- Novel 1,8-naphthalimide dye for multichannel sensing of H+ and Cu2+
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A novel 1,8-naphthalimide dye with simple structure has been produced by a facile synthetic method for colorimetric and fluorescent sensing of H+ and Cu2+. In CH3CN/H2O (1/1, v/v), the dye could monitor H+ using dual channels (ratiometric absorbance and fluorescence intensity change) from pH 6.2 to 12.0. Meanwhile, in the pH range of 1.9–5.2, the dye could also be used to detect Cu2+ using triple channels [ultraviolet–visible (UV–Vis) absorption, fluorescence intensity reduction, as well as fluorescence blueshift]. The detection limits for Cu2+ evaluated by colorimetric and fluorescent titration were 6.10?×?10?7 and 2.62?×?10?7?M, respectively. The dye exhibited specific selectivity and sensitivity for H+ and Cu2+ over various coexisting metal ions. Moreover, the sensing mechanism of the dye for H+ and Cu2+ was carefully examined.
- Chen, Yufen,Tang, Tengxuan,Chen, Yuhua,Xu, Dongmei
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- Development of naphthalimide-functionalized thermochromic conjugated polydiacetylenes and their reversible green-to-red chromatic transition in the solid state
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Development of PDAs has received great attention in many fields due to their optical and chromatic properties towards external stimuli. In this article, two novel PDAs (NPI-PDA1 and NPI-PDA2) containing naphthalimide as a head group are designed and synthesized through self-assembly followed by topochemical polymerization, and these compounds show a reversible green-to-red colorimetric transition upon heating. PEO-embedded films are fabricated to facilitate the investigation of the thermochromic properties, and the surface morphologies of the films are observed by SEM analysis. The thermochromic behavior and color transitions are observed using photography and electronic absorption spectroscopy. The changes in the extended ene-yne conjugated system of the polymer during heat treatment are successfully monitored by Raman spectrometry. Moreover, PDA-embedded crayon wax-based hand-writable pens are fabricated and used efficiently on a solid substrate. NPI-PDA1 and NPI-PDA2 display excellent reversibility in the temperature ranges of 25–120 °C and 25–160 °C, respectively in the PEO polymer and paraffin wax matrices.
- Mergu, Naveen,Kim, Hyorim,Heo, Gisu,Son, Young-A.
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- Combination of sensor potential and antimicrobial activity of a new 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide
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A blue emitting 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide bearing a dimethylaminoethyloxy group as a receptor fragment for metal ions and protons has been designed and synthesized. The basic photophysical properties of the compound have been investigated in organic solvents of different polarity. The detection of different metal cations (Pb2+, Cu2+, Cd2+, Co2+, Zn2+and Mn2+) has been studied by fluorescence spectroscopy. Depending on pH, the new compound shows "off-on" switching from alkaline to acid media. A new complex of Cu(II) with the 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide has been synthesized and characterized. The antibiotic activity of the complex was evaluated against some bacterial and yeast cultures.
- Staneva, Desislava,Vasileva-Tonkova, Evgenia,Makki, Mohamad S.I.,Asiri, Abdullah M.,Grabchev, Ivo
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- Fluoride ion activated CO2 sensing using sol-gel system
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CO2 detection has drawn a lot of attention due to its important role in the environment and in medical diagnosis. Two amino substituted naphthalimides are reported as new anion-induced CO2 selective chemosensors. The new naphthalimides contain either a hydrazinecarbothiourea or a hydrazinecarboxylate group which served as an anion recognition site. The addition of F? induced a distinct color change and a fluorescent quenching effect, which was revived by subsequent addition of CO2. The naphthalimide bearing a hydrazinecarboxylate group also served as an organo gelator, which showed a unique sol-gel transition as well as color/fluorescent changes with F? and CO2.
- Liu, Yifan,Lee, Dayoung,Zhang, Xin,Yoon, Juyoung
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- A novel ratiometric fluorescent probe for quantitative detection of isocyanates in air
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Isocyanates are important industrial raw materials, but they are hazardous to human health. Especially, gaseous isocyanates cause serious public health problems. Therefore, it is significant to monitor isocyanates in air. In this work, a novel ratiometric fluorescent probe based on a new fluorophore platform, which is designed by inserting a styryl π-bridge between donor and acceptor units of 1, 8-naphthalimide, was developed for quantitative detection of gaseous isocyanates. In the presence of isocyanates, fluorescence of probe solution changed from orange to yellow-green, which caused by alteration of substituent at the 4th position of styryl group resulted from reaction between isocyanates and probe, thus achieving ratiometric detection for isocyanates. And this probe exhibited a fast, sensitive and selective response towards isocyanates. Furthermore, probe solution absorption method was employed to detect quantitatively isocyanates in air. This strategy may be a powerful tool for monitoring isocyanates in air, and also provide a referable approach for detection of volatile organic compounds in air.
- Chen, Kai,Chen, Wanjuan,Sun, Jin,Bai, Mingyang,Gao, Zhenzhong,Hou, Xianfeng
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- Fabrication of double emission enhancement fluorescent nanoparticles with combined pet and aiee effects
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The major challenge in the fabrication of fluorescent silica nanoparticles (FSNs) based on dye-doped silica nanoparticles (DDSNs) is aggregation-caused fluorescence quenching. Here, we constructed an FSN based on a double emission enhancement (DEE) platform. A thio-reactive fluorescence turn-on molecule, N-butyl-4-(4-maleimidostyryl)-1,8-naphthalimide (CS), was bound to a silane coupling agent, (3-mercaptopropyl)-trimethoxysilane (MPTMS), and the product N-butyl-4-(3-(trimethoxysilyl-propylthio)styryl)-1,8-naphthalimide (CSP) was further used to fabricate a core–shell nanoparticle through the St?ber method. We concluded that the turn-on emission by CSP originated from the photoinduced electron transfer (PET) between the maleimide moiety and the CSP core scaffold, and the second emission enhancement was attributed to the aggregation-induced emission enhancement (AIEE) in CSP when encapsulated inside a core–shell nanoparticle. Thus, FSNs could be obtained through DEE based on a combination of PET and AIEE effects. Systematic investigations verified that the resulting FSNs showed the traditional solvent-independent and photostable optical properties. The results implied that the novel FSNs are suitable as biomarkers in living cells and function as fluorescent visualizing agents for intracellular imaging and drug carriers.
- Chang, Cheng-Chung,Wu, Hsing-Ju
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- Green synthesis of fluorescent N,O-chelating hydrazone Schiff base for multi-analyte sensing in Cu2+, F? and CN? ions
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A colorimetric and fluorometric hydrazone Schiff's base derived from dehydroacetic acid by three-steps and high-yield syntheses under green approach employing ethanol as a solvent has been prepared. Multi-analyte sensing for both metal cation (Cu2+) and anions (F? and CN?), with high sensitivity and competitive selectivity, was encountered. The sensing mechanism of anion detection found to be deprotonation of N–H and O–H moieties in the presence of ions. However, metal cation like copper(II) ions chelation with sensor, leads to diminish intra-molecular charge transfer (ICT) with chelation induced quenching of fluorescence (CHQF). Contrary, anionic interaction ensued in heightened ICT as well as photo-induced electron transfer (PET) processes. The Job's plots interpretation rendered stoichiometry of 2:1 with Cu2+/F? and 1:1 with CN?. Moreover, the detection limits of 0.962 ppm (Cu2+), 0.023 ppm (F?) and 0.073 ppm (CN?) were much lower than WHO guidelines. Further, either water or methanol was employed to differentiate F?/CN? ions with sensor in THF, with prominent visible naked eye and fluorometric responses.
- Saini, Neeraj,Prigyai, Nicha,Wannasiri, Chidchanok,Ervithayasuporn, Vuthichai,Kiatkamjornwong, Suda
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- Cis/trans Fluorescent Recognition by Naphthalimide Dyes???CB [7] Assembly
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A novel method to recognize cis/trans isomers was studied here. The naphthalimide dye as guest could bind with host cucurbit [7]uril (CB [7]) and 1:1 naphthalimide dye???CB [7] assembly was formed. Moreover, this assembly was used as a fluorescent probe to recognized Fumaric acid (FA) and maleic acid (MA) via fluorescence titration. Two carboxyls in MA are in the same side, they could form stable interaction with the assembly and the fluorescence intensity decreased obviously when naphthalimide dye???CB [7] was titrated by MA (nearly quenched in 1.5 equiv). But two carboxyls in FA are in opposite sides, the interaction between FA and the assembly was weak and not stable, and the fluorescence intensity changed inconspicuously when the assembly was titrated by FA.
- Li, Junyong,Gu, Xiaomin,Yuan, Xiaosheng,Qiu, Qiqi,Sun, Jie,Wang, Haibo
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- A two-channel chemosensor for the optical detection of carboxylic acids, including cholic acid
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A neutral receptor, in which a urea fragment has been equipped with two naphthaleneimide subunits, on interaction with acetate, in a DMSO solution, undergoes deprotonation of one of the N-H fragments; an event which is signalled by a yellow-to-red colour change and by the quenching of the blue fluorescence of the naphthalneimide subunit, with no competition by a number of anions (phosphate, nitrate, sulfate, chloride or bromide). This procedure can be employed for the visual and spectroscopic detection of cholic acid, even in presence of the other competing bile acids, such as glycocholic and taurocholic. The Royal Society of Chemistry 2005.
- Esteban-Gomez, David,Fabbrizzi, Luigi,Licchelli, Maurizio,Sacchi, Donatella
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- Ratiometric chemodosimeter: An organic-nanofiber platform for sensing lethal phosgene gas
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Herein, we report the fabrication of organic nanofibrils, using electrospun 3-oxime-4-hydroxy-1,8-naphthalic-n-butylimide (R1)-doped polycaprolactone (PCL), for application as a gaseous phosgene-specific sensing device. The phosgene-mediated adsorption of the nanofibers gives rise to an observable colorimetric switch from brown-red to pale greenish-yellow and a synchronized ratiometric spectral emission with significantly high Stokes shift. The high surface to volume ratio and innovative properties of the nanofiber mats lead to the diminution of response time in comparison to the composite film of the same materials. Proficient gas penetration allows a fast chemical reaction, which is proportional to the phosgene concentration and delivers a very low detection limit of 0.087 ppm. To the best of our knowledge, this is the lowest limit of detection of gaseous phosgene for any robust protocol to date. Confocal fluorescence imaging and scanning electron microscopy (SEM) studies revealed partial deformation on the surface of the nanomaterials upon the adsorption of phosgene, indicating the phosgene-mediated chemical transformation. The fluorescent naphthalic-oxime with an elevated specific surface area of nanofibrous polymeric supports proffers fast optical and visual phosgene detection for industrial and environment application. Importantly, the LOD of gaseous phosgene in all solid protocols used is far lower than the safe phosgene concentration levels for human exposure.
- Maiti, Kalipada,Ghosh, Debasish,Maiti, Rituparna,Vyas, Veena,Datta, Pallab,Mandal, Debabrata,Maiti, Dilip K.
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- Turn-on fluorescent detection of strong acids based on a naphthalimide-indoline hybrid
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A naphthalimide-indoline hybrid (1) was developed as a pH-sensitive turn-on fluorescent probe. Probe 1 displays a weak fluorescence intensity in pH span of 2.5–11.0 owing to a photo-induced electron transfer (PET) from the indoline moiety to the naphthalimide. However, the PET process is suppressed under the pH of 2.5, showing a strong fluorescence signal at 430?nm. The turn-on fluorescent change of 1 is selective for the acidity (H+) over other anions, metal ions, redox species and it displays a good reversibility. Moreover, glass TLC plates coated with probe 1 can readily detect acid vapors at an ambient atmosphere.
- Lee, Jinju,Lee, Min Hee
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- Paintable Room-Temperature Phosphorescent Liquid Formulations of Alkylated Bromonaphthalimide
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Organic phosphors have been widely explored with an understanding that crystalline molecular ordering is a requisite for enhanced intersystem crossing. In this context, we explored the room-temperature phosphorescence features of a solvent-free organic liquid phosphor in air. While alkyl chain substitution varied the physical states of the bromonaphthalimides, the phosphorescence remained unaltered for the solvent-free liquid in air. As the first report, a solvent-free liquid of a long swallow-tailed bromonaphthalimide exhibits room-temperature phosphorescence in air. Doping of the phosphor with carbonyl guests resulted in enhanced phosphorescence, and hence a large-area paintable phosphorescent liquid composite with improved lifetime and quantum yield was developed.
- Goudappagouda,Manthanath, Ananthakrishnan,Wakchaure, Vivek Chandrakant,Ranjeesh, Kayaramkodath Chandran,Das, Tamal,Vanka, Kumar,Nakanishi, Takashi,Babu, Sukumaran Santhosh
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- An o-hydroxyl aldehyde structure based naphthalimide derivative: Reversible photochromic properties and its application in ClO? detection in living cells
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A bifunctional organic compound 2-butyl-6-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de] isoquinoline-5-carbaldehyde (BHC) with photochromic properties in solid state and probe detection for ClO? in complete water solution was synthesized and fully characterized. A ‘white–yellow–white’ reversible photochromic behavior could be observed when alternating UV/vis light irradiation on the solid BHC powder. Good fatigue resistance and adjustable bleaching rate were shown when heating conditions changes. In addition, BHC displayed a high selectivity and low detection limit (1.16 × 10?8 M) for ClO?. The photoluminescent fluorescence “on-off” recognition result can be easily identified and BHC has been tested for safely imaging living cells and detecting hypochlorite anion in vitro and vivo. A better water solubility of BHC effectively reduces damage caused by organic solvent in cell imaging progress.
- Tang, Xinxue,Sun, Hao,Nie, Jing,Han, Xiang'en,Zhao, Yun,Zhang, Ran,Ni, Zhonghai
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- A rapid and highly sensitive fluorescent imaging materials for thiophenols
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Thiophenols, a class of toxic and polluting compounds, are widely used in industrial production. Meanwhile, some aliphatic thiols play important roles in living organisms. Therefore, the development of probes for specific thiophenol detection is of great importance. Herein, a novel highly sensitive and selective 'off-on' fluorescent probe for detecting thiophenols has been developed by an ICT mechanism through a rational design. The probe displays a large Stokes shift (140 nm) and 60-fold fluorescence intensity enhancement. More importantly, the probe features a rapid signal response time (within 100 s), a good linearity range and the detection limit is as low as 13 nM. In addition, the ability of the probe to detect thiophenols in living cells (HepG2 cells) via an enhancement of the fluorescence has also been demonstrated.
- Zhang, Weijie,Huo, Fangjun,Liu, Tao,Wen, Yin,Yin, Caixia
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- A highly selective fluorescent probe based on Michael addition for fast detection of hydrogen sulfide
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A new 4-hydroxy-1,8-naphthalimide-based compound (probe 1) has been designed and synthesized. The colorimetric and fluorescent properties of probe 1 towards hydrogen sulfide (H2S) were investigated in detail. The results show that the probe 1 c
- Gao, Baozhen,Cui, Lixia,Pan, Yong,Xue, Minjie,Zhu, Boyu,Zhang, Guomei,Zhang, Caihong,Shuang, Shaomin,Dong, Chuan
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- Highly selective fluorescence turn-on chemosensor based on naphthalimide derivatives for detection of trivalent chromium ions
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A new fluorescent probe, NPQ-C, was synthesized. NPQ-C was based on the naphthalimide derivatives and exhibited high selectivity and sensitivity for Cr3+ ions. As a Cr3+-amplified fluorescent probe, Its fluorescence spectrum showed 5.5-fold enhancement in the intensity of the signal at 500 nm on binding with the Cr3+. Based on the fluorescence titration spectra and Job's-plot analysis, binding mode of NPQ-C with Cr 3+ was proposed. Fluorescence intensity was linear with concentration of Cr3+ cation in a range from 0 to 10 μmol·L -1. NPQ-C was also sensitive for Cr3+. The detection limit was calculated to be 0.20 μmol·L-1 which indicated that NPQ-C was sensitive to Cr3+. Copyright
- Chen, Zhijun,Wang, Limin,Zou, Gang,Teng, Mingshuang,Yu, Jianjun
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- A novel flavin derivative reveals the impact of glucose on oxidative stress in adipocytes
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We present the synthesis and characterisation of naphthalimide-flavin redox sensor 1 (NpFR1), a novel flavin molecule that is almost non-fluorescent in reduced form, but oxidation gives rise to a 125-fold increase in fluorescence. Confocal microscopy experiments confirm that NpFR1 is sensitive to redox changes within living cells. This journal is the Partner Organisations 2014.
- Yeow, Jonathan,Kaur, Amandeep,Anscomb, Matthew D.,New, Elizabeth J.
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- A two-photon off-on fluorescence probe for imaging thiols in live cells and tissues
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A two-photon (TP) fluorescence imaging probe (Z1) was designed to detect biothiols through a photoinduced electron transfer pathway utilizing N-butyl-naphthalimide as the fluorophore and 2,4-dinitrobenzene-sulfonyl as the responsive group, which were linked together by piperazine. The synthesized Z1 displayed high selectivity to biothiols, significant fluorescence off-on properties, and a marked two-photon absorption cross section (δ = 110 GM). Moreover, Z1 showed good biocompatibility and insensitivity toward changes in the biologically relevant pH range (7.2-8.4), which enabled the utilization of Z1 to monitor biothiol levels not only in live cells but also in tissues at depths of 50-250 μm.
- Zhu, Xinyue,Li, Yan,Zan, Wenyan,Zhang, Jianjian,Chen, Zhenjie,Liu, Xiaoyan,Qi, Fengchao,Yao, Xiaojun,Zhang, Xiaoyu,Zhang, Haixia
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- Controlling photophysics of styrylnaphthalimides through TICT, fluorescence and: E, Z -photoisomerization interplay
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The photophysical properties of naphthalimide dyes NI1-3 with electron releasing 4-methoxy- (NI1), 3,4-dimethoxystyryl- (NI2) and dimethylaminostyryl (NI3) groups are examined in a variety of protic and aprotic solvents. All compounds demonstrate positive solvatochromism in the steady-state absorption and fluorescence spectra. The analysis of the dependence of the Stokes shift on the polarity of the solvent using the Lippert-Mataga equation allowed us to determine the change in the dipole moment upon excitation. The obtained data correspond to the formation of highly polar charge transfer states. Based on the transient absorption spectra and time-resolved fluorescence measurements, the presence of two different emissive states was definitely proved. The primarily formed planar Local Excited (LE) state dominates in non-polar solvents like cyclohexane and toluene where it relaxes mostly through fluorescence and E,Z-isomerisation pathways. In polar solvents, an alternative relaxation channel emerges that consists of twisting around single bond between styryl and naphthalimide fragments, which leads to the formation of a Twisted Intramolecular Charge Transfer (TICT) state. The factors affecting the fluorescence of TICT states are discussed. The observed spectral effects are rationalized using quantum-chemical calculations, X-ray data and NMR spectroscopy.
- Panchenko, Pavel A.,Arkhipova, Antonina N.,Fedorova, Olga A.,Fedorov, Yuri V.,Zakharko, Marina A.,Arkhipov, Dmitry E.,Jonusauskas, Gediminas
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- A colorimetric and fluorescence turn-on probe for the detection of palladium in aqueous solution and its application in vitro and in vivo
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Palladium has attracted a growing number of attention due to its widely application and environmental toxicity. Consequently, a novel colorimetric and fluorescent turn-on probe (NT-Pd) was designed for sensing of palladium. This probe was capable of detecting palladium in aqueous solution (DMSO was less than 1%, v/v). Under this mild condition, NT-Pd displayed high selectivity and sensitivity for sensing of palladium in both colorimetric and fluorescent strategy, such as low detection limit (5.30 nM) and rapid response time (within 10 min). In addition, NT-Pd was successfully applied for imaging of exogenous palladium in living cells and zebrafishes with good biocompatibility and low toxicity, indicating this probe has satisfactory application potential to track palladium in the complicated biological system.
- Chen, Jun,Guo, Yan-Rong,Han, Xin-Ya,Luo, Xiao-Gang,Qiu, Yuan,Sun, Qi,Wang, Da-Wei,Wu, Feng-Shou
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- A highly selective colorimetric and ratiometric fluorescent chemodosimeter for detection of fluoride ions based on 1,8-naphthalimide derivatives
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A high selective colorimetric and ratiometric fluorescent probe based on 4-hydroxy-1, 8-naphthalimide was designed and synthesized to detect fluoride ions (F-). The sensing behavior of this probe was studied by UV-visible and fluorescence spect
- Kai, Yumei,Hu, Yonghong,Wang, Kai,Zhi, Wenbiao,Liang, Mengmeng,Yang, Wenge
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- A highly selective and sensitive fluorescent turn-off probe for Cu2+ based on a guanidine derivative
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A new highly selective and sensitive fluorescent probe for Cu2+, N-n-butyl-4-(10-cyclooctene-10,30,60-triazole)-1,8-naphthalimide (L), was synthesized and evaluated. The structure of compound L was characterized via IR, 1H-NMR, 13C-NMR and HRMS. The fluorescent probe was quenched by Cu2+ with a 1:1 binding ratio and behaved as a "turn-off" sensor. An efficient and sensitive spectrofluorometric method was developed for detecting and estimating trace levels of Cu2+ in EtOH/H2O. The ligand exhibited excitation and emission maxima at 447 and 518 nm, respectively. The equilibrium binding constant of the ligand with Cu2+ was 1.57 × 10 4 M -1, as calculated using the Stern-Volmer equation. Ligand L is stable and can be used to detect Cu2+ in the range of pH from 7 to 12. The sensor responded to Cu2+ rapidly and a large number of coexisting ions showed almost no obvious interference with the detection.
- Ye, Fei,Chai, Qiong,Liang, Xiao-Min,Li, Ming-Qiang,Wang, Zhi-Qiang,Fu, Ying
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- A novel fluorescent molecule based on 1,8-naphthalimide: Synthesis, spectral properties, and application in cell imaging
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A novel naphthalimide molecule, 4-(2-methoxyethoxy)-N-butyl-1,8- naphthalimide (MEBN), has been synthesized and characterized. The UV-visible absorption and fluorescence emission spectral properties in n-hexane, toluene, CHCl3, and CH3OH were studied. Its optical properties depend on solvent polarity. The application of MEBN in cell imaging was investigated.
- Xiao, Haibo,Chen, Minjuan,Shi, Guanghao,Wang, Lei,Yin, Hongyao,Mei, Chong
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- A highly selective ratiometric fluorescent probe for biothiol and imaging in live cells
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A new N-butyl-4-amino-1,8-naphthalimide-based colorimetric and ratiometric fluorescent probe for the detection of biothiols (cysteine, homocysteine, and glutathione) was designed and synthesized. The probe exhibited good selectivity and sensitivity toward biothiols over other non-thiol-bearing amino acids and common anions with significant changes in both color (from colorless to yellow) and fluorescence (from blue to yellow-green). The mechanism is based on cleavage of disulfide by thiols followed by an intramolecular cyclization to give the product, N-butyl-4-amino-1,8-naphthalimide, which showed outstanding intramolecular charge transfer (ICT). Therefore, ratiometric fluorescence signal was observed. Furthermore, the probes were successfully applied for visualizing endogenous thiols in living cells.
- Gao, Baozhen,Cui, Lixia,Pan, Yong,Zhang, Guomei,Zhou, Ying,Zhang, Caihong,Shuang, Shaomin,Dong, Chuan
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- UV and fluorescent spectra study the reaction between 1, 8-Naphthalimide derivative and hypochlorite their applications
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Two simple, efficient turn-on fluorescent probes for hypochlorite have been rationally designed and developed by utilizing the oxidation of hypochlorite. Notably, probe 1 and 2 displayed rapid and remarkable turn-on responses to ClO? in PBS buffer solution (pH 7.4). Further, the optical properties of two probes and their ClO?-addition products were confirmed by density functional theory calculations. And detection limits of two probes for ClO? based on the definition by IUPAC were calculated for 2.882 nM and 0.354 μM. More importantly, cell imaging experiments demonstrated that probe 1 was more suitable for detecting the ClO? in living A549 cells. And both two probes had the possibility of potentially applied in practical applications such as detecting the hypochlorite concentration of tap water and river water.
- Li, Jiawei,Liu, Tao,Huo, Fangjun,Chao, Jianbin,Zhang, Yongbin,Yin, Caixia
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- Synthesis and fluorescent studies of a low molecular weight rotor for living cancer cell imaging
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A fluorescent and low molecular weight rotor (9) based on 1, 8-napthalimide for living cancer cell imaging was designed and synthesized. The effects of solvent polarity and viscosity on the fluorescence spectra of compound 9 were investigated. Rotor 9 exhibited favorable photophysical properties with a large Stokes shift and induced high viscosity sensitivity in a glycerol-ethanol system with an approximately 10-fold increase in emission intensity. The addition of different concentrations of BSA to compound 9 in PBS elicited an 8-fold increase in fluorescence intensity, suggesting superior environmental sensitivity. Fluorescence lifetime measurements also confirmed these results. Furthermore, compound 9 showed time- and concentration-dependent in vitro cellular uptake behavior in MCF-7 cells and other cancer cell lines. CLSM assay of tumor sections from MCF-7 nude mice also confirmed the possibility of tumor imaging.
- He, Yang,Lu, Wei,Ma, Mingliang,Yu, Xumeng,Zhu, Shulei
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- Fluorescent photochromic donor-acceptor Stenhouse adduct controlled by visible light
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A novel photochromic fluorescent DASA (donor-acceptor Stenhouse adduct) switch controlled by visible light was successfully designed and synthesized. Using 1,8-naphthalimide fluorophore in combination with indoline-based “donor” and barbituric acid “acceptor”, the DASA molecule exhibits two independent absorption bands at 440 nm and 616 nm. The physical and thermodynamic properties of fluorescent donor-acceptor Stenhouse adduct (DASA-NDI) have been investigated in different solvents. In accordance with the unique fluorescent properties under visible light/heat and H+/Cu2+, using fluorescence intensity at 604 nm (I604) as an output and visible light, H+ and Cu2+ as inputs, a combinatorial logic gate consisting of NOR and AND logics can be described and operated.
- Yang, Shun,Liu, Jing,Cao, Zhanqi,Li, Mingming,Luo, Qianfu,Qu, Dahui
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- A small-molecule-based device for data storage and electro-optical switch applications
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A sandwich device fabricated with light sensitive organic molecules shows excellent dynamic random access memory and excellent electro-optical switch behavior with high ON/OFF current ratio (109) and long-term stability under continuous stress. We envision this type of organic molecules will be an important alternative to the traditional materials for electronic applications.
- Li, Hua,Jin, Zhengneng,Li, Najun,Xu, Qingfeng,Gu, Hongwei,Lu, Jianmei,Xia, Xuewei,Wang, Lihua
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- A novel ratiometric fluorescent probe based on 1, 8-naphthalimide for the detection of Ho3 + and its bioimaging
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A ratiometric fluorescent probe for the detection of Ho3 + in DMSO-aqueous medium was designed and synthesized based on 1, 8-naphthalimide. The probe displayed response to Ho3 + with a fluorescence decrease at 512 nm and enhancement at 480 nm, accompanying with a distinct fluorescence change from bright yellow-green to cyan. Besides, the probe exhibited a lower detection limit (6 × 10? 8 M) and could be used in intracellular fluorescence imaging. To the best of the knowledge, it was the first ratiometric fluorescent probe for Ho3 + detection. This probe was expected to be a useful tool for further elucidating the roles of Ho3 + in materials, biology and environment.
- Zhang, Huifang,Liu, Tao,Yin, Caixia,Wen, Yin,Chao, Jianbin,Zhang, Yongbin,Huo, Fangjun
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- A colorimetric probe for copper(II) ion based on 4-amino-1,8-naphthalimide
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A novel fluorescent probe with naphthalimide as fluorophore and di(2-picolyl)amino unit as receptor for Cu(II) was designed and synthesized. In water/acetonitrile solution, the presence of Cu2+ ions induced significant blue shift on the maximum absorption band as well as complete fluorescence quenching due to the formation of a 1:1 metal-ligand complex. It exhibited high selectivity toward Cu(II) and no interference from other metal ions was observed. The structure of the complex was characterized by single crystal X-ray diffraction experiments. The results of this research demonstrate successfully that excellent sensing properties can be achieved by a small organic compound with very simple structure. This is also the first single crystal structure which reveals directly the coordination pattern of fluorescent probe bearing di-2-picoly-amine unit with Cu(II).
- Wang, Haixia,Yang, Lin,Zhang, Wenbo,Zhou, Yu,Zhao, Bing,Li, Xiyou
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- Four-, five- and six-coordinated transition metal complexes based on naphthalimide Schiff base ligands: Synthesis, crystal structure and properties
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Two bidentate Schiff base ligands (HL1?=?N-n-butyl-4-[(E)-2-(((2-aminoethyl)imino)methyl)phenol]-1,8-naphthalimide; and HL2?=?N-n-butyl-4-[(E)-2-(((2-aminoethyl)imino)methyl)-6-methoxyphenol]-1,8-naphthalimide) with their metal complexes [Cu(L1)2] (1), [Zn(L1)2(Py)]2?H2O (2) and [Ni(L2)2(DMF)2] (3) have been synthesized and characterized. Single-crystal X-ray structure analysis reveals that complex 1 has a four-coordinated square geometry, while complex 2 is a five-coordinated square pyramidal structure and complex 3 is a distorted six-coordinated octahedral structure. Cyclic voltammograms of 1 indicate an irreversible Cu2+/Cu+ couple. In vitro antioxidant activity assay demonstrates that the ligands and the two complexes 1 and 3 display high scavenging activity against hydroxyl (HO?) and superoxide (O2 ??) radicals. Moreover, the fluorescence properties of the ligands and complexes 1–3 were studied in the solid state. Metal-mediated enhancement is observed in 2, whereas metal-mediated fluorescence quenching occurs with 1 and 3.
- Xu, Yuling,Zhang, Han,Shen, Kesheng,Mao, Shanshan,Shi, Xinkui,Wu, Huilu
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- A fluorescent PET chemosensor for Zn2+ cations based on 4-methoxy-1,8-naphthalimide derivative containing salicylideneamino receptor group
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New 4-methoxy-1,8-naphthalimide derivative containing a salicylideneamino receptor group at the imide nitrogen atom demonstrated selective fluorescent response to Zn2+ cations due to the formation of 1: 2 and 2: 1 ligand–metal complexes.
- Panchenko, Pavel A.,Ignatov, Pavel A.,Zakharko, Marina A.,Fedorov, Yurii V.,Fedorova, Olga A.
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- A Water-Soluble, Two-Photon Probe for Imaging Endogenous Hypochlorous Acid in Live Tissue
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Detection of hypochlorous acid (HClO) in the living system may help to uncover its essential biological functions. However, current imaging agents suffer from poor water solubility that limit their live-tissue applications. Here, a water-soluble probe (NNH) is devised through innovative hydrazone modification of 1,8-naphthalimide at 3′ position. NNH was successfully applied to tracking endogenous HClO in both cultured macrophages and a liver injury model in mice. NNH demonstrated remarkably increased water solubility and multiple desirable features including two-photon absorbance, anti-bleaching capability, rapid cellular uptake, and low cytotoxicity. NNH is the first hydrazone-based probe for real-time imaging of HClO in live tissue.
- Xing, Panfei,Feng, Yanxian,Niu, Yiming,Li, Qiu,Zhang, Zhe,Dong, Lei,Wang, Chunming
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- A Highly Selective and Sensitive Fluorescent Turn-on Probe for Al3+ Based on Naphthalimide Schiff Base
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A simple and highly selective aluminium ion fluorescent probe (N-n-butyl-4-[3,3′-((2-aminoethyl)azanediyl)bis(N′-(2-hydroxy-3-methoxybenzylidene)-propanehydrazide)]-1,8-naphthalimide) (P-1) employing 1,8-naphthalimide as the fluorophore group and Schiff base as the recognition group has been successfully synthesized and systemically characterized. The structure of probe P-1 has been established by single crystal X-ray. The photophysical properties of probe P-1 revealed that the values of the fluorescence quantum yield are higher in non-polar solvents than in polar solvents. Compared with the free P-1, the fluorescence intensity of P-1 shows a significant fluorescence enhancement in the presence of Al3+ without any significant interference from other cations and anions. In addition, from the UV–vis titration, fluorescence titration,Job’s plot and 1H NMR spectra analysis, we could primarily confirm that three important coordinative sites of P-1 for Al3+ were from imine nitrogen and tertiary amine nitrogen and formed a 1:1 complex. The fluorescence intensity for the (P-1) showed a good linearity with the concentration of Al3+ in the range of 3.0–10.0?μM, with a detection limit of 8.65?×?10?8?M and a binding constant (Kb) of 4.95?×?104?M?1. It is worthy of note that the probe P-1 was successfully applied in detection of Al3+ in Yellow River and tap water samples.
- Peng, Hongping,Shen, Kesheng,Mao, Shanshan,Shi, Xinkui,Xu, Yuling,Aderinto, Stephen Opeyemi,Wu, Huilu
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- A 4-hydroxynaphthalimide-derived ratiometric fluorescent chemodosimeter for imaging palladium in living cells
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A highly selective ratiometric fluorescent chemodosimeter derived from 4-hydroxynaphthalimide was designed and synthesized to image palladium species in living cells by virtue of a palladium-catalyzed depropargylation reaction, and it could monitor three typical palladium species (0, + 2 and + 4) without additional reagents. The Royal Society of Chemistry 2011.
- Zhu, Baocun,Gao, Chenchen,Zhao, Yunzhou,Liu, Caiyun,Li, Yamin,Wei, Qin,Ma, Zhenmin,Du, Bin,Zhang, Xiaoling
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- A highly selective wavelength-ratiometric and colorimetric probe for cysteine
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Based on the nucleophilic aromatic substitution reaction mechanism, a new highly selective probe for cysteine (Cys), N-butyl-4-bromo-3-nitro-1,8- naphthalimide (1), was designed and synthesized. The probe displayed a remarkable (58 nm) red-shift in the absorption spectra and the color changes from colorless to yellow upon reaction with Cys. The probe could detect Cys quantitatively in the range of 0-0.9 mM by both normal and ratiometric absorption spectrometry methods. Moreover, 1 could also serve as a "naked-eye" probe for Cys with a minimum detectable concentration of approximately 50 μM.
- Zeng, Xiaodan,Zhang, Xiaoling,Zhu, Baocun,Jia, Hongying,Li, Yamin
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- Identification and Isolation of Glucosytransferases (GT) Expressed Fungi Using a Two-Photon Ratiometric Fluorescent Probe Activated by GT
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As is well-known, fungi are an important biocatalysis model of glucosylation and have been widely applied for bioactive compounds glucosylation mediated by the intracellular glucosytransferases (GTs). However, there is no efficient method for the real-time detection of GTs and the rapid isolation of the target fungi strains with the high expression of GTs. In the present work, we first developed a two-photon ratiometric fluorescent probe N-(n-butyl)-4-hydroxy-1,8-naphthalimide (NHN) for detecting the glucosyltransferases activity and intracellular imaging of GTs. Under UV light (365 nm), the transformed product of NHN mediated by intracellular glucosyltransferase displayed blue emission to guide the rapid isolation of fungal strains possessing overexpression of GTs from complex soil samples. Finally, by using the fluorescent probe, two target fungi were isolated and identified to be Rhizopus oryzae and Mucor circinelloides by molecular analysis, and they exhibited a robust capability for regio- and stereospecific O-glycosylation. Our results fully demonstrated that NHN may be a promising tool for guiding real-time GTs activity in fungal strains and even for developing natural fungal strains with GTs overexpression.
- Feng, Lei,Li, Ping,Hou, Jie,Cui, Yong-Lei,Tian, Xiang-Ge,Yu, Zhen-Long,Cui, Jing-Nan,Wang, Chao,Huo, Xiao-Kui,Ning, Jing,Ma, Xiao-Chi
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- A highly sensitive and selective fluorescence turn-on probe for the sensing of H2S in vitro and in vivo
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A fluorescence turn-on probe, 2-butyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl 2,4-dinitrobenzenesulfonate (NT-SH), has been constructed for sensing of hydrogen sulfide (H2S). NT-SH exhibited excellent detection performance including favorable water solubility, low fluorescence background, high enhancement (45-fold), large linear response range (0–50 μM) and low detection limit (80.01 nM) for H2S in aqueous. In addition, the response mechanism of NT-SH for H2S was confirmed by the theoretical calculation and mass spectral analysis. More importantly, the imaging experiments of H2S in vitro and in vivo confirmed that NT-SH had low cytotoxicity, and favorable biocompatibility. In addition, it illustrated that NT-SH was able to detected exogenous H2S in living cells and zebrafish. These results suggested that NT-SH can be act as a potential molecular tool for detecting of H2S in aqueous solution, in vitro and in vivo.
- Sun, Qi,Liu, Heng,Qiu, Yuan,Chen, Jun,Wu, Feng-Shou,Luo, Xiao-Gang,Wang, Da-Wei
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- Colorimetric fluoride sensor based on 1,8-naphthalimide derivatives
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A colorimetric chemosensor TBS-NA, 4-(tert-butyldimethylsilyloxy)-N-butyl- naphthalimide was designed and synthesized. Addition of fluoride ion to a CH3CN solution of TBS-NA can result in an obvious color change (from colorless to yellow) and UV-Vis absorption spectral change in a short time. This indicated that TBS-NA had highly selectivity for fluoride detection over other anions, such as Cl-, Br-, I-, HSO4-, ClO4- and AcO- in CH3CN solutions, and the selectively detection was due to the selective cleavage of Si-O bond in TBS-NA by fluoride. The detection limit was calculated to be 0.59 μM.
- Ren, Jun,Wu, Zhen,Zhou, Ying,Li, Yan,Xu, Zuxun
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- Enabling Light Work in Helical Self-Assembly for Dynamic Amplification of Chirality with Photoreversibility
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Light-driven transcription and replication are always subordinate to a delicate chirality transfer. Enabling light work in construction of the helical self-assembly with reversible chiral transformation becomes attractive. Herein we demonstrate that a hel
- Cai, Yunsong,Guo, Zhiqian,Chen, Jianmei,Li, Wenlong,Zhong, Liubiao,Gao, Ya,Jiang, Lin,Chi, Lifeng,Tian, He,Zhu, Wei-Hong
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- A naphthimide-based ratiometric fluorescent probe for selective and visual detection of phosgene in solution and the gas phase
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As a colorless, highly toxic and widely used chemical reagent, phosgene poses a potentially serious threat to public health and environmental safety. Therefore, there is an urgent need to develop a simple and sensitive method for detecting phosgene. In this work, a ratiometric fluorescent probe (NED) for phosgene was developed by utilizing 4-substituted 1,8-naphthimide unit as the fluorophore and ethylenediamine as the recognition moiety. The probe NED undergoes intramolecular cyclization reaction with phosgene, resulting in a remarkable ratiometric fluorescence response. The probe NED displays high sensitivity (LOD = 4.9 nM), excellent ratiometric fluorescence signal, and high selectivity toward phosgene over other relevant analytes. In addition, paper test strip capable of visually detecting gaseous phosgene has also been fabricated.
- Gu, Shuang-Xi,Hong, Yu,Liu, Ziru,Luo, Yabin,Xu, Zhiqiang,Yin, Jun,Zhang, Ming-Xing
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- Organic photoredox catalytic amino-heteroarylation of unactivated olefins to access distal amino ketones
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Here we describe a metal-free amino-heteroarylation of unactivated olefins via organic photoredox catalysis, providing a concise and efficient approach for the rapid synthesis of various δ (β, ?)-amino ketones under mild conditions. This protocol demonstrates that the new photocatalyst Cz-NI developed by our group has an excellent photoredox catalytic performance. Finally, a series of mechanistic experiments and DFT calculations indicate that this transformation undergoes a photoredox catalytic sequential radical addition/functional group migration process.
- Chen, Han-Nan,Ji, Zi-Qin,Luo, Yong-Chun,Xiao, Teng-Fei,Xu, Guo-Qiang,Xu, Peng-Fei,Yan, Pen-Ji,Zhang, Ji-Hua
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supporting information
p. 2882 - 2885
(2022/03/09)
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- Piperazine-bridged naphthalimide aminothiazole oxime compound as well as preparation method and application thereof
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The invention relates to piperazine bridged naphthalimide aminothiazole oxime compounds as well as a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The piperazine-bridged naphthalimide aminothiazole oxime compound is shown as a general formula I, has certain inhibitory activity on one or more of gram-positive bacteria, gram-negative bacteria and fungi, and can be used for preparing antibacterial and/or antifungal drugs, so that more efficient and safe candidate drugs are provided for clinical antimicrobial treatment, and the clinical treatment problems of increasingly serious drug resistance, stubborn pathogenic microorganisms, newly appearing harmful microorganisms and the like are favorably solved. The preparation raw materials are simple, cheap and easy to obtain, the synthetic route is short, and the method has important significance in anti-infection application.
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Paragraph 0036-0040
(2021/03/13)
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- Ligand-free Suzuki-Miyaura cross-coupling with low Pd content: rapid development by a fluorescence-based high-throughput screening method
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Suzuki-Miyaura (SM) cross-coupling is one of the most effective strategies for carbon-carbon bond formation, but previous methods have several drawbacks, such as the requirement of complicated ligands, toxic organic solvents, and high-content-Pd catalysts. Thus, in this study, a highly efficient SM cross-coupling was developed using metal oxide catalysts: 0.02 mol% Pd, aqueous solvent, no ligand, and room temperature. Metal oxides containing low Pd content (ppm scale) were prepared by a simple co-precipitation method and used as a catalyst for the SM reaction. A fluorescence-based high-throughput screening (HTS) method was developed for the rapid evaluation of catalytic activity and reaction conditions. Among the various metal oxides, Pd/Fe2O3showed the highest activity for the SM reaction. After further optimization by HTS, various biaryl compounds were obtained under optimal conditions: Pd/Fe2O3(0.02 mol% Pd) in aqueous ethanol at mild temperature without any ligands.
- Lim, Taeho,Ryoo, Jeong Yup,Jang, Mingyeong,Han, Min Su
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p. 1009 - 1016
(2021/02/16)
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- An HDAC8-selective fluorescent probe for imaging in living tumor cell lines and tissue slices
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Histone deacetylase 8 (HDAC8) has been used as a therapeutic target for many cancers as it is highly expressed in neuroblastoma cells and breast cancer cells. HDAC8-selective fluorescent probes need to be urgently developed. Herein, two novel fluorescent probes, namelyNP-C6-PCIandAM-C6-PCI, based on the conjugation of 1,8-naphthalimide with a highly selective inhibitor of HDAC8 (PCI-34051) were reported. Compared withPCI-34051(KD= 6.25 × 10?5M),NP-C6-PCI(KD= 8.05 × 10?6M) andAM-C6-PCI(KD= 7.42 × 10?6M) showed great selectivity toward HDAC8. Two fluorescent probes exhibited high fluorescence intensity underλex= 450 nm and a large Stokes shift (100 nm).NP-C6-PCIwas selected for cell and tissue imaging due to the similarity in the bioactivity ofNP-C6-PCIwithPCI-34051. The ability ofNP-C6-PCIto target imaging HDAC8 in SH-SY5Y and MDA-MB-231 tumor cells was demonstrated. Furthermore,NP-C6-PCIwas applied to imaging SH-SY5Y tumor tissue slices to indicate the relative expression level of HDAC8. Therefore, this HDAC8-selective fluorescent probe can be expected for applications in HDAC8-targeted drug screening as well as in pathologic diagnoses.
- Huang, Chaoqun,Li, Wei,Liu, Jian,Shan, Chenxiao,Shu, Yi,Wang, Xinzhi,Wen, Hongmei,Yan, Yinyu
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p. 8352 - 8366
(2021/10/14)
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- A palate of fluorescent corannulene derivatives: Synthesis, spectroscopic properties, and bio-imaging application
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Reported here is a palate of fluorescent corannulene derivatives suitable for cellular imaging. They are derived from "tagging"corannulene with known fluorophores. The tagged corannulenes display strong fluorescence (?F > 0.25 in MeOH), good photostability and long emission wavelength (500 nm to 600 nm). Cell staining experiments indicate that several of them have excellent cell membrane permeability and targeting ability. In addition, we have found an unexpected, highly efficient energy transfer from corannulene to the pendant fluorophore. This has implications for many areas of corannulene research.
- Finney, Nathaniel S.,Gao, Yan,Jiang, Haiyan,Liu, Xueling,Wang, Yali,Xu, Jun
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supporting information
p. 5818 - 5821
(2021/06/16)
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- A mitochondrial-targeted ratiometric probe for detecting intracellular H2S with high photostability
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Based on 4-bromo-1,8-naphthalic anhydride, one novel ratiometric fluorescence H2S-probe (IDNA) was designed and synthesized. Further studies indicate that IDNA can sensitively recognize H2S (detection limit of 7 μmol/L) with good selectivity and anti-interference ability. In addition, IDNA has satisfactory photostability in HeLa cells, ability of mitochondrial co-localization, and can be utilized in fluorescence imaging of H2S.
- Bu, Dandan,Wang, Yuying,Wu, Na,Feng, Wei,Wei, Donghui,Li, Zhanxian,Yu, Mingming
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supporting information
p. 1799 - 1802
(2021/03/09)
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- Fluorescent probe for detecting mercury ions and hypochlorite ions as well as preparation method and application of fluorescent probe
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The invention belongs to the technical field of organic synthesis, and particularly relates to a fluorescent probe for detecting mercury ions and hypochlorite ions as well as a preparation method and an application of the fluorescent probe. The molecular formula of the fluorescent probe is C19H19NO3S2, and the structural formula of the fluorescent probe is shown in the specification. The fluorescent probe disclosed by the invention realizes specific recognition response to mercury ions and hypochlorite ions, is not influenced by interference ions, can judge whether the mercury ions and the hypochlorite ions exist or not by directly observing with naked eyes, and has a wide application prospect in the field of biomolecule detection.
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Paragraph 0011; 0043-0046
(2021/06/13)
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- LED with aggregation-induced luminescence enhancement Naphthoyl imine compound with discoloring property and self-restoring force and application thereof
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The invention relates to a naphthyl imide compound with aggregation-induced emission enhancement, solvent discoloring and self-resilience photochromic properties and an application. The naphthyl imidecompound has a structure shown as formula I. The compou
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Paragraph 0035-0038; 0042
(2021/04/14)
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- BROMONAPHTHALIMIDE COMPOUNDS AND PHOSPHORESCENT LIQUID FORMULATION THEREOF
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The present invention provides a large scale paintable formulation of bromonapthalimide derivative compounds of formula (I) that shows phosphorescence in liquid state at 25-30° C. as well as their use as an indicator of temperature change in a visually enabled temperature measuring device.
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Paragraph 0091; 0092; 0093
(2021/05/07)
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- Ferrous iron fluorescent probe and application thereof
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The invention discloses a ferrous iron fluorescent probe and application thereof. The structural formula of the ferrous fluorescent probe is shown as a formula I, a ferrous fluorescence probe technology is applied to breeding of functional microorganisms
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Paragraph 0022; 0025-0027
(2021/01/24)
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- 1,8-Naphthalimide appended propiolate-based fluorescent sensor for selective detection of cysteine over glutathione and homocysteine in living cells
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Herein, a novel 1,8-naphthalimide-based fluorogenic compound, chemoprobeNASP, was designed and developed as a sensor platform for the selective detection of biologically important cysteine (Cys) over glutathione (GSH) and homocysteine (Hcy) in living-cells. In the presence of Hcy or Cys, the chemoprobeNASPdemonstrated a remarkable response in EtOH?:?H2O (90?:?10, v/v, 0.0670 M PBS buffer pH = 7.0) media at 416 nm (λmax), while the competitive amino acids showed no significant emission. To assess the fluorescence parameters, a validation study was also carried out. The chemoprobeNASPoffered a great sensitivity towards Cys and Hcy with ultra-low detection limits (Cys, 9.06 nM; Hcy, 57.5 nM), and it was highly selective over natural amino acids. The proposed sensing mechanism was confirmed using the MALDI-TOF-MS method. The molecular and electronic structures of the chemoprobeNASPandNASP-OH(Cys)were confirmed through DFT study. More importantly, the bio-imaging of intracellular Cys and Hcy by the chemoprobeNASPwas successfully applied with low cytotoxicity in living cells (human normal hepatocytes (THLE2) and human hepatocellular carcinoma (HepG2) cells). The results indicated that the developed chemoprobe will be a promising fluorogenic sensor for the diagnosis of biothiol-related illnesses.
- Aydin, Duygu,Karuk Elmas, Sukriye Nihan,Akin Geyik, Gonul,Bostanci, Aykut,Arslan, Fatma Nur,Savran, Tahir,Sadi, Gokhan,Yilmaz, Ibrahim
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supporting information
p. 16617 - 16624
(2021/09/28)
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- Strategic engineering of alkyl spacer length for a pH-tolerant lysosome marker and dual organelle localization
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Long-term visualization of lysosomal properties is extremely crucial to evaluate diseases related to their dysfunction. However, many of the reported lysotrackers are less conducive to imaging lysosomes precisely because they suffer from fluorescence quenching and other inherent drawbacks such as pH-sensitivity, polarity insensitivity, water insolubility, slow diffusibility, and poor photostability. To overcome these limitations, we have utilized an alkyl chain length engineering strategy and synthesized a series of lysosome targeting fluorescent derivatives namelyNIMCsby attaching a morpholine moiety at theperiposition of the 1,8-naphthalimide (NI) ring through varying alkyl spacers between morpholine and 1,8-naphthalimide. The structural and optical properties of the synthesizedNIMCswere explored by1H-NMR, single-crystal X-ray diffraction, UV-Vis, and fluorescence spectroscopy. Afterward, optical spectroscopic measurements were carefully performed to identify a pH-tolerant, polarity sensitive, and highly photostable fluoroprobes for further live-cell imaging applications.NIMC6displayed excellent pH-tolerant and polarity-sensitive properties. Consequently, allNIMCswere employed in kidney fibroblast cells (BHK-21) to investigate their applicability for lysosome targeting and probing lysosomal micropolarity. Interestingly, a switching of localization from lysosomes to the endoplasmic reticulum (ER) was also achieved by controlling the linker length and this phenomenon was subsequently applied in determining ER micropolarity. Additionally, the selected probeNIMC6was also employed in BHK-21 cells for 3-D spheroid imaging and inCaenorhabditis elegans(C. elegans) forin vivoimaging, to evaluate its efficacy for imaging animal models.
- Bhowal, Rohit,Biswas, Suprakash,Chopra, Deepak,Dutta, Tanoy,Koner, Apurba L.,Silswal, Akshay
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p. 9630 - 9644
(2021/07/28)
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- Study on synthesis and fluorescence property of rhodamine–naphthalene conjugate
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In this study, a novel ligand (HL) consisting of 2-methyl quinoline-4-carboxylic acid, rhodamine and naphthalene moiety, was designed and synthesized, it could be developed a ratiometric fluorescent sensor for selective detection of Al3+ via fluorescence resonance energy transfer (FRET) from naphthalimide moiety to rhodamine moiety. The addition of Al3+ trigger the significant fluorescence enhancement of HL at 550 nm at the expense of the fluorescent emission of HL centered at 524 nm.
- Qin, Jing-can,Fu, Zhen-hai,Tian, Li-mei,Yang, Zheng-yin
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- Fluorescent probe for detecting fluorine ions and preparation method and application thereof
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The invention relates to a fluorescent probe for detecting fluorine ions and a preparation method and application thereof. The chemical name of the fluorescent probe is 2-(2-butyl-1, 3-dioxocarbonyl-2, 3-dihydro-1H-benzo [de] isoquinoline-6-yl)-3-(4-((ter
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Paragraph 0040; 0042-0046; 0071; 0073; 0079; 0081
(2020/08/29)
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- Efficient Intersystem Crossing in the Tr?ger's Base Derived From 4-Amino-1,8-naphthalimide and Application as a Potent Photodynamic Therapy Reagent
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Intersystem crossing (ISC) was observed for naphthalimide (NI)-derived Tr?ger's base, and the ISC was confirmed to occur by a spin-orbital charge-transfer (SOCT) mechanism. Conventional electron donor/acceptor dyads showing SOCT-ISC have semirigid linkers. In contrast, the linker between the two chromophores in Tr?ger's base is rigid and torsion is completely inhibited, which is beneficial for efficient SOCT-ISC. Femtosecond transient absorption (TA) spectra demonstrated charge-separation and charge-recombination-induced ISC processes. Nanosecond TA spectroscopy confirmed the ISC, and the triplet state is long-lived (46 μs, room temperature). The ISC quantum yield is dependent on solvent polarity (8–41 %). The triplet state was studied by pulsed-laser-excited time-resolved EPR spectroscopy, and both the NI-localized triplet state and triplet charge-transfer state were observed, which is in good agreement with the spin-density analysis. The Tr?ger's base was confirmed to be a potent photodynamic therapy reagent with HeLa cells (EC50=5.0 nm).
- Barbon, Antonio,Chen, Kepeng,Hou, Yuqi,Li, Shujing,Wang, Zhijia,Wu, Huijian,Yaglioglu, Halime Gul,Yildiz, Elif Akhuseyin,Zhang, Xue,Zhao, Jianzhang,Zhao, Yingjie
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supporting information
(2020/03/05)
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- Peroxynitrite (ONOO-) generation from the HA-TPP@NORM nanoparticles based on synergistic interactions between nitric oxide and photodynamic therapies for elevating anticancer efficiency
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Due to biological safety and negligible toxicity, nitric oxide (NO) therapy has gained increasing interest in the field of cancer therapy during the past few years. However, individual NO cancer therapy normally exhibited limited therapeutic efficiency. In order to acquire satisfactory therapeutic outcomes, the NO therapy is usually combined with other therapeutic treatments, mostly chemotherapy. Herein, we constructed HA-TPP@NORM nanoparticles based on the co-assembly of an NO donor (NORM) and tetraphenylporphyrin (TPP)-modified hyaluronic acid, which can efficiently generate a highly biocidal molecule of peroxynitrite (ONOO-) via the synergistic interactions of the nitric oxide (NO) therapy and photodynamic therapy (PDT) to enhance the cancer therapeutic efficiency. In addition, MTT results exhibited that without light irradiation, the HA-TPP@NORM nanoparticles have favourable biocompatibility with the cell viability above 95% at the maximum TPP concentration (20 μg mL-1). Under simultaneous irradiation with 365 nm and 650 nm light, ONOO- can be efficiently produced in cancer cells via the direct coupling reaction of the generated NO and superoxide anion radical (O2-), which significantly enhanced the anticancer effect, when compared with individual NO therapy or PDT therapy. Therefore, the HA-TPP@NORM nanoparticles may provide a new insight into the design of efficiently NO-related cancer therapeutic systems.
- Jiang, Dawei,Yue, Tao,Wang, Guichen,Wang, Chaochao,Cao, Hongliang,Gao, Yun,Chen, Chao
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supporting information
p. 162 - 170
(2019/12/26)
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- 1,8-NAPHTHALIMIDE DERIVATIVE, PREPARATION METHOD THEREFOR AND USE THEREOF
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Disclosed are a 1,8-naphthalimide derivative, a preparation method therefor and a use thereof. The 1,8-naphthalimide derivative is easy to prepare, and is an enhanced Cu2+ fluorescent probe, which can detect Cu2+ by two wavelengths and be applied to almost-all-water systems. According to atitration experiments and blank experiments at 392 nm and 754 nm, the detection limit of the 1,8-naphthalimide derivative of the present invention for Cu2+ is 2.6368×10?7 mol/L and 2.0156×10?7 mol/L, respectively, indicating that same can perform quantitative detection for Cu2+ with a high selectivity and a high sensitivity by using two wavelengths. In addition, a pH colorimetric switch based on 1,8-naphthalimide can rapidly and reversibly respond to a pH by means of three ways: a maximum absorption wavelength, absorbance and color change. Same has a narrow switching pH range, a good selectivity and a high sensitivity, can be used in almost-all-water systems.
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Paragraph 0055; 0063
(2020/12/20)
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- A ratiometric fluorescent probe for the quantitative detection of styrene in air
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A ratiometric fluorescent probe (N-butyl-4-(4-amino-styryl)-1,8-naphthalimide) was developed for the quantitative detection of styrene in air. The sensing mechanism was found to involve a Heck reaction between the pretreated probe (diazotization) and styr
- Chen, Kai,Gao, Zhenzhong,Sun, Jin,Hou, Xianfeng,Chen, Jian
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supporting information
p. 13037 - 13039
(2020/11/05)
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- A fluorogenic probe for tracking GSH flux in developing neurons
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Understanding GSH flux in developing neurons is prerequisite to reveal its role in neuronal development but necessiates an ultrasensitive assay. By systematically exploring key structural factors determing probe sensitivity in live cells, we developed a fluorogenic probe capable of imaging subtle GSH fluctuations in developing neurons.
- Zong, Haichao,Peng, Jiayi,Li, Xiao-Rong,Liu, Meng,Hu, Yongzhou,Li, Jia,Zang, Yi,Li, Xin,James, Tony D.
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supporting information
p. 515 - 518
(2020/01/29)
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- For detecting glutathione fluorescence probe and its preparation method and application
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The invention provides a fluorescence probe for detecting glutathione. The structural formula of the fluorescence probe is as shown in the specification. A preparation process and an aftertreatment process are relatively simple, selectivity is good, sensi
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Paragraph 0045-0049
(2019/04/10)
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- Containing 4 - (biphenyl ethynyl) - 1, 8 naphthalene imide liquid crystal compound, preparation method and application thereof
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The invention discloses a liquid crystal compound containing 4-(biphenyl acetenyl)-1,8 naphthalimide, a preparing method and application. Solubility of molecules in mixed liquid crystal is improved by the compound, the linear structure of the molecules is
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Paragraph 0029; 0039; 0040; 0041
(2019/02/21)
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- Substituted naphthalimide derivatives as well as preparation method and application thereof
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The invention discloses substituted naphthalimide derivatives as well as a preparation method and application thereof. The substituted naphthalimide derivatives have a structure of a general formula D, wherein R1 is selected from n-butyl, phenyl, p-methyl
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Paragraph 0025; 0027; 0028; 0029
(2019/01/21)
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- Compound containing N-n-alkyl-4-phenylethynyl-1,8-naphthalimide, and preparation method and application thereof
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The invention discloses a compound containing N-n-alkyl-4-phenylethynyl-1,8-naphthalimide, and a preparation method and application thereof. The compound has a structure as shown in C which is described in the specification. According to the invention, 1,
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Paragraph 0029; 0031-0033
(2019/01/20)
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- A class of substituted 4 - styryl - 1, 8 - naphthalene imide compound, preparation method and application thereof (by machine translation)
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The invention discloses a substituted 4 - styryl - 1, 8 - naphthalene imide compound, preparation method and application thereof, it has C structure. The invention relates to a 1, 8 - naphthalene bitter wine as parent, design preparation the new structure
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Paragraph 0031; 0032; 0033
(2019/01/23)
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- Naphthalimide derivative containing 4-(alkylbicyclohexyl) substitute, and preparation method and application thereof
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The invention discloses a naphthalimide derivative containing a 4-(alkylbicyclohexyl) substitute, and a preparation method and application thereof. The naphthalimide derivative is of a structure represented by the general formula B, wherein R1 is one of a
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Paragraph 0025; 0027; 0028; 0029
(2019/02/26)
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- A nitroreductase and acidity detecting dual functional ratiometric fluorescent probe for selectively imaging tumor cells
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Nitroreductase and acidity are common features of a tumor, which is associated with serious disease with a high mortality rate. However, solo detection of nitroreductase or acidic environments may cause false-positive results. Thus, it is very meaningful to develop dual functional probes for detecting nitroreductase and acidity, as these could be used for accurate tumor imaging. Here we report on the first dual functional ratiometric fluorescent probe, NAFP, for acidity and nitroreductase detection. This probe enables the measurement of the acidic microenvironment and the concentration of nitroreductase at the same time and the same site. The probe can obviously distinguish acidity, nitroreductase, and nitroreductase in an acidic environment. Furthermore, confocal fluorescence imaging of A549 cells indicates that NAFP can detect acidity and expressed nitroreductase in living cells.
- He, Zhaoshuai,Chou, Yajie,Zhou, Hanxin,Zhang, Han,Cheng, Tanyu,Liu, Guohua
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p. 3266 - 3272
(2018/05/22)
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- Amino acid detection reagent naphthalimide derivative as well as synthesis method and application thereof
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The invention provides an amino acid detection reagent naphthalimide derivative as well as a synthesis method and application thereof. The naphthalimide derivative is 5-butyl-4,6,10-trioxo-5,6-dihydro-4H, 10H-benzopyran-isoquinoline-9-formate (NC-1). The invention further provides a method for detecting amino acid in a proportion mode, wherein in a PBS-DMSO (1:1, v/v) buffer solution with a pH value being 7.4, content of amino acid is quantitatively detected through a fluorospectrophotometer. The detecting method can effectively identify amino acid in a living body. The detecting method has the advantages of being high in sensitivity, high in selectivity, non-invasive, simple and convenient in operation, capable of performing real-time imaging and the like.
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Paragraph 0028; 0030
(2018/10/19)
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- 1,8-naphthalimide derivative as well as preparation method and application thereof
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The invention discloses a 1,8-naphthalimide derivative as well as a preparation method and application thereof. The 1,8-naphthalimide derivative disclosed by the invention is relatively easy to prepare, is an enhanced Cu fluorescent probe, can detect Cu by dual wavelengths, and in particular can be applied to an almost total-water system; and according to estimation of a titration experiment and a blank experiment at 392 nm and 754 nm, detection limits of the 1,8-naphthalimide derivative for the Cu are separately 2.6368 x 10 mol/L and 2.0156 x 10 mol/L, and the results indicate that the 1,8-naphthalimide derivative can utilize the dual wavelengths to perform high-selectivity high-sensitivity quantitative detection on the Cu.
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Paragraph 0017; 0019; 0026
(2018/09/08)
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- Mercaptan fluorescent probe, preparation method, and application thereof
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The invention discloses a mercaptan fluorescent probe, a preparation method, and an application thereof. The fluorescent probe has a molecular formula of C29H20N4O9S2 and has the structure representedas the specification. The probe is very weak in autoflu
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Paragraph 0057; 0058; 0059; 0060
(2019/01/08)
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- Synthesis and photophysical properties of blue-emitting fluorescence dyes derived from naphthalimide derivatives containing a diacetylene linkage group
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Four naphthalimide-based dyes with a diacetylene linkage at the 3- or 4-position were synthesized to improve the thermal stability of the fluorescence dye as well as the efficiency of fluorescent emission at blue region. The absorption and fluorescence properties of the synthesized dyes were also investigated. The geometries and molecular orbitals of the dyes prepared were simulated using by density functional theory and time-dependent density functional theory using Gaussian 09. Furthermore, the suitability of the dyes for application in light-conversion films was examined. N-Phenyl groups were found to have a greater effect on the fluorescence of naphthalimide-based dyes than analogue containing an N-alkyl group. In addition, investigation of the effect of diacetylene linkages at the 3- or 4-positions of naphthalimide-based dyes showed that the fluorescence was influenced by the electron-donating effect of the diacetylene linkage which could afford more conjugation of π orbitals of the dyes. Four blue fluorescence dyes derived from 1,8-naphthalimide containing a diacetylene linkage were synthesized and then coated in PE film. The photophysical properties were analyzed using density functional theory (DFT) calculations, and excitations from the highest occupied molecular orbitals (HOMOs) to the lowest unoccupied molecular orbitals (LUMOs) of the dyes were simulated at the B3LYP/6-31G level of theory via the Gaussian 09 suite of programs. Using these methods, the influences of the position of the ethynyl linkages, alkyl groups, and phenyl groups on the electronic and fluorescence properties of the dyes were also clarified.
- Kim, Kyung-Won,Kim, Geun-Hyeong,Kwon, Su-Hyeon,Yoon, Hyo-In,Son, Jung-Eek,Choi, Jae-Hong
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p. 353 - 361
(2018/06/06)
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- Naphthalimide derivatives as well as preparation method and application thereof
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The invention discloses naphthalimide derivatives with structures shown as formulae I-IV in the description and pharmaceutical salts of the naphthalimide derivatives. The compounds have certain inhibition activity on gram-positive bacteria, gram-negative bacteria and fungi and can be used for preparing antibacterial and/or anti-fungal drugs. Preparation raw materials of the compounds are high in commercialized degree, cheap and available, a preparation route is short, and a method is simple and convenient.
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Paragraph 0044; 0045; 0046
(2018/01/17)
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- Design and synthesis of a fluorescent probe based on naphthalene anhydride and its detection of copper ions
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Copper, as the third most abundant transition metal ions of human, plays an essential role in the redox reaction, signal transduction, hematopoiesis, and other physiological processes. Abnormal content of copper ions in the body will cause some diseases such as anemia, coronary heart disease, Menkes’ syndrome. In this article, a new fluorescence probe L for Cu2+ was designed and synthetized by using 4-bromo-1,8 naphthalene anhydride and 2-thio-phene formaldehyde as raw materials. Fluorescent probe L itself exhibited strong fluorescence, upon the addition of Cu2+ ions, the fluorescence was quenched. The fluorescent detection limit for Cu2+ ions was determined to be 1.8 μM based on a 3δ/S method. UV-vis absorption and fluorescence spectra indicated that probe L showed good selectivity and sensitivity for Cu2+, and this selectivity was not interfered by other metal ions and anions. Further cell fluorescence imaging experiments indicated that the probe L had potential to be used to examine copper ions in vivo.
- He, Guangjie,Liu, Chenxi,Liu, Xiaobo,Wang, Qingzhi,Fan, Aiying,Wang, Songjun,Qian, Xinlai
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- Fluorescence probe NASA as well as preparation and application thereof
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The invention discloses a fluorescence probe NASA as well as preparation and application thereof. The invention provides a fluorescence probe for detecting in-vitro S-adenosyl-L-homocysteine hydrolase which is called as SAHH for short. A main synthesis method comprises the following steps: connecting 1,8-naphthalimide with adenosine at an acting part of SAHH through a C-S band so as to generate a compound of a structure as shown in the specification; under the action of SAHH, generating a substance of a formula as shown in the specification, and detecting SAHH according to differences of fluorescence properties before and after reaction. By adopting the fluorescence probe, the content of SAHH in red blood cells can be quantified, and screening of an SAHH inhibitor can be achieved.
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Paragraph 0012
(2017/08/29)
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