- Targeted tumor detection: guidelines for developing biotinylated diagnostics
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The challenge in achieving precision medicine relies on how to advance and/or enhance new as well as old therapeutic strategies. Here, we highlight the significant role hydrophilicity of biotinylated fluorescent probe's plays on their cellular uptake behaviour.
- Jang, Joo Hee,Kim, Woo Ri,Sharma, Amit,Cho, Suk Hee,James, Tony D.,Kang, Chulhun,Kim, Jong Seung
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- Naphthalimide-based macrophage nucleus imaging probes
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The photophysical properties of naphthalimide-based fluorophores can be easily tuned by chemical manipulation of the substituents on that privileged scaffold. Replacement of a OMe group at position 6 in 2-(hydroxyl)ethyl-naphthalimide derivatives by diverse amines, including 2-(hydroxyl)ethylamine, trans-(4-acetamido)cyclohexylamine and azetidine increases the solvatochromic (ICT) character, while this replacement in 2-(dimethylamino)ethyl-naphthalimide analogues (PET fluorophores) decrease their solvent polarity sensitivity or even reversed them to solvatochromic fluorophores. These fluorophores resulted macrophage nucleus imaging probes, which bind DNA as intercalants and showed low cytotoxicity in human cancer cells.
- Herranz, Rosario,Orte, Angel,Fernández-Gutiérrez, Mar,Fueyo-González, Francisco,García-Puentes, Diego,González-Vera, Juan A.
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- Solid fluorescence sensors obtained by functionalization of photocrosslinked water-swollen acrylic membranes with 4-piperazine naphthalimide derivatives
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A photocrosslinked membrane (M-Cl) based on vinyl-pyrrolidone/butyl acrylate containing ethylene glycol dimethacrylate as a crosslinking agent and methacryloyl chloride as reactive monomer has been prepared for further functionalization. A series of hydroxy substituted piperazine naphthalimide compounds have been synthetized as pH sensitive Off-On fluorescence probes using two methods: microwave and reflux. Three of the derivatives were selected to be anchored to the M-Cl membrane through the acid chloride groups by the Schotten-Baumann reaction. All the obtained water-swollen membranes were characterized using different techniques. Photo-induced electron transfer (PET) and its pH-dependent optical changes were investigated and various photochemical parameters were determined by using pH-dependent absorption and fluorescence spectroscopies. In the pH range of 9.0–4.0, these solid sensors undergo PET process from the piperazine to the naphthalimide moiety leading to a fluorescence quenching. However, in the pH range of 4.0–1.0, the PET is inhibited to give a fluorescence enhancement. The sensitivity of the functionalized membranes to pH changes depended on the size and position of the naphthalimide substituents.
- Fernández-Alonso,Corrales,Pablos,Catalina
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- pH-responsive intramolecular FRET-based self-tracking polymer prodrug nanoparticles for real-time tumor intracellular drug release monitoring and imaging
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An intramolecular fluorescence resonance energy transfer (FRET)-based macromolecular theranostic prodrug was designed by directly conjugating Doxorubicin (DOX) as the FRET acceptor onto the naphthalimide side groups in the fluorescent copolymer PPEGMA20-PNAP8 as the FRET energy donor via an acid-labile imine bond, without a fluorogenic linker. The proposed PPEGMA20-PNAP8-DOX theranostic prodrug showed a high DOX content of 24.3% owing to a conjugation efficiency of > 93% under mild conjugation conditions. It could easily self-assemble into unique theranostic nanoparticles with a Dh of 71 nm. The theranostic nanoparticles showed excellent pH-triggered DOX release performance with very low premature drug leakage of 6.3% in normal physiological medium over 129 h, while>91% of the conjugated DOX was released in the acidic tumor intracellular microenvironment. MTT assays indicated the enhanced antitumor efficacy of the proposed theranostic nanoparticles compared with free DOX. Furthermore, because drug release was triggered by pH, orange fluorescence was restored to the blue fluorescence of the backbone copolymer. Such self-tracking pH-responsive colorful fluorescence variations during intracellular drug delivery and release are expected to allow real-time tumor intracellular drug release monitoring and imaging diagnosis.
- Dong, Yuman,Du, Pengcheng,Liu, Peng
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- A ratiometric lysosomal pH chemosensor based on fluorescence resonance energy transfer
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In this work, we presented a naphthalimide-rhodamine based fluorescence resonance energy transfer system (FRET) NR1 as a ratiometric and intracellular pH probe, in which 1,2,3-triazole was identified as an ideal bridge and biocompatibility. It could selectively monitor pH variations in methanol/HEPES solution at room temperature. When the pH changed from 6.20 to 2.00, both the fluorescence intensities at 580 nm and the intensity ratios, R (I 580 nm/I538 nm) increased, which allowed the detection of pH changes by both normal fluorescence and ratiometric fluorescence methods. The observation is consistent with the increased FRET from the 1,8-naphthalimide (donor) to the ring-opened, colored form of rhodamine (acceptor). Moreover, as NR1 is lysosomal with low cytotoxicity, it will be helpful for investigating the pivotal role of H+ in a biological context, especially in lysosomes through direct intracellular imaging.
- Fan, Jiangli,Lin, Chunying,Li, Honglin,Zhan, Peng,Wang, Jingyun,Cui, Shuang,Hu, Mingming,Cheng, Guanghui,Peng, Xiaojun
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- Conjugates of 3,4-dimethoxy-4-styrylnaphthalimide and bacteriochlorin for theranostics in photodynamic therapy
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New conjugates of fluorophore based on 3,4-dimethoxy-4-styryl-1,8-naphthalimide and photosensitizer bacteriochlorin e differing in the nature of spacer fragments were synthesized and their spectral-luminescent properties were studied. The conjugates effic
- Fedorova, O. A.,Grin, M. A.,Mironov, A. F.,Nenajdenko, V. G.,Panchenko, P. A.,Pritmov, D. A.,Zakharko, M. A.,Zarezin, D. P.
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- A dual pH and temperature responsive polymeric fluorescent sensor and its imaging application in living cells
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A polymeric fluorescent sensor PNME, consisting of A4 and N-isopropylacrylamide (NIPAM) units, was synthesized. PNME exhibited dual responses to pH and temperature, and could be used as an intracellular pH sensor for lysosomes imaging. Moreover, it also could sense different temperature change in living cells at 25 and 37°C, respectively.
- Yin, Liyan,He, Chunsheng,Huang, Chusen,Zhu, Weiping,Wang, Xin,Xu, Yufang,Qian, Xuhong
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- Colorimetric and fluorescent detection of hydrazine with high sensitivity and excellent selectivity
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It is critical to develop probes for rapid, selective, and sensitive detection of the highly toxic hydrazine in both environmental and biological science. In this work, under mild condition, a novel colorimetric and off-on fluorescent probe was synthesized for rapid recognition of hydrazine with excellent selectivity over other various species including some biological species, metal ions and anions. The limit of quantification (LOQ) value was 1.5?×?10??4?M–3.2?×?10??3?M (colorimetric method) and 1.5?×?10??4?M???3.2?×?10??3?M (fluorescent method) with as low as detection limit of 46.2?μM.
- Shi, Bingjie,Qi, Sujie,Yu, Mingming,Liu, Chunxia,Li, Zhanxian,Wei, Liuhe,Ni, Zhonghai
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- Ratiometric fluorescent detection of acidic pH in lysosome with carbon nanodots
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It is significant for cell physiology to keep the homeostasis of pH, and it is highly demanded to develop ratiometric fluorescent sensors toward pH. In this work, under mild condition, through the electrostatic interaction between carbon nanodots (CDs) and organic molecules, two novel ratiometric fluorescence hybrid nanosensors were fabricated for sensing acidic pH. These nanohybrid systems possess dual emission peaks at 455 and 527 nm under a single excitation wavelength of 380 nm in acidic pH condition. With the increasing of pH, the fluorescence of the 1,8-naphthalimide derivative completely quenches, while the blue fluorescence of CDs keeps constant. Furthermore, the CDs?organic molecular nanohybrids exhibit excellent anti-disturbance ability, reversible pH sensing ability, and a linear response range in wide pH range respectively. Besides the ability to target lysosome, with one of the nanosensor, stimulated pH change has been successfully tracked in a ratiometric manner via fluorescence imaging.
- He, Yangyang,Li, Zhanxian,Jia, Qingyan,Shi, Bingjie,Zhang, Hongyan,Wei, Liuhe,Yu, Mingming
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- A guanidine derivative of naphthalimide with excited-state deprotonation coupled intramolecular charge transfer properties and its application
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A new fluorophore based on guanidine substituted 1,8-naphthalimide was synthesized and characterized. In aqueous solution, the guanidine group undergoes deprotonation/protonation with a pKa of ~8.5 in the ground-state and ~0.9 in the excited-state. The emission of its protonated and deprotonated forms exhibits a large Stokes shift (Ex/Em: 350/460 nm and 400/580 nm) due to the excited-state intramolecular charge transfer (ICT) process. The protonated form of this fluorophore exhibits dual fluorescence emission (Em: 460 and 580 nm; Ex: 350 nm) that is contributed to by an excited-state deprotonation coupled ICT process. The emission properties of this fluorophore are strongly dependent on the solvent environment, which make it possible to tune the luminescence of the materials made using this fluorophore. The absorption and emission spectra of this fluorophore respond to fluoride ions ratiometrically, showing the potential application as a fluoride ion sensor.
- Zhou, Jin,Liu, Huiying,Jin, Bing,Liu, Xiangjun,Fu, Hongbing,Shangguan, Dihua
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- Different Steric-Twist-Induced Ternary Memory Characteristics in Nonconjugated Copolymers with Pendant Naphthalene and 1,8-Naphthalimide Moieties
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Herein, novel random copolymers PMNN and PMNB were designed and synthesized, and the memory devices Al/PMNN and PMNB/ITO both exhibited ternary memory performance. The switching voltages of the OFF–ON1 and ON1–ON2 transitions for both memory devices are around ?2.0 and ?3.5 V, respectively, and the ON1/OFF, ON2/ON1 current ratios are both up to 103. The observed tristable electrical conductivity switching could be attributed to field-induced conformational ordering of the naphthalene rings in the side chains, and subsequent charge trapping by 1,8-naphthalimide moieties. More interestingly, by adjusting the connection sites of 1,8-naphthalimide moieties to tune the steric-twist effect, different memory properties were achieved (PMNN showed nonvolatile write once, read many (WORM) memory behavior, whereas PMNB showed volatile static RAM (SRAM) memory behavior). This result will offer a guideline for the design of different high-performance multilevel memory devices by tuning the steric effects of the chemical moieties.
- Wang, Ming,Li, Zhuang,Li, Hua,He, Jinghui,Li, Najun,Xu, Qingfeng,Lu, Jianmei
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- Nanomolar detection of Hcy, GSH and Cys in aqueous solution, test paper and living cells
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A novel naphthalimide-based fluorescent probe was designed and synthesized for thiol recognition with high sensitivity and excellent selectivity. The probe can detect thiol quantitatively in a concentration range of 0-6.0 μM and the detection limit could
- Liu, Xingjiang,Zhang, Wenying,Li, Chunxiao,Zhou, Wan,Li, Zhanxian,Yu, Mingming,Wei, Liuhe
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- Synthesis of novel C4-benzazole naphthalimide derivatives with potent anti-tumor properties against murine melanoma
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Novel C4-benzazole naphthalimide derivatives were synthesized and tested in vitro and in vivo as anti-cancer drugs. Among these synthetic molecules, compounds 9 and 10 exhibited cytotoxicity against murine B16F10 melanoma cells. In addition, the above-mentioned compounds significantly suppressed lung tumor metastasis with no visible sign of toxicity.
- Lu, Yen-Ta,Chen, Tien-Ling,Chang, Kuo-Song,Chang, Chia-Ming,Wei, Tsai-Yin,Liu, Jen-Wei,Hsiao, Chih-Ang,Shih, Tzenge-Lien
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- Bifunctional fluorescent probes for hydrogen peroxide and diols based on a 1,8-naphthalimide fluorophore
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This report discloses a series of naphthalimide-based bifunctional fluorescent probes for hydrogen peroxide and diols. As a result, these molecules not only demonstrated high turn-on fluorescent response and good selectivity towards hydrogen peroxide over other relevant reactive oxygen species, but also displayed different responses to diols. Therefore, these fluorescent probes could be served as sensitive, selective and practical chemosensors for both hydrogen peroxide and diols under physiological-like conditions.
- Sun, Wei,Ma, Zhao,Li, Jing,Li, Wenhua,Du, Lupei,Li, Minyong
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- A New Reactive 1,8-Naphthalimide Derivative for Highly Selective and Sensitive Detection of Hg2+
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A 1,8-naphthalimide derivative with a reactive aliphatic hydroxyl was designed and synthesized as a fluorescent probe. Its structure was characterized by IR, 1H NMR, 13C NMR, LC-MS and HPLC. The probe showed high selectivity and sensitivity to Hg2+ over other metal ions such as Pb2+, Na+, K+, Cd2+, Cr3+, Zn2+, Cu2+, Ni2+, Ca2+, Fe3+, Fe2+, Co2+, Mn2+ and Mg2+ in MeCN/H2O (15/85, v/v). The increase in fluorescence intensity was linearly proportional to the concentration of Hg2+ in the range of 18–40?μM with a detection limit of 1.38?×?10?7?mol/L. The probe could work in a pH span of 4.3–9.0 and respond to Hg2+ quickly with strong anti-interference ability. Job’s plot suggested a 1:2 complex of the probe and Hg2+.
- Lv, Feng,Chen, Yufen,Tang, Tengxuan,Chen, Yuhua,Xu, Dongmei
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- 1,8-Naphthalimide Derivative Dyes with Large Stokes Shifts for Targeting Live-Cell Mitochondria
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An ideal fluorescent dye for staining cell organelles should have multiple properties including specificity, stability, biocompatibility, and a large Stokes shift. Tunable photophysical properties enable 1,8-naphthalimide to serve as an excellent fluorophore in biomedical applications. Many naphthalimide derivatives have been developed into drugs, sensors, and other dyes. In this study, a series of 1,8-naphthalimide derivatives targeting live cell mitochondria were synthesized. Among these probes, Mt-4 was characterized as the best one, with highly specific mitochondrial localization, low cytotoxicity, and a large Stokes shift. More importantly, Mt-4 stood out as a potential mitochondrial dye for living-cell experiments involving induced mitochondrial stress arising from the treatments because Mt-4 shows enhanced fluorescence in mitochondrial stress situations.
- Zhang, Liqiang,Su, Fengyu,Kong, Xiangxing,Lee, Fred,Sher, Steven,Day, Kevin,Tian, Yanqing,Meldrum, Deirdre R.
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- A novel bacteriochlorin-styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging
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Propargyl-152,173-dimethoxy-131-amide of bacteriochlorin e (BChl) and a 4-(4-N,N-dimethylaminostyryl)-N-alkyl-1,8-naphthalimide bearing azide group in the N-alkyl fragment were conjugated by the copper(i)-catalyzed 1,3-dipolar cycloaddition to produce a novel dyad compound BChl-NI for anticancer photodynamic therapy (PDT) combining the modalities of a photosensitizer (PS) and a fluorescence imaging agent. A precise photophysical investigation of the conjugate in solution using steady-state and time-resolved optical spectroscopy revealed that the presence of the naphthalimide (NI) fragment does not decrease the photosensitizing ability of the bacteriochlorin (BChl) core as compared with BChl; however, the fluorescence of naphthalimide is completely quenched due to resonance energy transfer (RET) to BChl. It has been shown that the BChl-NI conjugate penetrates into human lung adenocarcinoma A549 cells, and accumulates in the cytoplasm where it has a mixed granular-diffuse distribution. Both NI and BChl fluorescence in vitro provides registration of bright images showing perfectly intracellular distribution of BChl-NI. The ability of NI to emit light upon excitation in imaging experiments has been found to be due to hampering of RET as a result of photodestruction of the energy acceptor BChl unit. Phototoxicity studies have shown that the BChl-NI conjugate is not toxic for A549 cells at tested concentrations (8 μM) without light-induced activation. At the same time, the concentration-dependent killing of cells is observed upon the excitation of the bacteriochlorin moiety with red light that occurs due to reactive oxygen species formation. The presented data demonstrate that the BChl-NI conjugate is a promissing dual function agent for cancer diagnostics and therapy.
- Panchenko, Pavel A.,Grin, Mikhail A.,Fedorova, Olga A.,Zakharko, Marina A.,Pritmov, Dmitriy A.,Mironov, Andrey F.,Arkhipova, Antonina N.,Fedorov, Yuri V.,Jonusauskas, Gediminas,Yakubovskaya, Raisa I.,Morozova, Natalia B.,Ignatova, Anastasia A.,Feofanov, Alexey V.
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- Surface modification of poly(ethylene-butyl acrylate) copolymers by microwave methodology and functionalization with 4-dimethylamino-N-(2-hydroxyethyl)-1,8-naphthalimide for acidity sensing
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A new procedure was developed for functionalization in the solid phase by using microwave irradiation. Heterogeneous chemical modification of poly(ethylene-butyl acrylate) copolymer (EBA), hydrolysis, chlorination, and Schotten–Baumann reactions were monitored by attenuated total reflection Fourier transform infrared (ATR-FTIR) spectroscopy. EBA was superficially functionalized by a previously synthesized fluorescent dye, 4-dimethylamino-N-(2-hydroxyethyl)-1,8-naphthalimide, and the depth profile of the functionalized polymer was determined by confocal Raman spectroscopy. The new functionalized materials were also evaluated as an acidic pH sensor by determining the change in the spectroscopic properties of absorption and fluorescence with pH of the solution and vapor phases. To improve the wettability of the EBA surface, oxygen plasma treatment was used and the response time of the solid sensor was analyzed.
- Fernández-Alonso,Corrales,Pablos,Catalina
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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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- A 1,8-naphthalimide-based chemosensor with an off-on fluorescence and lifetime imaging response for intracellular Cr3+ and further for S2-
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A novel 1,8-naphthalimide-based chemosensor was designed and synthesized for rapid recognition of Cr3+. The desired sensor showed off-on fluorescent and lifetime-based response upon Cr3+ and S2- in solution, on test paper and in cells. With the intensity-based method, the limit of quantification (LOQ) value was 0-5.5 × 10-5 M and the detection limit could be as low as 0.60 ppm. The 'in situ' prepared Cr3+ complex can recognize S2- among a series of common anions with high selectivity and sensitivity, the LOD can be as low as 307 nM. The lifetime of the sensor changes from 4.95 to 4.89 and further to 5.88 ns upon addition of Cr3+ and S2- in turn.
- Yu, Mingming,Du, Weiwei,Zhou, Wan,Li, Haixia,Liu, Chunxia,Wei, Liuhe,Li, Zhanxian,Zhang, Hongyan
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- A pH sensitive ratiometric fluorophore and its application for monitoring the intracellular and extracellular pHs simultaneously
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Intracellular and extracellular pH plays a key role in many cell biological processes. Probes for simultaneously monitoring the pH change inside and outside living cells are rarely available. In this paper, we describe a new ratiometric pH fluorophore that was synthesized by condensation of 4-bromine-1,8-naphthalimides and 3-amino-1,2,4-triazole. In the range of pH 5-8, the only N-H in the heterocycle-fused aromatic ring system of this fluorophore undergoes a reversible deprotonation-protonation process, which results in a large red shift of the absorption and emission spectra. In aqueous solution, this fluorophore exhibits good pH selectivity, high photostability, high tolerance to ionic strength, and high fluorescence quantum yield in both the acid and base forms. A long chain derivative of this fluorophore (HNNA) was designed for cellular pH sensing. HNNA was found to locate on the membrane structure of the cells, and was successfully used for mapping the pH change in both the extracellular microenvironment and the inner cells by confocal imaging. The Royal Society of Chemistry 2013.
- Zhou, Jin,Fang, Canliang,Chang, Tianjun,Liu, Xiangjun,Shangguan, Dihua
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- A high-performance polyurethane sponge for the detection, adsorption and separation of Cu2+ ions
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The simultaneous detection and separation of copper ions is important. In this study, a fluorescent chemosensor (a copper sensitive molecule), was prepared using 6-bromo-benzo[de]isochromene-1,3-dione as a precursor. The as-prepared fluorescent molecule contains a hydroxyl group and an aminoquinoline moiety. The hydroxyl group enables the fluorescent molecule to anchor to a porous polyurethane (PU) sponge. The chemosensors still retained their recognition ability after they were introduced to PU. Upon the addition of Cu2+ ions to the PU sponge, both the color and the fluorescence intensity changed, suggesting that the chemosensor-functionalized PU sponges could be used as a Cu2+ ion sensor. The copper ions could also accumulate and be enriched on the sponges. The adsorption capacity of the PU sponge (containing 2 wt% of the chemosensor) reached 97.26 mg g-1, which was higher than that of the solid PU membranes (52.62 mg g-1). These polymeric, highly sensitive chemosensors may potentially be applied in the detection of water pollution generated by sources such as electroplating and drain outflow.
- Yu, Yun,Wang, Jianrui,Lian, Jiansheng,Cheng, Xinjian
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- A probe with hydrazinecarbothioamide and 1,8-naphthalimide groups for “turn-on” fluorescence detection of Hg2+ and Ag+ ions and live-cell imaging studies
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The probe (L) having hydrazinecarbothioamide and 1,8-naphthalimide moieties was synthesized and evaluated for its metal ion sensing ability. It exhibits a selective and sensitive colorimetric as well as fluorescent recognition of Hg2+ and Ag+ ions in CH3OH - HEPES buffer solution (5 mM, 7:3, v/v, pH = 7.4) in presence of other metal ions. Probe L is weakly fluorescent upon excitation with 410 nm light, but after gradual addition of HgCl2 and AgNO3 enhancement in fluorescent intensity was observed. Detection limits of Hg2+ and Ag+ using L have been found to be 20 nM (Hg2+) and 40 nM (Ag+) over the pH range of 6 – 10 that is suitable for practical application under physiological pH conditions. The reversibility of interaction of L with Hg2+ ion was monitored using Na2EDTA by emission titration. The “OFF-ON’’ fluorescence switching can be observed with naked eye, in which fluorescent “OFF’’ is due to operation of PET process in free L. Whereas upon complexation with these two metal ions, PET is restricted and CHEF process becomes operational. Mass spectral analysis and Job's plot yielded a binding ratio of 1:1 for both metal ions. NMR titration studies are consistent with binding of Hg2+ or Ag+ to NH group (attached with naphthalimide moiety) and sulfur atom of hydrazinecarbothioamide group. From cytotoxicity assay, 5 μM solution of L was considered in cellular imaging study and the potentiality of the probe L was established by using human breast cancer cell line (MDA-MB-231) and primary human dermal fibroblasts (HDF), through fluorescence cell imaging experiments for tracking both Hg2+ and Ag+ in living cells.
- Dey, Souradeep,Kumar, Sandeep,Mahata, Satyajit,Mandal, Biman B.,Manivannan, Vadivelu
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- An unanticipated discovery towards novel naphthalimide corbelled aminothiazoximes as potential anti-MRSA agents and allosteric modulators for PBP2a
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Available therapeutic strategies are urgently needed to conquer multidrug resistance of MRSA. A visible effort was guided towards the advancement of novel antibacterial framework of naphthalimide corbelled aminothiazoximes, and desired to assert some insight on the conjunction of individual pharmacophore with distinct biological activities and unique action mechanism. Preliminary assessment displayed that dimethylenediamine derivative 13d presented a wonderful inhibition on MRSA (MIC = 0.5 μg/mL), and showed excellent membrane selectivity (HC50 > 200 μg/mL) from an electrostatic distinction of the electronegative bacterial membranes and the electroneutral mammalian membranes. Moreover, 13d could effectually relieve the development of MRSA resistance. Investigations into explaining the mechanism of anti-MRSA disclosed that 13d displayed strong lipase affinity, which facilitated its permeation into cell membrane, causing membrane depolarization, leakage of cytoplasmic contents and lactate dehydrogenase (LDH) inhibition. Meanwhile, 13d could exert interaction with DNA to hinder biological function of DNA, and disrupt the antioxidant defense system of MRSA through up-regulation of ROS subjected the strain to oxidative stress. In particular, the unanticipated mechanism for naphthalimide corbelled aminothiazoximes that 13d could suppress the expression of PBP2a by inducing allosteric modulation of PBP2a and triggering the open of the active site, was discovered for the first time. These findings of naphthalimide corbelled aminothiazoximes as a small-molecule class of anti-MRSA agents held promise in strategies for treatment of MRSA infections.
- Zhang, Peng-Li,Gopala, Lavanya,Zhang, Shao-Lin,Cai, Gui-Xin,Zhou, Cheng-He
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supporting information
(2021/12/20)
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- Naphthaleimide compounds with active ends and preparation methods and applications thereof
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The present invention provides an active end of the naphthaleneimide compound and preparation method and application thereof, the compound to 1,8-naphthalene dimethylamide as an electron absorber, to 9,9-dimethylfluorene as the electron body, by changing
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Paragraph 0092-0094
(2022/01/04)
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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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- Labeled naphthalimide fluorescent probe as well as preparation method and application thereof
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The invention discloses a labeled naphthalimide fluorescent probe as well as a preparation method and application thereof. A naphthalimide fluorescent probe taking iodoacetamide as a sulfydryl reaction group is firstly disclosed. The structural formula of the naphthalimide fluorescent probe is shown as a formula I. The invention further discloses a method for preparing the labeled naphthalimide fluorescent probe and application of the fluorescent probe in qualitative or quantitative detection of sulfydryl-containing protein. The preparation method disclosed by the invention is simple and easyto obtain in quantity, the prepared probe compound contains a hydroxyl hydrophilic group, has little influence on an electrophoresis result and subsequent instrument detection, and contains a relatively long carbon chain as a connecting arm to reduce steric hindrance of fluorophore on sulfhydryl alkylation on the surface of protein. When the probe compound is applied to detection, the sampling amount of the detection method is small, the influence of coexisting ions, active oxygen and matrixes in the environment is avoided, and the probe compound has very high selectivity and sensitivity and can be used for qualitative and quantitative detection of various proteins containing sulfydryl.
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Paragraph 0027
(2020/12/30)
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- Hydrazone-based bridged naphthalimide imidazole compounds and preparation method and application thereof
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The invention relates to hydrazone-based bridged naphthalimide imidazole compounds and a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The hydrazone-based bridged naphthalimide imidazole compound is
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Paragraph 0043-0046
(2020/05/29)
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- Cation fluorescent dye based on benzyl naphthal imide structure as well as preparation and application thereof
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The invention relates to a cationic fluorescent dye based on a benzyl naphthal imide structure as well as preparation and application thereof. The structure is shown as a general formula I in the specification. The fluorescent cation dye is used for dyeing a modified polyester fabric, is high in dye-uptake and color yield, uniform in dyeing and strong in fluorescence, and fills the application blank of a fluorescent dye with a naphthal imide structure on a modified polyester fabric.
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Paragraph 0013; 0050-0051
(2021/01/15)
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- Introducing aldehyde functionality to proteins using ligand-directed affinity labeling
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Aldehyde is a versatile chemical handle for protein modification. Although many methods have been developed to label proteins with aldehyde, target-specific methods amenable to endogenous proteins are limited. Here, we report a simple affinity probe strategy to introduce aldehydes to native proteins. Notably, the probe contains a latent aldehyde functionality that is only exposed upon target binding, thereby enabling a one-pot labeling procedure.
- Fung, Yi Man Eva,Huang, Yiran,Li, Xiaoyu,Peng, Jianzhao,Song, Yinan,Xiong, Feng
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supporting information
p. 6134 - 6137
(2020/06/10)
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- Modulation of the lifespan of: C. elegans by the controlled release of nitric oxide
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The frontier of nitric oxide biology has gradually shifted from mechanism elucidation to biomanipulation, e.g. cell-proliferation promotion, cell-apoptosis induction, and lifespan modulation. This warrants biocompatible nitric oxide (NO) donating materials, whose NO release is not only controlled by a bioorthogonal trigger, but also self-calibrated allowing real-time monitoring and hence an onset/offset of the NO release. Additionally, the dose of NO release should be facilely adjusted in a large dynamic range; flux and the dose are critical to the biological outcome of NO treatment. Via self-assembly of a PEGylated small-molecule NO donor, we developed novel NO-donating nanoparticles (PEG-NORM), which meet all the aforementioned criteria. We showcased that a low flux of NO induced cell proliferation, while a high flux induced cell oxidative stress and, ultimately, death. Notably, PEG-NORM was capable of efficiently modulating the lifespan of C. elegans. The average lifespan of C. elegans could be fine-tuned to be as short as 15.87 ± 0.29 days with a high dose of NO, or as long as 21.13 ± 0.41 days with a low dose of NO, compared to an average life-span of 18.87 ± 0.46 days. Thus, PEG-NORM has broad potential in cell manipulation and life-span modulation and could drive the advancement of NO biology and medicine.
- Chen, Chao,Cheng, Lei,Gao, Yun,Jiang, Dawei,Wang, Chaochao,Xu, An,Xue, Yudong,Yang, Guoliang,Yang, Youjun,Zhang, Weian
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p. 8785 - 8792
(2020/09/04)
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- Self-assembled amphiphilic fluorescent probe: Detecting pH-fluctuations within cancer cells and tumour tissues
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Abnormal anaerobic metabolism leads to a lowering of the pH of many tumours, both within specific intracellular organelles and in the surrounding extracellular regions. Information relating to pH-fluctuations in cells and tissues could aid in the identification of neoplastic lesions and in understanding the determinants of carcinogenesis. Here we report an amphiphilic fluorescent pH probe (CS-1) that, as a result of its temporal motion, provides pH-related information in cancer cell membranes and selected intracellular organelles without the need for specific tumour targeting. Time-dependent cell imaging studies reveal that CS-1 localizes within the cancer cell-membrane about 20 min post-incubation. This is followed by migration to the lysosomes at 30 min before being taken up in the mitochondria after about 60 min. Probe CS-1 can selectively label cancer cells and 3D cancer spheroids and be readily observed using the green fluorescence channel (λem = 532 nm). In contrast, CS-1 only labels normal cells marginally, with relatively low Pearson's correlation coefficients being found when co-incubated with standard intracellular organelle probes. Both in vivo and ex vivo experiments provide support for the suggestion that CS-1 acts as a fluorescent label for the periphery of tumours, an effect ascribed to proton-induced aggregation. A much lower response is seen for muscle and liver. Based on the present results, we propose that sensors such as CS-1 may have a role to play in the clinical and pathological detection of tumour tissues or serve as guiding aids for surgery.
- Bhuniya, Sankarprasad,Cho, Youn-Joo,Han, Eun Hee,Hong, Kwan Soo,Khatun, Sabina,Kim, Soo Yeon,Lee, Hyunseung,Podder, Arup,Sessler, Jonathan L.
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p. 9875 - 9883
(2020/10/06)
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- Anticancer activity and topoisomerase II inhibition of naphthalimides with Ω-hydroxylalkylamine side-chains of different lengths
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Background: The substituted 1,8-Naphthalimides (1H-benzo[de]isoquinoline-1,3(2H)- diones) are known as DNA intercalators stabilizing DNA-Topoisomerase II complexes. This interaction disrupts the cleavage-relegation equilibrium of Topo II, resulting in formation of broken strands of DNA. Objective: To investigate the influence of type of substituents and substitution positions in 1,8- naphthalimde skeleton on the inhibition of Topoisomerase II activity. Method: The starting 1,8-naphthalimide were prepared from acenaphthene by introduction of appropriate substituents followed by condensation with ω-hydroxylakylamines of different chain length. The substituents were introduced to 1,8-naphthalimide molecule by nucleophilic substitution of leaving groups like nitro or bromo present in 4 or 4,5- positions using the ω- hydroxylalkylamines. The bioactivity of obtained compounds was examined in model cell lines. Results: Antiproliferative activity of selected compounds against HCT 116 human colon cancer cells, human non-small cell lung cells A549 and non-tumorigenic BEAS-2B human bronchial epithelium cells was examined. Several of investigated compounds exhibit a significant activity (IC50 μM to 7 μM) against model cancer cell lines. It was demonstrated that upon treatment with concentration of 200 μM, all derivatives display Topo II inhibitory activity, which may be compared with activity of Amonafide. Conclusion: The replacement of the nitro groups in the chromophore slightly reduces its anticancer activities, whereas the presence of both nitro group and ω-hydroxylalkylamine chain resulted in seriously increased anticancer activity. Obtained compounds showed Topo II inhibitory activity, moreover, influence of the substitution pattern on the ability to inhibit Topo II activity and cancer cells proliferation was observed.
- Kasprzycki, Przemys?aw,Strama, Klaudia,Tomczyk, Mateusz D.,Walczak, Krzysztof Z.,Wawszków, Martyna,Wyrostek, Anna Byczek
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p. 550 - 560
(2019/07/12)
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- Supramolecular Nanowires from an Acceptor–Donor–Acceptor Conjugated Chromophore
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Oligothiophene derivatives have been extensively studied as p-type semiconducting materials in organic electronics applications. This work reports the synthesis, self-assembly and photophysical properties of acceptor–donor–acceptor (A–D–A)-type oligothiop
- Chakraborty, Saptarshi,Varghese, Shinto,Ghosh, Suhrit
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supporting information
p. 16725 - 16731
(2019/12/24)
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- Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug
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A novel approach to the synthesis of pH-sensitive prodrugs has been proposed: thiourea drug modification. Resulting prodrugs can release the cytotoxic agent and the biologically active 2-thiohydantoin in the acidic environment of tumor cells. The concept of acid-catalyzed cyclization of thioureas to 2-thiohydantoins has been proven using a FRET model. Dual prodrugs of model azidothymidine, cytotoxic doxorubicin, and 2-thiohydantoin albutoin were obtained, which release the corresponding drugs in the acidic environment. The resulting doxorubicin prodrug was tested on prostate cancer cells and showed that the thiourea-modified prodrug is less cytotoxic (average IC50 ranging from 0.5584 to 0.9885 μM) than doxorubicin (IC50 ranging from 0.01258 to 0.02559 μM) in neutral pH 7.6 and has similar toxicity (average IC50 ranging from 0.4970 to 0.7994 μM) to doxorubicin (IC50 ranging from 0.2303 to 0.8110 μM) under mildly acidic conditions of cancer cells. Cellular and nuclear accumulation in PC3 tumor cells of Dox prodrug is much higher than accumulation of free doxorubicin.
- Krasnovskaya, Olga O.,Malinnikov, Vladislav M.,Dashkova, Natalia S.,Gerasimov, Vasily M.,Grishina, Irina V.,Kireev, Igor I.,Lavrushkina, Svetlana V.,Panchenko, Pavel A.,Zakharko, Marina A.,Ignatov, Pavel A.,Fedorova, Olga A.,Jonusauskas, Gediminas,Skvortsov, Dmitry A.,Kovalev, Sergey S.,Beloglazkina, Elena K.,Zyk, Nikolay V.,Majouga, Alexander G.
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p. 741 - 750
(2019/03/02)
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- Acid-base indicator prepared by utilizing vanillic aldehyde, and synthetic method of acid-base indicator
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The invention provides an acid-base indicator prepared by utilizing vanillic aldehyde, and a synthetic method of the acid-base indicator. The acid-base indicator shows yellow in an acid environment and shows dark red in a base environment, the color rende
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Paragraph 0017-0019
(2019/12/25)
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- The Effect of Random and Block Copolymerization with Pendent Carbozole Donors and Naphthalimide Acceptors on Multilevel Memory Performance
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Polymeric materials have been widely used in the fabrication of data-storage devices, owing to their unique advantages and defined conduction mechanisms. To date, the most-functional polymers that have been reported for memory devices were synthesized through random copolymerization, whilst there have been no reports regarding the memory effect of block polymers. Herein, we synthesized a random copolymer (PMCz8-co-PMBNa2) and its corresponding block copolymer (PMCz8-b-PMBNa2) to study the effect of the method of polymerization on the memory properties of the corresponding devices. Interestingly, both devices (ITO/PMCz8-co-PMBNa2/Al and ITO/PMCz8-b-PMBNa2/Al) exhibited ternary memory performance, with threshold voltages of ?1.7 V/?3.3 V and ?2.7 V/?3.8 V, respectively. However, based on comprehensive measurements, the memory properties of PMCz8-co-PMBNa2 and PMCz8-b-PMBNa2 were found to be owing to the operation of different conduction mechanisms, which resulted from different molecular stacking in the film state. Therefore, we expect that this work will be helpful for improving our understanding of the conduction mechanisms in polymer-based data-storage devices.
- Zhang, Qi-Jian,Zhou, Jia-Hui,Li, Hui,He, Jing-Hui,Li, Na-Jun,Xu, Qing-Feng,Chen, Dong-Yun,Li, Hua,Lu, Jian-Mei
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supporting information
p. 853 - 860
(2018/03/13)
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- Based on 1, 8 - naphthalene imide derivative of the probe molecule, preparation method and application (by machine translation)
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The invention discloses a based on the 1, 8 - naphthalene imide derivative of the probe molecule, preparation method and application. The 4 - bromo - 1, 8 - naphthalenedicarboxylic anhydride with ethanolamine to carry out the condensation reaction, to obtain the 4 - bromo - N - 2 - [...] - 1, 8 - naphthalene imide, then reaction with hydrazine hydrate to obtain 4 - hydrazino - N - 2 - [...] - 1, 8 - naphthalene imide, through the pyrrole - 2 - formaldehyde and 4 - hydrazino - N - 2 - [...] - 1, 8 - naphthalene imide primary amine condensation reaction to obtain the 4 bit in order to Schiff base forms of modified naphthalimide derivatives as probe molecules, it to pyrrole heterocyclic as the acceptor, naphthalimide as the fluorescence patterns, by absorbance, fluorescent and to realize the change of the color of Cu2 + The specificity of the response to the identification and concentration. The present invention has the synthetic method is simple, low cost, simple and convenient operation, good selectivity, high sensitivity and low detection limit and the like, can be used for complex real-time and quick detection of the sample. (by machine translation)
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Paragraph 0016; 0017
(2018/08/04)
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- Benzothiazole and triazole double-heterocyclic fused ring compound and use thereof
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The invention relates to a benzothiazole and triazolediheterocycle-containing fused ring compound which has a structure of a general formula Y shown in the specification. According to the compound, cyclic amine with bioactivity is connected to the site 4 of naphthalimide, a structure that an imine nitrogen atom of naphthalimide is spaced from a triazole nitrogen atom connected with a side chain by two carbon atoms is kept, and molecules are introduced into sulfur-containing heterocyclic benzothiazole through linkage of triazole, so that the diversity of naphthalimide derivatives, the bioactivity of naphthalimide and the DNA identification and intercalation capability are improved; the compound has a relatively good inhibition effect on normal growth of tumor cells, with different tissue sources, of cervical cancers, liver cancers, breast cancers and the like.
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Paragraph 0054; 0055; 0056
(2017/08/25)
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- Blue emitting 1,8-naphthalimides with electron transport properties for organic light emitting diode applications
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In this article, the synthesis, characterization and use of two novel naphthalimides as electron-transporting emitter materials for organic light emitting diode (OLED) applications are reported. The molecules were obtained by substituting electron donating chloro-phenoxy group at the C-4 position. A detailed optical, thermal, electrochemical and related properties were systematically studied. Furthermore, theoretical calculations (DFT) were performed to get a better understanding of the electronic structures. The synthesized molecules were used as electron transporters and emitters in OLEDs with three different device configurations. The devices with the molecules showed blue emission with efficiencies of 1.89?cdA-1, 0.98?lmW?1, 0.71% at 100?cdm-2. The phosphorescent devices with naphthalimides as electron transport materials displayed better performance in comparison to the device without any electron transporting material and were analogous with the device using standard electron transporting material, Alq3. The results demonstrate that the naphthalimides could play a significant part in the progress of OLEDs.
- Ulla, Hidayath,Kiran, M. Raveendra,Garudachari,Ahipa,Tarafder, Kartick,Adhikari, Airody Vasudeva,Umesh,Satyanarayan
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p. 344 - 354
(2017/05/08)
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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 0062; 0063; 0064
(2018/01/17)
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- Versatile Room-Temperature-Phosphorescent Materials Prepared from N-Substituted Naphthalimides: Emission Enhancement and Chemical Conjugation
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Purely organic materials with room-temperature phosphorescence (RTP) are currently under intense investigation because of their potential applications in sensing, imaging, and displaying. Inspired by certain organometallic systems, where ligand-localized
- Chen, Xiaofeng,Xu, Cheng,Wang, Tao,Zhou, Cao,Du, Jiajun,Wang, Zhongping,Xu, Hangxun,Xie, Tongqing,Bi, Guoqiang,Jiang, Jun,Zhang, Xuepeng,Demas, James N.,Trindle, Carl O.,Luo, Yi,Zhang, Guoqing
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supporting information
p. 9872 - 9876
(2016/08/16)
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- Naphthalimide derivative, preparation method and application of naphthalimide derivative in preparation of fluorescent polyacrylonitrile fibers
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The invention discloses a naphthalimide derivative, a preparation method and an application of the naphthalimide derivative in preparation of fluorescent polyacrylonitrile fibers. The fluorescent polyacrylonitrile fibers are prepared through subjecting a 1,8-naphthalimide derivative containing double bonds to free-radical polymerization with an acrylonitrile monomer so as to obtain a fluorescent polymer, then, preparing a spinning solution of proper concentration from the obtained polymer, and carrying out electrostatic spinning. According to the naphthalimide derivative, the preparation method and the application of the naphthalimide derivative, the prepared polyacrylonitrile nano-fibers have relatively high fluorescence, a tedious dyeing procedure is avoided, and the operation is simple, so that resource saving and environmental protection are facilitated.
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Paragraph 0016
(2017/07/22)
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- Naked-eye and fluorescence detection of basic pH and F- with a 1,8-naphthalimide-based multifunctional probe
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Based on 1,8-naphthalimide, a novel multifunctional colorimetric and fluorescent probe was designed and synthesized for basic pH and F- naked-eye and fluorescence recognition with high sensitivity and excellent selectivity. The probe can detect F- quantitatively in a concentration range of 0-16.7 μM and 0-20 μM in different methods, and the detection limit could be as low as 25 nM for F-. The detection of F- on chromatography plates and the preliminary application of the probe to detect fluoride contents in toothpaste have been successfully demonstrated.
- Du, Weiwei,Xu, Jie,Li, Haixia,Feng, Chengcheng,Yu, Mingming,Li, Zhanxian,Wei, Liuhe
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p. 15077 - 15083
(2015/02/19)
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- Visible-light-induced cleavage of 4-α-amino acid substituted naphthalimides and its application in DNA photocleavage
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A new kind of visible-light photocleavable molecule, 4-α-amino acid substituted naphthalimide, is reported. The cleavage occurred at the C-N bond between the 4-amino and the amino acid residue and released a 4-aminonaphthalimide. A lysine substituted naphthalimide exhibited a strong DNA photocleavage activity when irradiated with a blue light LED. This journal is
- Zhou, Jin,Fang, Canliang,Liu, Ying,Zhao, Yao,Zhang, Nan,Liu, Xiangjun,Wang, Fuyi,Shangguan, Dihua
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p. 3931 - 3935
(2015/03/30)
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- A fluorescent probe for benzenethiols and its application on test paper, in water samples and living cells
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It is important to develop probes for rapid, selective, and sensitive detection of highly toxic benzenethiols in both environmental and biological science. In this work, based on the selective cleavage reaction by benzenethiols under mild conditions, a no
- Zhang, Wenying,Liu, Xingjiang,Zhang, Hongyan,Feng, Chengcheng,Liu, Chunxia,Yu, Mingming,Wei, Liuhe,Li, Zhanxian
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p. 8248 - 8254
(2015/08/06)
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- Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination
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Successful amination of 4-bromo-1,8-naphthalimides with 'lengthy' imide N-functionality has been achieved using a general palladium mediated approach (conventional thermal protocols were sub-optimal). Only readily available Pd/ligand combinations were considered and the resulting Buchwald-Hartwig procedure using Pd2(dba)3, Xantphos and Cs 2CO3 is high yielding, relatively mild (40-80 °C, 24 h, yields 50-90%), requires only a modest excess of amine (3.0 equiv) and works equally well with other imide N-substituents. As such, the protocol complements existing methods but is superior for more complex substrates. Herein we compare this Pd mediated approach to the methods most commonly used and further demonstrate its utility by synthesising a number of new, highly fluorescent, 4-aminonaphthalimides.
- Fleming, Cassandra L.,Ashton, Trent D.,Pfeffer, Frederick M.
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p. 135 - 143
(2014/06/23)
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- Carbon-dot-based ratiometric fluorescent sensor for detecting hydrogen sulfide in aqueous media and inside live cells
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A FRET ratiometric fluorescent sensor was developed for detecting H 2S in aqueous media and serum, as well as inside live cells. For this sensor, carbon dots serve as the energy donor and also the anchoring site for the probe. This sensor is highly selective and sensitive with a detection limit of 10 nM which is the lowest among fluorescent H2S sensors. This journal is
- Yu, Changmin,Li, Xizhen,Zeng, Fang,Zheng, Fangyuan,Wu, Shuizhu
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supporting information
p. 403 - 405
(2013/02/22)
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- A new Schiff base based on vanillin and naphthalimide as a fluorescent probe for Ag+ in aqueous solution
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A new Schiff base based on vanillin and naphthalimide was designed and synthesized as fluorescent probe. The probe showed high selectivity for Ag + over other metal ions such as Pb2+, Na+, K+, Cd2+, B
- Zhou, Yanmei,Zhou, Hua,Ma, Tongsen,Zhang, Junli,Niu, Jingyang
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scheme or table
p. 56 - 59
(2012/03/07)
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