- Study on the synthesis and spectra of a novel kind of carbozole benzothiazole indole styryl cyanine dye with a carbazole bridged Chain
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Based on the frequently-used cyanine dye probe thiazole orange (TO) and Cy3, a novel kind of styryl cyanine dye was designed and synthesized. Carbazole was inserted into the structures of two cyanine dyes, TO and Cy3, to act as a bridge to link the benzothiazole and indole. This modification resulted in a novel kind of carbozole benzothiazole indole cyanine dye with a carbazole-bridged chain. The dyes were characterized by HNMR and MS. The spectra of the novel dyes were also studied and the results showed that the fluorescence wavelength of novel carbazole benzothiazole indole cyanine dye shifted red, the Stokes shift and Fluorescence quantum yields increased and the fluorescence intensity was enhanced compared to that of TO. These results indicated that the novel dye could be used as an excellent fluorescent probe in biological labeling.
- Fei, Xuening,Hao, Yachao,Gu, Yingchun,Li, Chao,Yu, Lu
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- The effect of bis-carboxylic groups of squarylium dyes on the efficiency of dye-sensitized solar cells
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Symmetric squarylium dye (SQIND1) with bi-carboxylic groups has been synthesized and photoelectrochemical properties have been studied in comparison with its non-functionalized analog groups (SQIND2). The experimental results showed that the introduction of anchor carboxylic groups in SQIND1 sensitizer provides a more intimate contact with nanoparticles TiO2 which increases the number of charge carriers transferred from the SQIND1 to the semiconductor. The theoretical calculations and absorbance results show that the electron density of LUMO of SQIND1 is delocalized in the whole chromophore, leading to strong electronic coupling between SQIND1 sensitizer and conducting band of TiO2, resulting in improved dye-sensitized solar cell efficiency compared to SQIND2. Hence, the SQIND1 sensitized exhibit better photovoltaic performance. Although, the absence of any linker groups in the SQIND1, then SQIND1 was perfect efficiently sensitized on porous TiO2 with the long UV–Vis and NIR region up to 800?nm of the spectrum and showed higher remarkable performance of values, such as η of 3.3%, a Jsc of 7.6?mA/cm2, a Voc of 0.59, and FF of 0.73.
- Al-horaibi, Sultan A.,Garoon, Eman M.,Bhise, Narendra A.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.
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- Benz[c,d]indolium-containing monomethine cyanine dyes: Synthesis and photophysical properties
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Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.
- Soriano, Eduardo,Holder, Cory,Levitz, Andrew,Henary, Maged
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- A carbazole-hemicyanine dye based ratiometric fluorescent probe for selective detection of bisulfite (HSO3 ?) in cells and C. elegans
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Bisulfite (HSO3 ?) is an important sulfur dioxide (SO2) derivative, which plays a major role in many physiological processes and is also closely associated with a variety of diseases. Thus the development of highly selective and sensitive fluorescent probes is essential to detect HSO3ˉ in living cells. In this work, we report the synthesis and analysis of a ratiometric fluorescent probe for selective detection of HSO3ˉ based on the 1,4-nucleophilic addition reaction with the carbazole as an electron donor (D) and aldehyde group as an electron acceptor (A). The addition of HSO3ˉ and other ions to our probe can be observed by UV - vis and fluorescence spectrometry. Our investigation proved that the probe is highly selective and sensitive for HSO3ˉ and ratiometric changes. Moreover, the probe has good cell permeability and was successfully applied to the detection of exogenous HSO3ˉ in Hela cells and C. elegans.
- Bi, Keying,Tan, Rui,Hao, Ruiting,Miao, Lanxi,He, Yanqi,Xianghua, Wu,Zhang, Junfeng,Rui, Xu
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- Ultrabright and Serum-Stable Squaraine Dyes
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Highly stable symmetric and asymmetric squaraine fluorophores have been synthesized featuring an internal salt bridge between a quaternary ammonium cation and the central oxycyclobutenolate ring of the chromophore. Some of our newly synthesized symmetric and asymmetric compounds display increased molar absorptivity, quantum yield in serum, and thermal/photochemical stability over previously reported squaraine-based dyes. Consequently, both classes show great promise in resurfacing the normal environment-labile squaraine dyes as novel imaging agents and scaffolds for fluorescence sensing. Furthermore, incorporating a covalent attachment point away from the conjugated system allows for biological tagging applications without disturbing the optimum optical characteristics of the newly designed fluorophore.
- Yadav, Yogesh,Owens, Eric,Nomura, Shinsuke,Fukuda, Takeshi,Baek, Yoonji,Kashiwagi, Satoshi,Choi, Hak Soo,Henary, Maged
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- Photophysical characterization and BSA interaction of the direct ring carboxy functionalized unsymmetrical NIR cyanine dyes
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Novel near infrared (NIR) sensitive unsymmetrical cyanine dyes bearing direct –COOH functionalized indole ring were synthesized, characterized and subjected to photophysical investigations. These unsymmetrical cyanine dyes were then subjected to investigate their interaction with bovine serum albumin (BSA) as a model protein in Phosphate buffer solutions. Apart from NIR absorption and emission with high molar extinction coefficients they exhibit a blue shift in PBS solution owing to their enhanced dye aggregation. Interaction of these dyes with BSA leads to not only enhanced emission intensity but also bathochromically shifted absorption maximum due to formation of dye-BSA conjugate. These dyes bind strongly with BSA having about an order of magnitude higher binding constant as compared to the typical cyanine dyes. Amongst the unsymmetrical cyanine dyes investigated in this work one bearing substituents like Iodo and carboxylic acid in the terminal Indole rings (UCD-3) exhibited highest association with the BSA having very high binding constant of 1.01?×?107?M?1.
- Saikiran, Maryala,Sato, Daisuke,Pandey, Shyam S.,Ohta, Takeshi,Hayase, Shuzi,Kato, Tamaki
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- An indocyanine-based turn-on fluorescent probe for specific detection of biothiols
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A novel heptamethine cyanine-based turn-on fluorescent probe Cy-DNBS was designed and synthesized, which was used successfully to detect biothiols with high selectivity and sensitivity. With the addition of biothiols, the probe displayed ~30-fold fluorescence enhancement at 625 nm. Meanwhile, the solution color changed remarkably from green to red, which provides a method to recognize biothiols by the ‘naked eye’. The detection limit of Cys, GSH and Hcy are 2.24 nM, 1.99 nM and 4.46 nM, respectively.
- Wang, Xiaojing,Jin, Di,Li, Xue,Yan, Xilong,Wang, Bowei
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- Near-infrared squaraine fluorescent probe for imaging adenosine 5′-triphosphate in live cells
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Adenosine 5′-triphosphate (ATP), as a “molecular currency” for intracellular energy transfer, not only participates in various physiological activities, but also involves in various pathological processes of living cells. Therefore, the establishment of a simple, rapid, sensitive and accurate ATP analysis method is of great significance for the study of its physiological functions. In this work, we rationally design a near-infrared phenylboronic acid group-functionalized dicyanovinyl squaraine (SQ-PBA3), with which a supramolecular assembly was constructed for fluorescent imaging of ATP. In PBS buffer, SQ-PBA3 changes self-assembly when adding cetyltrimethyl ammonium bromide (CTAB) deriving fluorescence response of SQ-PBA3 to ATP with the maximum emission at 700 nm, due to the specificity of phenylboronic acid to diols and the multiple electrostatic interactions between SQ-PBA3, ATP and CTAB molecules. Meanwhile, the probe was successfully applied to monitor intracellular ATP level in MCF-7 cells with high sensitivity and selectivity.
- Wang, Guimei,Jiang, Xiaoxue,Fu, Nanyan
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- Photochromism of neutral spiropyran in the crystalline state at room temperature
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Solid-state photochromic materials are very attractive due to their promising future in advanced functional materials with reversible and tunable optical properties. However, the development of photochromic material in the solid state, especially in the crystalline state, is still a great challenge due to dense molecular packing. In this study, a solid-state optical switch based on the methanol-esterified spiropyran derivative S1 is constructed, which exhibits reversible photochromic properties in the solid-state product without further recrystallization. Moreover, the cultured single crystal (S1-C) can unexpectedly undergo photochromism at room temperature, which is a very rare example in a neutral spiropyran crystal. The crystallographic analysis reveals that weak van der Waals forces dominate in the crystal of S1-C, resulting in a relatively loose packing mode and photochromic properties. Mechanical force can destroy the restricted environment of the crystalline state and allow the S1 compound to achieve more efficient photochromism. Our study opens up an avenue for relating the molecular structure/packing mode to photochromic properties. Consequently, by utilizing the reversible and efficient photochromic properties, we successfully demonstrate the application of S1 as optical printing materials. This journal is
- Fang, Bing,Li, Pengyu,Wang, Qian,Wu, Zhen,Yin, Meizhen
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- Squaraine-based polymer dots with narrow, bright near-infrared fluorescence for biological applications
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This article describes the design and development of squaraine-based semiconducting polymer dots (Pdots) that show large Stokes shifts and narrow-band emissions in the near-infrared (NIR) region. Fluorescent copolymers containing fluorene and squaraine units were synthesized and used as precursors for preparing the Pdots, where exciton diffusion and likely through-bond energy transfer led to highly bright and narrow-band NIR emissions. The resulting Pdots exhibit the emission full width at half-maximum of ～36 nm, which is ～2 times narrower than those of inorganic quantum dots in the same wavelength region (～66 nm for Qdot705). The squaraine-based Pdots show a high fluorescence quantum yield (QY) of 0.30 and a large Stokes shift of ～340 nm. Single-particle analysis indicates that the average per-particle brightness of the Pdots is ～6 times higher than that of Qdot705. We demonstrate bioconjugation of the squaraine Pdots and employ the Pdot bioconjugates in flow cytometry and cellular imaging applications. Our results suggest that the narrow bandwidth, high QY, and large Stokes shift are promising for multiplexed biological detections.
- Wu, I-Che,Yu, Jiangbo,Ye, Fangmao,Rong, Yu,Gallina, Maria Elena,Fujimoto, Bryant S.,Zhang, Yong,Chan, Yang-Hsiang,Sun, Wei,Zhou, Xing-Hua,Wu, Changfeng,Chiu, Daniel T.
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- Synthesis of novel pyrazolo[3,4-b]pyridine derivatives in aqueous medium
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A synthesis of 5-(3,3-dimethyl-3H-indol-2-yl)-3-methyl-1H-pyrazolo[3,4-b]pyridines by the reaction of variously substituted aminomethylene malondialdehydes [2-(3,3-dimethyl-3H-indol-2-ylidene)malondialdehydes] with 5-amino-1-aryl-3-methylpyrazoles in the presence of p-toluenesulfonic acid in water is described.
- Baradarani, Mehdi M.,Fazlelahi, Hadi Zare,Rashidi, Ahmad,Joule, John A.
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- Light-Driven Expansion of Spiropyran Hydrogels
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The incorporation of molecular switches in organic structures is of great interest in the chemical design of stimuli-responsive materials that mimic the complex functions of living systems. Merocyanine dyes that convert to spiropyran moieties upon exposure to visible light have been extensively studied as they can be incorporated in hydrated covalent networks that will expel water when this conversion occurs and induce a volumetric shrinkage. We report here on a sulfonate-based water-soluble photoswitch that, in contrast to the well-known systems, triggers a volumetric expansion in hydrogels upon exposure to photons. Contraction is in turn observed under dark conditions in a highly reversible manner. The novel behavior of the photoswitch incorporated in the covalent network was predicted by coarse-grained simulations of the system's chemical structure. Using pH control and polymeric structures that differ in lower critical solution temperature, we were able to develop hydrogels with highly tunable volumetric expansion. The novel molecular function of the systems developed here led to materials with the negative phototaxis observed in plants and could expand the potential use of hydrogels as sensors, soft robots, and actuators.
- Li, Chuang,Iscen, Aysenur,Palmer, Liam C.,Schatz, George C.,Stupp, Samuel I.
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- Mitochondria-targeted prostate cancer therapy using a near-infrared fluorescence dye–monoamine oxidase A inhibitor conjugate
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Prostate cancer (PCa) is the most frequent malignant cancer among men in the USA, leading to substantial morbidity and mortality, while the existing treatments have restricted therapeutic benefits for patients with hormone-refractory PCa (HRPC) and metast
- Lv, Qingzhi,Yang, Xiaoguang,Wang, Menglin,Yang, Jincheng,Qin, Zhilin,Kan, Qiming,Zhang, Haotian,Wang, Yongjun,Wang, Dun,He, Zhonggui
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- Glucosamine modified near-infrared cyanine as a sensitive colorimetric fluorescent chemosensor for aspartic and glutamic acid and its applications
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A glucosamine modified near-infrared cyanine fluorescent probe has been synthesized and developed as an efficient and visual sensor for the trace level determination of glutamic acid (Glu) and aspartic acid (Asp) with no interference by other amino acids. A prominent fluorescence enhancement at 805 nm and a remarkable color change from pale red to colorless were observed in the presence of Glu and Asp respectively. This probe may also serve as a highly sensitive acidic pH probe with a pKa value of 5.82. Furthermore, the chemosensor has been successfully applied for the imaging of Glu and Asp in living cells, and the cytotoxicity assay exhibited that it is of low toxicity under the experimental conditions. This journal is
- Zhao, Xu,Wei, Ruisong,Chen, Ligong,Jin, Di,Yan, Xilong
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- A mitochondria-targeted fluorescent dye naphthalimide-thioether-cyanine for NIR-activated photodynamic treatment of cancer cells
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In this work, an NIR-activated fluorescent dye naphthalimide-thioether-cyanine (NPSCY) was developed for the photodynamic treatment of cancer cells. In this dye, naphthalimide and cyanine were selected as the two fluorophores, which were linked by the thioether group. Under 660 nm irradiation,NPSCYcould produce1O2rapidly, suggesting the potential for photodynamic therapy. Cys can be considered as one of the markers of cancer cells andNPSCYcould distinguish Cys from three channels (433 nm, 475 nm, 733 nm) due to the bilateral recognition of the thioether group, which was helpful for accurately locating cancer cells. Fortunately,NPSCYcould also produce1O2after being reacted with the intracellular biological thiols, which also avoided the inactivation of the photosensitizer in cancer cells. The co-localization coefficient of 0.873 indicated that the cyanine group promoted the aggregation ofNPSCYin mitochondria. This photosensitizer showed low dark toxicity and high phototoxicity. Meanwhile, the half-maximal inhibitory concentration (IC50) was calculated to be 3.7 μM.NPSCYcould inhibit cell migration after irradiation at 660 nm.
- Shen, Ronghua,Bai, Jin,Qian, Ying
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- Iodine-Promoted Domino Oxidative Cyclization for the One-Pot Synthesis of Novel Fused Four-Ring Quinoxaline Fluorophores by sp3 C?H Functionalization
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A method for the synthesis of novel fused four-ring quinoxaline skeleton has been described by an I2 promoted sp3 C?H functionalization between 1,2,3,3-tetramethyl-3H-indolium iodides and 1,2-diamines. This transformation proceeds smoothly under metal- and peroxide-free conditions through a sequential iodination, oxidation, annulation and rearrangement. Moreover, 8,9-dichloro-5,12,12-trimethyl-2-(trifluoromethyl)-5,12-dihydroquinolino[2,3-b]quinoxaline showed good photophysical properties and was used in live cell imaging, indicating the potential value of this skeleton as a fluorophore in probes.
- Zhang, Yong,Yang, Min,Jia, Chengli,Ji, Min
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- A Cyanine Dye Encapsulated Porous Fibrous Mat for Naked-Eye Ammonia Sensing
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Electrospun ultrathin fiber-based sensors are desirable because of their practicality and sensitivity. Ammonia-detection systems are in high demand in different areas, including the industrial and agricultural fields. However, current technologies rely on large and complex instruments that restrict their actual utilization. Herein, we report a flexible naked-eye ammonia sensor, the polylactic acid–cyanine (PLA-Cy) fibrous mat, which was fabricated by blending a carboxyl-functionalized cyanine dye (D1) into electospun PLA porous fibers. The sensing mat was shown to undergo a naked-eye-detectable color change from white to blue upon exposure to ammonia vapor. The mat showed high selectivity to ammonia gas with a detection limit of 3.3 ppm. Aggregated D1 was first encapsulated by PLA and was then ionized by NH3. These mechanisms were examined by photophysical studies and scanning electron microscopy. The aggregation–deaggregation process of D1 in the PLA-Cy fibrous mat led to the color change. This work provides a facile method for the naked-eye detection of ammonia and a novel strategy for the use of organic dyes in ammonia sensing.
- Ji, Chendong,Ma, Lijing,Yin, Meizhen,Yang, Wantai,Pan, Kai
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- Preparation of a spirooxazine grafted PMMA and its photochromic properties
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A novel spirooxazine (SO) compound was designed and synthesized. Macromolecular materials, called SO-g-hPMMAs (where the g means grafting and the h means partial hydrolysis), were prepared using PMMA (polymethylmethacrylate) with different degrees of hydrolysis. SO-g-5%hPMMA was prepared by reacting SO-containing active C-Br bonds with 5% partially hydrolyzed PMMA. The SO was characterized using1H NMR and infrared. Beyond that, photochromic properties were studied in detail. We discuss the effects of hydrochloric acids and hPMMAs of different hydrolysis degrees on photochromic properties of SO-g-hPMMA. Additionally, mechanical properties of the material were studied. Results indicate that the colored ring-opening form (PMC) of SO-g-hPMMA exhibits a good performance in terms of thermal stability, in contrast to the homologous SO. Experiments additionally demonstrate that hydrochloric acid improves the PMC’s thermal stability. SO-g-9%hPMMA demonstrated a good performance of photochromic properties compared to those with different degrees of hydrolysis.
- Wu, Liang,Zhang, Sai,Gao, Jun,Qiang, Peirong,Lei, Jingxin
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- A fluorescent chemosensor for fluoride anions based on a hemicyanine dye
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A hemicyanine dye with imidazole as the acceptor was designed and prepared as a chemosensor for fluoride anions. The experimental results demonstrated that it is a fluorometric probe for fluoride anion with good sensitivity and high selectivity. This probe showed obvious changes in UV-Vis absorption and fluorescence spectra in the presence of fluoride anions, which are attributed to the deprotonation of N-H on the imidazole moiety with fluoride anions.
- Yu, Liang,Li, Tingting,Chen, Ligong
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- Two near-infrared highly sensitive cyanine fluorescent probes for pH monitoring
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Two near-infrared (NIR) pH-activated heptamethine indocyanine probes with quaternary ammonium unit were designed and synthesized. The absorption and emission titrations indicate that cationic structure improves the cyanine dye's aqueous solubility and these two probes exhibit highly sensitive response to pH in acid condition. Their fluorescence intensities both gradually increase about 25-fold from pH 7.60 to 3.00 with pKa values of 4.72 and 4.45 respectively, which are suitable for studying acidic organelles in living cells. Moreover, their fluorescence intensities are linearly proportional to pH values in the range of 5.50–4.00. These results are probably attributed to the protonation of the indole nitrogen atoms, which are verified by 1H NMR spectra. Furthermore, these two probes can achieve real-time imaging of cellular pH and detection of pH in situ in living HeLa cells due to their excellent properties, including good reversibility, desirable photostability, high selectivity, low cytotoxicity and remarkable membrane permeability.
- Hou, Jing-Ru,Jin, Di,Chen, Bo,Si, Lei-Lei,Jin, Yue-Hua,Chen, Li-Gong,Yan, Xi-Long,Wang, Bo-Wei,Li, Yang
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- Application of benz[c,d]indolenine-based unsymmetrical squaraine dyes to near-infrared dye-sensitized solar cells
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Novel benz[c,d]indolenine-based unsymmetrical near-infrared squaraine dyes having germinal butyl (η?=?0.55%) and octyl (η?=?0.58%) groups at another indolenine ring exhibited higher conversion efficiency than the usually used methyl derivative (η?=?0.38%)
- Matsui, Masaki,Haishima, Yuki,Kubota, Yasuhiro,Funabiki, Kazumasa,Jin, Jiye,Kim, Taek Hyeon,Manseki, Kazuhiro
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- Synthesis and characterization of new squaraine dyes with bis-pendent carboxylic groups for dye-sensitized solar cells
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In the present study, we introduce a new plan to boost the charge transfer between squaraine sensitizers and the conduction band of TiO2 by increasing the anchoring number. Two new symmetric squaraine sensitizers (SQIND-1 and SQIND-2) derived from indoline and having pendant bis-COOH as anchor groups to inject the electron into the TiO2 nanoparticles were tested as DSSC. The theoretical calculations and absorbance results showed that the electron density of LUMO of SQIND-1 is delocalized in the whole carboxylic group resulting in strong electronic interaction between SQIND-1 sensitizer and the conducting band of TiO2. Also, the relatively longer alkyl chain present in SQIND-1 would lower the aggregation of the dye on the TiO2 surface compared to SQIND-2. Hence, the SQIND-1 sensitized exhibit better photovoltaic performance. Dye-sensitized solar cell base fabricated in SQIND-1 was on TiO2 with the long wavelength and NIR region up to 750 nm of the spectrum and showed higher noteworthy performance properties, such as energy conversion efficiency (η) of 6.2% (AM 1.5 G), a short-circuit photocurrent density of 6.64 mA/cm2, an open-circuit photovoltage of 0.53, a fill factor of 0.72 and an incident photon-to-current conversion efficiency of 45% at 668 nm.
- Al-horaibi, Sultan A.,Asiri, Abdullah M.,El-Shishtawy, Reda M.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.
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- Ratiometric fluorescent detection of intracellular hydroxyl radicals based on a hybrid coumarin-cyanine platform
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The first ratiometric fluorescent probe for hydroxyl radical ratiometric imaging in living cells was rationally designed based on a hybrid coumarin-cyanine platform.
- Yuan, Lin,Lin, Weiying,Song, Jizeng
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- Erlotinib-Guided Self-Assembled Trifunctional Click Nanotheranostics for Distinguishing Druggable Mutations and Synergistic Therapy of Nonsmall Cell Lung Cancer
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The outcome of molecular targeted therapies is restricted by the ambiguous molecular subtypes of nonsmall cell lung cancer (NSCLC), which are difficult to be defined with druggable mutations, and the inevitable emergence of drug-resistance. Here we used the Cu-catalyzed click chemistry to synthesize a chitosan-based self-assembled nanotheranostics (CE7Ns) composed of a near-infrared (NIR) fluorescent photosensitizer Cy7 and molecular targeted drug erlotinib. The well-characterized CE7Ns can release erlotinib and Cy7 fast under acidic condition in the presence of lysozyme, distinguish three molecular subtypes of NSCLC, and specifically bind to the erlotinib-sensitive epidermal growth factor receptor (EGFR)-mutated PC-9 cells. The uptake of CE7Ns is much more in PC-9 cells than in other NSCLC cells, thus generating a notable fluorescence signal in PC-9 cells. Upon NIR irradiation, Cy7 in CE7Ns produces high reactive oxygen species in PC-9 cells. The synergistic effect between erlotinib-targeted therapy and photodynamic therapy significantly up-regulates cancer suppressor p53 and inhibits Survivin, which results in more apoptosis and cell cycle arrest. Upon intravenous administration, the erlotinib-guided CE7Ns significantly accumulate in PC-9-seeded mouse lungs and produce strong fluorescence. Upon NIR irradiation, CE7Ns significantly inhibit the subcutaneously implanted PC-9 tumor growth. This study provides, for the first time, a novel strategy to synthesize a multifunctional theranostic entity to simultaneously distinguish and image druggable mutations and combine targeted therapy with photodynamic therapy to overcome drug resistance.
- Gao, Yu,Zhang, Huijuan,Zhang, Yingying,Lv, Tingting,Zhang, Lu,Li, Ziying,Xie, Xiaodong,Li, Fengqiao,Chen, Haijun,Jia, Lee
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- Design, synthesis and biological evaluation of novel heptamethine cyanine dye-erlotinib conjugates as antitumor agents
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Epidermal growth factor receptor tyrosine kinase (EGFR-TK) has been proved as a target for the treatment of non-small cell lung cancer (NSCLC) with specific gene mutations. However, EGFR-TK inhibitors (EGFR-TKIs) need to enter cancer cells and then competitively interact with the active site of tyrosine kinase receptors to suppress the downstream signaling pathway to inhibit tumor proliferation. In this study, in order to improve the tumor cell targeting ability of EGFR-TKI, EGFR-TKI erlotinib was conjugated with the cancer cell-targeting heptamethine cyanine dyes to form seventeen novel erlotinib-dye conjugates. The efficiency of tumor targeting properties of conjugates against cancer cell growth and EGFR-TK inhibition was evaluated in vitro. The result revealed that most erlotinib-dye conjugates exhibited stronger inhibitory effect on A549, H460, H1299 and MDA-MB-231 cell lines than the parent drug erlotinib. Meanwhile, representative compounds exhibited weak cytotoxicity on human normal mammary epithelial MCF-10A cells. Moreover, the conjugate CE17 also showed ~14-fold higher EGFR-TK inhibition activity (IC50 = 0.124 μM) than erlotinib (IC50 = 5.182 μM) in A549 cell line. Finally, molecular docking analysis verified that the erlotinib moiety of compound CE17 could form hydrogen bond with Met-769 and occupy active cavity of EGFR-TK. Therefore, we believed the integration strategy between heptamethine cyanine dyes and EGFR-TKI will contribute to enhancing the therapeutic effect of EGFR-TKI for NSCLC treatment.
- Guo, Chun,Hou, Zhuang,Mou, Yanhua,Wang, Dun,Yang, Xiaoguang
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- Highly selective visual detection of Cu(II) utilizing intramolecular hydrogen bond-stabilized merocyanine in aqueous buffer solution
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A Cu2+-specific colorimetric sensor 1, which is stabilized by an intramolecular hydrogen bonding, was designed and developed. The color of 1 changes from purple to blue on addition of 1.0 μM Cu2+ in aqueous buffer solution, which can be detected by the naked eye. The analytical detection limit for Cu2+ by the naked eye is as low as 1.0 μM. The stoichiometry for 1 and Cu2+ in complex is 2:1 in aqueous solution.
- Guo, Zhao-Qi,Chen, Wei-Qiang,Duan, Xuan-Ming
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- The investigation of unique water-soluble heptamethine cyanine dye for use as NIR photosensitizer in photodynamic therapy of cancer cells
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In this paper, a unique water-soluble heptamethine cyanine dye as NIR photosensitizer was synthesized to explore its properties associated with potential applications in photodynamic therapy (PDT). In the strategy of designing this photosensitizer, a sulfonic acid was used as a water soluble functional group and linked to the fluorophore through alkyl chains. 4-amino-2,2,6,6-tetramethylpiperidine-N-oxyl(Tempo) moiety was used as the a nitroxide spin label in obtaining biochemical reaction information in vivo due to it could greatly increase the inter-system crossing (ISC) process for triplet-state photosensitizers and low toxicity. As expected, the photosensitizers performed well in vitro photodynamic therapy. There were a remarkable absorbance band located at 692 nm and emission peaks falls at 762 nm, the quantum yield (Φf) was calculated to be 12.12% in pure aqueous solution using ICG as standards. The photosensitizer also has high singlet oxygen quantum yield (Φ△) for 16.96% with NIR LED irradiation. This photosensitizer can rapidly produce singlet oxygen and exhibit high phototoxicity under NIR light irradiation. It has excellent cellular uptake ability and better cell compatibility. It was also successfully applied in Near-infrared fluorescence imaging and AO/EB staining. In a whole, the organic dye based on Heptamethine cyanine used as photosensitizer has great potential in vivo cancer treatment.
- Yang, Xin,Bai, Jin,Qian, Ying
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- Light-Switchable Buffers
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A visible light-switchable buffer system based on a merocyanine photoacid is presented. Para-substitution of the indolium side with a methoxy group affords a compound suitable for making hydrolytically stable aqueous buffers whose pH can be tuned between 7 and 4 using 500 nm light.
- Berton, Cesare,Busiello, Daniel Maria,Fadaei-Tirani, Farzaneh,Pezzato, Cristian,Scopelliti, Rosario,Severin, Kay,Zamuner, Stefano
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- New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria
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In this communication, the synthesis of three unknown polyfluorinated cyanine dyes and their application as selective markers for mitochondria are presented. By incorporating fluorous side chains into cyanine dyes, their remarkable photophysical properties were enhanced. To investigate their biological application, several different cell lines were incubated with the synthesized cyanine dyes. It was discovered that the presented dyes can be utilized for selective near-infrared-light (NIR) staining of mitochondria, with very low cytotoxicity determined by MTT assay. This is the first time that polyfluorinated cyanine fluorophores are presented as selective markers for mitochondria. Due to the versatile applications of polyfluorinated fluorophores in bioimaging and materials science, it is expected that the presented fluorophores will be stimulating for the scientific community.
- Braun, Alexander B.,Wehl, Ilona,K?lmel, Dominik K.,Schepers, Ute,Br?se, Stefan
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- Unraveling the Hydrolysis of Merocyanine-Based Probes in Biological Assay
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Merocyanine dyes, owing to their unique photochemical properties, are widely used to fabricate probes for the detection of biologically active small molecules and bioimaging. In this paper, merocyanine-based probes were proved of undergoing unwanted hydrolysis. To explore the strategies toward avoiding the hydrolysis, the detailed hydrolysis mechanism was first investigated, which was also confirmed by density functional theory (DFT) calculation. Then a series of merocyanine dyes were rationally designed. Influences of molecular structures of the probes, the analytical media such as pH and components of the solution on the hydrolysis were systematically studied. The experimental results suggest that merocyanine based probes with low electron density are more likely to suffer the hydrolysis, which could be exacerbated by the well-accepted strategy for constructing type-II probes. It is worth noting that chemical surroundings could also exert distinctive influence on the hydrolysis. The hydrolysis could be obviously aggravated when fetal calf serum or DMSO was deployed. Our findings will definitely provide an effective and reliable approach for guiding the rational design of highly robust merocyanine-based probes and the optimization of the analytical media, which is helpful in terms of avoiding the hydrolysis of the probes and hydrolysis caused analytical errors.
- Wang, Liqiang,Hao, Yuanqiang,Huang, Jianhan,He, Yonghui,Zeng, Ke,Li, Juan,Chabu, Johnny Muya,Chen, Wansong,Yang, Minghui,Deng, Liu,Liu, You-Nian
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- A near-infrared fluorescent probe for the discrimination of cysteine in pure aqueous solution and imaging of cysteine in hepatocellular carcinoma cells with facile cell-compatible ability
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A unique near-infrared fluorescence sensor named AySA was designed and synthesized for selectively detecting cysteine over Hcy and GSH in aqueous solution with fast response and long emission wavelength of 701 nm. In this strategy of designing the probe, sulfonic acid was introduced to the cyanine structure through multiple methylene flexible chains as the water soluble functional group, and an acryl group was introduced through nucleophilic substitution reaction to serve as an efficient reaction site for Cys. Finally, a new NIR fluorescence sensor was constructed for the discrimination of Cys in aqueous solution. The probe shows excellent properties in 100% aqueous solution. It shows evident discrimination of Cys over Hcy and GSH, which is accompanied with fluorescence intensity enhancement and visible color change. The detection limit was calculated for 21.1 nm using the linear relationship of concentration of 1-3 μM (3σ/κ). The proposed mechanism based on conjugated addition, intramolecular cyclization and the sensing mechanism was confirmed by high-resolution mass spectrometry. In addition, the probe can work at a wide range of pH 7-10 and react with Cys in a few minutes. The probe was also successfully applied to Bel 7402 imaging with low toxicity. An outstanding red fluorescence appeared when the Bel 7402 cells were incubated with the probe or when Cys was added to the NEM-pretreated cells, indicating that the probe has a good ability to penetrate cells and react with Cys quickly. Considering the above results, we have the confidence to say that the probe can be used as an ultra-sensitive, near-infrared fluorescence sensor to selectively sense Cys in pure aqueous solutions in living systems.
- Yang, Xin,Qian, Ying
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Read Online
- A near-infrared, colorimetric and ratiometric fluorescent sensor with high sensitivity to hydrogen peroxide and viscosity for solutions detection and imaging living cells
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Considering to the importance of hydrogen peroxide (H2O2) in a number of pathological processes and fluorescence sensor as a powerful tool for imaging and therapy of H2O2-related diseases, herein, a near-infrared fluorescent sensor for colorimetric and ratiometric detecting H2O2 and viscosity, named NCR, was constructed and reported. Its long emission wavelength (670 nm) avoids the interference of biological autofluorescence. When NCR interacted with 10 equiv. of H2O2, colorimetric characteristic provides a clear naked eye recognition (colourless turned to green under UV light and light purple turned to colorless under visible light). In addition, NCR shows high sensitivity to viscosity with or without the addition of H2O2. It was also found alkaline environment contribute to enhance fluorescence response to H2O2. A suitable water-octanol partition coefficient (logP, 0.521 ± 0.003) and low cytotoxicity displayed that NCR is very favorable to image living cells. Furthermore, exogenous and endogenous H2O2 was detected successfully by NCR in living Hela cells. These studies indicate that NCR has great potential to develop as a practical tool for monitoring H2O2 level in biological process.
- Liu, Daili,Chen, Gaofei,Fang, Guiqian
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- Method for preparing indoline
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The invention relates to a method for preparing indoline. The metho is characterized by comprising the following steps of: a, performing condensation and cyclization on phenylhydrazine hydrochloride or substituted phenylhydrazine hydrochloride and a methyl ketone compound in a solvent under a non-catalytic condition to generate C2-methylindole or a derivative thereof, and conducting cooling, salting-out, suction filtration and desolventizing successively; b, subjecting the condensation ring-closing product C2-methylindole or the derivative thereof to reacting with chloromethane under the conditions of pressurization, solvent presence and catalysis to generate corresponding quaternary ammonium salt or quaternary ammonium salt containing substituent groups; and c, dissolving the salt generated in the step b in water, then carrying out alkaline hydrolysis in a solvent and alkali liquor, and successively performing layering, desolvation and distillation to obtain a product, namely 1,3,3-trimethyl-2-methyleneindoline or a derivative thereof. The whole technological process is simple, the amount of three wastes is small, the cost is low, the yield is high, and the method is a green technology suitable for industrial amplification and outstanding in economic benefit.
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Paragraph 0022
(2021/01/12)
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- Novel hemicyanine sensitizers based on benzothiazole-indole for dye-sensitized solar cells: Synthesis, optoelectrical characterization and efficiency of solar cell
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Synthesis, characterization, and photovoltaic properties of three new hemicyanine sensitizers based benzothiazole-indoline (HC-TH, HC-IND1 and HC-IND2) were tested in DSSC with TiO2 film. These sensitizers have a higher molar absorption coefficient, and thus have better light harvesting properties. Electrochemical, theoretical, and spectroscopic methods were used to calculate energy levels of the dye molecules both in the excited state and in the ground state. The results obtained from the spectroscopy and Tafel studies show a marked increase in overall photoelectro-chemical cell output with Br-substitute at p-position in the hemicyanine sensitizer. Interestingly, HC-IND2 showed absorption of UV–Vis at a longer wavelength than HC-IND1 and HC-TH. This structural feature, as well as optical properties, would result in an improved efficiency of DSSC with a better photovoltaic output (4.01percent) solar to electricity conversion efficiency compared to HC-IND1 and HC-TH.
- Al-Ostoot, Fares H.,Al-horaibi, Sultan A.,Alghamdi, Mohammed T.,Alrabie, Ali A.,Garoon, Eman M.,Rajbhoj, Anjali S.
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- FLUORESCENTLY LABELED POLYSACCHARIDE, PREPARATION METHOD THEREFOR, AND USE THEREOF
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Disclosed is a fluorescently labeled polysaccharide. The fluorescently labeled polysaccharide is formed by covalently coupling a polysaccharide to a fluorescent dye having a structure as shown in Formula I. A stable covalent bond is form between the polysaccharide molecule and the fluorescent dye molecule. The fluorescently labeled polysaccharide has high stability in serum and other detection environments, has high biocompatibility, and is applicable to the detection of carbohydrate molecules inside and outside cells. Due to a large Stokes shift of the fluorescent dye molecule, the fluorescently labeled polysaccharide has advantages of high fluorescence stability, high fluorescence quantum yields, and achieves high signal-to-noise ratios in imaging results. Further disclosed is a method for preparing the fluorescently labeled polysaccharide. The method has mild reaction conditions and high reaction selectivity, is simple to execute, and can be used to prepare a fluorescently labeled polysaccharide in high yield.
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Paragraph 0035-0038
(2021/07/17)
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- Near-Infrared Heptamethine Cyanine Dyes for Nanoparticle-Based Photoacoustic Imaging and Photothermal Therapy
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We have synthesized and characterized a library of near-infrared (NIR) heptamethine cyanine dyes for biomedical application as photoacoustic imaging and photothermal agents. These hydrophobic dyes were incorporated into a polymer-based nanoparticle system to provide aqueous solubility and protection of the photophysical properties of each dye scaffold. Among those heptamethine cyanine dyes analyzed, 13 compounds within the nontoxic polymeric nanoparticles have been selected to exemplify structural relationships in terms of photostability, photoacoustic imaging, and photothermal behavior within the NIR (～650-850 nm) spectral region. The most contributing structural features observed in our dye design include hydrophobicity, rotatable bonds, heavy atom effects, and stability of the central cyclohexene ring within the dye core. The NIR agents developed within this project serve to elicit a structure-function relationship with emphasis on their photoacoustic and photothermal characteristics aiming at producing customizable NIR photoacoustic and photothermal tools for clinical use.
- St. Lorenz, Anna,Buabeng, Emmanuel Ramsey,Taratula, Oleh,Taratula, Olena,Henary, Maged
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p. 8798 - 8805
(2021/06/28)
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- Synthesis, characterization, and photochromism study of two spiropyran molecules with a terminal alkynyl functional group and their new 1,2,3-triazoline-containing derivatives
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The spiropyran derivatives are known for their good photochromic properties. These photochromic compounds are isomerized between two forms; merocyanine is the open-ring form and spiropyran is the closed-ring form. In this work, two spiropyran derivatives (compounds 1 and 2) with the N-alkynyl functional group are prepared. The click reactions of these spiropyran derivatives with 1-azido-4-nitrobenzene and (azidomethyl)benzene are studied. For this purpose, 3,3-dimethyl-2-methylene-1-prop-2-ynyl-2,3-dihydro-1H-indole is synthesized, which is then reacted with 3- and 5-nitrosalicylaldehyde. The FT-IR, 1H-NMR, and 13C-NMR spectra of the reaction products are used for their characterization. The solutions of the products in methanol are prepared, and their UV–visible spectra are investigated. The darkening of the crystals of compound 1 upon exposure to the UV irradiation indicates that the spiro C–O bond in this compound is weaker than that in compound 2, which is due to the presence of the nitro group in the para position relative to this bond, and consequently, the stabilization of the open-ring form.
- Mahdavian, Ali Reza,Nasr-Isfahani, Hossein,Notash, Behrouz,Sepehr, Zeinalabedin
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- NARROW ABSORPTION POLYMER NANOPARTICLES AND RELATED METHODS
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Polymers, monomers, narrow-band absorbing polymers, narrow-band absorbing monomers, absorbing units, polymer dots, and related methods are provided. Bright, luminescent polymer nanoparticles with narrow-band absorptions are provided. Methods for synthesizing absorbing monomers, methods for synthesizing the polymers, preparation methods for forming the polymer nanoparticles, and applications for using the polymer nanoparticles are also provided.
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Page/Page column 187
(2020/04/25)
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- Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria
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The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.
- Chatterjee, Sudipta,Das, Rabi Sankar,Guha, Samit,Mukherjee, Ayan,Saha, Pranab Chandra,Sepay, Nayim
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supporting information
(2020/08/05)
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- Four-condensed-ring quinoxaline derivative and preparation method therefor
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In view of the problem that the existing quinoxaline compounds are single in structure, the invention provides a full-novel structure-diversified four-condensed-ring quinoxaline derivative and a preparation method therefor. The four-condensed-ring quinoxaline derivative has a structural general formula represented by a formula (I). The four-condensed-ring quinoxaline derivative provided by the invention has cytotoxic activity to tumor cells in vitro and in vivo and can serve as an antitumor drug.
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Paragraph 0058; 0060-0062
(2020/03/05)
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- A novel mitochondrial targeting fluorescent probe for ratiometric imaging SO2 derivatives in living cells
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As an important endogenous signaling molecule, SO2 plays a key role in many physiological processes. However, excessive intake of SO2 and its derivatives lead to serious health complications of various diseases. In order to study the role of SO2 and its derivatives in the biological environment, it is of great significance to develop new and effective monitoring methods. Here, a new red emission fluorescent probe (TNPI) based on pyrazoline and hemicyanine dyes for the high selective detection of SO2 derivatives was developed. The probe TNPI showed some advantages such as long emission wavelength (640 nm), obvious color and fluorescence changes after reaction with SO2 derivatives, high selectivity and sensitivity toward SO2 derivatives (detection limit = 80 nM), and large fluorescence emission shift (160 nm) and signal ratio change (from 0.45–445, about 989 times). Intriguingly, the probe was successfully exploited for the fluorescence imaging of SO2 derivatives in the mitochondria of living cells with low cytotoxicity.
- Wang, Xiao-Bo,Li, Hui-Jing,Chi, Zhenxing,Zeng, Xianshun,Wang, Li-Juan,Cheng, Yun-Fei,Wu, Yan-Chao
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- Long afterglow nano-composite and application thereof in multi-modal imaging and synergistic treatment of tumors
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The invention discloses a long-afterglow nano-composite, which is prepared by loading a near-infrared absorption dye and Fe on human serum albumin and coating the surface of a long-afterglow nano-material with the human serum albumin, the long-afterglow nano-composite is in a core-shell structure, the long-afterglow nano-material is a core, and the human serum albumin loaded with the near-infrared absorption dye and the Fe is a shell. After use, multi-modal imaging can be realized, and more comprehensive biological tissue characteristics can be obtained, so that the biological tissuestructure, functional characteristics and early lesions can be imaged; and integration of multi-modal imaging and multi-means collaborative treatment can be realized.
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Paragraph 0050; 0051
(2020/04/17)
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- Evaluation of asymmetric orthogonal cyanine fluorophores
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Pentamethine cyanine (Cy5) fluorophores have proven to be versatile imaging agents (i.e., tracers) for a range of micro- and macroscopic imaging applications, including image-guided surgery. In this study the relationship between the structure of asymmetric Cy5 fluorophores and their photophysical properties was studied. To this end, seven Cy5 analogues, bearing orthogonal N-indole substituents (H, SO3?, or benzene), were synthesised and evaluated. In-depth analysis revealed that introduction of sulfonates enhanced the fluorescence brightness and photostability, while reducing the lipophilicity, serum binding and stacking tendency. The addition of benzene moieties induced a bathochromic shift of 10–20 nm, increased the lipophilicity (LogP = -1.56–1.23) and serum binding (67.3–93.8percent bound), as well as negatively impacted the brightness (0.74–42.9 · 103 M?1 cm?1), photostability (24.4–90.6percent remaining), and stacking tendency. Chemical stability was uninfluenced by the substitution pattern. Additionally, the generation of a c[RGDyK]-based hybrid tracer based on one of these fluorophores in combination with a diethylenetriaminepentaacetic acid (DTPA) chelate and an 111In-isotope was reported. This compound was evaluated in vitro using αvβ3-overexpressing Geβ3 cells and in vivo using a 4T1 mouse tumour model. Overall, the presented results imply that alterations of the asymmetrical orthogonal Cy5 fluorophore structure have impact on the (photo)physical properties. Furthermore, the orthogonal Cy5 fluorophore framework can readily be applied in tracer development.
- Boutkan, Michael S.,Buckle, Tessa,Hensbergen, Albertus W.,Welling, Mick M.,Wester, Hans-Jürgen,de Kleer, Mathijs A. C.,van Leeuwen, Fijs W. B.,van Willigen, Danny M.,van der Wijk, Felicia A.
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- Preparation of Indolenines via Nucleophilic Aromatic Substitution
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An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution.
- Huber, Florian,Roesslein, Joel,Gademann, Karl
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p. 2560 - 2564
(2019/03/19)
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- Second Generation G-Quadruplex Stabilizing Trimethine Cyanines
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G-Quadruplex DNA has been recognized as a highly appealing target for the development of new selective chemotherapeutics, which could result in markedly reduced toxicity toward normal cells. In particular, the cyanine dyes that bind selectively to G-quadruplex structures without targeting duplex DNA have attracted attention due to their high amenability to structural modifications that allows fine-tuning of their biomolecular interactions. We have previously reported pentamethine and symmetric trimethine cyanines designed to effectively bind G-quadruplexes through end stacking interactions. Herein, we are reporting a second generation of drug candidates, the asymmetric trimethine cyanines. These have been synthesized and evaluated for their quadruplex binding properties. Incorporating a benz[c,d]indolenine heterocyclic unit increased overall quadruplex binding, and elongating the alkyl length increases the quadruplex-to-duplex binding specificity.
- Owens, Eric A.,Huynh, Hang T.,Stroeva, Ekaterina M.,Barman, Arghya,Ziabrev, Kostiantyn,Paul, Ananya,Nguyen, Sarah V.,Laramie, Matthew,Hamelberg, Donald,Germann, Markus W.,Wilson, W. David,Henary, Maged
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p. 2647 - 2663
(2019/10/11)
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- Pyridinium ion modified near infrared squaric acid dye as well as preparation and application thereof
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The invention discloses pyridinium ion modified near infrared squaric acid dye as well as a preparation method and application thereof. Pyridinium ion modified trimethyl dihydroindole derivatives anddicyanovinyl square acid derivatives are used as raw materials to prepare the near infrared squaric acid dye. The near infrared squaric acid dye has high stability and excellent optical performance; particularly pyridinium ion groups can enhance the dye water solubility; when the near infrared squaric acid dye is used for aquacide detection, aquacide molecules and dye molecules can mutually act, so that the absorption spectrum and fluorescence spectrum change can be caused, so that the materials can be used as fluorescence probes for aquacide detection, can be used for aquacide fluorescence detection in the environment, and has higher detection sensitivity.
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Paragraph 0025
(2019/06/07)
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- IR780 ketone form cyanine dye molecule, and preparation method and crystal structure thereof
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The invention relates to the field of fluorescent dyes, and discloses an IR780 ketone form cyanine dye molecule, and a preparation method and crystal structure thereof. The cyanine dye is simple in synthetic method, less in by-product, high in yield and stable in structure; and an emission spectrum can be in a near infrared region under an acidic condition, and the crystal structure obtained by adopting dichloromethane and diethyl ether diffusion methods through cultivation is stable. Based on the above advantages, the cyanine dye molecule can have good application prospects in the field of fluorescent dyes and bioluminescent imaging studies.
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Paragraph 0037; 0038; 0040
(2019/05/08)
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- MEANS AND METHODS FOR VISUALIZATION OF TISSUE STRUCTURES
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The present invention relates to a chemical compound comprising (i) a polycationic polymer, coupled to (ii) a dye. The present invention further relates to a method for visualizing a glycosamine-containing structure in a biological sample comprising a) contacting an inner lumen of said biological sample with a dye-conjugated polycationic polymer, preferably with the chemical compound according to the present invention; b) tissue-clearing said biological sample; and, thereby, c) visualizing an internal glycosamine-containing structure in said biological sample. The present invention also relates to a method for determining the number and/or size of glomeruli in a kidney or a sample thereof making use of the method for visualizing a glycosamine-containing structure; and also relates to kits and uses related to said chemical compounds and said methods.
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Paragraph 0103-0104
(2019/12/02)
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- Effects of Substituents on Metastable-State Photoacids: Design, Synthesis, and Evaluation of their Photochemical Properties
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Recently, metastable-state photoacids have been widely used to control proton transfer in numerous chemical and biological processes as well as applications with visible light. Generally, substituents have a great influence on the photochemical properties of molecules, which will further affect their applications. Yet, the effects of substituents on metastable-state photoacids have not been studied systematically. In this work, 16 metastable-state photoacid derivatives were designed and synthesized on the basis of substituents having a large range of σ–π electron–donor–acceptor capabilities. The effects of substituents on the color display [or maximum absorption band(s)], solubility, pKa values, dark/photoacidity, photosensitivity, and relaxation kinetic(s) were investigated in detail. This study will be helpful for the targeted design and synthesis of promising photoacids and the application of their photocontrolled proton-release processes in functional materials/devices.
- Liu, Junning,Tang, Wenqi,Sheng, Lan,Du, Zhen,Zhang, Ting,Su, Xing,Zhang, Sean Xiao-An
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supporting information
p. 438 - 445
(2019/01/08)
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- Novel near-infrared pH-sensitive cyanine-based fluorescent probes for intracellular pH monitoring
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Real-time monitoring of intracellular pH fluctuation is of great significance for diagnosis of diseases and study of related physiological and pathological processes. A novel near-infrared (NIR) pH-activated parent probe 4 was developed, and further functionalized to afford probes 6 and 7. With the decrease of pH from 11 to 2, they all exhibited a new absorption peak and strong fluorescence emission in NIR region, accompanied by rapid solution color change from pink to pale green. Moreover, the probes’ fluorescence responses toward pH fluctuations were reversible and stable, and the pseudo-linear relationship between the fluorescence intensity and pH value can be used to detect pH value in 2.76–6.45 range quantitatively. Finally, probe 6 and 7 were successfully applied to monitor the fluctuation of intracellular pH by a fluorescence turn-on mode, and the imaging results confirmed their low cytotoxicity and satisfactory cell-membrane permeability, as well as their application prospect in disease diagnosis (such as tumor specific imaging) or assist in study of pH-related biological processes in wide acidic environment.
- Jin, Di,Wang, Bowei,Hou, Yuqing,Du, Yuchao,Li, Xue,Chen, Ligong
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- Siliceous nanoparticle drug carrier, diagnostic and therapeutic preparation thereof and preparation method
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The invention discloses a siliceous nanoparticle drug carrier, a diagnostic therapeutic preparation thereof and a preparation method. The carrier is a vesicle having a lipid bilayer structure formed by doping hydration and self-assembly of a fluorescent amphiphilic molecule and a silicon-containing composite liposome, wherein the fluorescent amphiphilic molecule is a compound taking a glycerol skeleton structure as a core and formed by a bonded hydrophobic long chain and a fluorescent group; the silicon-containing composite liposome is composed of a silicon-containing inorganic precursor, a hydrophobic lipid chain, and a linking group coupling the silicon-containing inorganic precursor and the hydrophobic lipid chain, and the silicon-containing inorganic precursor of the silicon-containingcomposite liposome is hydrolyzed and then hydrolysis products are condensed to form an inorganic silicate network structure distributed on the surface of the vesicle. The diagnostic and therapeutic preparation prepared by using the carrier to load a drug has high stability, combines two drug controlled release mechanisms, that is pH and photothermal response, and enhances the stability of the fluorescent group. Through combination of chemotherapy and photothermal therapy, the recurrence rate of tumors is effectively reduced.
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Paragraph 0057; 0059; 0061
(2019/04/26)
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- Near-infrared fluorescent molecule for controlled release of singlet oxygen and preparation method thereof
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The invention discloses a near-infrared fluorescent molecule for controlled release of singlet oxygen and a preparation method thereof. specifically, cyanine is used as a main structure to synthesizea compound B2, and then the compound B2 reacts with malononitrile to form a C=N double bonds to obtain a target product C2. The target compound C2 can release singlet oxygen under the irradiation of near-infrared light. Through laser irradiation with the wavelength of 635 nm, the absorbancy value reduction rate of C2 molecules at the maximum absorption wavelength is higher than that of rose bengalmolecules; the absorbancy value reduction rate of C2 molecules at 410 nm is faster than that of rose bengal molecules, i.e., the singlet oxygen generation rate is faster than that of rose bengal molecules, wherein the singlet oxygen yield of C2 molecules is 0.56.
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Paragraph 0034-0036
(2020/01/08)
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- Compound with fluorescence resonance energy transfer performance and its application
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The invention relates to a compound with fluorescence resonance energy transfer performance and its application. The compound is prepared by trimethine cyanine dye and pentamethine cyanine dye througha proper connecting arm. The compound provided by the invention can be applied to detect active oxygen and active nitrogen, and is not influenced by probe concentration, background fluorescence, instrumental error and other factors; moreover, the compound has relatively high FRET efficiency.
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Paragraph 0041; 0042; 0043
(2018/03/28)
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- SQUARAINE DYES AND APPLICATIONS THEREOF
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The present invention disclosed a squaraine dye of formula (I) and process for the preparation thereof. Further, the present invention disclosed to an electronic device comprising dye of formula (I).
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Page/Page column 22
(2018/02/28)
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- Synthesis and optical properties of near-infrared meso-phenyl-substituted symmetric heptamethine cyanine dyes
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Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF) probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored for particular applications. Generally, modifications at the meso-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and SRN1 nucleophilic substitution of the chlorine atom at the meso-position of the dye. Herein, a series of 15 meso phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds.
- Levitz, Andrew,Marmarchi, Fahad,Henary, Maged
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- Phenylboronic acid modified near-infrared squaraine dyes as well as preparation method and application thereof
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The invention discloses phenylboronic acid modified near-infrared squaraine dyes as well as a preparation method and application thereof. The preparation method comprises the following steps: mixing an indole-modified phenylboronic acid derivative with a dicyanyl vinyl squaraine derivative; carrying out dissolution, backflow, pressure-reduction evaporation-removal on a solvent and silica gel column chromatography purification to obtain the near-infrared squaraine dyes. The squaraine dyes have the advantages of better stability and excellent optical performance, in particular to contraposition-substituted phenylboronic acid groups; the squaraine dyes can be partially combined with cis-glycol in an ATP (adenosinetriphosphate) molecule, so that change of absorption spectrum and fluorescence spectrum of the dyes is induced through multiple electrostatic interactions among the dyes, the ATP and CTAB (Cetyl Trimethyl Ammonium Bromide), so that the dyes can be used as fluorescent probes for ATP detection, and the fluorescent probes are used for carrying out fluorescent imaging detection on the ATP in cells; moreover, the probes have the advantages of better biocompatibility and cellular permeability and lower biotoxicity, and has better detection sensitivity on ATP.
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Paragraph 0028
(2018/11/03)
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- Isopropyl spirooxazine photochromic compound and synthetic method thereof
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The invention discloses an isopropyl spirooxazine photochromic compound and a synthetic method thereof. The compound has a chemical name of N isopropyl[2,3,3-trimethyl-3H-indole] spirooxazine, and hasa structural formula in a following figure. The isopropyl spirooxazine photochromic compound and the synthetic method thereof have the advantages of a simple preparation process, an easy treatment process and good-stability products; as a photochromic material with excellent performance, the spirooxazine obtained by a reaction has the number of repeated cycles of 3*10 or above, and an important step is achieved in practical researches of the spirooxazine.
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Paragraph 0009; 0031-0033
(2018/11/27)
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- Photooxidation of oxazolidine molecular switches: Uncovering an intramolecular ionization facilitated cyclization process
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Photooxidation of oxazoline (OXA) molecular switches through media-induced intramolecular ionization is reported. The formation of the photooxidation product occurs by attack of the flexible donor group (-CH2CH2OH) to the adjacent CC with 1O2 as the oxidant. The novel seven-membered ring sub-structure of the photooxidation product was inferred by HRMS, IR and 1H NMR spectroscopy. Additionally, acid released from solvent photolysis was found to affect the product formation and efficiency of the photooxidation.
- Chen, Qiaonan,Sheng, Lan,Du, Jiahui,Xi, Guan,Zhang, Sean Xiao-An
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supporting information
p. 5094 - 5097
(2018/05/26)
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- Fluorescent dye as well as preparation method and application thereof
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The invention relates to the field of an optical function material, in particular to fluorescent dye. The fluorescent dye has the structure shown in a formula (I). The fluorescent dye with the structure is covalently bonded with a biological macromolecule, has a stable structure and high flexibility, can be applied to different application fields of cell imaging, fluorescent probes, laser dye, fluorescent sensors and the like, and shows excellent practicability. The preparation method provided by the invention is low in raw material cost, free of pollution, simple in process and high in yield;the prepared fluorescent dye has a novel structure and excellent performance, and is suitable for being widely applied to the fields of biology, environment and the like.
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Paragraph 0043; 0047; 0048; 0049; 0050
(2018/11/22)
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- Fluorescent-labeled amino acid as well as preparation method and application thereof
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The invention discloses a fluorescent-labeled amino acid. The fluorescent-labeled amino acid has the structure shown in a formula I: (the formula is shown in the description); stable covalent bondingis formed between an amino acid molecule and a fluorescence dye molecule; the fluorescent-labeled amino acid has high stability and high biocompatibility in the detection environments such as serum, and is suitable for detection of biological molecules such as protein and polypeptide inside and outside cells. Because the strokes shift of the fluorescence dye molecule is large, the fluorescent-labeled amino acid has the advantages of high fluorescence stability, high fluorescence quantum yield and high imaging result signal-to-noise ratio. The invention discloses a preparation method of the fluorescent-labeled amino acid. The preparation method is mild in reaction condition, simple to operate and high in reaction selectivity; the high-yield fluorescent-labeled amino acid can be prepared.
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Paragraph 0147; 0151; 0152; 0153; 0154
(2018/12/13)
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- Fluorescently-labeled nucleotide as well as preparation method and application thereof
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The invention discloses fluorescently-labeled nucleotide. The fluorescently-labeled nucleotide has a structure represented as the formula I in the description. Stable covalent bonding is formed between dNTP (deoxyribonucleoside triphosphate) and fluorescent dye molecules represented as the formula Q, and the fluorescently-labeled nucleotide has high stability in detection environments such as serum and the like, and is high in biocompatibility and suitable for detecting nucleic acid molecules in and out of cells. Due to large Stokes shift of the fluorescent dye molecules, the fluorescently-labeled nucleotide further has the advantages of good fluorescent stability, high fluorescent quantum yield and high signal-to-noise ratio of an imaging result. The invention further discloses a preparation method of the fluorescently-labeled nucleotide. The compound with the structure shown as the formula I is prepared by a click chemical reaction, reaction conditions are mild, operation is simple,reaction selectivity is high, and the fluorescently-labeled nucleotide with high yield can be prepared.
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Paragraph 0097-0100
(2018/11/22)
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- Method for preparing indoline polymethin dye via one-pot method
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The invention discloses a method for preparing an indoline polymethin dye via a one-pot method. The method comprises the following steps of: carrying out condensation and ring closing on phenylhydrazine or para-substituted phenylhydrazine hydrochloride and methyl isopropyl ketone in an alcohol solvent under the catalysis of sulfuric acid so as to generate 2,3,3-trimethylindole or a derivative thereof, adding alkali to carry out neutralization, and carrying out filtration to remove salt; adding an appropriate acid-binding agent in the filtrate, dropwise adding dimethyl sulfate to generate 1,3,3-trimethyl-2--methylene indoline or a derivative thereof; and directly adding 1-phenyl-3-methyl-4-formyl-5-pyrazolone, and carrying out acid catalysis and condensation to generate a target dye. The method has the advantages of being easy to operate, high in yield, low in cost and less in wastewater.
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Paragraph 0075; 0076; 0094; 0095; 0096
(2019/01/14)
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