1640-39-7Relevant articles and documents
Study on the synthesis and spectra of a novel kind of carbozole benzothiazole indole styryl cyanine dye with a carbazole bridged Chain
Fei, Xuening,Hao, Yachao,Gu, Yingchun,Li, Chao,Yu, Lu
, p. 563 - 568 (2014)
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.
Benz[c,d]indolium-containing monomethine cyanine dyes: Synthesis and photophysical properties
Soriano, Eduardo,Holder, Cory,Levitz, Andrew,Henary, Maged
, (2016)
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.
Ultrabright and Serum-Stable Squaraine Dyes
Yadav, Yogesh,Owens, Eric,Nomura, Shinsuke,Fukuda, Takeshi,Baek, Yoonji,Kashiwagi, Satoshi,Choi, Hak Soo,Henary, Maged
, p. 9436 - 9445 (2020)
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.
An indocyanine-based turn-on fluorescent probe for specific detection of biothiols
Wang, Xiaojing,Jin, Di,Li, Xue,Yan, Xilong,Wang, Bowei
, p. 707 - 715 (2018)
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.
Photochromism of neutral spiropyran in the crystalline state at room temperature
Fang, Bing,Li, Pengyu,Wang, Qian,Wu, Zhen,Yin, Meizhen
, p. 6290 - 6296 (2021)
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
Synthesis of novel pyrazolo[3,4-b]pyridine derivatives in aqueous medium
Baradarani, Mehdi M.,Fazlelahi, Hadi Zare,Rashidi, Ahmad,Joule, John A.
, p. 114 - 122 (2018)
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.
Mitochondria-targeted prostate cancer therapy using a near-infrared fluorescence dye–monoamine oxidase A inhibitor conjugate
Lv, Qingzhi,Yang, Xiaoguang,Wang, Menglin,Yang, Jincheng,Qin, Zhilin,Kan, Qiming,Zhang, Haotian,Wang, Yongjun,Wang, Dun,He, Zhonggui
, p. 234 - 242 (2018)
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
A mitochondria-targeted fluorescent dye naphthalimide-thioether-cyanine for NIR-activated photodynamic treatment of cancer cells
Shen, Ronghua,Bai, Jin,Qian, Ying
, p. 2462 - 2468 (2021)
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.
A Cyanine Dye Encapsulated Porous Fibrous Mat for Naked-Eye Ammonia Sensing
Ji, Chendong,Ma, Lijing,Yin, Meizhen,Yang, Wantai,Pan, Kai
, p. 2316 - 2321 (2016)
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.
Preparation of a spirooxazine grafted PMMA and its photochromic properties
Wu, Liang,Zhang, Sai,Gao, Jun,Qiang, Peirong,Lei, Jingxin
, p. 818 - 830 (2016)
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.
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Nakazaki
, p. 334,336 (1961)
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Two near-infrared highly sensitive cyanine fluorescent probes for pH monitoring
Hou, Jing-Ru,Jin, Di,Chen, Bo,Si, Lei-Lei,Jin, Yue-Hua,Chen, Li-Gong,Yan, Xi-Long,Wang, Bo-Wei,Li, Yang
, p. 1681 - 1687 (2017)
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.
Synthesis and characterization of new squaraine dyes with bis-pendent carboxylic groups for dye-sensitized solar cells
Al-horaibi, Sultan A.,Asiri, Abdullah M.,El-Shishtawy, Reda M.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.
, p. 850 - 858 (2019)
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.
Ratiometric fluorescent detection of intracellular hydroxyl radicals based on a hybrid coumarin-cyanine platform
Yuan, Lin,Lin, Weiying,Song, Jizeng
, p. 7930 - 7932 (2010)
The first ratiometric fluorescent probe for hydroxyl radical ratiometric imaging in living cells was rationally designed based on a hybrid coumarin-cyanine platform.
Design, synthesis and biological evaluation of novel heptamethine cyanine dye-erlotinib conjugates as antitumor agents
Guo, Chun,Hou, Zhuang,Mou, Yanhua,Wang, Dun,Yang, Xiaoguang
, (2020)
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.
The investigation of unique water-soluble heptamethine cyanine dye for use as NIR photosensitizer in photodynamic therapy of cancer cells
Yang, Xin,Bai, Jin,Qian, Ying
, (2020)
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.
New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria
Braun, Alexander B.,Wehl, Ilona,K?lmel, Dominik K.,Schepers, Ute,Br?se, Stefan
, p. 7998 - 8002 (2019)
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.
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
Yang, Xin,Qian, Ying
, p. 3725 - 3732 (2019)
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.
Novel hemicyanine sensitizers based on benzothiazole-indole for dye-sensitized solar cells: Synthesis, optoelectrical characterization and efficiency of solar cell
Al-Ostoot, Fares H.,Al-horaibi, Sultan A.,Alghamdi, Mohammed T.,Alrabie, Ali A.,Garoon, Eman M.,Rajbhoj, Anjali S.
, (2020/08/11)
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.
Near-Infrared Heptamethine Cyanine Dyes for Nanoparticle-Based Photoacoustic Imaging and Photothermal Therapy
St. Lorenz, Anna,Buabeng, Emmanuel Ramsey,Taratula, Oleh,Taratula, Olena,Henary, Maged
, p. 8798 - 8805 (2021/06/28)
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.
