84-83-3Relevant academic research and scientific papers
Synthesis and characterization of a novel indoline based nonlinear optical chromophore with excellent electro-optic activity and high thermal stability by modifying the π-conjugated bridges
Hu, Chaolei,Chen, Zhuo,Xiao, Hongyan,Zhen, Zhen,Liu, Xinhou,Bo, Shuhui
, p. 5111 - 5118 (2017)
Two novel second order nonlinear optical (NLO) chromophores based on indoline donors and tricyanofuran (TCF) acceptors linked together via modified polyene π-conjugation bridges have been synthesized in good overall yields and systematically characterized. Thermal stability, optical property and electro-optic property were measured to investigate the effects of the introduced rigid benzene derivative steric hindrance group on the bridge. Besides, density functional theory (DFT) was used to calculate the HOMO-LUMO energy gaps and first-order hyperpolarizability (β) of these chromophores. After introducing the benzene derivative steric hindrance group into the bridge, chromophore CLH-2 showed very good thermal stability with a decomposition temperature of 250 °C, which was 83 °C higher than chromophore CLH-1 without the isolation group on the bridge. In electro-optic activity, the introduction of rigid steric hindrance groups can effectively reduce dipole-dipole interactions to translate the relatively small β values into bulk high EO activities. By doping chromophores CLH-1 and CLH-2 with a high loading of 45 wt% in APC, EO coefficients (r33) of up to 63 and 102 pm V-1 at 1310 nm can be achieved, respectively. The r33 value of the new chromophore CLH-2 was about 1.6 times that of chromophore CLH-1. The high r33 value, good thermal stability and high yield suggest the promising applications of the new chromophore in nonlinear optical areas.
A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near-IR Light
Mitra, Koushambi,Lyons, Charles E.,Hartman, Matthew C. T.
supporting information, p. 10263 - 10267 (2018/07/31)
Controlled generation of cytotoxic agents with near-IR light is a current focus of photoactivated cancer therapy, including that involving cytotoxic platinum species. A heptamethine cyanine scaffolded PtII complex, IR797-Platin exhibits unprecedented Pt?O bond scission and enhancement in DNA platination in near-IR light. This complex also displayed significant singlet oxygen quantum yield thereby qualifying as a near-IR photodynamic therapeutic agent. The complex showed 30–60 fold enhancement of cytotoxicity in near-IR light in various cancer cell lines. The cellular imaging properties were also leveraged to observe its significant co-localization in cytoplasmic organelles. This is the first demonstration of a near-IR light-initiated therapy involving the cytotoxic effects of both active cisplatin and singlet oxygen.
A Rhodium-Cyanine Fluorescent Probe: Detection and Signaling of Mismatches in DNA
Nano, Adela,Boynton, Adam N.,Barton, Jacqueline K.
supporting information, p. 17301 - 17304 (2017/12/15)
We report a bifunctional fluorescent probe that combines a rhodium metalloinsertor with a cyanine dye as the fluorescent reporter. The conjugate shows weak luminescence when free in solution or with well matched DNA but exhibits a significant luminescence increase in the presence of a 27-mer DNA duplex containing a central CC mismatch. DNA photocleavage experiments demonstrate that, upon photoactivation, the conjugate cleaves the DNA backbone specifically near the mismatch site on a 27-mer fragment, consistent with mismatch targeting. Fluorescence titrations with the 27-mer duplex containing the CC mismatch reveal a DNA binding affinity of 3.1 × 106 M-1, similar to that of other rhodium metalloinsertors. Fluorescence titrations using genomic DNA extracted from various cell lines demonstrate a clear discrimination in fluorescence between those cell lines that are proficient or deficient in mismatch repair. This differential luminescence reflects the sensitive detection of the mismatchrepair-deficient phenotype.
Development and applications of a near-infrared dye-benzylguanine conjugate to specifically label SNAP-tagged proteins
Song, Xinbo,Bian, Hui,Wang, Chao,Hu, Mingyu,Li, Ning,Xiao, Yi
, p. 8091 - 8101 (2017/10/13)
Near-infrared (NIR) fluorescent probes are advantageous over visible ones, for they can avoid the interference from the short-wavelength background emission in biological systems. However, there are a very limited number of NIR probes that can specifically label target proteins in living cells. In this work, a series of long-wavelength dyes (N-NIR, S-NIR, and K-NIR) analogous to the novel Changsha NIR family are synthesized conveniently through a new approach that is different from the previously reported one. These three dyes have similar conjugation structures but exhibit tunable photophysical properties. N-NIR and S-NIR have large extinction coefficients over 100000, and high fluorescence quantum yields. Although NIR absorption and emission of K-NIR are inferior to the former two, it emits in a much longer wavelength region. And all the three dyes can easily pass through the cell membranes to obtain the high-resolution NIR fluorescence images. Furthermore, N-NIR is chosen as the NIR fluorophore to develop a protein-labeling reagent PYBG-D, since it demonstrates the highest fluorescence quantum yield of up to 0.4 (in methanol). PYBG-D is efficiently synthesized through Sonogashira coupling between bromo-substituted N-NIR and alkyne-substituted benzylguanine (PYBG). The conjugate PYBG-D proves to be a specific and efficient label for O6-alkylguanine-DNA alkyltransferase (SNAP-tag) that fused to target proteins in living cells, which contributes to high resolution NIR fluorescence images under a laser confocal microscope.
INDOLE-BASED COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME
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, (2016/11/17)
Disclosed in the present invention are a novel indole-based compound, a colorant composition comprising the same, and a resin composition comprising the same. Provided in an embodiment of the present invention is the compound represented by chemical formula 1. According to an embodiment of the present invention, the compound can be acted as a dye, and can be used as a material of a color filter. Specifically, the resin composition comprising the compound has a high color reproduction rate, high luminance, a high contrast ratio, etc.(AA) Comparative example 1(BB) Example 1(CC) Example 2(DD) Example 3(EE) Example 4(FF) Example 5(GG) Example 7(HH) Example 8(II) Example 9(JJ) Example 10COPYRIGHT KIPO 2016
Reactive species involved in the regioselective photooxidation of heptamethine cyanines
Nani, Roger R.,Kelley, James A.,Ivanic, Joseph,Schnermann, Martin J.
, p. 6556 - 6563 (2015/10/28)
Heptamethine cyanines are important near-IR fluorophores used in many fluorescence applications. Despite this utility, these molecules are susceptible to light-promoted reactions (photobleaching) involving photochemically generated reactive oxygen species (ROS). Here, we have sought to define key chemical aspects of this nearly inescapable process. Near-IR photolysis of a model heptamethine cyanine leads to the regioselective oxidative cleavage of the characteristic polyene. We report the first quantitative analysis of the major reaction pathway following either photolysis or exposure to candidate ROS. These studies clearly indicate that only singlet oxygen (1O2), and not other feasible ROS, recapitulates the direct photolysis pathway. Computational studies were employed to investigate the regioselectivity of the oxidative cleavage process, and the theoretical ratio is comparable to observed experimental values. These results provide a more complete picture of heptamethine cyanine photooxidation, and provide insight for the design of improved compounds for future applications.
Exploration of cyanine compounds as selective inhibitors of protein arginine methyltransferases: Synthesis and biological evaluation
Hu, Hao,Owens, Eric A.,Su, Hairui,Yan, Leilei,Levitz, Andrew,Zhao, Xinyang,Henary, Maged,Zheng, Yujun George
, p. 1228 - 1243 (2015/03/04)
Protein arginine methyltransferase 1 (PRMT1) is involved in many biological activities, such as gene transcription, signal transduction, and RNA processing. Overexpression of PRMT1 is related to cardiovascular diseases, kidney diseases, and cancers; therefore, selective PRMT1 inhibitors serve as chemical probes to investigate the biological function of PRMT1 and drug candidates for disease treatment. Our previous work found trimethine cyanine compounds that effectively inhibit PRMT1 activity. In our present study, we systematically investigated the structure-activity relationship of cyanine structures. A pentamethine compound, E-84 (compound 50), showed inhibition on PRMT1 at the micromolar level and 6- to 25-fold selectivity over CARM1, PRMT5, and PRMT8. The cellular activity suggests that compound 50 permeated the cellular membrane, inhibited cellular PRMT1 activity, and blocked leukemia cell proliferation. Additionally, our molecular docking study suggested compound 50 might act by occupying the cofactor binding site, which provided a roadmap to guide further optimization of this lead compound.
Synthesis and effect of heterocycle modification on the spectroscopic properties of a series of unsymmetrical trimethine cyanine dyes
Levitz, Andrew,Ladani, Safieh Tork,Hamelberg, Donald,Henary, Maged
, p. 238 - 249 (2014/04/03)
Carbocyanine dyes are a class of organic compounds that contain two heterocycles that act as electron donors and acceptors connected by a conjugated methine bridge. Herein the synthesis of a series of 16 novel unsymmetrical trimethine cyanine dyes is reported. Their structures were characterized by various spectroscopic techniques, and their optical properties were measured. Absorption maxima of the dyes were calculated using the time-dependent density-functional theory method and the computational absorption maxima are consistent with the experimental data. The addition of electron withdrawing substituents such as halogens on the heterocycle gave more favorable optical properties such as higher quantum yield and molar absorptivity. The aggregation of these cyanine dyes was studied and compared to a similar series of symmetric cyanine dyes. It was determined that the heterocycle has more effect on aggregation than the side chain and a dye with two different heterocycles will aggregate less than a dye with the same heterocycle. The dyes were also investigated for Lipinski Rule violations as their use is becoming more prevalent for in vivo applications.
Reversible synthesis and characterization of dynamic imino analogues of trimethine and pentamethine cyanine dyes
Meguellati, Kamel,Spichty, Martin,Ladame, Sylvain
supporting information; experimental part, p. 1123 - 1126 (2009/07/25)
A new family of unsymmetrical imine-based trimethine and pentamethine cyanine dye analogues is reported that can form under reversible and thermodynamically controlled conditions from non-or weakly emissive amine and aldehyde building blocks. These dynami
Photooxygenation of α,α'-dimethylstilbenes sensitised by photochromic compounds
Salemi-Delvaux, Christiane,Luccioni-Houze, Barbara,Baillet, Gilles,Giusti, Gerard,Guglielmetti, Robert
, p. 5127 - 5130 (2007/10/03)
A convincing evidence of the ability of the coloured open forms or photomerocyanines of photochromic compounds to act as sensitiser of singlet oxygen is provided by photosensitised oxidation of reference olefins, cis- and trans-α,α'-dimethylstilbenes, to a hydroperoxide.
