- Two different donor subunits substituted unsymmetrical squaraines for solution-processed small molecule organic solar cells
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Two unsymmetrical squaraines (USQs) with different donor (D) subunits as photovoltaic materials, namely USQ-11 and USQ-12, were designed and synthesized to investigate the effect of different D subunits on the optoelectronic properties of USQs for the first time. The two USQs compounds were characterized for optical, electrochemical, quantum chemical and optoelectronic properties. By changing the two different D subunits attached to the squaric acid core from 2,3,3-trimethylindolenine to 2-methylbenzothiazole, the HOMO energy levels could be tuned with a stepping of 0.07 eV, and quite different solid state aggregations (H-or J-aggregation) were observed in the thin film by UV-Vis absorption spectra, which were attributed to their distinct steric effects and dipole moments. Solution-processed bulk-heterojunction small molecule organic solar cells fabricated with the USQ-11/PC71BM (1:5, wt%) exhibited extremely higher PCE (4.27%) than that of the USQ-12/PC71BM (2.78%). The much enhanced PCE should be attributed to the simultaneously improved Voc, Jsc and FF.
- Yang, Daobin,Jiao, Yan,Huang, Yan,Zhuang, Taojun,Yang, Lin,Lu, Zhiyun,Pu, Xuemei,Sasabe, Hisahiro,Kido, Junji
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Read Online
- Spectroscopic study of a novel bis(heptamethine cyanine) dye and its interaction with human serum albumin
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A newly synthesized near-infrared (NIR) bis(heptamethine cyanine) dye 7 was evaluated for its utility as a non-covalent label for proteins. This dye forms inter- and intramolecular H-aggregates in polar solvents, even at very low concentrations. The intra
- Patonay, Gabor,Kim, Jun Seok,Kodagahally, Ravikumar,Strekowski, Lucjan
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Read Online
- Synthesis of asymmetric monomethine cyanine dyes with red-shifted optical properties
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Six novel asymmetrical monomethine cyanine dyes were synthesized via the condensation reaction of 1-butyl-2-(methylthio)benzo[c,d]indol-1-ium iodide and various 1,5-substituted indolenine salts under basic conditions. The dyes were characterized using UV-vis spectroscopy, fluorescence, 1H NMR, 13C NMR, and mass spectrometry; furthermore, the purity of these compounds was observed using LC/ELSD/MS.
- Soriano, Eduardo,Outler, Loretta,Owens, Eric A.,Henary, Maged
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Read Online
- “Turn on” fluorescence response of monomethine cyanines caused by noncovalent binding to ct-DNA
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Monomethine cyanines have been extensively studied for their use as probes for nucleic acids among other biological systems. Four monomethine cyanine dyes were synthesized with various heterocyclic moieties including quinoline, benzoxazole, benzothiazole, and 3,3-dimethylindolenine adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. The dyes were characterized by 1H and 13C NMR and HRMS. In this study the twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the benzoxazole containing sensor displayed up to 700-fold increase in fluorescence when bound to the DNA compared to the unbound form.
- Levitz, Andrew,Holder, Cory,Soriano, Eduardo,Henary, Maged
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Read Online
- Fluorescence properties of indolenine semi-squarylium dyes
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3-Butoxy-4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-cyclobut-1, 2-dione exhibited the most intense florescence at fluorescence maxima 536 and 563 nm with fluorescence quantum yield 0.21 among any indolenine semi-squarylium dyes in the crystalline form due to the isolated dimer-type molecular packing and its suitable melting point. This compound showed aggregation-induced emission enhancement.
- Matsui, Masaki,Shibata, Toshihiro,Fukushima, Masato,Kubota, Yasuhiro,Funabiki, Kazumasa
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Read Online
- Symmetrical and asymmetrical cyanine dyes. Synthesis, spectral properties, and bsa association study
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New cyanines were prepared by an efficient and practical route with satisfactory overall yield from low-cost starting materials. The photophysical behavior of the cyanines was investigated using UV-vis and steady-state fluorescence in solution, as well as
- Pisoni, Diego S.,Todeschini, Letícia,Borges, Antonio César A.,Petzhold, Cesar L.,Rodembusch, Fabiano S.,Campo, Leandra F.
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Read Online
- Acridinium-conjugated aromatic heterocycles as highly potent FtsZ inhibitors: Design, synthesis, and biological evaluation
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The epidemic of multidrug resistance (MDR) is a serious threat to public health, and new classes of antibiotics with novel mechanisms of action are in critical need. We rationally designed and efficiently synthesized three series of new chemical entities with potential antibacterial activity targeting filamenting temperature-sensitive mutant Z (FtsZ). Evaluation of these compounds against a panel of Gram-positive bacteria including MDR and vancomycin-resistant Enterococcus?strains indicated that most compounds showed enhanced antibacterial efficacy, comparable or even superior to the reference drugs. The newly synthesized compounds proved to be substrates of the Escherichia coli efflux pump AcrB, thus affecting the activity. Their structure–activity relationships?were summarized in detail. The most potent compound 10f quickly eliminated bacteria in a bactericidal mode, with low susceptibility to induce bacterial resistance. Further mechanistic studies with the BsFtsZ protein revealed that 10f functioned as an effective FtsZ inhibitor through altering the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which leads to inhibition of cell division and cell death. Besides, 10f not only displayed no obvious cytotoxicity to mammalian cells but also had a high efficacy in a murine model of bacteremia in vivo. Regarded as a whole, our findings highlight 10f as a promising new FtsZ-targeting bactericidal agent.
- Chen, Weijin,Guo, Ting,Ma, Shutao,Ma, Yangchun,Song, Di,Zhang, Nan,Zhang, Shenyan
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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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- NOVEL SQUARYLIUM COMPOUNDS, AND COMPOSITIONS COMPRISING SAME
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The present disclosure is disclosed herein. The present invention relates to a novel squarylium compound and a near infrared absorbing resin composition containing the squarylium compound.
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Paragraph 0142; 0144-0146
(2021/04/29)
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- N-alkylated linear heptamethine polyenes as potent non-azole leads against Candida albicans fungal infections
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In this study, eighteen heptamethine dyes were synthesised and their antifungal activities were evaluated against three clinically relevant yeast species. The eighteen dyes were placed within classes based on their core subunit i.e. 2,3,3-trimethylindolenine (5a-f), 1,1,2-trimethyl-1H-benzo[e]indole (6a-f), or 2-methylbenzothiazole (7a-f). The results presented herein imply that the three families of cyanine dyes, in particular compounds 5a-f, show high potential as selective scaffolds to treat C. albicans infections. This opens up the opportunity for further optimisation and investigation of this class compounds for potential antifungal treatment.
- Critchley, Megan E.,Lawrence, Clare L.,McKenna, Sean T.,Okoh, Adeyi Okoh,Smith, Robert B.,Vishwapathi, Vinod
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supporting information
(2020/07/21)
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- Tuning lipophilicity for optimizing the H2S sensing performance of coumarin-merocyanine derivatives
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Hydrogen sulfide (H2S) is an endogenous signaling molecule involved in various physiopathological processes; coumarin-based merocyanines have been successfully utilized for developing fluorescent H2S sensors. However, subtle changes in the chemical structure of merocyanines could induce distinct difference in the H2S sensing behavior. Investigation of the structure-property relationship of merocyanine dyes is of great importance for the development of ideal sensors with desirable performance. In this work, a series of coumarin/merocyanine (CMC) hybrid fluorescent probes with different lipophilicities have been developed. By altering the N-alkyl chain, the reaction rate with H2S and intracellular distribution of CMC sensors are optimized. The results showed that increasing the lipophilicity by attaching longer N-alkyl chains leads to a faster sensing response as well as a higher efficiency of the mitochondrial targeting ability. By virtue of rapid sensing of H2S and impressive mitochondrial co-localization ability, CM-NC6 could monitor H2S levels via a dual channel ratiometric mode. In addition, CM-NC6 is also capable of in vivo imaging of exogenous H2S. The work provided a powerful strategy for developing H2S sensors with optimized performance, which would be helpful for understanding the complicated roles of H2S in various physiological processes.
- Fang, Hongbao,Chen, Yuncong,Shi, Xiangchao,Bai, Yang,Chen, Zhongyan,Han, Zhong,Zhang, Yuming,He, Weijiang,Guo, Zijian
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supporting information
p. 14800 - 14805
(2019/09/30)
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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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- 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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- Investigation of the minimum driving force for dye regeneration utilizing model squaraine dyes for dye-sensitized solar cells
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Combined theoretical and experimental approaches were implemented to design model far-red sensitive unsymmetrical squaraine dyes in order to estimate the minimum energy barrier required for dye regeneration. Our logical molecular design indicated that it is possible to have a fine control on the energetics within 0.2 eV only by the judicious selection of substituents and alkyl chain length keeping the main π-molecular framework the same. The utilization of the LSDA functional under TD-DFT calculations offered an effective and economical computational method for the reliable prediction of the energetics as well as the absorption maximum of the sensitizers. Among the designed dyes under investigation, SQ-75 exhibited the best photovoltaic performance, having a short-circuit current density of 10.92 mA cm-2, open circuit voltage of 0.57 V and a fill factor of 0.67, leading to a photoconversion efficiency of 4.25% despite having photon harvesting mainly in the far-red region. The best photon harvesting by SQ-75, even with an energy difference of only 0.12 eV between the energy of its highest occupied molecular orbital and redox energy level I-/I3- electrolyte, corroborates the possibility for dye regeneration with such a small driving force.
- Pradhan, Anusha,Morimoto, Takuya,Saikiran, Maryala,Kapil, Gaurav,Hayase, Shuzi,Pandey, Shyam S.
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p. 22672 - 22682
(2017/11/14)
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- Dye salt (by machine translation)
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This invention is a kind of type (0) to express perabrodil due to high absorbance, the concentration of said light units are removed the concentration of the high concentration, in particular can be used as a liquid crystal display device of the display device of the dye for color filter use. (0) (by machine translation)
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Page/Page column 49
(2016/10/09)
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- Exploration of cyanine compounds as selective inhibitors of protein arginine methyltransferases: Synthesis and biological evaluation
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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.
- Hu, Hao,Owens, Eric A.,Su, Hairui,Yan, Leilei,Levitz, Andrew,Zhao, Xinyang,Henary, Maged,Zheng, Yujun George
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p. 1228 - 1243
(2015/03/04)
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- Correlating molecular character of NIR imaging agents with tissue-specific uptake
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Near-infrared (NIR) fluorescent contrast agents are emerging in optical imaging as sensitive, cost-effective, and nonharmful alternatives to current agents that emit harmful ionizing radiation. Developing spectrally distinct NIR fluorophores to visualize sensitive vital tissues to selectively avoid them during surgical resection of diseased tissue is of great significance. Herein, we report the synthetic variation of pentamethine cyanine fluorophores with modifications of physicochemical properties toward prompting tissue-specific uptake into sensitive tissues (i.e., endocrine glands). Tissue-specific targeting and biodistribution studies revealed localization of contrast agents in the adrenal and pituitary glands, pancreas, and lymph nodes with dependence on molecular characteristics. Incorporation of hydrophobic heterocyclic rings, alkyl groups, and halogens allowed a fine-tuning capability to the hydrophobic character and dipole moment for observing perturbation in biological activity in response to minor structural alterations. These NIR contrast agents have potential for clinical translation for intraoperative imaging in the delineation of delicate glands.
- Owens, Eric A.,Hyun, Hoon,Tawney, Joseph G.,Choi, Hak Soo,Henary, Maged
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p. 4348 - 4356
(2015/06/08)
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- Synthesis and effect of heterocycle modification on the spectroscopic properties of a series of unsymmetrical trimethine cyanine dyes
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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.
- Levitz, Andrew,Ladani, Safieh Tork,Hamelberg, Donald,Henary, Maged
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p. 238 - 249
(2014/04/03)
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- Selective G-quadruplex DNA recognition by a new class of designed cyanines
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A variety of cyanines provide versatile and sensitive agents acting as DNA stains and sensors and have been structurally modified to bind in the DNA minor groove in a sequence dependent manner. Similarly, we are developing a new set of cyanines that have been designed to achieve highly selective binding to DNA G-quadruplexes with much weaker binding to DNA duplexes. A systematic set of structurally analogous trimethine cyanines has been synthesized and evaluated for quadruplex targeting. The results reveal that elevated quadruplex binding and specificity are highly sensitive to the polymethine chain length, heterocyclic structure and intrinsic charge of the compound. Biophysical experiments show that the compounds display significant selectivity for quadruplex binding with a higher preference for parallel stranded quadruplexes, such as cMYC. NMR studies revealed the primary binding through an end-stacking mode and SPR studies showed the strongest compounds have primary KD values below 100 nM that are nearly 100-fold weaker for duplexes. The high selectivity of these newly designed trimethine cyanines for quadruplexes as well as their ability to discriminate between different quadruplexes are extremely promising features to develop them as novel probes for targeting quadruplexes in vivo.
- Nanjunda, Rupesh,Owens, Eric A.,Mickelson, Leah,Dost, Tyler L.,Stroeva, Ekaterina M.,Huynh, Hang T.,Germann, Markus W.,Henary, Maged M.,Wilson, W. David
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p. 13588 - 13607
(2014/01/06)
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- N-Alkylated 2,3,3-trimethylindolenines and 2-methylbenzothiazoles. Potential lead compounds in the fight against Saccharomyces cerevisiae infections Dedication in memory of the late Derek Bennett 17-07-1931 to 05-04-2013.
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The synthesis of a variety of N-alkylated 2,3,3-trimethylindolenines and 2-methylbenzothiazoles is reported herein. Their potential as antifungal agents is evaluated by preliminary screening against Saccharomyces cerevisiae (S. cerevisiae), Schizosaccharomyces pombe (S. pombe), and Candida albicans (C. albicans). Statistical analyses illustrate a strong relationship between chain length and growth inhibition for S. cerevisiae and S. pombe (p 0.0001 in every case). Of particular interest is the activity of both sets of compounds against S. cerevisiae, as this is emerging as an opportunistic pathogen, especially in immunosuppressed and immunocompromised patients. Bioassays were set up to compare the efficacy of our range of N-alkylated compounds against classic antifungal agents; Amphotericin B and Thiabendazole.
- Tyler, Andrew R.,Okoh, Adeyi Okoh,Lawrence, Clare L.,Jones, Vicky C.,Moffatt, Colin,Smith, Robert B.
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supporting information
p. 222 - 227
(2013/07/27)
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- 2-Styrylindolium based fluorescent probes visualize neurofibrillary tangles in Alzheimer's disease
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We evaluated 2-styrylindolium derivatives (6-11) as novel and selective probes for neurofibrillary tangles (NFTs) on brain sections of AD patients. The staining experiments indicated that these compounds may bind selectively to NFTs in the presence of ss-amyloid (Ass) plaques. Cell free binding assays confirmed that 2-[2-[4-(1-pyrrolidinyl)phenyl]ethenyl]-1,3,3-trimethyl-3H- indolium iodide (9) and 2-[2-[4-(diethylamino)phenyl]ethenyl]-1-butyl-3,3- dimethyl-3H-indolium iodide (11) display excellent affinities to Tau-aggregates (IC50 values of 5.1 and 1.4 nM, respectively) in the displacement of Thiazin Red R. These probes have good solubility in distilled water and low or no cytotoxicity in zebrafish embryo and liver hepatocellular carcinoma cell assays.
- Gu, Jiamin,Anumala, Upendra Rao,Lo Monte, Fabio,Kramer, Thomas,Heyny Von Haussen, Roland,Hoelzer, Jana,Goetschy-Meyer, Valerie,Mall, Gerhard,Hilger, Ingrid,Czech, Christian,Schmidt, Boris
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p. 7667 - 7671
(2013/02/22)
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- Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents
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Protein arginine methylation regulates multiple biological processes. Deregulation of protein arginine methyltransferase (PRMT) activities has been observed in many disease phenotypes. Small molecule probes that target PRMTs with strong affinity and selectivity can be used as valuable tools to dissect biological mechanisms of arginine methylation and establish the role of PRMT proteins in a disease process. In this work, we report synthesis and evaluation of a class of carbocyanine compounds containing indolium, benz[e]indolium or benz[c,d]indolium heterocyclic moieties that bind to the predominant arginine methyltransferase PRMT1 and inhibit its methyltransferase activity at low micromolar potencies. In particular, the developed molecules have long wavelength colorimetric and fluorometric photoactivities, which can be used for optical and near-infrared fluorescence imaging in cells or biological tissues. Together, these new chemical probes have potential application in PRMT studies both as enzyme inhibitors and as fluorescent dyes for microscope imaging.
- Sinha, Sarmistha Halder,Owens, Eric A.,Feng, You,Yang, Yutao,Xie, Yan,Tu, Yaping,Henary, Maged,Zheng, Yujun George
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experimental part
p. 647 - 659
(2012/09/08)
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- Solid-state fluorescence of squarylium dyes
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An N-butyl indolenine squarylium dye could include toluene and p-xylene and exhibited the solid-state fluorescence in near-infrared region (F max=761 nm) in crystalline form due to inhibition of π/π-interactions between the fluorophores.
- Matsui, Masaki,Fukushima, Masato,Kubota, Yasuhiro,Funabiki, Kazumasa,Shiro, Motoo
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scheme or table
p. 1931 - 1935
(2012/04/10)
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- Synthesis and characterization of heptamethine NIR absorbing cyanine dye compounds
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In this work, new heptamethine near infrared (NIR) absorbing cyanine dye compounds were designed and synthesized by the reaction of bis-aldehyde, (1-formyl-3-hydroxymethylene)cyclohexene with benzindole derivatives. These dyes contained different Nalkyl c
- Shin, Joung-Il,Park, Soo-Youl,Shin, Seung-Rim,Jun, Kun,Youn, Hye-Soo,An, Kyoung-Lyong,Son, Young-A
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experimental part
p. 621 - 625
(2011/10/30)
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- Structural properties and degree of intramolecular charge transfer of an N-Alkyl indoline-tricyanoquinodimethane system
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A series of intramolecular charge-transfer compounds comprised of 1-alkyl-3,3-dimethyl-2-methyleneindoline (In, donor, n = alkyl chain length; 1-8, 10, 14, 16, 18, 20, and 22) and 7,8,8-tricyanoquinodimethane (=2-(4′-cyanomethylene-2′,5′-cyclohexadienylidene) malononitrile (3CNQ), acceptor) moieties linked through a π-bond, I n-3CNQ were prepared, and their structures are discussed. The melting points of the In-3CNQ solids decreased with increasing alkyl chain length until reaching a minimum point (95°C) at n = 18, and then began to gradually increase, indicating self-aggregation of the alkyl chains. The I n-3CNQ derivatives with long alkyl chains (n ≥ 6) produced supercooled liquids displaying conspicuous color changes after melting. Diverse molecular packing patterns were observed in the crystal structures. Most I n-3CNQ derivatives formed face-to-face and/or side-by-side dimeric motifs to cancel net dipole moments. I20-3CNQ formed a two-dimensional bilayer structure by π-stacking and self-assembly of the alkyl chains. Two types of molecular conformation, which significantly affect the electronic structures, were observed to be dependent on the alkyl chain length. A parameter to evaluate the degree of intramolecular charge transfer, namely bond length ratio, was proposed; it exhibited good agreement with solvatochromic shifts and molecular orbital calculations.
- Murata, Tsuyoshi,Nishimura, Kazukuni,Enomoto, Yuichiro,Honda, Genki,Shimizu, Yasuhito,Otsuka, Akihiro,Saito, Gunzi
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experimental part
p. 869 - 884
(2009/04/14)
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- Dyeing method using a specific cationic derivative and a compound selected among a specific aldehyde, a specific ketone, a quinone and a di-imino-isoindoline or 3-amino-isoindolone derivative
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Compositions, methods, and kits for dyeing at least one keratin fiber, comprising at least one specific cationic compound and at least one compound chosen from specific aldehydes, specific ketones, quinones, diiminoisoindoline derivatives, and 3-aminoisoindolone derivatives, with the proviso that the inventive compositions do not comprise an oxidizing agent.
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- SYNTHESE DE QUELQUES SPIRO ET SPIRO PHOTOCHROMIQUES. APPLICATION DE LA METHODOLOGIE DE LA RECHERCHE EXPERIMENTALE
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Some spiro I and spiro II substituted by different groups were synthesized in order to evaluate their photochromic properties and to optimize the preparation of spiroheterocyclic systems.In addition, some spiro III were also prepared as reference compounds.Their physical and spectroscopic characteristics (UV, 1H and 13C) were determined.A study using the experimental design methodology allowed to point out the most important factors for improving the reaction yields. KEYWORDS: Photochromism, spirooxazines, spiropyrans, synthesis, 1H NMR, experimental design methodology.
- Pottier, E.,Sergent, M.,Luu, R. Phan Tan,Guglielmetti, R.
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p. 719 - 740
(2007/10/02)
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