2785-06-0Relevant articles and documents
Aggregation and photoisomerization of amphiphilic crown-ether styryl dye in monolayers at the interface
Yu Kryukov,Feofanov,Oleinikov,Vereshchetin,Yu Zaitsev,Gromov,Fedorova,Maskevichf,Kivach,Zubov,Nablev,Alfimov
, p. 2362 - 2368 (1996)
The molecules of trans-isomer of styryl dye la, containing the benzo-18-crown-6 moiety and the methoxybenzothiazole residue with the //-octadecyl substituent, were shown to form stable, highly ordered monolayers at the water/air interface. Increasing the surface pressure of the monolayer results in the formation of the H-aggregated molecules of compound la. The H-aggregates tend to dissociate to the monomeric trans-form. when the monolayer forms in the Langmuir-Blodgett film (LB film). The light irradiation of the LB films leads to the partially reversible trans-cw-photoisomerization of compound la, whose efficiency is much lower than that observed in an acetonitrile solution of la. The aggregation of cis-la isomers in the LB film is suggested to hamper the reverse cis-rra/u-isomerization. The aggregation of trans-l molecules in the LB films does not occur in air, but, after dipping in an aqueous solution, molecules of the LB film slowly form J-aggregates. A model of the structural organization of trans-l molecules in the LB films was proposed.
Antibacterial activity of 3-methylbenzo[d]thiazol-methylquinolinium derivatives and study of their action mechanism
Sun, Ning,Du, Ruo-Lan,Zheng, Yuan-Yuan,Guo, Qi,Cai, Sen-Yuan,Liu, Zhi-Hua,Fang, Zhi-Yuan,Yuan, Wen-Chang,Liu, Ting,Li, Xiao-Mei,Lu, Yu-Jing,Wong, Kwok-Yin
, p. 879 - 889 (2018)
The increasing incidence of multidrug resistant bacterial infection renders an urgent need for the development of new antibiotics. To develop small molecules disturbing FtsZ activity has been recognized as promising approach to search for antibacterial of high potency systematically. Herein. series of novel quinolinium derivatives were synthesized and their antibacterial activities were investigated. The compounds show strong antibacterial activities against different bacteria strains including MRSA, VRE and NDM-1 Escherichia coli. Among these derivatives. compound bearin. 4-fluorophenyl group (A2) exhibite. superior antibacterial activity and its MICs to the drug-resistant strains are found lower than those of methicillin and vancomycin. The biological results suggest that these quinolinium derivatives can disrupt the GTPase activity and dynamic assembly of FtsZ, and thus inhibit bacterial cell division and then cause bacterial cell death. These compounds deserve further evaluation for the development of new antibacterial agents targeting FtsZ.
Turn-on fluorescent probes that can light up endogenous RNA in nucleoli and cytoplasm of living cells under a two-photon microscope
Feng, Ruiqing,Li, Longlong,Li, Bing,Li, Jinhui,Peng, Dan,Yu, Yitao,Mu, Qiuhong,Zhao, Ning,Yu, Xiaoqiang,Wang, Zhenhua
, p. 16730 - 16736 (2017)
We have synthesized two-photon organic molecule probes (IMT-E and IMT-M), which selectively stain endogenous RNA in the nucleolus and cytoplasm of living cells in a short incubation time. Using these probes, bright two-photon excitation fluorescence (TPEF) images of living cells have been developed. Titrations and digest tests of ribonuclease indicate the markedly higher affinity of these probes for RNA, especially when using IMT-E. Upon binding to RNA, the fluorescence intensity of IMT-E increases by about 15-fold, showing that IMT-E is a turn-on probe for the detection of RNAs. MTT assays demonstrate that the mitochondria of cells maintain their electron mediating ability after being stained with the probes. These results demonstrate that IMT-E is an attractive two-photon turn-on fluorescent probe for visualizing RNA in living cells.
Simple benzothiazole chemosensor for detection of cyanide anions via nucleophilic addition
Yu, Xueying,Wang, Kangnan,Cao, Duxia,Wu, Qianqian,Guan, Ruifang,Xu, Yongxiao,Sun, Yatong,Liu, Zhiqiang
, p. 42 - 45 (2017)
[Figure not available: see fulltext.] A benzothiazolium salt containing carbazole group has been synthesized in a good yield via simple condensation reaction. Its photophysical properties and affinity for cyanide anion (tetrabutylammonium cyanide) have been investigated. The compound exhibited quick and well visible UV/Vis absorption and fluorescence responses to cyanide anion in MeCN, as the yellow color faded and the orange fluorescence disappeared. The in situ analysis by 1H NMR indicated that the cyanide anion was added to the C=N bond in the benzothiazolyl group.
A novel water-soluble AIE-based fluorescence probe with red emission for the sensitive detection of heparin in aqueous solution and human serum samples
Yang, Shuqi,Gao, Tang,Dong, Jie,Xu, Huan,Gao, Feng,Chen, Qian,Gu, Yonghong,Zeng, Wenbin
, p. 3681 - 3686 (2017)
Heparin is widely used to anticoagulation treatment in clinic, while the overdoses of heparin can cause potentially catastrophic complications. Thus, the selective and sensitive detection of heparin is of great importance. Herein, a novel water-soluble AIE-based fluorescent probe (TIBI) with red emission (650 nm) has been rationally developed to detect heparin by the electrostatic-interaction and ion replacing strategy. TIBI exhibited excellent selectivity and low detection limit (0.08 μM) for detection of heparin. Moreover, TIBI was successfully applied to detect heparin in complicated serum samples with satisfactory results. This study holds great promise for real time monitoring heparin in clinical application.
Highly selective reaction based colorimetric and fluorometric chemosensors for cyanide detection via ICT off in aqueous solution
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In the present work, thiazole functionalized receptors, S1 and S2, containing aminophenol as a signaling unit have been prepared and evaluated by UV–vis and fluorescence methods. These receptors consisting of conjugated benzothiazol-aminophenol system, which exhibited rapid and selective response towards cyanide anion. These two probes showed dramatic color change from wine red/purple to colorless, and optical quenching was also observed upon addition of CN? ions based on intramolecular charge transfer (ICT) transition in aqueous media. The detection limit of the probe S1 and S2 for CN? was calculated as 3.6 and 4.2 μM by spectrophotometric, 0.5 and 0.6 μM by spectrofluorophotometric methods, respectively. The binding stoichiometry between probes and cyanide was found to be 1:1, and the binding mechanism was also proposed.
Benzothiazole merocyanine dyes as middle pH optical sensors
Coelho, Felipe Lange,da Costa Duarte, Rodrigo,de ávila Braga, Cláudia,Toldo, Josene Maria,Bruno Gon?alves, Paulo Fernando,da Silveira Santos, Fabiano,Rodembusch, Fabiano Severo
, (2020)
Substituted merocyanine dyes were obtained by Knoevenagel condensation between formylated arylbenzothiazole and quaternary 2-alkylbenzothiazoles. The condensations were performed in the presence of sodium methoxide and the products were obtained with exce
Non-cytotoxic photostable monomethine cyanine platforms: Combined paradigm of nucleic acid staining and in vivo imaging
Ilic-Tomic, Tatjana,Kamounah, Fadhil S.,Kurutos, Atanas,Nikodinovic-Runic, Jasmina,Vasilev, Aleksey A.
, (2020)
Cyanine based chemosensing platforms have successfully been employed over the past couple of decades in various fields of biomolecular sciences. Still a substantial number of recent advances and improvements on this class of compounds are reported in the art. This paper presents our latest work on the improved synthetic approach, study on photophysical properties, and biosensing applicability of monomethine cyanine dyes. The series of mono-, di- and tricationic dyes showed up to 5-fold enhanced resistance against photobleaching compared to the commercially available Thiazole Orange (TO). The title compounds were studied as potential molecular probes for the detection of deoxyribonucleic acid, demonstrating their capacity as excellent fluorescent labeling agents. Depending on the dye chemical structure, current Cl-TO compounds exhibit up to 834-fold enhanced fluorescence emission and form stable complexes with Calf Thymus-DNA. The calculated binding constants were found to be higher than several conventional fluorogenic dyes for nucleic acid detection. All studied derivatives appeared as less cytotoxic than the Thiazole Orange. IC50 concentrations in human fibroblasts MRC5 cell line were calculated up to 50 μM for the synthesized Cl-TO dyes, and 0.5 μM for the parental Thiazole Orange. Two of the dyes were found very competent in post-electrophoretic visualization of DNA. As demonstrated by the agarose gel electrophoresis, the staining efficiency and detection limits of the dyes were comparable to the widely used Ethidium Bromide. The tricationic dye revealed great potential for cell cycle analysis in G1, S and G2 phases. The chlorinated TO derivatives readily stain human cells in vivo, while they can effectively be applied for eukaryotic and microbial cell staining.
Highly selective turn-on red fluorescence probes for visualization of the G-quadruplexes DNA in living cells
Kang, Yongqiang,Wei, Chunying
, (2021/10/27)
Studies on small molecule fluorescent probes for detecting G-quadruplexes DNA have bring about an extensive attention in recent years. In this paper, we designed and synthesized three benzothiazole derivatives named 2a-2c under moderate reaction conditions and investigated their interactions with DNA (single-stranded, duplex, i-motif and G-quadruplex) and distribution in living cell. Three compounds present a large Stokes shift (～90 nm) and a weak red fluorescence emission, and they exhibit a good selectivity and sensitive turn-on fluorescence response for the promoter G-quadruplex DNA (bcl-2, c-myc and c-kit 2) and mitochondria G-quadruplex (KSS). The affinity of 2a and 2b with N-alkyl side chain group to DNA is stronger than that of 2c with an anion group, therefore, they also increase the stability of the G-quadruplex structure. 2b induces the conformational change of both bcl-2 and KSS G-quadruplexes, while all compounds induce the folding of bcl-2 from the coiled structure to the hybrid G-qrudruplex. Three compounds interact with the G-quadruplex DNA mainly by end-stacking mode. Furthermore, MTT assays and confocal fluorescence images show that these compounds can enter the living HepG2 cells with low cytotoxicity. 2a-2c are mainly located in the mitochondrion and interacted with mitochondria G-quadruplex DNA, while only weak fluorescence can be found in cell nucleus. In a word, 2a-2c can be implied in image of G-quadruplex DNA in living cells.
Benzothiazolium Derivative-Capped Silica Nanocomposites for β-Amyloid ImagingIn Vivo
Ma, Lijun,Yang, Shu,Ma, Yufan,Chen, Yuzhi,Wang, Zhenguo,James, Tony D.,Wang, Xuefei,Wang, Zhuo
, p. 12617 - 12627 (2021/09/30)
Alzheimer’s disease (AD) is a neurodegenerative disease, and β-amyloid (Aβ) is believed to be a causative factor in AD pathology. The abnormal deposition of Aβ is believed to be responsible for progression of AD. In order to facilitate the imaging of Aβin vivo, suitable probe molecules with a near-infrared emission wavelength that can penetrate the blood-brain barrier (BBB) were utilized. The commercial fluorescent probe thioflavin-T (ThT) is used to image Aβ; however, because of its short emission wavelength and poor BBB penetration, ThT can only be usedin vitro. With this research, based on ThT, we design three fluorescent probes (SZIs) having a longer emission wavelength in order to image Aβ aggregates. SZIs with different numbers of double bonds respond to Aβ aggregates. The SZIs have a structure similar to ThT, and as such, the SZIs are also unable to penetrate the BBB. To deal with the problem, we develop nanocomposites (MSN-Lf@SZIs) to deliver SZIs into the brain of AD mouse and image Aβ successfully. These new nanocomposites are able to deliver the dyes into the brain and facilitate Aβ imagingin vivo.
