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.
Multicationic monomethine dyes as sensitizers in two- and three-component photoinitiating systems for multiacrylate monomers
Kabatc, Janina
, p. 74 - 85 (2010)
This paper is focused on the description of the synthesis, spectroscopic and electrochemical properties, and the free radical photoinitiation abilities of new multi-cationic monomethine dyes. The new monomethine dyes were employed both as the visible light photoinitiators of acrylate monomer polymerization and as fluorescence probes for monitoring the progress of polymerization. A degree of polymer cure from the measurement of the changes in the probe emission intensity and position shift during the thermally initiated polymerization of monoacrylate was obtained. A distinct increase in the intensity of the dyes fluorescence was observed during polymerization when the degree of monomer conversion was gradually increasing. The second part of this work is the possibility of an application of the dyes synthesized in combination with borate anions, as photoinitiating systems. Novel multi-cationic monomethine dyes paired with n-butyltriphenylborate anions are very efficient visible light photoinitiators of free radical polymerization of acrylate monomers. Their photoinitiating abilities were compared with the photoinitiation ability of Rose Bengal derivative, e.g. typical triplet state photoinitiator. The addition of a second co-initiator to the two-component photoinitiating system (monomethine borate salts) enhances their photoinitiating abilities.
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.
Clickable styryl dyes for fluorescence labeling of pyrrolidinyl PNA probes for the detection of base mutations in DNA
Ditmangklo, Boonsong,Taechalertpaisarn, Jaru,Siriwong, Khatcharin,Vilaivan, Tirayut
, p. 9712 - 9725 (2019)
Fluorescent hybridization probes are important tools for rapid, specific and sensitive analysis of genetic mutations. In this work, we synthesized novel alkyne-modified styryl dyes for conjugation with pyrrolidinyl peptide nucleic acid (acpcPNA) by click chemistry for the development of hybridization responsive fluorescent PNA probes. The free styryl dyes generally exhibited weak fluorescence in aqueous media, and the fluorescence was significantly enhanced (up to 125-fold) upon binding with DNA duplexes. Selected styryl dyes that showed good responses with DNA were conjugated with PNA via sequential reductive alkylation-click chemistry. Although these probes showed little fluorescence change when hybridized to complementary DNA, significant fluorescence enhancements were observed in the presence of structural defects including mismatched, abasic and base-inserted DNA targets. The largest increase in fluorescence quantum yield (up to 14.5-fold) was achieved with DNA carrying base insertion. Although a number of probes were designed to give fluorescence response to complementary DNA targets, probes that are responsive to mutations such as single nucleotide polymorphism (SNP), base insertion/deletion and abasic site are less common. Therefore, styryl-dye-labeled acpcPNA is a unique probe that is responsive to structural defects in the duplexes that may be further applied for diagnostic purposes.
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.
Molecular Engineering of Thiazole Orange Dye: Change of Fluorescent Signaling from Universal to Specific upon Binding with Nucleic Acids in Bioassay
Lu, Yu-Jing,Deng, Qiang,Hou, Jin-Qiang,Hu, Dong-Ping,Wang, Zheng-Ya,Zhang, Kun,Luyt, Leonard G.,Wong, Wing-Leung,Chow, Cheuk-Fai
, p. 1019 - 1029 (2016)
The universal fluorescent staining property of thiazole orange (TO) dye was adapted in order to be specific for G-quadruplex DNA structures, through the introduction of a styrene-like substituent at the ortho-position of the TO scaffold. This extraordinary outcome was determined from experimental studies and further explored through molecular docking studies. The molecular docking studies help understand how such a small substituent leads to remarkable fluorescent signal discrimination between G-quadruplex DNA and other types of nucleic acids. The results reveal that the modified dyes bind to the G-quadruplex or duplex DNA in a similar fashion as TO, but exhibit either enhanced or quenched fluorescent signal, which is determined by the spatial length and orientation of the substituent and has never been known. The new fluorescent dye modified with a p-(dimethylamino)styryl substituent offers 10-fold more selectivity toward telomeric G-quadruplexes than double-stranded DNA substrates. In addition, native PAGE experiments, FRET, CD analysis, and live cell imaging were also studied and demonstrated the potential applications of this class of thiazole-orange-based fluorescent probes in bioassays and cell imaging.
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.
Fluorescent probe for biological gas SO2 derivatives bisulfite and sulfite
Sun, Yuan-Qiang,Liu, Jing,Zhang, Jingyu,Yang, Ting,Guo, Wei
, p. 2637 - 2639 (2013)
A coumarin-hemicyanine dye 1 was reported for ratiometric fluorescent detection of SO2 derivatives HSO3- and SO 32- based on a novel addition-rearrangement cascade reaction. The Royal Society of Chemistry 2013.
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.
Smart phone assisted quinoline-hemicyanine based fluorescent probe for the selective detection of glutathione and the application in living cells
Ilanchelian, Malaichamy,Jothi, Mathivanan,Mani, Kailasam Saravana,Muralidharan, Narenkumar,Rajamanikandan, Ramar,Rajendran, Subramaniam Parameswaran
, (2020)
Quinoline appended hemicyanine 6MIM with strong ICT character was successfully synthesized through simple condensation reaction of 6-methoxy-2-chloro-3-formyl quinoline with 2-benzothiazolinium iodide. The photophysical characteristics of synthesized probe revealed that it would selectively detect glutathione (GSH) when it compared with different amino acids including biothiols and the detection limit is found to be 100 nM. The turn off sensor is due to thiol-halogen SNAr nucleophilic substitution between 6MIM and thiol group in glutathione. More importantly, the biosensor 6MIM was effectively applied in the fluorescence bioimaging of GSH in living cells with low cell toxicity. The colorimetric detectable color change of 6MIM-GSH has been effectively integrated with smartphone assisted RGB color value application with lowest detection value of 120 nM.
