- On the use of 2,1,3-benzothiadiazole derivatives as selective live cell fluorescence imaging probes
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Newly designed 2,1,3-benzothiadiazole-containing fluorescent probes with four excited state intramolecular proton transfer (ESIPT) sites were successfully tested in live cell-imaging assays using a confluent monolayer of human stem-cells (tissue). All tes
- Oliveira, Felipe F.D.,Santos, Diego C.B.D.,Lapis, Alexandre A.M.,Corrêa, José R.,Gomes, Alexandre F.,Gozzo, Fabio C.,Moreira Jr., Paulo F.,De Oliveira, Virgínia C.,Quina, Frank H.,Neto, Brenno A.D.
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- Synthesis, bioactivities, DFT and in-silico appraisal of azo clubbed benzothiazole derivatives
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Six new azo clubbed benzothiazole dyes were synthesized by diazotization reaction. These six novel compounds were characterized using 1H NMR, FTIR, UV–Visible, fluorescence spectroscopy, LC-MS, and elemental analysis. The in-vitro antimicrobial
- Ghanavatkar, Chaitannya W.,Mishra, Virendra R.,Mali, Suraj N.,Chaudhari, Hemchandra K.,Sekar, Nagaiyan
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- Benzimidazole and benzothiazole conjugated Schiff base as fluorescent sensors for Al3+ and Zn2+
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Two benzimidazole/benzothiazole based azomethines, (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(4-(diethylamino)-2-hydroxybenzylideneamino)phenol (HBZA) and (E)–2-(benzo[d]thiazol–2-yl)–4-(4-(diethylamino)–2-hydroxybenzylideneamino)phenol (HBTA) were designed and
- Suman,Bubbly,Gudennavar,Gayathri
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- An excited state intramolecular proton transfer dye based fluorescence turn-on probe for fast detection of thiols and its applications in bioimaging
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In this study, a new fluorescent probe 2-(2′-hydroxy-5′-N-maleimide phenyl)-benzothiazole (probe 1), was designed and synthesized by linking the excited state intramolecular proton transfer (ESIPT) fluorophore to the maleimide group for selective detectio
- Zhao, Yun,Xue, Yuanyuan,Li, Haoyang,Zhu, Ruitao,Ren, Yuehong,Shi, Qinghua,Wang, Song,Guo, Wei
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- Proton-Transfer-Based Azides with Fluorescence Off-On Response for Detection of Hydrogen Sulfide: An Experimental, Theoretical, and Bioimaging Study
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This work describes the synthesis of photoactive proton transfer compounds based on the benzazolic core containing the azide group. The compounds present absorption in the UV region and fluorescence emission in the visible region of the spectra with large
- Brito Da Silva, Cláudia,Gil, Eduarda Sangiogo,Da Silveira Santos, Fabiano,Morás, Ana Moira,Steffens, Luiza,Bruno Gon?alves, Paulo Fernando,Moura, Dinara Jaqueline,Lüdtke, Diogo Seibert,Rodembusch, Fabiano Severo
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- ESIPT-based fluorescence probe for the rapid detection of peroxynitrite ‘AND' biological thiols
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An ESIPT-based ‘AND' logic fluorescence probe (GSH-ABAH) was developed for the simultaneous detection of ONOO? and biological thiols. GSH-ABAH was shown to have good cell permeability and with the addition of just SIN-1 (ONOO? donor)
- Wu, Luling,Han, Hai-Hao,Liu, Liyuan,Gardiner, Jordan E.,Sedgwick, Adam C.,Huang, Chusen,Bull, Steven D.,He, Xiao-Peng,James, Tony D.
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- UV protective heterocyclic disperse azo dyes: Spectral properties, dyeing, potent antibacterial activity on dyed fabric and comparative computational study
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Disperse azo dyes are synthesized and characterized by 1H NMR, 13C NMR, LC-MS, Elemental analysis, UV–visible, and fluorescence spectroscopy methods. The azo dyes show absorption maxima in the range of 460–493 nm. Dye with benzothiaz
- Mishra, Virendra R.,Ghanavatkar, Chaitannya W.,Sekar, Nagaiyan
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- Schiff base clubbed benzothiazole: synthesis, potent antimicrobial and MCF-7 anticancer activity, DNA cleavage and computational study
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Schiff bases containing benzothiazole unit are synthesized and characterized by 1H NMR, 13C NMR, LC–MS, UV–visible and fluorescence spectroscopy methods. Synthesized compounds were evaluated for in vitro antibacterial activities on f
- Mishra, Virendra R.,Ghanavatkar, Chaitannya W.,Mali, Suraj N.,Chaudhari, Hemchandra K.,Sekar, Nagaiyan
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- Benzothiazole-pyridone and benzothiazole-pyrazole clubbed emissive azo dyes and dyeing application on polyester fabric: UPF, biological, photophysical and fastness properties with correlative computational assessments
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Positional isomers of benzothiazole-pyridone and benzothiazole-pyrazole containing disperse azo dyes are reported. These heterocyclic azo dyes are decorated with ‘separate ESIPT core’ and show emission in seven solvents of different polarity. After applic
- Ghanavatkar, Chaitannya W.,Mishra, Virendra R.,Sekar, Nagaiyan
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- A ratiometric fluorescent probe for alkaline phosphatase with high sensitivity
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Alkaline phosphatase (ALP) is one of essential biomarkers in mammalian tissue. Here we report a ratiometric probe for ALP, which is rationally designed and synthesized by employing ESIPT fluorophore N-(3-(benzo[d]thiazol-2-yl)-4-hydroxyphenyl)benzamide (B
- Yangyang, Yang,Chen, Zhang,Rizhao, Pan,Shiwei, Zhang,Shengtao, Yao,Yao, Tang,Weilong, Zhu,Liyue, Wang,Weiping, Zhu,Yufang, Xu,Xuhong, Qian
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supporting information
(2019/05/07)
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- Fluorescence sensing of Ag+ ions by desulfurization of an acetylthiourea derivative of 2-(2-hydroxyphenyl)benzothiazole
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A novel Ag+-selective reaction-based probe based on an acetylthiourea derivative of 2-(2-hydroxyphenyl)benzothiazole dye was investigated. The designed probe showed pronounced off-on type fluorescence signaling behavior towards Ag+ i
- Hwang, Keum Saem,Park, Ka Young,Kim, Da Bin,Chang, Suk-Kyu
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p. 413 - 419
(2017/09/02)
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- Synthesis and photophysical characterization of proton transfer-based thiourea derivatives: Potential application as colorimetric naked-eye chemosensor for fluoride detection in solution
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Two new thiourea derivatives were synthesized through the reaction of photoactive aminohydroxybenzazoles and p-isothiocyanate benzoic acid via nucleophilic addition reaction. The compounds were characterized using high resolution mass spectrometry with el
- Da Silva, Cláudia B.,Kroetz, Thais,Santos, Fabiano S.,Rodembusch, Fabiano S.
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p. 1830 - 1841
(2017/07/17)
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- Luminescent properties of benzothiazole derivatives and their application in white light emission
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Three benzothiazole derivatives, N-[4-(benzothiazol-2-yl)-3-hydroxyphenyl]-octanamide (BHPO1), N-[3-(benzothiazol-2-yl)-4-hydroxyphenyl]-octanamide (BHPO2), N-[4-(benzothiazol-2-yl)phenyl]-octanamide (BPO) were prepared and their luminescence properties w
- Lu, Fengxian,Hu, Rui,Wang, Shuangqing,Guo, Xudong,Yang, Guoqiang
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p. 4196 - 4202
(2017/02/05)
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- Confinement effect on the photophysics of ESIPT fluorophores
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The photophysics of three benzothiazole derivatives that exhibit excited state intramolecular proton transfer (ESIPT) were investigated in a confined medium afforded by the water soluble supramolecular host octaacid (OA). The dye@(OA)2 inclusion complexes were probed by UV-Vis absorption, steady-state and time resolved fluorescence emission techniques. Comparison studies of the free dyes in solution were also conducted. All three benzothiazole derivatives free in solution and as OA complexes in water absorb in the UV region. The fluorescence maxima of the OA complexes in water are similar to those in an apolar environment. This is different from the emission behavior of the dyes dissolved alone in water. The observed Stokes shift when confined within OA is related to the intramolecular proton transfer mechanism. Within OA only neutral species are present, indicating that these compounds are shielded from the bulk water. The excited state behavior of the benzothiazole derivatives in a confined medium indicates that supramolecular effects significantly alter the nature of the fluorescence emission.
- Santos, Fabiano S.,Ramasamy, Elamparuthi,Ramamurthy,Rodembusch, Fabiano S.
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p. 2820 - 2827
(2016/04/26)
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- Synthesis and photophysical properties of novel succinimidyl benzazole derivatives, evaluated by Candida albicans ATCC 10231 fluorescent staining
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New fluorescent succinimidyl benzazole derivatives were synthesised and successfully used to stain Candida albicans ATCC 10231 cells. The dyes were characterised by means of infrared, 13C and 1H NMR spectroscopies and elemental analy
- Santos, Rosane Catarina Dos,Faleiro, Nalva Vivian Da Silva,Campo, Leandra Franciscato,Scroferneker, Maria Lúcia,Corbellini, Valeriano Antonio,Rodembusch, Fabiano Severo,Stefani, Valter
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scheme or table
p. 3048 - 3053
(2011/06/26)
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- BENZOXAZOLE AND BENZOTHIAZOLE COMPOUNDS AND METHODS THEREFOR
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A compound of Formula (I): wherein R1 is selected from the group consisting of an aliphatic functionality having 2 to 12 carbons, an aromatic functionality having 3 to 20 carbons, and a cycloaliphatic functionality having 3 to 20 carbons; with
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(2008/06/13)
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- Synthesis and screening of quinolone antibiotic isosteres
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Condensation of either 4-(benzothiazol-2-yl)phenylamine 1 or 4-amino-2-(benzothiazol-2-yl)-phenol 2 with ethyl cyanoethoxyacrylate or diethyl ethoxymethylenemalonate (EMME) followed by intra molecular thermal cyclisation results in substituted quinolones
- Shaban, Mohamed A.,Al Badry, Ossama M.,Kamal, Aliaa M.,El-Gawad, Mohamd Abd El Wahap Abd
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scheme or table
p. 715 - 718
(2009/09/25)
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- 2-arylbenzothiazole analogues and uses thereof
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The present invention relates to compounds of the general formula (I) and salts, prodrugs, and stereoisomers thereof, wherein Y independently represents S, O, NR2, SO, SO2; A independently represents a fife- or six-membered aromatic carbocycle or heterocycle and wherein R1 to R20 in formula (I) represent independently of each other a variety of different substituents comprising alkyl, aryl, aralkyl, alkylaryl, heteroaryl groups and monofunctional moieties.
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(2008/06/13)
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- 2-Arylbenzothiazole analogues and uses thereof in the treatment of cancer
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The present invention relates to anticancer compounds of the general formula (I) and salts and physiologically functional derivatives thereof, wherein Y independently represents S, O, NR 2 , SO, SO 2 ; A independently represents a five- or six-membered aromatic carbocycle or heterocycle and wherein R 1 in formula (I) represents one of the heteroaryl groups defined in the claims.
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(2010/11/25)
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- Antitumor benzothiazoles. Part 2. Formation of 2,2'-diaminobiphenyls from the decomposition of 2-(4-azidophenyl)benzazoles in trifluoromethanesulfonic acid
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Decomposition of 2-(2-azidophenyl)- and 2-(3-azidophenyl)-benzothiazoles in trifluoromethanesulfonic acid generates ?-carbocations.These reactive intermediates have been trapped by triflate anion with the nucleophile substituting para to the original azido group to yield triflate-substituted arylamines. 2-(4-Azidophenyl)-benzothiazoles and -benzoxazoles behave differently: triflate-substituted arylamines are accompanied by symmetrical or unsymmetrical benzazolyl-substituted 2,2'-diaminobiphenyls as major products.These biphenyls have been identified by their characteristic 1H and 13C NMR spectra. 2,2'-Diaminobiphenyls are formed by initial C-C coupling interactions between the ?-carbocations and undecomposed 2-(4-azidophenyl)benzazoles and not by benzidine-type rearrangements as originally proposed.Symmetrical 2,2'-diaminobiphenyls have been oxidized by (diacetoxyiodo) benzene to give novel benzazolyl-substituted benzocinnolines.
- Stevens, Malcolm F. G.,Shi, Dong-Fang,Castro, Angeles
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- Solid-state Fluorescent Photophysics of Some 2-Substituted Benzothiazoles
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The solid-state fluorescence properties of a series of benzothiazoles with phenyl, napthalene, and coumarin moieties substituted at the 2-position have been investigated.The necessity for a 2'-OH substituent for fluorescence has been confirmed and the effects of further substitution in the 2-phenyl ring are reported.
- Anthony, Kevin,Brown, Robert G.,Hepworth, John D.,Hodgson, Kevin W.,May, Bernadette,West, Michael A.
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p. 2111 - 2118
(2007/10/02)
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