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Highly selective isomer fluorescent probes for distinguishing homo-/cysteine from glutathione based on AIE.
Dong, Fangdi; Lai, Huiyan; Liu, Yun; Li, Qiuhong; Chen, Huahui; Ji, Shaomin; Zhang, Jianye; Huo, Yanping.
Afiliación
  • Dong F; School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, PR China.
  • Lai H; School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, PR China.
  • Liu Y; Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences and the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China.
  • Li Q; School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, PR China.
  • Chen H; School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, PR China.
  • Ji S; School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, PR China. Electronic address: smji@gdut.edu.cn.
  • Zhang J; Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences and the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China. Electronic address: jianyez@163.com.
  • Huo Y; School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, PR China. Electronic address: yphuo@gdut.edu.cn.
Talanta ; 206: 120177, 2020 Jan 01.
Article en En | MEDLINE | ID: mdl-31514882
Two highly selective OFF-ON isomer fluorescent probes (1 and 2) for homo-/cysteine were designed and synthesized. The pyrene modified tetraphenylethylene derivative with AIE was used as luminescent group while maleimide was used as recognition group. These two isomer probes were found to be nearly nonfluorescent when treated with GSH. However, upon interaction with Cys or Hcy, the fluorescence was enhanced by 2000 folds in a wide pH range from 3 to 10. Experimental results and DFT calculation have demonstrated that the fluorescence OFF-ON switch of such thiol probes is resulted from the termination of the PET (photo-induced electron transfer) effect through the Michael addition reaction of maleimide unit and thiols. In addition, probe 1 and 2 exhibit excellent selectivity and sensitivity towards Cys, Hcy over GSH and other amino acids, which was confirmed by mass MS. We suggested that Michael addition reaction of these probes with GSH was prevented because of the stereo-hindrance effect. Furthermore, these two isomer probes were successfully used for imaging biothiols in living H1299 lung cancer cells.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Cisteína / Colorantes Fluorescentes / Glutatión / Homocisteína Límite: Humans Idioma: En Revista: Talanta Año: 2020 Tipo del documento: Article Pais de publicación: Países Bajos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Cisteína / Colorantes Fluorescentes / Glutatión / Homocisteína Límite: Humans Idioma: En Revista: Talanta Año: 2020 Tipo del documento: Article Pais de publicación: Países Bajos