Highly selective isomer fluorescent probes for distinguishing homo-/cysteine from glutathione based on AIE

TALANTA

卷:206

Article

Dong, Fangdi¹  Lai, Huiyan¹  Liu, Yun^2,3  Li, Qiuhong¹  Chen, Huahui¹  Ji, Shaomin¹  Zhang, Jianye^2,3  Huo, Yanping¹ 

[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Guangdong, Peoples R China

[2] Guangzhou Med Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab Mol Target & Clin Pharmaco, Guangzhou 511436, Guangdong, Peoples R China

[3] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China

关键词: Fluorescent probe;    Thiols;    AIE;    Bioimaging;   

DOI  :  10.1016/j.talanta.2019.120177

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

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