| 一种还原型谷胱甘肽荧光探针的合成及应用 |
| Synthesis and application of a fluorescent probe for the detection of reduced glutathione |
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| 摘要: 以三苯胺基作为供电子基团，2，4二硝基苯磺酰基作为吸电子基团和反应位点，基于分子内电荷转移(ICT)机理，通过Knoevenagel缩合反应合成检测还原型谷胱甘肽(GSH)的荧光探针CDAS。探针CDAS本身在561 nm处没有荧光，当加入GSH后，探针CDAS中的2，4二硝基苯磺酰基与之发生亲核取代反应，同时释放出3[4(二苯基氨基)苯基]2苯基丙烯腈(CDA)，荧光强度在561 nm处显著增强。在磷酸盐缓冲溶液(PBS)和乙腈混合液(体积比1∶1，10 mmol·L-1，pH=7.4)中，探针CDAS对GSH具有高的灵敏度(最低检测限为7.70 μmol·L-1)、高选择性和较大的斯托克斯位移(179 nm)。更重要的是，探针CDAS能够用于人宫颈癌细胞(HeLa细胞)中GSH的细胞成像。 |
| 关键词: 三苯胺 分子内电荷转移 荧光探针 还原型谷胱甘肽 细胞成像 |
| 基金项目: 山西省基础研究计划(No.202203021212184)、 忻州市科技局基础研究计划(No.20240502)和忻州师范学院培育项目(No.XJ2024001201)资助。 |
| Abstract: In this study, a fluorescent probe, CDAS, was synthesized to detect reduced glutathione (GSH). CDAS was designed by incorporating triphenylamine as an electrondonating group and a 2,4dinitrobenzenesulfonyl moiety as an electronwithdrawing group, with the response mechanism based on intramolecular charge transfer (ICT). These components were linked through Knoevenagel condensation. The probe exhibited no fluorescence; however, upon interaction with GSH, a nucleophilic substitution reaction occurred between GSH and probe CDAS, significantly enhancing fluorescent intensity at 561 nm. In a mixture of phosphatebuffered saline (PBS) and acetonitrile (1∶1, V/V, 10 mmol·L-1， pH=7.4), CDAS demonstrated a low detection limit of 7.70 μmol·L-1, high selectivity for GSH, and a large Stokes shift of 179 nm. Notably, CDAS can be effectively utilized to detect GSH in human cervical cancer cells (HeLa cells) via fluorescent cell imaging. |
| Keywords: triphenylamine intramolecular charge transfer fluorescent probe reduced glutathione cell imaging |
| 投稿时间：2024-12-27 修订日期：2025-04-10 |
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