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引用本文:   郭靖, 刘庆文, 杜建时, 孔祥怡, 宋岩, 杨清彪, 赵晴, 李耀先. 基于萘酰亚胺的生物硫醇探针的合成及对含硫醇氨基酸的检测. 分析化学, 2017, 45(9): 1330-1338. doi:  10.11895/j.issn.0253-3820.170319 [复制]

Citation:   GUO Jing, LIU Qing-Wen, DU Jian-Shi, KONG Xiang-Yi, SONG Yan, YANG Qing-Biao, ZHAO Qing, LI Yao-Xian. Synthesis of Naphthalimide-based Biothiols Probe and Detection of Amino Acids Containing Sulfhydryl Groups. Chinese Journal of Analytical Chemistry, 2017, 45(9): 1330-1338. doi: 10.11895/j.issn.0253-3820.170319 [复制]

基于萘酰亚胺的生物硫醇探针的合成及对含硫醇氨基酸的检测

通讯作者:  赵晴, qingzhao888@hotmail.com

收稿日期: 2017-05-19

接受日期: 2017-07-20

出版日期: 2017-09-20

基金项目: 本文系吉林省自然科学基金(No.20160101311JC)和吉林省科技厅重点项目(Nos.20170204039GX,201307270299YY,20150204057SF)资助

Synthesis of Naphthalimide-based Biothiols Probe and Detection of Amino Acids Containing Sulfhydryl Groups

Corresponding author:  ZHAO Qing, qingzhao888@hotmail.com

Received Date:  2017-05-19

Accepted Date:  2017-07-20

Published Date:  2017-09-20

合成了以4-羟基萘酰亚胺为荧光团,2,4-二硝基苯磺酰氧基为特异性识别基团的生物硫醇探针4-(2,4-二硝基苯磺酰氧基)-正丁基-1,8-萘酰亚胺(DNSBN)。吸收光谱和荧光光谱结果表明,DNSBN对半胱氨酸(Cys)、同型半胱氨酸(Hcy)和谷胱甘肽(GSH)3种生物硫醇分子具有高效的检测识别能力,不受其它17种天然氨基酸的干扰。同时,通过荧光滴定实验证实了此探针是一种比率型探针,555 nm处的荧光强度与溶液中的生物硫醇分子浓度在0~20 μmol/L范围内呈良好的线性关系,对Cys、Hcy和GSH的检出限(3σ)分别为25.9、92.0和77.9 nmol/L。而吸收光谱、荧光光谱和质谱表征数据显示,生物硫醇与2,4-二硝基苯磺酸酯发生亲核取代反应并导致磺酸酯的分解。随着识别基团的解离,探针分子的d-PeT(donor-excited photoinduced electron transfer)效应被解除,并出现非常明显的比色与荧光变化。HeLa细胞成像实验表明,探针DNSBN具有良好的生物相容性,能够对细胞外源性生物硫醇分子进行检测。

关键词:   荧光探针, 萘酰亚胺, 半胱氨酸, 同型半胱氨酸, 谷胱甘肽
Key words:   Fluorescent probe, Naphthalimide, Cysteine, Homocysteine, Glutathione
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基于萘酰亚胺的生物硫醇探针的合成及对含硫醇氨基酸的检测

郭靖, 刘庆文, 杜建时, 孔祥怡, 宋岩, 杨清彪, 赵晴, 李耀先

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