文献类型：期刊文献

中文题名：基于菁染料高选择性检测半胱氨酸的近红外荧光探针

英文题名：Near-infrared Cyanine-based Fluorescent Probe for Cysteine with High Selectivity

作者：马亚光[1];张玉涛[1];马一宇[1];郭志前[1];朱为宏[1]

机构：[1]华东理工大学精细化工研究所,上海200237

年份：2018

卷号：36

期号：3

起止页码：236

中文期刊名：影像科学与光化学

外文期刊名：Imaging Science and Photochemistry

收录：CSTPCD;;Scopus;CSCD:【CSCD_E2017_2018】；

基金：国家自然科学基金项目(21622602)资助

语种：中文

中文关键词：近红外;半胱氨酸;荧光探针;菁染料

外文关键词：near-infrared;cysteine;fluorescent probe;cyanine

摘要：本文设计合成了以菁染料为荧光团,以4-(三氟甲基)苯硫基为半胱氨酸响应识别基团的近红外荧光探针(Cy-CF_3)。利用探针分子Cy-CF_3与半胱氨酸和谷胱甘肽反应发生的机理不同,实现了对半胱氨酸特异性识别。探针分子Cy-CF_3与半胱氨酸发生芳香亲核取代反应生成巯基取代产物,进一步通过分子内重排反应生成氨基取代产物Cy-Cys。光谱研究结果表明,探针分子Cy-CF_3与半胱氨酸作用后发生明显的吸收波长蓝移(160nm),并且可观察到明显的颜色变化;荧光光谱中,随着半胱氨酸的加入,探针分子Cy-CF_3在780nm处的近红外荧光显著增强。Cy-CF_3能高选择性检测半胱氨酸,并且不受其它氨基酸尤其是结构类似的谷胱甘肽干扰。探针分子Cy-CF_3被成功地应用于活体细胞中检测半胱氨酸。
We developed a turn-on cyanine-based near-infrared（NIR）probe which can selectively detect cysteine.In this probe Cy-CF3,4-（trifluoromethyl）thiophenol moiety is employed as both the recognition unit and fluorescence quenching group.With the titration of cysteine,a large blue shift（160 nm）is observed in the absorption spectra of Cy-CF3,accompanying with significant color changes.The probe Cy-CF3 shows obviously fluorescent enhancement at 780 nm in emission spectra.Over all,the probe Cy-CF3 exhibits high selectivity for cysteine over glutathione and other potential interferences.The reaction mechanism of Cy-CF3 with cysteine is verified by mass spectra,1 HNMR spectra and absorption spectra,indicating that 4-（trifluoromethyl）thiophenol in the probe Cy-CF3 could be replaced by cysteine,and then the PET process from 4-（trifluoromethyl）thiophenol to cyanine is blocked.The cell experiments also demonstrate that this probe could be successfully applied for the detection of cysteine in living cells.