用于在肿瘤小鼠中成像半胱氨酸的具有大斯托克斯位移的近红外荧光探针。
A near-infrared fluorescent probe with large Stokes shift for imaging Cys in tumor mice.
机构信息
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, 411105, PR China.
Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, PR China.
出版信息
Anal Chim Acta. 2021 Aug 1;1171:338655. doi: 10.1016/j.aca.2021.338655. Epub 2021 May 21.
Cysteine (Cys), a kind of small molecule biological thiol, not only involves in the regulation of physiological processes, but also is considered a marker of tumor. However, it is challenging to develop suitable probe for detecting Cys in tumors. In this paper, a near-infrared (NIR) fluorescent probe named IX for Cys has been designed and synthesized. The probe shows a NIR emission peak at 770 nm with large Stokes shift (180 nm) upon adding Cys. It displays high sensitivity to Cys with 6-fold increase of fluorescence intensity. Meanwhile, IX has the high selectivity to Cys over other potential interference such as Hcy and GSH, which have similar structure with Cys. In addition, a possible mechanism of fluorescence enhancement is the reaction of IX with Cys to release IX-OH, which is verified by fluorescence spectra, MS and HPLC. Next, IX can selectively image Cys in HCT-116 cells thanks to the low cytotoxicity. Most important of all, the fluorescent probe IX has visualized Cys in HCT116-xenograft tumor mice due to the near-infrared properties with large Stokes shift.
半胱氨酸（Cys）是一种小分子生物硫醇，不仅参与生理过程的调节，而且被认为是肿瘤的标志物。然而，开发用于检测肿瘤中 Cys 的合适探针具有挑战性。在本文中，设计并合成了一种近红外（NIR）荧光探针，命名为 IX，用于检测 Cys。探针在加入 Cys 后，在 770nm 处显示出近红外发射峰，具有大的斯托克斯位移（180nm）。它对 Cys 具有高灵敏度，荧光强度增加了 6 倍。同时，IX 对 Cys 具有高选择性，对其他潜在干扰物如 Hcy 和 GSH 具有高选择性，这些干扰物与 Cys 具有相似的结构。此外，荧光增强的可能机制是 IX 与 Cys 的反应释放出 IX-OH，这通过荧光光谱、MS 和 HPLC 得到验证。接下来，由于低细胞毒性，IX 可以选择性地对 HCT-116 细胞中的 Cys 进行成像。最重要的是，由于具有大斯托克斯位移的近红外特性，荧光探针 IX 可以在 HCT116 异种移植肿瘤小鼠中可视化 Cys。
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