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用于体内区分检测 Cys/Hcy 和 GSH 的具有多个结合位点的比色和近红外荧光探针。

Colorimetric and NIR Fluorescence Probe with Multiple Binding Sites for Distinguishing Detection of Cys/Hcy and GSH in Vivo.

机构信息

Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province , Shanxi University , Taiyuan 030006 , People's Republic of China.

Research Institute of Applied Chemistry (RIAC) , Shanxi University , Taiyuan , 030006 , People's Republic of China.

出版信息

Anal Chem. 2019 Jan 15;91(2):1472-1478. doi: 10.1021/acs.analchem.8b04485. Epub 2018 Dec 31.

Abstract

Although some progress has been made in distinguishing the detection of biothiols, NIR biothiol fluorescent probes for simultaneously distinguishing detection of Cys, Hcy, and GSH in vivo have not been reported. The design of these probes involves the introduction of NIR fluorophores and multiple binding sites; thus, the integrated design of probes remains a challenge. Although Cys, Hcy, and GSH have common functional groups, a sulfydryl group and an amino group, due to their differences in spatial structure, they may react with multiple binding site probes to produce different reaction products in different bonding mechanisms, resulting in different colors and fluorescent signal changes of the system. Therefore, multiple binding site fluorescent probes can realize their discrimination detection. For an NIR fluorescent probe, it is easier to realize in vivo imaging to promote the research of biothiols in clinical diagnosis. In our work, not only were multiple binding sites constructed in the compound but also NIR fluorophores were introduced. This enables the probe to not only efficiently distinguish detection of Cys/Hcy and GSH but also achieve fluorescence imaging in vivo. We believe this result is a milestone in the discrimination detection of biothiols.

摘要

虽然在区分生物硫醇的检测方面已经取得了一些进展,但尚未有报道能够同时区分检测体内的半胱氨酸、同型半胱氨酸和谷胱甘肽的近红外生物硫醇荧光探针。这些探针的设计涉及到近红外荧光团和多个结合位点的引入;因此,探针的整体设计仍然是一个挑战。尽管半胱氨酸、同型半胱氨酸和谷胱甘肽具有共同的官能团,即巯基和氨基,但由于它们在空间结构上的差异,它们可能与多个结合位点探针反应,在不同的键合机制下产生不同的反应产物,导致体系颜色和荧光信号变化不同。因此,多个结合位点荧光探针可以实现它们的区分检测。对于近红外荧光探针,在体内成像中更容易实现,从而促进了临床诊断中生物硫醇的研究。在我们的工作中,不仅在化合物中构建了多个结合位点,还引入了近红外荧光团。这使得探针不仅能够高效地区分检测半胱氨酸/同型半胱氨酸和谷胱甘肽,还能够实现体内荧光成像。我们相信这一结果是生物硫醇区分检测的一个里程碑。

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