Fluorescence turn-on probe for biothiols: intramolecular hydrogen bonding effect on the Michael reaction

被引：27

作者：

Ha, Hyun-Joon ^{[1
,2
]}

Yoon, Doo-Ha ^{[1
]}

Park, Seokan ^{[1
]}

Kim, Hae-Jo ^{[1
]}

机构：

[1] Hankuk Univ Foreign Studies, Dept Chem, Yongin 449719, South Korea

[2] Hankuk Univ Foreign Studies, Prot Res Ctr Bioind, Yongin 449719, South Korea

来源：

TETRAHEDRON | 2011年 / 67卷 / 40期

基金：

新加坡国家研究基金会;

关键词：

Biothiol; Coumarinyl enone; Fluorescence; Hydrogen bond; Michael addition; GLUTATHIONE; CHEMOSENSOR; CYSTEINE;

D O I：

10.1016/j.tet.2011.08.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Weakly fluorescent coumarinyl enones are rapidly transformed into strongly fluorescent molecules through the Michael addition reaction of a thiol group, where an intramolecular hydrogen bond plays a critical role in the reaction rate. The molecular probe (3) with an ortho hydroxyl group to a carbonyl group exhibits a rapid response toward GSH owing to the stabilization of the possible oxyanion intermediate by a preferable intramolecular hydrogen bond. Probe 1 with an o-hydroxyl group also showed a moderately enhanced reaction rate with GSH and soluble in HEPES buffer to exhibit a highly selective and sensitive fluorescence turn-on response toward biothiols. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：7759 / 7762

页数：4

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