The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study

被引：30

作者：

Garcia-Beltran, Olimpo ^{[1
,2
]}

Mena, Natalia ^{[3
]}

Perez, Edwin G. ^{[4
,5
]}

Cassels, Bruce K. ^{[2
,4
]}

Nunez, Marco T. ^{[3
,4
]}

Werlinger, Francisca ^{[5
]}

Zavala, Daniel ^{[5
]}

Aliaga, Margarita E. ^{[5
]}

Pavez, Paulina ^{[5
]}

机构：

[1] Univ Andres Bello, Fac Ciencias Exactas, Dept Ciencias Quim, Santiago, Chile

[2] Univ Chile, Fac Sci, Dept Chem, Santiago, Chile

[3] Univ Chile, Fac Sci, Dept Biol, Santiago, Chile

[4] Univ Chile, Inst Cell Dynam & Biotechnol, Santiago, Chile

[5] Pontificia Univ Catolica Chile, Fac Quim, Santiago 6094411, Chile

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 49期

关键词：

Biothiols; Coumarin-based derivatives; Fluorescence probes; Michael addition; PROBE; HOMOCYSTEINE; DISEASE; THIOLS; WATER;

D O I：

10.1016/j.tetlet.2011.09.137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6606 / 6609

页数：4

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