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Molecular modulated cysteine-selective fluorescent probe

Authors
Jung, Hyo SungPradhan, TuhinHan, Ji HyeHeo, Kyung JunLee, Joung HaeKang, ChulhunKim, Jong Seung
Issue Date
11월-2012
Publisher
ELSEVIER SCI LTD
Keywords
Thiol; Cysteine; Cellular detection; Fluorescence; DFT calculations
Citation
BIOMATERIALS, v.33, no.33, pp.8495 - 8502
Indexed
SCIE
SCOPUS
Journal Title
BIOMATERIALS
Volume
33
Number
33
Start Page
8495
End Page
8502
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/107152
DOI
10.1016/j.biomaterials.2012.08.009
ISSN
0142-9612
Abstract
We have synthesized a series of coumarins (1-3) that can emit fluorescence in a turn-on manner through a Michael-type reaction with thiol-containing compounds. The only difference among the coumarins is the position of a carboxyl group on its benzene ring moiety near the double-bond conjugated coumarin. Their selectivity for Cys, GSH, and Hcy as well as the associated fluorogenic mechanism were illustrated by fluorescence spectroscopy. DFT calculations, and kinetic studies. All isomers prefer Cys over GSH in the reaction from 48.6 (probe 3) to 111-fold (probe 1) as demonstrated in a second order kinetics. The high selectivity of probe 1 to Cys might be achieved since the ortho carboxyl group on its benzene ring prefers a less negatively charged nucleophile. During intracellular Cys detection using 1, a possible interference by a large amount of GSH in the HepG2 cells was evaluated. The cells were treated with L-buthionine sulfoximine (BSO), an inhibitor of gamma-glutamylcysteine synthetase, providing an experimental condition where the cells could not synthesize GSH from Cys or other species. Then, the fluorescence intensity of 1 in HepG2 cells under BSO-H2O2 treatment was strongly enhanced by N-acetylcysteine (NAC), a precursor of Cys, implicating that the fluorescence signal from the cells is mainly associated with changes in intracellular [Cys] rather than that in intracellular [GSH]. (C) 2012 Elsevier Ltd. All rights reserved.
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