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Org Lett. 2013 Jul 19;15(14):3630-3. doi: 10.1021/ol401480w. Epub 2013 Jun 28.

Highly fluorescent and specific molecular probing of (homo)cysteine or superoxide: biothiol detection confirmed in living neuronal cells.

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1
Molecular Logic Gate Laboratory, Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), 373-1 Guseong-dong, Yuseong-gu, Daejeon, 305-701, Republic of Korea.

Abstract

Chemodosimetric action in detection of cysteine and homocysteine (310- and 290-fold) and superoxide inputs (336-fold increase) gives significant fluorescence intensity increases. Detection limits of 2.13 × 10(-5) M, 1.37 × 10(-5) M, and 2.71 × 10(-5) M, respectively, are biorelevant and are consistent with "OR" logic gating, demonstrated in intracellular biothiol detection in neuronal cells by way of novel fluorescein derivatization. As per our knowledge, this is the first example of a novel fluorescent probe based on the nucleophilic substitution reaction of biothiols and superoxide through ester cleavage.

PMID:
23808645
DOI:
10.1021/ol401480w
[Indexed for MEDLINE]
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