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Issue 3, 2015
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Chemiluminescent probes for imaging H2S in living animals

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Abstract

Hydrogen sulphide (H2S) is an endogenous mediator of human health and disease, but precise measurement in living cells and animals remains a considerable challenge. We report the total chemical synthesis and characterization of three 1,2-dioxetane chemiluminescent reaction-based H2S probes, CHS-1, CHS-2, and CHS-3. Upon treatment with H2S at physiological pH, these probes display instantaneous light emission that is sustained for over an hour with high selectivity against other reactive sulphur, oxygen, and nitrogen species. Analysis of the phenol/phenolate equilibrium and atomic charges has provided a generally applicable predictive model to design improved chemiluminescent probes. The utility of these chemiluminescent reagents was demonstrated by applying CHS-3 to detect cellularly generated H2S using a multi-well plate reader and to image H2S in living mice using CCD camera technology.

Graphical abstract: Chemiluminescent probes for imaging H2S in living animals

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Supplementary files

Article information


Submitted
14 Nov 2014
Accepted
31 Dec 2014
First published
02 Jan 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 1979-1985
Article type
Edge Article

Chemiluminescent probes for imaging H2S in living animals

J. Cao, R. Lopez, J. M. Thacker, J. Y. Moon, C. Jiang, S. N. S. Morris, J. H. Bauer, P. Tao, R. P. Mason and A. R. Lippert, Chem. Sci., 2015, 6, 1979
DOI: 10.1039/C4SC03516J

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