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, A. R. Lippert

Research output: Contribution to journalArticle

72 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1979-1985
Number of pages7
JournalChemical Science
Volume6
Issue number3
DOIs
StatePublished - Mar 1 2015

ASJC Scopus subject areas

  • Chemistry(all)

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    Cao, J., Lopez, R., Thacker, J. M., Moon, J. Y., Jiang, C., Morris, S. N. S., Bauer, J. H., Tao, P., Mason, R. P., & Lippert, A. R. (2015). Chemiluminescent probes for imaging H2S in living animals. Chemical Science, 6(3), 1979-1985. https://doi.org/10.1039/c4sc03516j