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

doi:10.1039/c4sc03516j

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

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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.

Original language	English (US)
Pages (from-to)	1979-1985
Number of pages	7
Journal	Chemical Science
Volume	6
Issue number	3
DOIs	https://doi.org/10.1039/c4sc03516j
State	Published - Mar 1 2015

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General Chemistry

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title = "Chemiluminescent probes for imaging H2S in living animals",

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.",

author = "J. Cao and R. Lopez and Thacker, {J. M.} and Moon, {J. Y.} and C. Jiang and Morris, {S. N S} and Bauer, {J. H.} and P. Tao and Mason, {R. P.} and Lippert, {A. R.}",

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AU - Cao, J.

AU - Lopez, R.

AU - Thacker, J. M.

AU - Moon, J. Y.

AU - Jiang, C.

AU - Morris, S. N S

AU - Bauer, J. H.

AU - Tao, P.

AU - Mason, R. P.

AU - Lippert, A. R.

PY - 2015/3/1

Y1 - 2015/3/1

N2 - 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.

AB - 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.

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JO - Chemical Science

JF - Chemical Science

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Chemiluminescent probes for imaging H₂S in living animals

Abstract

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