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, andCHS-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 applyingCHS-3to detect cellularly generated H2S using a multi-well plate reader and to image H2S in living mice using CCD camera technology.
authors.affiliation: Department of Chemistry, Southern Methodist University, Dallas, TX 75275-0314, USA ; Center for Drug Discovery, Design, and Delivery (CD4), Southern Methodist University, Dallas, TX 75275-0314, USA.
authors.forename: J
authors.initials: J
authors.lastname: Cao
authors.affiliation: Laboratory of Prognostic Radiology, Pre-clinical Imaging Section, Department of Radiology, UT Southwestern Medical Center, Dallas, TX 75390-9058, USA.
authors.forename: R
authors.initials: R
authors.lastname: Lopez
authors.affiliation: Department of Chemistry, Southern Methodist University, Dallas, TX 75275-0314, USA.
authors.forename: J M
authors.initials: JM
authors.lastname: Thacker
authors.affiliation: Department of Chemistry, Southern Methodist University, Dallas, TX 75275-0314, USA.
authors.forename: J Y
authors.initials: JY
authors.lastname: Moon
authors.affiliation: Hockaday School, Dallas, TX 75229, USA.
authors.forename: C
authors.initials: C
authors.lastname: Jiang
authors.affiliation: Department of Biological Sciences, Southern Methodist University, Dallas, TX 75275-0314, USA.
authors.forename: S N S
authors.initials: SN
authors.lastname: Morris
authors.affiliation: Center for Drug Discovery, Design, and Delivery (CD4), Southern Methodist University, Dallas, TX 75275-0314, USA ; Department of Biological Sciences, Southern Methodist University, Dallas, TX 75275-0314, USA.
authors.forename: J H
authors.initials: JH
authors.lastname: Bauer
authors.affiliation: Department of Chemistry, Southern Methodist University, Dallas, TX 75275-0314, USA ; Center for Drug Discovery, Design, and Delivery (CD4), Southern Methodist University, Dallas, TX 75275-0314, USA.
authors.forename: P
authors.initials: P
authors.lastname: Tao
authors.affiliation: Laboratory of Prognostic Radiology, Pre-clinical Imaging Section, Department of Radiology, UT Southwestern Medical Center, Dallas, TX 75390-9058, USA.
authors.forename: R P
authors.initials: RP
authors.lastname: Mason
authors.affiliation: Department of Chemistry, Southern Methodist University, Dallas, TX 75275-0314, USA ; Center for Drug Discovery, Design, and Delivery (CD4), Southern Methodist University, Dallas, TX 75275-0314, USA.
authors.forename: A R
authors.initials: AR
authors.lastname: Lippert