title: Theoretical and Experimental Investigation of Thermodynamics and Kinetics of Thiol-Michael Addition Reactions: A Case Study of Reversible Fluorescent Probes for Glutathione Imaging in Single Cells.
abstract: Density functional theory (DFT) was applied to study the thermodynamics and kinetics of reversible thiol-Michael addition reactions. M06-2X/6-31G(d) with the SMD solvation model can reliably predict the Gibbs free energy changes (ΔG) of thiol-Michael addition reactions with an error of less than 1 kcal·mol(-1) compared with the experimental benchmarks. Taking advantage of this computational model, the first reversible reaction-based fluorescent probe was developed that can monitor the changes in glutathione levels in single living cells.
authors.affiliation: Department of Pharmacology, Dan L. Duncan Cancer Center, and Cardiovascular Research Institute, Baylor College of Medicine, Houston, TX 77030.
authors.forename: Jianwei
authors.initials: J
authors.lastname: Chen
authors.affiliation: Department of Pharmacology, Dan L. Duncan Cancer Center, and Cardiovascular Research Institute, Baylor College of Medicine, Houston, TX 77030.
authors.forename: Xiqian
authors.initials: X
authors.lastname: Jiang
authors.affiliation: Department of Pharmacology, Dan L. Duncan Cancer Center, and Cardiovascular Research Institute, Baylor College of Medicine, Houston, TX 77030.|Department of Chemistry, Rice University, Houston, TX 77251.
authors.forename: Shaina
authors.initials: S
authors.lastname: Carroll
authors.affiliation: Sciclotron LLC. Sugar Land, TX 77479.
authors.forename: Jia
authors.initials: J
authors.lastname: Huang
authors.affiliation: Department of Pharmacology, Dan L. Duncan Cancer Center, and Cardiovascular Research Institute, Baylor College of Medicine, Houston, TX 77030.|Center for Drug Discovery, Dan L. Duncan Cancer Center, and Cardiovascular Research Institute, Baylor College of Medicine, Houston, TX 77030.
authors.forename: Jin
authors.initials: J
authors.lastname: Wang
mesh_terms: D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D005978:Glutathione / Q000032:analysis*; D006367:HeLa Cells; D006801:Humans; D007700:Kinetics; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D005456:Fluorescent Dyes; D013438:Sulfhydryl Compounds; D005978:Glutathione