biostudies-literatureChen JU.S. Department of Health and Human ServicesNIA NIH HHSBaylor College of MedicineWelch FoundationNIGMS NIH HHSCancer Prevention and Research Institute of Texas5978-5981https://www.ebi.ac.uk/biostudies/studies/S-EPMC4727754biostudies-literatureUnknown17(24)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.Organic lettersTheoretical 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.PMC4727754R01 AG045183R01 GM115622Q-1798R01-GM115622R1104Chen JHuang JJiang XCarroll SWang JfalseTheoretical 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.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.2015-01-01T00:00:00Z2015 Dec2025-04-26T00:59:04.824Z2019-03-27T02:07:35ZS-EPMC47277542660617110.1021/acs.orglett.5b02910