Introduction of Intrinsic Kinetics of Protein–Ligand Interactions and Their Implications for Drug Design

Journal of Medicinal Chemistry
2018.0

Abstract

Structure-kinetic relationship analyses and identification of dominating interactions for optimization of lead compounds should ideally be based on intrinsic rate constants instead of the more easily accessible observed kinetic constants, which also account for binding-linked reactions. The intrinsic rate constants for sulfonamide inhibitors and pharmacologically relevant isoforms of carbonic anhydrase were determined by a novel surface plasmon resonance (SPR) biosensor-based approach, using chemodynamic analysis of binding-linked pH-dependent effects. The observed association rates ( kaobs) were pH-dependent and correlated with the fraction of deprotonated inhibitor and protonated zinc-bound water molecule. The intrinsic association rate constants ( kaintr) were pH independent and higher than kaobs. By contrast, the observed and intrinsic dissociation rate constants were identical and pH-independent, demonstrating that the observed association and dissociation mechanisms are inherently different. A model accounting for the differences between intrinsic and observed rate constants was developed, useful also for other interactions with binding-linked protonation reactions.

Knowledge Graph

Similar Paper

Introduction of Intrinsic Kinetics of Protein–Ligand Interactions and Their Implications for Drug Design
Journal of Medicinal Chemistry 2018.0
Relationships between Structure and Interaction Kinetics for HIV-1 Protease Inhibitors
Journal of Medicinal Chemistry 2002.0
Kinetic and Structural Insights into the Mechanism of Binding of Sulfonamides to Human Carbonic Anhydrase by Computational and Experimental Studies
Journal of Medicinal Chemistry 2016.0
Experimental and ‘in silico’ analysis of the effect of pH on HIV-1 protease inhibitor affinity: Implications for the charge state of the protein ionogenic groups
Bioorganic & Medicinal Chemistry 2012.0
Protein–ligand (un)binding kinetics as a new paradigm for drug discovery at the crossroad between experiments and modelling
MedChemComm 2017.0
Improved Structure−Activity Relationship Analysis of HIV-1 Protease Inhibitors Using Interaction Kinetic Data
Journal of Medicinal Chemistry 2004.0
Early Absorption and Distribution Analysis of Antitumor and Anti-AIDS Drugs:  Lipid Membrane and Plasma Protein Interactions
Journal of Medicinal Chemistry 2005.0
Characterization of human carbonic anhydrase XII stability and inhibitor binding
Bioorganic & Medicinal Chemistry 2013.0
Carbonic anhydrase inhibitors: Design, synthesis, kinetic, docking and molecular dynamics analysis of novel glycine and phenylalanine sulfonamide derivatives
Bioorganic & Medicinal Chemistry 2015.0
The binding of benzenesulfonamides to carbonic anhydrase enzyme. A molecular mechanics study and quantitative structure-activity relationships
Journal of Medicinal Chemistry 1989.0