Molecular modeling and 3D-QSAR studies on the interaction mechanism of tripeptidyl thrombin inhibitors with human alpha-thrombin

J Med Chem. 1997 Sep 12;40(19):3085-90. doi: 10.1021/jm960309m.

Abstract

The mechanism of inhibition of peptidyl inhibitors with thrombin was studied using molecular modeling, molecular mechanics, and CoMFA statistical analysis. A new procedure for the elucidation of binding conformations, BCSPL, is described and was employed to obtain the binding conformers of a series of 18 tripeptidyl thrombin inhibitors. Energetic studies and QSAR analysis of the BCSPL-derived conformers indicated a modest correlation between the calculated binding energies of the title compounds and their inhibitory activities to human alpha-thrombin. CoMFA analysis of the BCSPL alignment resulted in a satisfactory model of the thrombin active site.

Publication types

  • Comparative Study

MeSH terms

  • Antithrombins / chemistry*
  • Antithrombins / pharmacology
  • Binding Sites
  • Calorimetry
  • Computer Graphics
  • Computer Simulation
  • Crystallography, X-Ray
  • Humans
  • Kinetics
  • Models, Molecular
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology*
  • Protein Conformation*
  • Structure-Activity Relationship
  • Thermodynamics
  • Thrombin / antagonists & inhibitors*
  • Thrombin / chemistry*

Substances

  • Antithrombins
  • Oligopeptides
  • Thrombin