Macrocyclic inhibitors of HCV NS3 protease

Expert Opin Ther Pat. 2009 Sep;19(9):1277-303. doi: 10.1517/13543770903044994.

Abstract

Background: HCV NS3 is a serine protease that plays a pivotal role in catalyzing the cleavage of the single polyprotein encoded by HCV after infection of hepatocytes. Analysis of the X-ray crystal structure of the enzyme reveals a shallow catalytic site located on the surface of the protein, which has made development of inhibitors a formidable task. Attempts to discover leads by a traditional approach of screening of compound libraries have proved futile and, therefore, researchers have adopted a structure-based drug design. Analysis of the X-ray structure of NS3 protease reveals close proximity of S(1)-S(3) and S(2)-S(4) pockets. Various novel approaches have been used to design preorganized, depeptidized macrocyclic inhibitors linking the P(2)-P(4) groups and P(1)-P(3) residues.

Objective: The article summarizes efforts by various groups to develop inhibitors that bind to the active site and inhibit viral replication.

Method: Review of recent patents and scientific literature.

Conclusion: Macrocyclization has proved to be an effective tool for depeptidization of peptidic inhibitors with improved binding and pharmacokinetic properties.

Publication types

  • Review

MeSH terms

  • Animals
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Binding Sites
  • Drug Design
  • Hepacivirus / enzymology
  • Humans
  • Macrocyclic Compounds / chemistry
  • Macrocyclic Compounds / pharmacology*
  • Patents as Topic
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology
  • Protein Binding
  • Viral Nonstructural Proteins / antagonists & inhibitors*
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Macrocyclic Compounds
  • NS3 protein, hepatitis C virus
  • Protease Inhibitors
  • Viral Nonstructural Proteins