Design, synthesis, and evaluation of inhibitors of cathepsin L: Exploiting a unique thiocarbazate chemotype

Bioorg Med Chem Lett. 2008 Jun 15;18(12):3646-51. doi: 10.1016/j.bmcl.2008.04.065. Epub 2008 May 1.

Abstract

Recently, we identified a thiocarbazate that exhibits potent inhibitory activity against human cathepsin L. Since this structure represents a novel chemotype with potential for activity against the entire cysteine protease family, we designed, synthesized, and assayed a series of analogs to probe the mechanism of action, as well as the structural requirements for cathepsin L activity. Molecular docking studies using coordinates of a papain-inhibitor complex as a model for cathepsin L provided useful insights.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Binding Sites
  • Cathepsin L
  • Cathepsins / antagonists & inhibitors*
  • Crystallography, X-Ray
  • Cysteine Endopeptidases
  • Cysteine Proteinase Inhibitors* / chemical synthesis
  • Cysteine Proteinase Inhibitors* / chemistry
  • Cysteine Proteinase Inhibitors* / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Design
  • Drug Evaluation, Preclinical
  • Humans
  • Hydrazines* / chemical synthesis
  • Hydrazines* / chemistry
  • Hydrazines* / pharmacology
  • Inhibitory Concentration 50
  • Models, Molecular
  • Molecular Structure
  • Papain / antagonists & inhibitors
  • Papain / chemistry
  • Structure-Activity Relationship
  • Sulfhydryl Compounds* / chemical synthesis
  • Sulfhydryl Compounds* / chemistry
  • Sulfhydryl Compounds* / pharmacology

Substances

  • Cysteine Proteinase Inhibitors
  • Hydrazines
  • Sulfhydryl Compounds
  • carbazic acid
  • Cathepsins
  • Cysteine Endopeptidases
  • CTSL protein, human
  • Cathepsin L
  • Papain