Arginine-based structures are specific inhibitors of cathepsin C. Application of peptide combinatorial libraries

Eur J Biochem. 2000 Jun;267(11):3330-6. doi: 10.1046/j.1432-1327.2000.01364.x.

Abstract

Novel synthetic peptide inhibitors of lysosomal cysteine proteinase cathepsin C have been designed through the use of soluble peptide combinatorial libraries. The uncovered structural inhibitory module consists of the N-terminal cluster of L-arginine residues. Its modification with D-amino acids or arginine derivatives did not increase the inhibition strength. Inhibitory potency of oligoarginines improves with the elongation of peptide chain reaching a maximum for octa-L-arginine. The oligoarginines specifically interact with the cathepsin C active site as shown by competitive-type inhibition kinetics (Ki approximately 10-5 M) and intrinsic fluorescence measurements. The inhibitory interaction of oligoarginines is established through the specific spatial contact of a net of guanidino groups in the arginine side-chains, as indicated by comparison with inhibitory action of low molecular mass guanidine derivatives (Ki approximately 10-3 M). Nonarginine polyionic compounds cannot mimic the inhibitory effect of oligoarginines. The arginine-based peptide inhibitors were selective towards cathepsin C among other cysteine proteinases tested.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arginine / chemistry*
  • Binding Sites / drug effects
  • Cathepsin C / antagonists & inhibitors*
  • Cattle
  • Combinatorial Chemistry Techniques
  • Cysteine Proteinase Inhibitors / chemistry*
  • Cysteine Proteinase Inhibitors / pharmacology
  • Drug Design
  • Peptides / pharmacology*
  • Structure-Activity Relationship

Substances

  • Cysteine Proteinase Inhibitors
  • Peptides
  • polyarginine
  • Arginine
  • Cathepsin C