Structure-based optimization of a peptidyl inhibitor against calcineurin-nuclear factor of activated T cell (NFAT) interaction

J Med Chem. 2014 Sep 25;57(18):7792-7. doi: 10.1021/jm500743t. Epub 2014 Sep 4.

Abstract

Calcineurin inhibitors such as cyclosporine A and FK506 are effective immunosuppressants but produce severe side effects. Rational modification of a previously reported peptide inhibitor, GPHPVIVITGPHEE (KD ∼ 500 nM), by replacing the two valine residues with tert-leucine and the C-terminal proline with a cis-proline analogue, gave an improved inhibitor ZIZIT-cisPro, which binds to calcineurin with a KD value of 2.6 nM and is more resistant to proteolysis.

Publication types

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

MeSH terms

  • Active Transport, Cell Nucleus / drug effects
  • Amino Acid Sequence
  • Amino Acid Substitution
  • Binding Sites
  • Calcineurin / metabolism*
  • Calcineurin Inhibitors / blood
  • Calcineurin Inhibitors / chemistry*
  • Calcineurin Inhibitors / pharmacology*
  • Cell Nucleus / drug effects
  • Cell Nucleus / metabolism
  • Drug Stability
  • HeLa Cells
  • Humans
  • Models, Molecular
  • NFATC Transcription Factors / metabolism*
  • Peptides / blood
  • Peptides / chemistry*
  • Peptides / pharmacology*
  • Protein Binding
  • Protein Conformation
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Calcineurin Inhibitors
  • NFATC Transcription Factors
  • Peptides
  • Calcineurin