An alpha-helical peptidomimetic inhibitor of the HIV-1 Rev-RRE interaction

J Am Chem Soc. 2006 Mar 22;128(11):3496-7. doi: 10.1021/ja0582051.

Abstract

The interaction between the HIV-1 Rev protein and the Rev-Responsive Element (RRE) RNA is an attractive target for anti-viral therapy. We have designed alpha-helical peptidomimetics of Rev-like peptides using side chain-side chain macrolactam formation between positions i and i+4. One peptidomimetic having an appropriate location, orientation, and length of the macrolactam exhibited both significant helical character and specific RRE binding. This molecule displays 2-fold greater RNA specificity than the wild-type Rev peptide and more than 20-fold greater specificity than an uncyclized control peptide. Thus, specific, high affinity recognition of the RRE is feasible utilizing a small, relatively rigid peptidomimetic scaffold.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / metabolism
  • Anti-HIV Agents / pharmacology
  • Biomimetic Materials / chemistry
  • Biomimetic Materials / metabolism
  • Biomimetic Materials / pharmacology
  • Circular Dichroism
  • Gene Products, rev / antagonists & inhibitors*
  • Gene Products, rev / genetics
  • Gene Products, rev / metabolism
  • Genes, env*
  • HIV-1 / genetics*
  • HIV-1 / metabolism
  • Molecular Sequence Data
  • Oligopeptides / chemistry*
  • Oligopeptides / metabolism
  • Oligopeptides / pharmacology*
  • Protein Structure, Secondary
  • RNA, Viral / genetics
  • RNA, Viral / metabolism
  • rev Gene Products, Human Immunodeficiency Virus

Substances

  • Anti-HIV Agents
  • Gene Products, rev
  • Oligopeptides
  • RNA, Viral
  • rev Gene Products, Human Immunodeficiency Virus