Structure-guided optimization of small molecules inhibiting human immunodeficiency virus 1 Tat association with the human coactivator p300/CREB binding protein-associated factor

J Med Chem. 2007 May 17;50(10):2285-8. doi: 10.1021/jm070014g. Epub 2007 Apr 20.

Abstract

Human immunodeficiency virus 1 (HIV-1) trans-activator Tat recruits the human transcriptional coactivator PCAF (p300/CREB binding protein-associated factor) to facilitate transcription of the integrated HIV-1 provirus. We report here structure-based lead optimization of small-molecule inhibitors that block selectively Tat and PCAF association in cells. Our lead optimization was guided by grand-canonical ensemble simulation of the receptor/lead complex that leads to definition of chemical modifications with improved lead affinity through displacing weakly bound water molecules at the ligand-receptor interface.

Publication types

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

MeSH terms

  • Cell Cycle Proteins / chemistry*
  • Cell Cycle Proteins / metabolism
  • Gene Products, tat / chemistry*
  • Gene Products, tat / genetics
  • Gene Products, tat / metabolism
  • Genes, Reporter
  • HIV Long Terminal Repeat
  • HIV-1 / genetics
  • HIV-1 / metabolism*
  • Histone Acetyltransferases / chemistry*
  • Histone Acetyltransferases / metabolism
  • Humans
  • Ligands
  • Luciferases / genetics
  • Luciferases / metabolism
  • Models, Molecular*
  • Monte Carlo Method
  • Promoter Regions, Genetic
  • Propylamines / chemistry*
  • Propylamines / pharmacology
  • Protein Structure, Tertiary
  • Transcription Factors / chemistry*
  • Transcription Factors / metabolism
  • Transcription, Genetic
  • Water / chemistry
  • p300-CBP Transcription Factors
  • tat Gene Products, Human Immunodeficiency Virus

Substances

  • Cell Cycle Proteins
  • Gene Products, tat
  • Ligands
  • Propylamines
  • Transcription Factors
  • tat Gene Products, Human Immunodeficiency Virus
  • Water
  • Luciferases
  • Histone Acetyltransferases
  • p300-CBP Transcription Factors
  • p300-CBP-associated factor