Small-molecule inactivation of HIV-1 NCp7 by repetitive intracellular acyl transfer

Nat Chem Biol. 2010 Dec;6(12):887-9. doi: 10.1038/nchembio.456. Epub 2010 Oct 17.

Abstract

The zinc fingers of the HIV-1 nucleocapsid protein, NCp7, are prime targets for antiretroviral therapeutics. Here we show that S-acyl-2-mercaptobenzamide thioester (SAMT) chemotypes inhibit HIV by modifying the NCp7 region of Gag in infected cells, thereby blocking Gag processing and reducing infectivity. The thiol produced by SAMT reaction with NCp7 is acetylated by cellular enzymes to regenerate active SAMTs via a recycling mechanism unique among small-molecule inhibitors of HIV.

Publication types

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

MeSH terms

  • Acetylation
  • Acylation
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Benzamides / chemistry
  • Benzamides / pharmacology*
  • Genes, gag / genetics
  • Molecular Sequence Data
  • Small Molecule Libraries
  • Zinc Fingers / drug effects
  • gag Gene Products, Human Immunodeficiency Virus / antagonists & inhibitors*

Substances

  • Anti-HIV Agents
  • Benzamides
  • NCP7 protein, Human immunodeficiency virus 1
  • S-acyl-2-mercaptobenzamide thioester
  • Small Molecule Libraries
  • gag Gene Products, Human Immunodeficiency Virus

Associated data

  • PubChem-Substance/99351096
  • PubChem-Substance/99351097
  • PubChem-Substance/99351098
  • PubChem-Substance/99351099
  • PubChem-Substance/99351100
  • PubChem-Substance/99351101
  • PubChem-Substance/99351102
  • PubChem-Substance/99351103
  • PubChem-Substance/99351104
  • PubChem-Substance/99351105
  • PubChem-Substance/99351106
  • PubChem-Substance/99351107
  • PubChem-Substance/99351108
  • PubChem-Substance/99351109