Evaluation of potential genotoxicity of HIV entry inhibitors derived from natural sources

PLoS One. 2014 Mar 25;9(3):e93108. doi: 10.1371/journal.pone.0093108. eCollection 2014.

Abstract

AIDS is a global pandemic that has seen the development of novel and effective treatments to improve the quality of life of those infected and reduction of spread of the disease. Palmitic Acid (PA), which we identified and isolated from Sargassum fusiforme, is a naturally occurring fatty acid that specifically inhibits HIV entry by binding to a novel pocket on the CD4 receptor. We also identified a structural analogue, 2-bromopalmitate (2-BP), as a more effective HIV entry inhibitor with a 20-fold increase in efficacy. We have used the structure-activity relationship (SAR) of 2-BP as a platform to identify new small chemical molecules that fit into the various identified active sites in an effort to identify more potent CD4 entry inhibitors. To validate further drug development, we tested the PA and 2-BP scaffold molecules for genotoxic potential. The FDA and International Conference on Harmonisation (ICH) recommends using a standardized 3-test battery for testing compound genotoxicity consisting of the bacterial reverse mutation assay, mouse lymphoma assay, and rat micronucleus assay. PA and 2-BP and their metabolites tested negative in all three genotoxicty tests. 2-BP is the first derivative of PA to undergo pre-clinical screening, which will enable us to now test multiple simultaneous small chemical structures based on activity in scaffold modeling across the dimension of pre-clinical testing to enable transition to human testing.

Publication types

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

MeSH terms

  • Animals
  • Biological Products / chemistry*
  • Biological Products / pharmacology
  • Biological Products / toxicity*
  • Drug Discovery
  • Female
  • HIV / drug effects*
  • HIV / physiology*
  • HIV Fusion Inhibitors / chemistry*
  • HIV Fusion Inhibitors / pharmacology
  • HIV Fusion Inhibitors / toxicity*
  • Lymphoma / pathology
  • Male
  • Mice
  • Micronucleus Tests
  • Palmitates / chemistry
  • Palmitates / pharmacology
  • Palmitates / toxicity
  • Palmitic Acid / chemistry
  • Palmitic Acid / pharmacology
  • Palmitic Acid / toxicity
  • Rats
  • Salmonella typhimurium / drug effects
  • Salmonella typhimurium / genetics
  • Structure-Activity Relationship
  • Virus Internalization / drug effects*

Substances

  • Biological Products
  • HIV Fusion Inhibitors
  • Palmitates
  • 2-bromopalmitate
  • Palmitic Acid