A novel molecule with notable activity against multi-drug resistant tuberculosis

Bioorg Med Chem Lett. 2015 Mar 15;25(6):1269-73. doi: 10.1016/j.bmcl.2015.01.050. Epub 2015 Jan 28.

Abstract

Multi-drug resistant tuberculosis (MDR-TB) is emerging as a serious global health problem, which has been elevated through co-infection involving HIV and MDR-Mtb. The discovery of new compounds with anti-MDR TB efficacy and favorable metabolism profiles is an important scientific challenge. Using computational biology and ligand docking data, we have conceived a multifunctional molecule, 2, as a potential anti-MDR TB agent. This compound was produced through a multi-step synthesis. It exhibited significant in vitro activity against MDR-TB (MIC 1.56μg/mL) and its half-life (t1/2) in human liver microsomes was 14.4h. The metabolic profiles of compound 2 with respect to human cytochrome P450 (CYP) and uridine 5'-diphospho-glucuronosyltransferase (UGT) isozymes were favorable. Compound 2 also had relatively low in vitro cytotoxicity in uninfected macrophages. It displayed synergistic behavior against MDR-TB in combination with PA-824. Interestingly, compound 2 also displayed in vitro anti-HIV activity.

Keywords: Anti-MDR TB; CYP and UGT profiles; Drug discovery; Synergism.

Publication types

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

MeSH terms

  • Antitubercular Agents / chemical synthesis
  • Antitubercular Agents / chemistry*
  • Antitubercular Agents / pharmacology
  • Cytochrome P-450 Enzyme System / chemistry
  • Cytochrome P-450 Enzyme System / metabolism
  • Drug Design
  • Drug Synergism
  • Glucuronosyltransferase / chemistry
  • Glucuronosyltransferase / metabolism
  • Half-Life
  • Humans
  • Microbial Sensitivity Tests
  • Microsomes, Liver / metabolism
  • Mycobacterium tuberculosis / drug effects
  • Nitroimidazoles / pharmacology
  • Piperazines / chemical synthesis
  • Piperazines / chemistry*
  • Piperazines / pharmacology
  • Pyridones / chemical synthesis
  • Pyridones / chemistry*
  • Pyridones / pharmacology
  • Tuberculosis, Multidrug-Resistant

Substances

  • 1-(4-(4-(1H-pyrrol-1-yl)phenyl)piperazin-1-yl)-4-(5-(3,5-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxybut-2-ene-1,4-dione
  • Antitubercular Agents
  • Nitroimidazoles
  • Piperazines
  • Pyridones
  • pretomanid
  • Cytochrome P-450 Enzyme System
  • Glucuronosyltransferase