A microbiological assessment of novel nitrofuranylamides as anti-tuberculosis agents

J Antimicrob Chemother. 2008 Nov;62(5):1037-45. doi: 10.1093/jac/dkn307. Epub 2008 Aug 7.

Abstract

Objectives: Nitrofuranylamides (NFAs) are nitroaromatic compounds that have recently been discovered and have potent anti-tuberculosis (TB) activity. A foundational study was performed to evaluate whether this class of agents possesses microbiological properties suitable for future antimycobacterial therapy.

Methods: Five representative compounds of the NFA series were evaluated by standard microbiological assays to determine MICs, MBCs, activity against anaerobic non-replicating persistent Mycobacterium tuberculosis, post-antibiotic effects (PAEs), antibiotic synergy and the basis for resistance.

Results: The antimicrobial activity of these compounds was restricted to bacteria of the M. tuberculosis complex, and all compounds were highly active against drug-susceptible and -resistant strains of M. tuberculosis, with MICs 0.0004-0.05 mg/L. Moreover, no antagonism was observed with front-line anti-TB drugs. Activity was also retained against dormant bacilli in two in vitro low-oxygen models for M. tuberculosis persistence. A long PAE was observed, which was comparable to that of rifampicin, but superior to isoniazid and ethambutol. Spontaneous NFA-resistant mutants arose at a frequency of 10(-5)-10(-7), comparable to that for isoniazid (10(-5)-10(-6)). Some of these mutants exhibited cross-resistance to one or both of the nitroimidazoles PA-824 and OPC-67683. Cross-resistance was associated with inactivation of the reduced F(420)-deazaflavin cofactor pathway and not with inactivation of the Rv3547, the nitroreductase for PA-824 and OPC-67683.

Conclusions: Based on these studies, NFAs have many useful antimycobacterial properties applicable to TB chemotherapy and probably possess a unique mode of action that results in good activity against active and dormant M. tuberculosis. Therefore, the further development of lead compounds in this series is warranted.

Publication types

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

MeSH terms

  • Antitubercular Agents / pharmacology*
  • Drug Resistance, Bacterial
  • Drug Synergism
  • Humans
  • Microbial Sensitivity Tests
  • Microbial Viability
  • Molecular Structure
  • Mycobacterium bovis / drug effects*
  • Mycobacterium tuberculosis / drug effects*
  • Nitro Compounds / pharmacology*
  • Nitroimidazoles / pharmacology
  • Oxazoles / pharmacology
  • Polycyclic Aromatic Hydrocarbons / pharmacology*

Substances

  • Antitubercular Agents
  • Nitro Compounds
  • Nitroimidazoles
  • OPC-67683
  • Oxazoles
  • Polycyclic Aromatic Hydrocarbons