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Issue 110, 2016
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Synthesis, characterization and biological activity of fluorescently labeled bedaquiline analogues

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Abstract

Diarylquinolines represent a new class of antibiotics with high potency against Mycobacterium tuberculosis. As such, they are of utmost importance in the treatment of drug-resistant bacterial pathogens. In this work, we report a strategy for preparing fluorescently labeled derivatives of the FDA-approved diarylquinoline-based tuberculosis drug bedaquiline. The labeled compounds were capable of blocking bacterial growth and interfered with the function of ATP synthase, the cellular target of diarylquinolines. This indicates that the chosen labeling strategy does not preclude the antibacterial activity of bedaquiline, and allowed us to investigate the effect of labeling on drug recognition by bacterial efflux pumps in living M. tuberculosis strains. These properties, coupled with the efficient fluorescence of the attached BODIPY fluorophore means that these compounds can be used as a research tool to gain deeper understanding into the mechanism of action of this class of drugs.

Graphical abstract: Synthesis, characterization and biological activity of fluorescently labeled bedaquiline analogues

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Publication details

The article was received on 11 Sep 2016, accepted on 01 Nov 2016 and first published on 02 Nov 2016


Article type: Paper
DOI: 10.1039/C6RA22693K
Citation: RSC Adv., 2016,6, 108708-108716
  • Open access: Creative Commons BY-NC license
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    Synthesis, characterization and biological activity of fluorescently labeled bedaquiline analogues

    J. A. Rombouts, Richard M. P. Veenboer, C. Villellas, P. Lu, A. W. Ehlers, K. Andries, A. Koul, H. Lill, E. Ruijter, R. V. A. Orru, K. Lammertsma, D. Bald and J. C. Slootweg, RSC Adv., 2016, 6, 108708
    DOI: 10.1039/C6RA22693K

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