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Twelve new Cyclophostin and Cyclipostins analogues ( CyC   19 - 30  ) were synthesized, thus extending our series to 38 CyCs . Their antibacterial activities were evaluated against four pathogenic mycobacteria ( Mycobacterium abscessus , Mycobacterium marinum , Mycobacterium bovis BCG, and Mycobacterium tuberculosis ) and two Gram negative bacteria. The CyCs displayed very low toxicity toward host cells and were only active against mycobacteria. Importantly, several CyCs were active against extracellular M. abscessus ( CyC   17  / CyC   18β  / CyC   25  / CyC   26  ) or intramacrophage residing mycobacteria ( CyC   7(α,β)  / CyC   8(α,β)  ) with minimal inhibitory concentrations (MIC 50 ) values comparable to or better than those of amikacin or imipenem, respectively. An activity-based protein profiling combined with mass spectrometry allowed identification of the potential target enzymes of CyC   17  / CyC   26  , mostly being involved in lipid metabolism and/or in cell wall biosynthesis. Overall, these results strengthen the selective activity of the CyCs against mycobacteria, including the most drug-resistan M. abscessus , through the cumulative inhibition of a large number of Ser- and Cys-enzymes participating in key physiological processes.

Cyclipostins and Cyclophostin Analogues as Multitarget Inhibitors That Impair Growth of Mycobacterium abscessus