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Design and synthesis of C10 modified and ring-truncated canthin-6-one analogues as effective membrane-active antibacterial agents.

Abstract：

:A series of canthin-6-one analogues were designed and synthesized in order to study their antibacterial activity and structure-activity relationships. Compound 22 showed a broad spectrum of antibacterial activity and exhibited better bactericidal effect (8-fold superiority against Staphylococcus aureus and 2-fold superiority against Ralstonia solanacearum) than fosfomycin sodium and propineb with a minimum inhibitory concentration value of 2 μg/mL. Moreover, it showed low cytotoxicity, stimulation on germination rates and good "drug-like" properties. Membrane-active mechanism was further studied by fluorescent microscopy, scanning electron microscopy, cytoplasmic β-galactosidase leakage assay and evaluation of the molecular docking. The results showed that 22 may exert its bactericidal effect by damaging bacterial cell membranes and influencing the membrane formation, both of which could lead to cell death. The in vivo antibacterial assay with a protective efficacy of 68% demonstrated the potential of C ring-truncated canthin-6-one 22 as a new bactericide.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Dai J,Dan W,Zhang Y,He M,Wang J

doi

10.1016/j.bmcl.2018.06.001

subject

Has Abstract

pub_date

2018-10-01 00:00:00

pages

3123-3128

issue

18

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(18)30478-5

journal_volume

28

pub_type

杂志文章

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