Antifouling bastadin congeners target blue mussel phenoloxidase and complex copper(II) ions

M. Bayer, Claire Hellio, J-P. Marechal, W. Lin, W. Frank, H. Weber, P. Proksch

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Abstract

Synthetically prepared congeners of sponge-derived bastadin derivatives such as 5,5′-dibromohemibastadin-1 (DBHB) that suppress the settling of barnacle larvae were identified in this study as strong inhibitors of blue mussel phenoloxidase that is involved in the firm attachment of mussels to a given substrate. The IC50 value of DBHB as the most active enzyme inhibitor encountered in this study amounts to 0.84 μM. Inhibition of phenoloxidase by DBHB is likely due to complexation of copper(II) ions from the catalytic centre of the enzyme by the α-oxo-oxime moiety of the compound as shown here for the first time by structure activity studies and by X-ray structure determination of a copper(II) complex of DBHB.
Original languageEnglish
Pages (from-to)1148-1158
Number of pages11
JournalMarine Biotechnology
Volume13
Issue number6
DOIs
Publication statusPublished - Dec 2011

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