caa a22 4500 445318120 CHVBK 20180317142654.0 cr unu---uuuuu 170323e20111201xx s 000 0 eng 10.1007/s10126-011-9378-3 doi (NATIONALLICENCE)springer-10.1007/s10126-011-9378-3 Antifouling Bastadin Congeners Target Mussel Phenoloxidase and Complex Copper(II) Ions [Elektronische Daten] [Mirko Bayer, Claire Hellio, Jean-Philippe Maréchal, Walter Frank, Wenhan Lin, Horst Weber, Peter Proksch] 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 0.84μM. 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. Springer Science+Business Media, LLC, 2011 Phenoloxidase nationallicence Antifouling nationallicence Bastadin nationallicence 5,5′-Dibromohemibastadin-1 nationallicence X-ray nationallicence Copper(II) nationallicence Bayer Mirko Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany aut Hellio Claire School of Biological Sciences, King Henry Building, Portsmouth University, PO1 2DY, Portsmouth, UK aut Maréchal Jean-Philippe School of Biological Sciences, King Henry Building, Portsmouth University, PO1 2DY, Portsmouth, UK aut Frank Walter Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany aut Lin Wenhan State Key Laboratory of Natural and Biomimetic Drugs, Peking University, No. 38 Xue Yuan Road, 100083, Beijing, People's Republic of China aut Weber Horst Institut für Pharmazeutische und Medizinische Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany aut Proksch Peter Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany aut Marine Biotechnology Springer-Verlag 13/6(2011-12-01), 1148-1158 1436-2228 13:6<1148 2011 13 10126 https://doi.org/10.1007/s10126-011-9378-3 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10126-011-9378-3 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Bayer Mirko Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany aut NATIONALLICENCE 700 1- Hellio Claire School of Biological Sciences, King Henry Building, Portsmouth University, PO1 2DY, Portsmouth, UK aut NATIONALLICENCE 700 1- Maréchal Jean-Philippe School of Biological Sciences, King Henry Building, Portsmouth University, PO1 2DY, Portsmouth, UK aut NATIONALLICENCE 700 1- Frank Walter Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany aut NATIONALLICENCE 700 1- Lin Wenhan State Key Laboratory of Natural and Biomimetic Drugs, Peking University, No. 38 Xue Yuan Road, 100083, Beijing, People's Republic of China aut NATIONALLICENCE 700 1- Weber Horst Institut für Pharmazeutische und Medizinische Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany aut NATIONALLICENCE 700 1- Proksch Peter Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany aut NATIONALLICENCE 773 0- Marine Biotechnology Springer-Verlag 13/6(2011-12-01), 1148-1158 1436-2228 13:6<1148 2011 13 10126 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer