Phidianidine A and Synthetic Analogues as Naturally Inspired Marine Antifoulants

Type Article
Date 2020-11
Language English
Author(s) Labriere Christophe1, Elumalai Vijayaragavan1, Staffansson Jannie1, Cervin Gunnar2, Le Norcy Tiffany3, Denardou Hugo1, Réhel Karine3, Moodie Lindon W. K.4, Hellio Claire5, Pavia Henrik2, Hansen Jørn H.1, Svenson Johan1, 6
Affiliation(s) 1 : Department of Chemistry, Chemical Synthesis and Analysis Group, UiT The Arctic University of Norway, N-9037 Tromsø, Norway
2 : Department of Marine Sciences, Tjärnö Marine Laboratory, University of Gothenburg, SE-452 96 Strömstad, Sweden
3 : Univ. Bretagne-Sud, EA 3884, LBCM, IUEM, F-56100 Lorient, France
4 : Department of Medicinal Chemistry and Uppsala Antibiotic Centre, Biomedical Centre, Uppsala University, 75123 Uppsala, Sweden
5 : Univ. Brest, Laboratoire des Sciences de l’Environnement MARin (LEMAR), CNRS, IRD, IFREMER, Brest 29285, France
6 : Department of Chemistry, Biomaterial & Textile, RISE Research Institutes of Sweden, Box 857, 501 15 Borås, Sweden
Source Journal Of Natural Products (0163-3864) (American Chemical Society (ACS)), 2020-11 , Vol. 83 , N. 11 , P. 3413-3423
DOI 10.1021/acs.jnatprod.0c00881
WOS© Times Cited 2
Abstract

Stationary and slow-moving marine organisms regularly employ a natural product chemical defense to prevent being colonized by marine micro- and macroorganisms. While these natural antifoulants can be structurally diverse, they often display highly conserved chemistries and physicochemical properties, suggesting a natural marine antifouling pharmacophore. In our current report, we investigate the marine natural product phidianidine A, which displays several chemical properties found in highly potent marine antifoulants. Phidianidine A and synthetic analogues were screened against the settlement and metamorphosis of Amphibalanus improvisus cyprids, and several of the compounds displayed inhibitory activities at low micromolar concentrations with IC50 values down to 0.7 μg/mL observed. The settlement study highlights that phidianidine A is a potent natural antifoulant and that the scaffold can be tuned to generate simpler and improved synthetic analogues. The bioactivity is closely linked to the size of the compound and to its basicity. The study also illustrates that active analogues can be prepared in the absence of the natural constrained 1,2,4-oxadiazole ring. A synthetic lead analogue of phidianidine A was incorporated in a coating and included in antifouling field trials, where it was shown that the coating induced potent inhibition of marine bacteria and microalgae settlement.

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Labriere Christophe, Elumalai Vijayaragavan, Staffansson Jannie, Cervin Gunnar, Le Norcy Tiffany, Denardou Hugo, Réhel Karine, Moodie Lindon W. K., Hellio Claire, Pavia Henrik, Hansen Jørn H., Svenson Johan (2020). Phidianidine A and Synthetic Analogues as Naturally Inspired Marine Antifoulants. Journal Of Natural Products, 83(11), 3413-3423. Publisher's official version : https://doi.org/10.1021/acs.jnatprod.0c00881 , Open Access version : https://archimer.ifremer.fr/doc/00655/76683/