FN Archimer Export Format PT J TI Phidianidine A and Synthetic Analogues as Naturally Inspired Marine Antifoulants BT AF 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 AS 1:1;2:1;3:1;4:2;5:3;6:1;7:3;8:4;9:5;10:2;11:1;12:1,6; FF 1:;2:;3:;4:;5:;6:;7:;8:;9:;10:;11:;12:; C1 Department of Chemistry, Chemical Synthesis and Analysis Group, UiT The Arctic University of Norway, N-9037 Tromsø, Norway Department of Marine Sciences, Tjärnö Marine Laboratory, University of Gothenburg, SE-452 96 Strömstad, Sweden Univ. Bretagne-Sud, EA 3884, LBCM, IUEM, F-56100 Lorient, France Department of Medicinal Chemistry and Uppsala Antibiotic Centre, Biomedical Centre, Uppsala University, 75123 Uppsala, Sweden Univ. Brest, Laboratoire des Sciences de l’Environnement MARin (LEMAR), CNRS, IRD, IFREMER, Brest 29285, France Department of Chemistry, Biomaterial & Textile, RISE Research Institutes of Sweden, Box 857, 501 15 Borås, Sweden C2 UNIV ARCTIC UIT NORWAY, NORWAY UNIV GOTHENBURG, SWEDEN UBS, FRANCE UNIV UPPSALA, SWEDEN UBO, FRANCE RISE, SWEDEN UM LEMAR IN WOS Cotutelle UMR copubli-france copubli-europe copubli-univ-france IF 4.05 TC 24 UR https://archimer.ifremer.fr/doc/00655/76683/77813.pdf https://archimer.ifremer.fr/doc/00655/76683/77814.pdf LA English DT Article AB 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. PY 2020 PD NOV SO Journal Of Natural Products SN 0163-3864 PU American Chemical Society (ACS) VL 83 IS 11 UT 000595546200024 BP 3413 EP 3423 DI 10.1021/acs.jnatprod.0c00881 ID 76683 ER EF