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Phidianidine A and synthetic analogues as naturally inspired marine antifoulants

Labriere, Chrostophe (author)
UiT The Arctic University of Norway, Norway,UiT Arctic Univ Norway, Dept Chem, Chem Synth & Anal Grp, N-9037 Tromso, Norway.
Elumalai, Vijayaragavan (author)
UiT The Arctic University of Norway, Norway,UiT Arctic Univ Norway, Dept Chem, Chem Synth & Anal Grp, N-9037 Tromso, Norway.
Staffansson, Jannie (author)
UiT The Arctic University of Norway, Norway,UiT Arctic Univ Norway, Dept Chem, Chem Synth & Anal Grp, N-9037 Tromso, Norway.
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Cervin, Gunnar, 1967 (author)
Gothenburg University,Göteborgs universitet,Institutionen för marina vetenskaper, Tjärnö marinlaboratoriet,Department of marine sciences, Tjärnö Marine Laboratory,University of Gothenburg, Sweden
Le Norcy, Tiffany (author)
University Bretagne-Sud, France,Univ Bretagne Sud, IUEM, LBCM, EA 3884, F-56100 Lorient, France.
Denardou, Hugo (author)
UiT The Arctic University of Norway, Norway,UiT Arctic Univ Norway, Dept Chem, Chem Synth & Anal Grp, N-9037 Tromso, Norway.
Réhel, Karine Vallée (author)
University Bretagne-Sud, France,Univ Bretagne Sud, IUEM, LBCM, EA 3884, F-56100 Lorient, France.
Moodie, Lindon W. K. (author)
Uppsala universitet,Läkemedelsdesign och läkemedelsutveckling,Uppsala Antibiotic Center,Uppsala University, Sweden
Hellio, Claire (author)
Université de Bretagne Occidentale, France,Univ Brest, Lab Sci Environm MARin LEMAR, IFREMER, CNRS,IRD, F-29285 Brest, France.
Pavia, Henrik, 1964 (author)
Gothenburg University,Göteborgs universitet,Institutionen för marina vetenskaper, Tjärnö marinlaboratoriet,Department of marine sciences, Tjärnö Marine Laboratory,University of Gothenburg, Sweden
Hansen, Jørn H. (author)
UiT The Arctic University of Norway, Norway,UiT Arctic Univ Norway, Dept Chem, Chem Synth & Anal Grp, N-9037 Tromso, Norway.
Svenson, Johan (author)
RISE,Kemi, biomaterial och textil,UiT The Arctic University of Norway, Norway,UiT Arctic Univ Norway, Dept Chem, Chem Synth & Anal Grp, N-9037 Tromso, Norway.;RISE Res Inst Sweden, Dept Chem Biomat & Text, S-50115 Borås, Sweden.
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UiT The Arctic University of Norway, Norway UiT Arctic Univ Norway, Dept Chem, Chem Synth & Anal Grp, N-9037 Tromso, Norway (creator_code:org_t)
2020-10-15
2020
English.
In: Journal of Natural Products. - : American Chemical Society. - 0163-3864 .- 1520-6025. ; 83:11, s. 3413-3423
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  • Journal article (peer-reviewed)
Abstract Subject headings
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  • 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.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)
NATURVETENSKAP  -- Biologi (hsv//swe)
NATURAL SCIENCES  -- Biological Sciences (hsv//eng)

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