Antifouling activity of sponge-derived polybrominated diphenyl ethers and synthetic analogues.
The antifouling (AF) activity of 2-hydroxy-4-(3-hydroxy-5-methylphenoxy)- 6-methylbenozoic acid methyl ester (1), 3,5-dibromo-2-(2',4'-dibromophenoxy)phenol (2); 3,4,5-tribromo-2-(2',4'-dibromophenoxy)phenol (3), 3,4,5-tribromo-2-(2'-bromophenoxy)phenol (4), 3,5-dibromo-2(2',4'-dibromophenoxy)phenol (5), 3,4,5,6-tetrabromo-2-(2'-bromophenoxy)phenol (6); 4-phenoxyphenol (7), 4-phenoxyaniline (9), 1-chloro-4-phenoxybenzene (10); 1-bromo-4-phenoxybenzene (13) was investigated against marine bacteria, a diatom, barnacle larvae and mussel juveniles. The naturally occurring compound 2 showed the strongest AF activity in all bioassays but lacked toxicity. It inhibited the growth of all tested bacterial strains (MIC = 0.02 - 1.52 microM) and its 50% effective concentrations (EC(50)) were 0.24 microM (diatom test), 0.66 microM (mussel test) and 1.26 microM (barnacle test). Among the commercially available derivates, compound 7 was the most active in bacterial and diatom bioassays but its activity was lower than that of compound 2. Overall, the naturally occurring compounds showed stronger activity than the commercially available analogues and could be possible future non-toxic AF candidates.
Ortlepp
Sofia
S
Institut für Pharmazeutische Biologie und Biotechnologie, Düsseldorf, Germany.
Pedpradap
Suwigarn
S
Dobretsov
Sergey
S
Proksch
Peter
P
D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology; D018441:Biofilms / Q000187:drug effects; D001688:Biological Products / Q000494:pharmacology*; D047128:Callyspongia / Q000737:chemistry; D017377:Diatoms / Q000187:drug effects; D055768:Halogenated Diphenyl Ethers; D049880:Mytilus edulis / Q000187:drug effects; D010636:Phenols / Q000494:pharmacology*; D010647:Phenyl Ethers / Q000494:pharmacology*; D001468:Thoracica / Q000187:drug effects
D000900:Anti-Bacterial Agents; D001688:Biological Products; D055768:Halogenated Diphenyl Ethers; D010636:Phenols; D010647:Phenyl Ethers; C085794:3,5-dibromo-2-(2,4-dibromophenoxy)phenol