title: Antifouling activity of bromotyrosine-derived sponge metabolites and synthetic analogues.
abstract: Eighteen brominated sponge-derived metabolites and synthetic analogues were analyzed for antilarval settlement of Balanus improvisus. Only compounds exhibiting oxime substituents including bastadin-3 (4), -4 (1), -9 (2), and -16 (3), hemibastadin-1 (6), aplysamine-2 (5), and psammaplin A (10) turned out to inhibit larval settling at 1 to 10 microM. Analogues of hemibastadin-1 (6) were synthesized and tested for structure activity studies. Debromohemibastadin-1 (8) inhibited settling of B. improvisus, albeit at lower concentrations than hemibastadin-1 (6). Both 6 and 8 also induced cyprid mortality. 5,5'-dibromohemibastadin-1 (7) proved to be nontoxic, but settlement inhibition was observed at 10 microM. Tyrosinyltyramine (9), lacking the oxime function, was not antifouling active and was non-toxic at 100 microM. Hemibastadin-1 (6) and the synthetic products showed no general toxicity when tested against brine shrimp larvae. In contrast to the lipophilic psammaplin A (10), the hydrophilic sulfated psammaplin A derivative (11) showed no antifouling activity even though it contains an oxime group. We therefore hypothesize that the compound needs to cross membranes (probably by diffusion) and that the target for psammaplin A lies intracellularly.
authors: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, Universitätstrasse 1, Geb. 26.23, D-40225 Düsseldorf, Germany.
authors: Sofia
authors: S
authors: Ortlepp
authors: Martin
authors: M
authors: Sjögren
authors: Mia
authors: M
authors: Dahlström
authors: Horst
authors: H
authors: Weber
authors: Rainer
authors: R
authors: Ebel
authors: RuAngelie
authors: R
authors: Edrada
authors: Carsten
authors: C
authors: Thoms
authors: Peter
authors: P
authors: Schupp
authors: Lars
authors: L
authors: Bohlin
authors: Peter
authors: P
authors: Proksch
mesh_terms: D000818:Animals; D001156:Artemia / Q000187:drug effects; D007814:Larva / Q000187:drug effects; D008386:Marine Biology; D010091:Oximes / Q000737:chemistry / Q000633:toxicity; D010647:Phenyl Ethers / Q000737:chemistry / Q000633:toxicity; D011161:Porifera / Q000737:chemistry*; D001468:Thoracica / Q000187:drug effects* / Q000502:physiology; D014443:Tyrosine / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*
chemical_list: D010091:Oximes; D010647:Phenyl Ethers; C475724:bromotyrosine; D014443:Tyrosine
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