Antifouling activity of synthesized peptide analogs of the sponge metabolite barettin
2006 (English)In: Peptides, ISSN 0196-9781, E-ISSN 1873-5169, Vol. 27, no 9, 2058-2064 p.Article in journal (Refereed) Published
Barettin (cyclo [(6-bromo-8-en-tryptophan) arginine]), a diketopiperazine isolated from the marine sponge Geodia barretti, is a potent inhibitor of barnacle larvae settlement with an EC50-value of 0.9 mu M. In the present study, 14 analogs of barettin and its structural congener dipodazine were synthezised and tested for their ability to inhibit larval settlement. Two of the analogs have an intact barettin skeleton. The remaining analogs have a dipodazine skeleton (a diketopiperazine where arginine is replaced with glycine). Six of the tested synthetic analogs displayed significant settlement inhibition with the most potent inhibitor being benzo[g]dipodazine, which displayed even stronger activity than barettin (EC50-value 0.034 mu M). The effect of benzo[g]dipodazine was also shown to be readily reversible, when cyprids were transferred to filtered seawater (FSW).
Place, publisher, year, edition, pages
2006. Vol. 27, no 9, 2058-2064 p.
barettin, dipodazine, marine sponges, Geodia barretti, synthesis, cyprid settlement
IdentifiersURN: urn:nbn:se:uu:diva-94327DOI: 10.1016/j.peptides.2006.03.027ISI: 000240379800002PubMedID: 16781016OAI: oai:DiVA.org:uu-94327DiVA: diva2:168141