Antifouling activity of synthesized peptide analogs of the sponge metabolite barettin

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• 作者：Martin Sj&#xf6 ; gren ; Ann-Louise Johnson ; Erik Hedner ; Mia Dahlstr&#xf6 ; m ; Ulf G&#xf6 ; ransson ; Hamid Shirani ; Jan Bergman ; Per R. Jonsson and Lars Bohlin
• 关键词：Barettin ; Dipodazine ; Marine sponges ; Geodia barretti ; Synthesis ; Cyprid settlement
• 刊名：Peptides
• 出版年：2006
• 出版时间：September 2006
• 年：2006
• 卷：27
• 期：9
• 页码：2058-2064
• 全文大小：217 K

文摘

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 μM. 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 μM). The effect of benzo[g]dipodazine was also shown to be readily reversible, when cyprids were transferred to filtered seawater (FSW).