Antifouling activity of synthesized peptide analogs of the sponge metabolite barettin.
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 microM. 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 microM). The effect of benzo[g]dipodazine was also shown to be readily reversible, when cyprids were transferred to filtered seawater (FSW).
Sjögren
Martin
M
Division of Pharmacognosy, Department of Medicinal Chemistry, Biomedical Centre, Uppsala University, P.O. Box 574, SE-751 23 Uppsala, Sweden.
Johnson
Ann-Louise
AL
Hedner
Erik
E
Dahlström
Mia
M
Göransson
Ulf
U
Shirani
Hamid
H
Bergman
Jan
J
Jonsson
Per R
PR
Bohlin
Lars
L
D000818:Animals; D054659:Diketopiperazines; D005998:Glycine / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007814:Larva / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry* / Q000166:cytology / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D001468:Thoracica / Q000166:cytology / Q000187:drug effects
D054659:Diketopiperazines; D007211:Indoles; D010456:Peptides, Cyclic; D010879:Piperazines; C484472:barettin; C514604:dipodazine; D005998:Glycine