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 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). (c) 2006 Elsevier Inc. All rights reserved.

Ämnesord

MEDICIN OCH HÄLSOVETENSKAP  -- Medicinska och farmaceutiska grundvetenskaper -- Farmaceutiska vetenskaper (hsv//swe)

MEDICAL AND HEALTH SCIENCES  -- Basic Medicine -- Pharmaceutical Sciences (hsv//eng)

NATURVETENSKAP  -- Biologi -- Ekologi (hsv//swe)

NATURAL SCIENCES  -- Biological Sciences -- Ecology (hsv//eng)

Nyckelord

barettin

dipodazine

marine sponges

Geodia barretti

synthesis

cyprid settlement

MARINE NATURAL-PRODUCTS

SECONDARY METABOLISM

BALANUS-IMPROVISUS

GEODIA-BARRETTI

EVOLUTION

RECEPTORS

DIKETOPIPERAZINE

CYCLOPEPTIDES

RECRUITMENT

DIPODAZINE

barettin

PHARMACY

Publikations- och innehållstyp

ref (ämneskategori)

art (ämneskategori)