Structure-Activity Relationship Probing of the Natural Marine Antifoulant Barettin.
Amphibalanus improvisus
Antifouling
Barettin
Marine natural product
Journal
Marine biotechnology (New York, N.Y.)
ISSN: 1436-2236
Titre abrégé: Mar Biotechnol (NY)
Pays: United States
ID NLM: 100892712
Informations de publication
Date de publication:
Dec 2021
Dec 2021
Historique:
received:
05
06
2021
accepted:
17
09
2021
pubmed:
3
11
2021
medline:
17
3
2022
entrez:
2
11
2021
Statut:
ppublish
Résumé
The sponge derived 2,5-diketopiperazine metabolite barettin is a potent antifouling compound effective against the settlement and metamorphosis of barnacles. Simplified derivatives of barettin have previously been shown to display similar inhibitory properties. The synthetic derivative benzo[g]dipodazine has been reported to display significantly improved antifouling properties in comparison with the native barettin with inhibitory activities as low a 0.034 µM reported against barnacle cyprid settlement. In the current study we report the antifouling activity of 29 synthetic analogs designed and inspired by the potent antifouling effect seen for benzo[g]dipodazine. The library contains mainly not only dipodazine derivatives but also disubstituted diketopiperazines and compounds incorporating alternative heterocyclic cores such as hydantoin, creatinine, and rhodanine. Several of the prepared compounds inhibit the settlement of Amphibalanus improvisus cyprids at low micromolar concentrations, in parity with the natural barettin. While several highly active compounds were prepared by incorporating the benzo[g]indole as hydrophobic substituent, the remarkable antifouling effect reported for benzo[g]dipodazine was not observed when evaluated in our study.
Identifiants
pubmed: 34727298
doi: 10.1007/s10126-021-10074-z
pii: 10.1007/s10126-021-10074-z
doi:
Substances chimiques
Peptides, Cyclic
0
barettin
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
904-916Subventions
Organisme : Norges Forskningsråd
ID : ES508288
Organisme : Norges Forskningsråd
ID : 275043
Informations de copyright
© 2021. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.
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