Effect of regio- and stereoisomerism on antifouling 2,5-diketopiperazines.
Org Biomol Chem
; 20(47): 9431-9446, 2022 12 07.
Article
en En
| MEDLINE
| ID: mdl-36408605
Marine biofouling is a problem that plagues all maritime industries at vast economic and environmental cost. Previous and current methods to prevent biofouling have employed the use of heavy metals and other toxic or highly persistent chemicals, and these methods are now coming under immense regulatory pressure. Recent studies have illustrated the potential of nature-inspired tetrasubstituted 2,5-diketopiperazines (2,5-DKPs) as eco-friendly marine biocides for biofouling control. These highly active symmetrically substituted 2,5-DKPs can be generated by combining structural motifs from cationic innate defence peptides and natural marine antifoulants. A balance between a threshold hydrophobic contribution and sufficient cationic charge has been established as key for bioactivity, and our current study further increases understanding of the antifouling mechanism by investigating the effect of both regio- and stereochemistry. Novel synthetic routes for the generation of unsymmetrical 2,5-DKPs were developed and a library of nine compounds was prepared. The compounds were screened against a series of four model macrofouling organisms (Ciona savignyi, Mytilus galloprovincialis, Spirobranchus cariniferus, and Undaria pinnatifida). Several of the evaluated compounds displayed inhibitory activity at sub-micromolar concentrations. The structural contributions to antifouling bioactivity were studied using NMR spectroscopy and molecular modelling, revealing a strong dependence on a stable amphiphilic solution structure regardless of substitution pattern.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Dicetopiperazinas
Idioma:
En
Revista:
Org Biomol Chem
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
2022
Tipo del documento:
Article
País de afiliación:
Nueva Zelanda
Pais de publicación:
Reino Unido