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Chalcone derivatives as promising antifoulants: Molecular optimization, bioactivity evaluation and performance in coatings.
Pereira, Daniela; Palmeira, Andreia; Lima, Érica; Vasconcelos, Vitor; Pinto, Madalena; Correia-da-Silva, Marta; Almeida, Joana R; Cidade, Honorina.
Afiliação
  • Pereira D; Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edifício do Termina
  • Palmeira A; Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edifício do Termina
  • Lima É; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos, S/N, Matosinhos 4450-208, Portugal.
  • Vasconcelos V; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos, S/N, Matosinhos 4450-208, Portugal; Department of Biology, Faculty of Sciences, University of Porto, Rua do Campo Alegr
  • Pinto M; Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edifício do Termina
  • Correia-da-Silva M; Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edifício do Termina
  • Almeida JR; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos, S/N, Matosinhos 4450-208, Portugal. Electronic address: jalmeida@ciimar.up.pt.
  • Cidade H; Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edifício do Termina
Ecotoxicol Environ Saf ; 280: 116560, 2024 Jul 15.
Article em En | MEDLINE | ID: mdl-38865941
ABSTRACT
Marine biofouling remains a huge concern for maritime industries and for environmental health. Although the current biocide-based antifouling coatings can prevent marine biofouling, their use has been associated with toxicity for the marine environment, being urgent to find sustainable alternatives. Previously, our research group has identified a prenylated chalcone (1) with promising antifouling activity against the settlement of larvae of the macrofouling species Mytilus galloprovincialis (EC50 = 16.48 µM and LC50 > 200 µM) and lower ecotoxicity when compared to Econea®, a commercial antifouling agent in use. Herein, a series of chalcone 1 analogues were designed and synthesized in order to obtain optimized antifouling compounds with improved potency while maintaining low ecotoxicity. Compounds 8, 15, 24, and 27 showed promising antifouling activity against the settlement of M. galloprovincialis larvae, being dihydrochalcone 27 the most potent. The effect of compound 24 was associated with the inhibition of acetylcholinesterase activity. Among the synthesized compounds, compound 24 also showed potent complementary activity against Navicula sp. (EC50 = 4.86 µM), similarly to the lead chalcone 1 (EC50 = 6.75 µM). Regarding the structure-activity relationship, the overall results demonstrate that the substitution of the chalcone of the lead compound 1 by a dihydrochalcone scaffold resulted in an optimized potency against the settlement of mussel larvae. Marine polyurethane (PU)-based coatings containing the best performed compound concerning anti-settlement activity (dihydrochalcone 27) were prepared, and mussel larvae adherence was reduced compared to control PU coatings.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Mytilus / Incrustação Biológica / Larva Idioma: En Ano de publicação: 2024 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Mytilus / Incrustação Biológica / Larva Idioma: En Ano de publicação: 2024 Tipo de documento: Article