Chalcone derivatives as promising antifoulants: Molecular optimization, bioactivity evaluation and performance in coatings

• Type: Article in International Scientific Journal
• Date: 2024

Authors

Pereira, D (Author) Other; Palmeira, A (Author) FFUP; Lima,É (Author) Other; Vitor Vasconcelos (Author) FCUP; Pinto, M (Author) Other; Marta Correia da Silva (Author) FFUP; Almeida, JR (Author) Other; Honorina Cidade (Author) FFUP

Journal

Title: Ecotoxicology and Environmental Safety

Vol. 280

ISSN: 0147-6513

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 0 Citations

Scopus - 0 Citations

Other information

Authenticus ID: P-010-KJE

DOI: 10.1016/j.ecoenv.2024.116560

Abstract (EN): 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 mu M and LC50 > 200 mu M) and lower ecotoxicity when compared to Econea (R), 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 mu M), similarly to the lead chalcone 1 (EC50 = 6.75 mu M). 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 14