Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents

• Tipo: Artigo em Revista Científica Internacional
• Data: 2021

Autores

Neves, AR (Autor) Outra; Pereira, D (Autor) Outra; Goncalves, C (Autor) Outra; Cardoso, J (Autor) Outra; Eugenia Pinto (Autor) FFUP; Vitor Vasconcelos (Autor) FCUP; Pinto, M (Autor) Outra; Emilia Sousa (Autor) FFUP; Almeida, JR (Autor) Outra; Honorina Cidade (Autor) FFUP; Marta Correia da Silva (Autor) FFUP

Revista

Título: Marine Drugs

Vol. 11

Página Final: 682

ISSN: 1660-3397

Editora: MDPI

Indexação

ISI Web of Knowledge - 2 Citações

Scopus - 3 Citações

Outras Informações

ID Authenticus: P-00V-RKR

DOI: 10.3390/md19120682

Abstract (EN): Marine biofouling is a natural process that represents major economic, environmental, and health concerns. Some booster biocides have been used in biofouling control, however, they were found to accumulate in environmental compartments, showing negative effects on marine organisms. Therefore, it is urgent to develop new eco-friendly alternatives. Phenyl ketones, such as benzophenones and acetophenones, have been described as modulators of several biological activities, including antifouling activity (AF). In this work, acetophenones were combined with other chemical substrates through a 1,2,3-triazole ring, a strategy commonly used in Medicinal Chemistry. In our approach, a library of 14 new acetophenone-triazole hybrids was obtained through the copper(I)-catalyzed alkyne-azide cycloaddition "click" reaction. All of the synthesized compounds were evaluated against the settlement of a representative macrofouling species, Mytilus galloprovincialis, as well as on biofilm-forming marine microorganisms, including bacteria and fungi. The growth of the microalgae Navicula sp. was also evaluated after exposure to the most promising compounds. While compounds 6a, 7a, and 9a caused significant inhibition of the settlement of mussel larvae, compounds 3b, 4b, and 7b were able to inhibit Roseobacter litoralis bacterial biofilm growth. Interestingly, acetophenone 7a displayed activity against both mussel larvae and the microalgae Navicula sp., suggesting a complementary action of this compound against macro- and microfouling species. The most potent compounds (6a, 7a, and 9a) also showed to be less toxic to the non-target species Artemia salina than the biocide Econea(R). Regarding both AF potency and ecotoxicity activity evaluation, acetophenones 7a and 9a were put forward in this work as promising eco-friendly AF agents.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 17