Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents
| Autor: | Joana F.M.F. Cardoso, Ana Rita Neves, Eugénia Pinto, Honorina Cidade, Catarina Gonçalves, Joana R. Almeida, Daniela Pereira, Emília Sousa, Vitor Vasconcelos, Madalena Pinto, Marta Correia-da-Silva |
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| Rok vydání: | 2021 |
| Předmět: |
Aquatic Organisms
Biocide 1 2 3-Triazole QH301-705.5 Biofouling Pharmaceutical Science acetophenones 1 2 3-triazole click chemistry antifouling ecotoxicity eco-friendly Article Structure-Activity Relationship chemistry.chemical_compound Drug Discovery Microalgae Animals Organic chemistry Biology (General) Pharmacology Toxicology and Pharmaceutics (miscellaneous) biology Acetophenones Triazoles Roseobacter litoralis biology.organism_classification Mytilus Bivalvia chemistry Navicula Biofilms Larva Ecotoxicity Artemia salina Disinfectants |
| Zdroj: | Marine Drugs Marine Drugs, Vol 19, Iss 682, p 682 (2021) Marine Drugs; Volume 19; Issue 12; Pages: 682 |
| ISSN: | 1660-3397 |
| DOI: | 10.3390/md19120682 |
| Popis: | 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®. Regarding both AF potency and ecotoxicity activity evaluation, acetophenones 7a and 9a were put forward in this work as promising eco-friendly AF agents. |
| Databáze: | OpenAIRE |
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