Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents
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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-11-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/19/12/682 |
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| author | Ana Rita Neves Daniela Pereira Catarina Gonçalves Joana Cardoso Eugénia Pinto Vitor Vasconcelos Madalena Pinto Emília Sousa Joana R. Almeida Honorina Cidade Marta Correia-da-Silva |
| author_facet | Ana Rita Neves Daniela Pereira Catarina Gonçalves Joana Cardoso Eugénia Pinto Vitor Vasconcelos Madalena Pinto Emília Sousa Joana R. Almeida Honorina Cidade Marta Correia-da-Silva |
| author_sort | Ana Rita Neves |
| collection | DOAJ |
| description | 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, <i>Mytilus galloprovincialis</i>, as well as on biofilm-forming marine microorganisms, including bacteria and fungi. The growth of the microalgae <i>Navicula</i> sp. was also evaluated after exposure to the most promising compounds. While compounds <b>6a, 7a</b>, and <b>9a</b> caused significant inhibition of the settlement of mussel larvae, compounds <b>3b</b>, <b>4b</b>, and <b>7b</b> were able to inhibit <i>Roseobacter litoralis</i> bacterial biofilm growth. Interestingly, acetophenone <b>7a</b> displayed activity against both mussel larvae and the microalgae <i>Navicula</i> sp., suggesting a complementary action of this compound against macro- and microfouling species. The most potent compounds (<b>6a</b>, <b>7a</b>, and <b>9a</b>) also showed to be less toxic to the non-target species <i>Artemia salina</i> than the biocide Econea<sup>®</sup>. Regarding both AF potency and ecotoxicity activity evaluation, acetophenones <b>7a</b> and <b>9a</b> were put forward in this work as promising eco-friendly AF agents. |
| first_indexed | 2024-03-10T03:40:53Z |
| format | Article |
| id | doaj.art-46dcca6845d8427f894e6622f20eb2f3 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T03:40:53Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-46dcca6845d8427f894e6622f20eb2f32023-11-23T09:18:11ZengMDPI AGMarine Drugs1660-33972021-11-01191268210.3390/md19120682Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling AgentsAna Rita Neves0Daniela Pereira1Catarina Gonçalves2Joana Cardoso3Eugénia Pinto4Vitor Vasconcelos5Madalena Pinto6Emília Sousa7Joana R. Almeida8Honorina Cidade9Marta Correia-da-Silva10Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalLaboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalCIIMAR—Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, PortugalLaboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalCIIMAR—Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, PortugalCIIMAR—Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, PortugalLaboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalLaboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalCIIMAR—Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, PortugalLaboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalLaboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalMarine 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, <i>Mytilus galloprovincialis</i>, as well as on biofilm-forming marine microorganisms, including bacteria and fungi. The growth of the microalgae <i>Navicula</i> sp. was also evaluated after exposure to the most promising compounds. While compounds <b>6a, 7a</b>, and <b>9a</b> caused significant inhibition of the settlement of mussel larvae, compounds <b>3b</b>, <b>4b</b>, and <b>7b</b> were able to inhibit <i>Roseobacter litoralis</i> bacterial biofilm growth. Interestingly, acetophenone <b>7a</b> displayed activity against both mussel larvae and the microalgae <i>Navicula</i> sp., suggesting a complementary action of this compound against macro- and microfouling species. The most potent compounds (<b>6a</b>, <b>7a</b>, and <b>9a</b>) also showed to be less toxic to the non-target species <i>Artemia salina</i> than the biocide Econea<sup>®</sup>. Regarding both AF potency and ecotoxicity activity evaluation, acetophenones <b>7a</b> and <b>9a</b> were put forward in this work as promising eco-friendly AF agents.https://www.mdpi.com/1660-3397/19/12/682acetophenones1,2,3-triazoleclick chemistryantifoulingecotoxicityeco-friendly |
| spellingShingle | Ana Rita Neves Daniela Pereira Catarina Gonçalves Joana Cardoso Eugénia Pinto Vitor Vasconcelos Madalena Pinto Emília Sousa Joana R. Almeida Honorina Cidade Marta Correia-da-Silva Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents Marine Drugs acetophenones 1,2,3-triazole click chemistry antifouling ecotoxicity eco-friendly |
| title | Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents |
| title_full | Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents |
| title_fullStr | Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents |
| title_full_unstemmed | Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents |
| title_short | Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents |
| title_sort | natural benzo acetophenones as leads for new synthetic acetophenone hybrids containing a 1 2 3 triazole ring as potential antifouling agents |
| topic | acetophenones 1,2,3-triazole click chemistry antifouling ecotoxicity eco-friendly |
| url | https://www.mdpi.com/1660-3397/19/12/682 |
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