Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://hdl.handle.net/10216/130448 |
Resumo: | The development of alternative ecological and effective antifouling technologies is still challenging. Synthesis of nature-inspired compounds has been exploited, given the potential to assure commercial supplies of potential ecofriendly antifouling agents. In this direction, the antifouling activity of a series of nineteen synthetic small molecules, with chemical similarities with natural products, were exploited in this work. Six (4, 5, 7, 10, 15 and 17) of the tested xanthones showed in vivo activity toward the settlement of Mytilus galloprovincialis larvae (EC50: 3.53–28.60 µM) and low toxicity to this macrofouling species (LC50 > 500 µM and LC50/EC50: 17.42–141.64), and two of them (7 and 10) showed no general marine ecotoxicity (<10% of Artemia salina mortality) after 48 h of exposure. Regarding the mechanism of action in mussel larvae, the best performance compounds 4 and 5 might be acting by the inhibition of acetylcholinesterase activity (in vitro and in silico studies), while 7 and 10 showed specific targets (proteomic studies) directly related with the mussel adhesive structure (byssal threads), given by the alterations in the expression of Mytilus collagen proteins (PreCols) and proximal thread proteins (TMPs). A quantitative structure-activity relationship (QSAR) model was built with predictive capacity to enable speeding the design of new potential active compounds. |
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Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthonesAntifouling activityChemical synthesisInvertebratesMolecular targetsXanthonesThe development of alternative ecological and effective antifouling technologies is still challenging. Synthesis of nature-inspired compounds has been exploited, given the potential to assure commercial supplies of potential ecofriendly antifouling agents. In this direction, the antifouling activity of a series of nineteen synthetic small molecules, with chemical similarities with natural products, were exploited in this work. Six (4, 5, 7, 10, 15 and 17) of the tested xanthones showed in vivo activity toward the settlement of Mytilus galloprovincialis larvae (EC50: 3.53–28.60 µM) and low toxicity to this macrofouling species (LC50 > 500 µM and LC50/EC50: 17.42–141.64), and two of them (7 and 10) showed no general marine ecotoxicity (<10% of Artemia salina mortality) after 48 h of exposure. Regarding the mechanism of action in mussel larvae, the best performance compounds 4 and 5 might be acting by the inhibition of acetylcholinesterase activity (in vitro and in silico studies), while 7 and 10 showed specific targets (proteomic studies) directly related with the mussel adhesive structure (byssal threads), given by the alterations in the expression of Mytilus collagen proteins (PreCols) and proximal thread proteins (TMPs). A quantitative structure-activity relationship (QSAR) model was built with predictive capacity to enable speeding the design of new potential active compounds.MDPI20202020-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10216/130448engISSN 2218-273Xhttps://doi.org/10.3390/biom10081126Almeida, J.R.Palmeira, A.Campos, A.Cunha, I.Freitas, M.Felpeto, A.B.Turkina, M.V.Vasconcelos, V.Pinto, M.Correia-Da-silva, M.Sousa, E.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-11-29T13:28:15Zoai:repositorio-aberto.up.pt:10216/130448Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:41:09.320245Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones |
title |
Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones |
spellingShingle |
Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones Almeida, J.R. Antifouling activity Chemical synthesis Invertebrates Molecular targets Xanthones |
title_short |
Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones |
title_full |
Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones |
title_fullStr |
Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones |
title_full_unstemmed |
Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones |
title_sort |
Structure-antifouling activity relationship and molecular targets of bio-inspired(Thio)xanthones |
author |
Almeida, J.R. |
author_facet |
Almeida, J.R. Palmeira, A. Campos, A. Cunha, I. Freitas, M. Felpeto, A.B. Turkina, M.V. Vasconcelos, V. Pinto, M. Correia-Da-silva, M. Sousa, E. |
author_role |
author |
author2 |
Palmeira, A. Campos, A. Cunha, I. Freitas, M. Felpeto, A.B. Turkina, M.V. Vasconcelos, V. Pinto, M. Correia-Da-silva, M. Sousa, E. |
author2_role |
author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Almeida, J.R. Palmeira, A. Campos, A. Cunha, I. Freitas, M. Felpeto, A.B. Turkina, M.V. Vasconcelos, V. Pinto, M. Correia-Da-silva, M. Sousa, E. |
dc.subject.por.fl_str_mv |
Antifouling activity Chemical synthesis Invertebrates Molecular targets Xanthones |
topic |
Antifouling activity Chemical synthesis Invertebrates Molecular targets Xanthones |
description |
The development of alternative ecological and effective antifouling technologies is still challenging. Synthesis of nature-inspired compounds has been exploited, given the potential to assure commercial supplies of potential ecofriendly antifouling agents. In this direction, the antifouling activity of a series of nineteen synthetic small molecules, with chemical similarities with natural products, were exploited in this work. Six (4, 5, 7, 10, 15 and 17) of the tested xanthones showed in vivo activity toward the settlement of Mytilus galloprovincialis larvae (EC50: 3.53–28.60 µM) and low toxicity to this macrofouling species (LC50 > 500 µM and LC50/EC50: 17.42–141.64), and two of them (7 and 10) showed no general marine ecotoxicity (<10% of Artemia salina mortality) after 48 h of exposure. Regarding the mechanism of action in mussel larvae, the best performance compounds 4 and 5 might be acting by the inhibition of acetylcholinesterase activity (in vitro and in silico studies), while 7 and 10 showed specific targets (proteomic studies) directly related with the mussel adhesive structure (byssal threads), given by the alterations in the expression of Mytilus collagen proteins (PreCols) and proximal thread proteins (TMPs). A quantitative structure-activity relationship (QSAR) model was built with predictive capacity to enable speeding the design of new potential active compounds. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020 2020-01-01T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://hdl.handle.net/10216/130448 |
url |
https://hdl.handle.net/10216/130448 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
ISSN 2218-273X https://doi.org/10.3390/biom10081126 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
MDPI |
publisher.none.fl_str_mv |
MDPI |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799135726525218816 |