Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10400.21/16089 |
Resumo: | This work describes the design, sustainable synthesis, evaluation of electrochemical and biological properties against HepG2 cell lines, and AChE enzymes of different substituted derivatives of 1,4- and 1,2-naphthoquinones (NQ). A microwave-assisted protocol was optimized with success for the synthesis of the 2-substituted-1,4-NQ series and extended to the 4-substituted-1,2-NQ family, providing an alternative and more sustainable approach to the synthesis of naphthoquinones. The electrochemical properties were studied by cyclic voltammetry, and the redox potentials related to the molecular structural characteristics and the biological properties. Compounds were tested for their potential anti-cancer activity against a hepatocellular carcinoma cell line, HepG2, using MTT assay, and 1,2-NQ derivatives were found to be more active than their 1,4-NQ homologues (3a-f), with the highest cytotoxic potential found for compound 4a (EC50 = 3 mu M). The same trend was found for the inhibitory action against acetylcholinesterase, with 1,2-NQ derivatives showing higher inhibition(50 mu M) than their 1,4-NQ homologues, with 4h being the most potent compound (Inhibition(50 mu M) = 85%). Docking studies were performed for the 1,2-NQ derivatives with the highest inhibitions, showing dual binding interactions with both CAS and PAS sites, while the less active 1,4-NQ derivatives showed interactions with PAS and the mid-gorge region. |
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Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivativesNaphthoquinonesElectrochemistry behaviorAcetylcholinesterase inhibitory activityCytotoxic activityBiological activityThis work describes the design, sustainable synthesis, evaluation of electrochemical and biological properties against HepG2 cell lines, and AChE enzymes of different substituted derivatives of 1,4- and 1,2-naphthoquinones (NQ). A microwave-assisted protocol was optimized with success for the synthesis of the 2-substituted-1,4-NQ series and extended to the 4-substituted-1,2-NQ family, providing an alternative and more sustainable approach to the synthesis of naphthoquinones. The electrochemical properties were studied by cyclic voltammetry, and the redox potentials related to the molecular structural characteristics and the biological properties. Compounds were tested for their potential anti-cancer activity against a hepatocellular carcinoma cell line, HepG2, using MTT assay, and 1,2-NQ derivatives were found to be more active than their 1,4-NQ homologues (3a-f), with the highest cytotoxic potential found for compound 4a (EC50 = 3 mu M). The same trend was found for the inhibitory action against acetylcholinesterase, with 1,2-NQ derivatives showing higher inhibition(50 mu M) than their 1,4-NQ homologues, with 4h being the most potent compound (Inhibition(50 mu M) = 85%). Docking studies were performed for the 1,2-NQ derivatives with the highest inhibitions, showing dual binding interactions with both CAS and PAS sites, while the less active 1,4-NQ derivatives showed interactions with PAS and the mid-gorge region.MDPIRCIPLCabral, Rafaela G.Viegas, GonçaloPacheco, RitaSousa, Ana CatarinaRobalo, Maria Paula2023-05-22T08:53:47Z2023-01-272023-01-27T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.21/16089engCABRAL, Rafaela G.; [et al] – Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives. Molecules. eISSN 1420-3049. Vol. 28, N.º 3 (2023), pp. 1-18.10.3390/molecules280312321420-3049info: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:RCAAP2023-08-03T10:14:23Zoai:repositorio.ipl.pt:10400.21/16089Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:23:41.316991Repositório 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 |
Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives |
title |
Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives |
spellingShingle |
Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives Cabral, Rafaela G. Naphthoquinones Electrochemistry behavior Acetylcholinesterase inhibitory activity Cytotoxic activity Biological activity |
title_short |
Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives |
title_full |
Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives |
title_fullStr |
Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives |
title_full_unstemmed |
Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives |
title_sort |
Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives |
author |
Cabral, Rafaela G. |
author_facet |
Cabral, Rafaela G. Viegas, Gonçalo Pacheco, Rita Sousa, Ana Catarina Robalo, Maria Paula |
author_role |
author |
author2 |
Viegas, Gonçalo Pacheco, Rita Sousa, Ana Catarina Robalo, Maria Paula |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
RCIPL |
dc.contributor.author.fl_str_mv |
Cabral, Rafaela G. Viegas, Gonçalo Pacheco, Rita Sousa, Ana Catarina Robalo, Maria Paula |
dc.subject.por.fl_str_mv |
Naphthoquinones Electrochemistry behavior Acetylcholinesterase inhibitory activity Cytotoxic activity Biological activity |
topic |
Naphthoquinones Electrochemistry behavior Acetylcholinesterase inhibitory activity Cytotoxic activity Biological activity |
description |
This work describes the design, sustainable synthesis, evaluation of electrochemical and biological properties against HepG2 cell lines, and AChE enzymes of different substituted derivatives of 1,4- and 1,2-naphthoquinones (NQ). A microwave-assisted protocol was optimized with success for the synthesis of the 2-substituted-1,4-NQ series and extended to the 4-substituted-1,2-NQ family, providing an alternative and more sustainable approach to the synthesis of naphthoquinones. The electrochemical properties were studied by cyclic voltammetry, and the redox potentials related to the molecular structural characteristics and the biological properties. Compounds were tested for their potential anti-cancer activity against a hepatocellular carcinoma cell line, HepG2, using MTT assay, and 1,2-NQ derivatives were found to be more active than their 1,4-NQ homologues (3a-f), with the highest cytotoxic potential found for compound 4a (EC50 = 3 mu M). The same trend was found for the inhibitory action against acetylcholinesterase, with 1,2-NQ derivatives showing higher inhibition(50 mu M) than their 1,4-NQ homologues, with 4h being the most potent compound (Inhibition(50 mu M) = 85%). Docking studies were performed for the 1,2-NQ derivatives with the highest inhibitions, showing dual binding interactions with both CAS and PAS sites, while the less active 1,4-NQ derivatives showed interactions with PAS and the mid-gorge region. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-05-22T08:53:47Z 2023-01-27 2023-01-27T00:00:00Z |
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 |
http://hdl.handle.net/10400.21/16089 |
url |
http://hdl.handle.net/10400.21/16089 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
CABRAL, Rafaela G.; [et al] – Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives. Molecules. eISSN 1420-3049. Vol. 28, N.º 3 (2023), pp. 1-18. 10.3390/molecules28031232 1420-3049 |
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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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