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Sustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivatives

2023-01-27Journal article Open access
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dc.contributor.authorCabral, Rafaela G.
dc.contributor.authorViegas, Gonçalo
dc.contributor.authorPacheco, Rita
dc.contributor.authorSousa, Ana Catarina
dc.contributor.authorRobalo, Maria Paula
dc.date.accessioned2023-05-22T08:53:47Z
dc.date.available2023-05-22T08:53:47Z
dc.date.issued2023-01-27
dc.description.abstractThis 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.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationCABRAL, 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.pt_PT
dc.identifier.doi10.3390/molecules28031232pt_PT
dc.identifier.eissn1420-3049
dc.identifier.urihttp://hdl.handle.net/10400.21/16089
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationIPL/2021/Naf4Med 3D_ISEL - Instituto Politécnico de Lisboapt_PT
dc.relationCentro de Química Estrutural
dc.relationCentro de Química Estrutural
dc.relation.publisherversionhttps://www.mdpi.com/1420-3049/28/3/1232pt_PT
dc.subjectNaphthoquinonespt_PT
dc.subjectElectrochemistry behaviorpt_PT
dc.subjectAcetylcholinesterase inhibitory activitypt_PT
dc.subjectCytotoxic activitypt_PT
dc.subjectBiological activitypt_PT
dc.titleSustainable synthesis, antiproliferative and acetylcholinesterase inhibition of 1,4-and 1,2-naphthoquinone derivativespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCentro de Química Estrutural
oaire.awardTitleCentro de Química Estrutural
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F00100%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F00100%2F2020/PT
oaire.citation.endPage18pt_PT
oaire.citation.issue3pt_PT
oaire.citation.startPage1pt_PT
oaire.citation.titleMoleculespt_PT
oaire.citation.volume28pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNamePacheco
person.familyNameSousa
person.familyNameRobalo
person.givenNameRita
person.givenNameAna Catarina
person.givenNameMaria Paula
person.identifier1022927
person.identifier.ciencia-id9F13-D310-B5A3
person.identifier.ciencia-idE81E-0596-BF29
person.identifier.ciencia-idE11C-A704-9C18
person.identifier.orcid0000-0001-5192-3006
person.identifier.orcid0000-0001-6133-7406
person.identifier.orcid0000-0002-8200-6910
person.identifier.ridC-3062-2012
person.identifier.ridU-3597-2017
person.identifier.ridB-2002-2012
person.identifier.scopus-author-id8853708300
person.identifier.scopus-author-id9269662100
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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relation.isAuthorOfPublication2ec1bb85-33cd-4e24-b84f-0c965d84d25b
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