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Xanthones for melanogenesis inhibition : Molecular docking and QSAR studies to understand their anti-tyrosinase activity

2021-01Journal article Open access
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dc.contributor.authorRosa, Gonçalo P.
dc.contributor.authorPalmeira, A.
dc.contributor.authorResende, Diana I. S. P.
dc.contributor.authorAlmeida, Isabel F.
dc.contributor.authorKane-Pagès, Aida
dc.contributor.authorBarreto, Maria do Carmo
dc.contributor.authorSousa, E.
dc.contributor.authorPinto, Madalena M. M.
dc.date.accessioned2021-09-14T11:52:32Z
dc.date.available2023-01-02T01:30:34Z
dc.date.issued2021-01
dc.description.abstractThe human skin is constantly exposed to external factors that affect its integrity, UV radiation being one of the main stress factors. The repeated exposure to this radiation leads to increased production of Reactive Oxygen Species (ROS) which activate a series of processes involved in photoaging. Excessive UV exposure also exacerbates melanin production leading to a variety of pigmentation disorders. Xanthones are reported to exhibit properties that prevent deleterious effects of UV exposure and high levels of ROS in the organism, so in this work a wide library of xanthones with different patterns of substitution was synthesized and tested for their inhibitory activity against the skin enzymes tyrosinase, elastase, collagenase and hyaluronidase, many of which were evaluated for the first time. Most of the compounds were tyrosinase inhibitors, with the best one (xanthone 27) presenting an IC50 of 1.9 µM, which is approximately 6 times lower than the IC50 of the positive control kojic acid. Concerning the other enzymes, only one compound presented IC50 lower than 150 µM in elastase inhibition (xanthone 14 = 91.8 µM) and none in collagenase and hyaluronidase inhibition. A QSAR model for tyrosinase inhibitory activity was built using six molecular descriptors, with a partial negative surface area descriptor and the relative number of oxygen atoms being positively contributing to the tyrosinase inhibitory activity. Docking using AutoDock Vina shows that all the tested compounds have more affinity to mushroom tyrosinase than kojic acid. Docking results implied that the tyrosinase inhibitory mechanisms of xanthonic derivatives are attributed to an allosteric interaction. Taken together, these data suggest that xanthones might be useful scaffolds for the development of new and promising candidates for the treatment of pigmentation-related disorders and for skin whitening cosmetic products.en
dc.description.sponsorshipThis research was supported by national funds through FCT, Foundation for Science and Technology, within the scope of UIDB/04423/2020 and UIDP/04423/2020 under the project PTDC/SAU-PUB/28736/2017 (reference POCI-01-0145-FEDER-028736), cofinanced by COMPETE 2020, Portugal 2020 and the European Union through the ERDF and by FCT through national funds, and supported by the Applied Molecular Biosciences Unit-UCIBIO which is financed by national funds from FCT/MCTES (UID/Multi/04378/2019). Thanks are also due to FCT, the European Union, QREN, FEDER, COMPETE, by funding cE3c center (Ref. UID/BIA/00329/2019) and Direção Regional da Ciência e Tecnologia (Azores Government) by funding Azorean Biodiversity Group.en
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationRosa, G.P., Palmeira, A., Resende, D.I.S.P., Almeida, I.F., Kane-Pagés, A., Barreto, M.C., Sousa, E. & Pinto, M.M.M. (2021). Xanthones for melanogenesis inhibition: molecular docking and QSAR studies to understand their anti-tyrosinase activity. "Bioorganic & Medicinal Chemistry", 29, 115873. DOI:10.1016/j.bmc.2020.115873en
dc.identifier.doi10.1016/j.bmc.2020.115873pt_PT
dc.identifier.issn0968-0896
dc.identifier.pmid33242700
dc.identifier.urihttp://hdl.handle.net/10400.3/6053
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relationPOCI-01-0145-FEDER-028736pt_PT
dc.relationAntimicrobials from the sea: models for innovative agents to revert multidrug resistance
dc.relationApplied Molecular Biosciences Unit
dc.relationInterdisciplinary Centre of Marine and Environmental Research
dc.relationInterdisciplinary Centre of Marine and Environmental Research
dc.relation.publisherversionhttps://www.sciencedirect.com/science/article/pii/S0968089620307033pt_PT
dc.subjectXanthonesen
dc.subjectMelanogenesisen
dc.subjectAnti-tyrosinaseen
dc.subjectQSARen
dc.subjectDockingen
dc.titleXanthones for melanogenesis inhibition : Molecular docking and QSAR studies to understand their anti-tyrosinase activityen
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleAntimicrobials from the sea: models for innovative agents to revert multidrug resistance
oaire.awardTitleApplied Molecular Biosciences Unit
oaire.awardTitleInterdisciplinary Centre of Marine and Environmental Research
oaire.awardTitleInterdisciplinary Centre of Marine and Environmental Research
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/9471 - RIDTI/PTDC%2FSAU-PUB%2F28736%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FMulti%2F04378%2F2019/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04423%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04423%2F2020/PT
oaire.citation.conferencePlaceUnited Kingdomen
oaire.citation.titleBioorganic & Medicinal Chemistryen
oaire.citation.volume29pt_PT
oaire.fundingStream9471 - RIDTI
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameRosa
person.familyNameBarreto
person.givenNameGonçalo
person.givenNameMaria do Carmo
person.identifier.ciencia-idC512-A6FD-4A68
person.identifier.orcid0000-0002-0706-8505
person.identifier.orcid0000-0001-5797-8913
person.identifier.ridN-8704-2015
person.identifier.scopus-author-id7004455600
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
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
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.embargofctDecisão baseada em informação Sherpa/Romeo.pt_PT
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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