Investigation of structure−activity relationships for benzoyl and cinnamoyl piperazine/piperidine amides as Tyrosinase inhibitors

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dc.contributorLab. Fisiopatologiapt_BR
dc.contributor.authorVarela, Marina Themoteopt_BR
dc.contributor.authorLevatti, Erica V. de Castropt_BR
dc.contributor.authorCardoso, Andre Gustavo Temponept_BR
dc.contributor.authorFernandes, João Paulo dos Santospt_BR
dc.date.accessioned2023-12-18T13:26:03Z-
dc.date.available2023-12-18T13:26:03Z-
dc.date.issued2023pt_BR
dc.identifier.citationVarela MT, Levatti EV.C, Cardoso AGT, Fernandes JPS. Investigation of structure−activity relationships for benzoyl and cinnamoyl piperazine/piperidine amides as Tyrosinase inhibitors. ACS Omega. 2023 Nov; 8(46):44265-44275. doi:10.1021/acsomega.3c06977.pt_BR
dc.identifier.urihttps://repositorio.butantan.gov.br/handle/butantan/5200-
dc.description.abstractMelanin is a substance that plays important roles in several organisms. Its function as an antioxidant and metal-complexing agent makes tyrosinase, the key enzyme that controls melanogenesis, an interesting target for designing inhibitors. In this article, we report a set of piperazine/piperidine amides of benzoic and cinnamic acid derivatives as tyrosinase inhibitors with improved potency and drug-likeness. The most potent compound 5b showed a pIC50 of 4.99 in the monophenolase assay, and only compound 3a showed reasonable potency in the diphenolase assay (pIC50, 4.18). These activities are not correlated to antiradical activity, suggesting that the activity is dependent on competition with the substrates. Molecular docking studies indicated that the benzyl substituent of 5b and other analogues perform important interactions in the enzyme that may explain the higher potency of these compounds. Moreover, the compounds present adequate lipophilicity and skin permeability and no relevant cytotoxicity (CC50 > 200 μM) to mammalian cells.pt_BR
dc.description.sponsorship(FAPESP) Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorship(CAPES) Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorpt_BR
dc.description.sponsorship(CNPq) Conselho Nacional de Desenvolvimento Científico e Tecnológicopt_BR
dc.format.extent44265–44275pt_BR
dc.language.isoEnglishpt_BR
dc.relation.ispartofACS Omegapt_BR
dc.rightsOpen accesspt_BR
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/pt_BR
dc.titleInvestigation of structure−activity relationships for benzoyl and cinnamoyl piperazine/piperidine amides as Tyrosinase inhibitorspt_BR
dc.typeArticlept_BR
dc.rights.licenseCC BY-NC-NDpt_BR
dc.identifier.doi10.1021/acsomega.3c06977pt_BR
dc.contributor.external(UNIFESP) Universidade Federal de São Paulopt_BR
dc.identifier.citationvolume8pt_BR
dc.identifier.citationissue46pt_BR
dc.relation.ispartofabbreviatedACS Omegapt_BR
dc.identifier.citationabntv. 8, n.46, 44265-44275, nov. 2023pt_BR
dc.identifier.citationvancouver2023 Nov; 8(46):44265-44275pt_BR
dc.contributor.butantanCardoso, Andre Gustavo Tempone|:Pesquisador|:Lab. Fisiopatologiapt_BR
dc.sponsorship.butantan(FAPESP) Fundação de Amparo à Pesquisa do Estado de São Paulo¦¦2019/24028-8pt_BR
dc.sponsorship.butantan(CAPES) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior¦¦001pt_BR
dc.sponsorship.butantan(CNPq) Conselho Nacional de Desenvolvimento Científico e Tecnológico¦¦307829/2021-9pt_BR
dc.sponsorship.butantan(CNPq) Conselho Nacional de Desenvolvimento Científico e Tecnológico¦¦307672/2021-2pt_BR
dc.identifier.bvsccBR78.1pt_BR
dc.identifier.bvsdbIBProdpt_BR
dc.description.dbindexedYespt_BR
item.languageiso639-1English-
item.fulltextCom Texto completo-
item.grantfulltextopen-
item.openairetypeArticle-
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