Two novel donepezil-lipoic acid hybrids: synthesis, anticholinesterase and antioxidant activities and theoretical studies

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dc.creatorBruna Silva Terra
dc.creatorAngelo de Fátima
dc.creatorPedro Henrique Correa da Silva
dc.creatorAnna Tramarin
dc.creatorLucas Lopardi Franco
dc.creatorElaine Fontes Ferreira da Cunha
dc.creatorFernando César de Macedo Júnior
dc.creatorTeodorico de Castro Ramalho
dc.creatorManuela Bartolini
dc.creatorMaria Laura Bolognesi
dc.date.accessioned2024-07-05T17:17:45Z
dc.date.accessioned2025-09-09T00:46:23Z
dc.date.available2024-07-05T17:17:45Z
dc.date.issued2018
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.format.mimetypepdf
dc.identifier.doihttp://dx.doi.org/10.21577/0103-5053.20170196
dc.identifier.issn0103-5053
dc.identifier.urihttps://hdl.handle.net/1843/69757
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.rightsAcesso Aberto
dc.subjectAntioxidantes
dc.subjectAlzheimer, Doença de
dc.subjectInibidores da colinesterase
dc.subject.otherDonepezil-lipoic acid hybrids
dc.subject.otherAlzheimer disease
dc.subject.otherMulti-target directed ligands
dc.titleTwo novel donepezil-lipoic acid hybrids: synthesis, anticholinesterase and antioxidant activities and theoretical studies
dc.typeArtigo de periódico
local.citation.epage747
local.citation.issue4
local.citation.spage738
local.citation.volume29
local.description.resumoAlzheimer disease (AD) is a complex disease related to multiple pathogenic mechanisms. A strategy to develop effective drugs is based on the so-called multi-target directed ligands (MTDL) by using hybrid compounds. So, in the present study, we have designed and synthesized two hybrids, containing the indanone-piperidine moiety of donepezil, a drug approved for the treatment of AD, and the lipoic acid scaffold, an antioxidant compound endowed with neuroprotective effects. One hybrid was synthesized in four steps with 42% global yield, and the other hybrid in six steps with 19% global yield. The latter hybrid displayed moderate inhibitory activity against human acetylcholinesterase (hAChE) and greater activity against human butyrylcholinesterases (hBuChE). The selectivity for hBuChE was further rationalized by theoretical study. Importantly, the second hybrid showed a good antioxidant activity, exhibiting better ability in scavenging 2,2-diphenyl 1-picrylhydrazyl (DPPH) radicals than lipoic acid.
local.identifier.orcidhttps://orcid.org/0000-0002-9608-1559
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0002-5196-9845
local.identifier.orcidhttps://orcid.org/0000-0002-3845-3801
local.identifier.orcidhttps://orcid.org/0000-0002-4230-1309
local.identifier.orcidhttps://orcid.org/0000-0002-7324-1353
local.identifier.orcidhttps://orcid.org/0000-0002-2890-3856
local.identifier.orcidhttps://orcid.org/0000-0002-1289-5361
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://jbcs.sbq.org.br/default.asp?ed=265

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