Redox center modification of lapachones toward the syntheses of nitrogen heterocycles as selective fluorescent mitochondrial imaging probes

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dc.creatorFabíola S. dos Santos
dc.creatorGleiston Gonçalves Dias
dc.creatorRossimiriam Pereira de Freitas
dc.creatorLucas da Silva Santos
dc.creatorGuilherme Ferreira de Lima
dc.creatorHélio Anderson Duarte
dc.creatorCarlos Alberto de Simone
dc.creatorLidia Maria Silva Lopes Rezende
dc.creatorMonique Jacob Xavier Vianna
dc.creatorJosé Raimundo Corrêa
dc.creatorBrenno Amaro da Silveira Neto
dc.creatorEufrânio Nunes da Silva Júnior
dc.date.accessioned2024-07-30T14:15:44Z
dc.date.accessioned2025-09-09T01:03:31Z
dc.date.available2024-07-30T14:15:44Z
dc.date.issued2017
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.sponsorshipINCT – Instituto nacional de ciência e tecnologia (Antigo Instituto do Milênio)
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1002/ejoc.201700227
dc.identifier.issn1875-6638
dc.identifier.urihttps://hdl.handle.net/1843/72109
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofEuropean Journal of Organic Chemistry
dc.rightsAcesso Restrito
dc.subjectQuinona
dc.subjectNaftoquinona
dc.subjectCompostos heterocíclicos
dc.subjectNitrogênio
dc.subjectFluorescência
dc.subjectSíntese
dc.subjectSondas fluorescentes
dc.subject.otherQuinones
dc.subject.otherHeterocycles
dc.subject.otherImaging agents
dc.subject.otherFluorescence
dc.subject.otherRedox modification
dc.titleRedox center modification of lapachones toward the syntheses of nitrogen heterocycles as selective fluorescent mitochondrial imaging probes
dc.typeArtigo de periódico
local.citation.epage3773
local.citation.issue26
local.citation.spage3763
local.citation.volume2017
local.description.resumoWe describe herein a synthetic strategy for the synthesis of new fluorescent imidazole and phenazine derivatives synthesized from lapachol, a naturally occurring naphthoquinone isolated from Tabebuia species (ipê tree). The photophysical properties and computational details of these compounds have been studied, aiming at gaining a complete understanding of the potential of these derivatives as probes capable of staining mitochondria selectively. Cell imaging experiments proved the capacity of the imidazole derivatives as selective fluorescent mitochondrial imaging probes. These heterocycles present the same staining patterns as MitoTracker Red, corroborating the potential of these compounds as new mitochondria markers permeable to the cell membrane.
local.identifier.orcidhttps://orcid.org/0000-0003-4952-756X
local.identifier.orcidhttps://orcid.org/0000-0001-6974-3724
local.identifier.orcidhttps://orcid.org/0000-0002-0311-3831
local.identifier.orcidhttps://orcid.org/0000-0001-8164-4454
local.identifier.orcidhttps://orcid.org/0000-0001-6622-710X
local.identifier.orcidhttps://orcid.org/0000-0003-2752-5395
local.identifier.orcidhttps://orcid.org/0000-0003-1281-5453
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201700227

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