Synthesis, anticancer activities and experimental-theoretical dna interaction studies of 2-amino-4-phenyl-4h-benzo[h]chromene-3-carbonitrile

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dc.creatorTaniris Cafiero Braga
dc.creatorFelipe Terra Martins
dc.creatorIsis Martins Figueiredo
dc.creatorThiago Mendonça de Aquino
dc.creatorCleiton Moreira da Silva
dc.creatorBhagirath Mandal
dc.creatorGoutam Brahmachari
dc.creatorJosué Carinhanha Caldas Santos
dc.creatorÂngelo de Fátima
dc.creatorMarina de Magalhães Silva
dc.creatorEduarda O.O. Nascimento
dc.creatorEdjan Carlos Dantas da Silva
dc.creatorYuri de Freitas Rego
dc.creatorMullicka Mandal
dc.creatorZaqueu Alves de Souza
dc.creatorAna Lúcia Tasca Góis Ruiz
dc.creatorJoão Ernesto de Carvalho
dc.date.accessioned2025-01-31T19:27:17Z
dc.date.accessioned2025-09-09T00:12:21Z
dc.date.available2025-01-31T19:27:17Z
dc.date.issued2022
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.doihttps://doi.org/10.1016/j.ejmcr.2022.100030
dc.identifier.issn2772-4174
dc.identifier.urihttps://hdl.handle.net/1843/79584
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofEuropean Journal of Medicinal Chemistry Reports
dc.rightsAcesso Aberto
dc.subjectCompostos heterocíclicos
dc.subjectDNA
dc.subjectAgentes antineoplásicos
dc.subjectRaios X - Difração
dc.subjectFluorescência
dc.subjectEspectrometria de ultra violeta
dc.subject.otherChromene
dc.subject.otherAntiproliferative activity
dc.subject.otherBioanalytical correlation
dc.subject.otherDNA interaction
dc.subject.otherIntercalation
dc.titleSynthesis, anticancer activities and experimental-theoretical dna interaction studies of 2-amino-4-phenyl-4h-benzo[h]chromene-3-carbonitrile
dc.typeArtigo de periódico
local.citation.spage100030
local.citation.volume4
local.description.resumoTwenty chromenes were synthesized with good to excellent yields (70–96%). From the series of chromenes herein tested, compounds 14, 12, 15, 16, 17, 18, and 20 were the most potent throughout the cancer human cell lines tested. In general, the para-position electron-withdrawing substituents on the phenyl ring are favored towards potency and selectivity for cancer cells. Biophysical studies were performed with eight chromene derivatives (13-20) and ctDNA to evaluate possible biological targets. The molecular fluorescence verified that compound 16 presented a higher binding constant (Kb) with the ctDNA, agreeing with in vitro biological results and that evaluated chromenes derivatives interact preferentially via intercalation. Finally, an inverse linear correlation (logKb vs. GI50) was observed for six human carcinogenic cell lines; hence, the mechanism of action of these compounds may be related to DNA interaction.
local.identifier.orcidhttps://orcid.org/0000-0002-4032-0100
local.identifier.orcidhttps://orcid.org/0000-0001-9004-0927
local.identifier.orcidhttps://orcid.org/0000-0002-1873-5342
local.identifier.orcidhttps://orcid.org/0000-0001-9138-8466
local.identifier.orcidhttps://orcid.org/0000-0001-9913-8971
local.identifier.orcidhttps://orcid.org/0000-0002-3491-2249
local.identifier.orcidhttps://orcid.org/0000-0001-9925-6281
local.identifier.orcidhttps://orcid.org/0000-0002-9525-5123
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0002-1087-4639
local.identifier.orcidhttps://orcid.org/0000-0003-4660-6852
local.identifier.orcidhttps://orcid.org/0000-0003-0698-5341
local.identifier.orcidhttps://orcid.org/0000-0002-0844-8702
local.identifier.orcidhttps://orcid.org/0000-0002-6901-6815
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S2772417422000024?via%3Dihub

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