Experimental and theoretical study on spectral features, reactivity, solvation, topoisomerase I inhibition and in vitro cytotoxicity in human HepG2 cells of guadiscine and guadiscidine aporphine alkaloids

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MetadadosDescriçãoIdioma
Autor(es): dc.contributorFederal University of Amazonas (DQ-UFAM)-
Autor(es): dc.contributorUniversidade Estadual de Campinas (UNICAMP)-
Autor(es): dc.contributorUniversidade Estadual Paulista (Unesp)-
Autor(es): dc.contributorOswaldo Cruz Fundation (IGM/FIOCRUZ-BA)-
Autor(es): dc.creatorCosta, Renyer A.-
Autor(es): dc.creatorBarros, Gabriel de A.-
Autor(es): dc.creatorda Silva, Jonathas N. [UNESP]-
Autor(es): dc.creatorOliveira, Kelson M.-
Autor(es): dc.creatorBezerra, Daniel P.-
Autor(es): dc.creatorSoares, Milena B.P.-
Autor(es): dc.creatorCosta, Emmanoel V.-
Data de aceite: dc.date.accessioned2022-02-22T00:45:03Z-
Data de disponibilização: dc.date.available2022-02-22T00:45:03Z-
Data de envio: dc.date.issued2021-06-25-
Data de envio: dc.date.issued2021-06-25-
Data de envio: dc.date.issued2021-04-05-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1016/j.molstruc.2020.129844-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/205695-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/205695-
Descrição: dc.descriptionIn this study, guadiscine (G1) and guadiscidine (G2), 7,7-dimethylaporphine alkaloids from Guatteria friesiana, have they geometric paramaters, vibrational behavior and quantum chemical properties (HOMO-LUMO, MEP, ALIE and Fukui indices) analyzed through a theoretical view, by density functional theory (DFT), using the Becker's three-parameter hybrid exchange functional combined with the Lee–Yang–Parr correlation functional (B3LYP) and 6–311G(2d,p) and 6–311G++(2df,3p) basis sets. The obtained geometry data were compared with x-ray data for (−)-N-acetyl-anonaine, showing close values. Vibrational analysis, together with potential energy distribution (PED) calculations, revealed several characteristic vibrations that characterize the 7,7 dimethylaporphine skeleton, besides enabling the observation of intermolecular H-bonds through dimers formation. Molecular dynamic simulations were carried out, allowing to evaluate the solvation free energies of G1 and G2 in water, methanol and ethanol, as well as H-bonds formation between G1 and G2 and the tested solvents. The antineoplastic potential of the title molecules was evaluated via molecular docking calculations with topoisomerase I complexed with DNA. Guadiscine and guadiscidine showed, respectively, binding free energies of -8.0 and -8.5 kcal/mol, while topotecan, a DNA topoisomerase I inhibitor, showed a binding free energy value of -12 kcal/mol, indicating that the studied molecules are good topoisomerase I inhibitors. In vitro cytotoxicity assay with HepG2 cell line were performed, revealing significant antitumor potential for G2.-
Descrição: dc.descriptionDepartment of Chemistry Federal University of Amazonas (DQ-UFAM)-
Descrição: dc.descriptionChemistry institute University of Campinas-
Descrição: dc.descriptionFaculty of Sciences and Letters - Araraquara Campus São Paulo State University (UNESP)-
Descrição: dc.descriptionGonçalo Moniz Institute Oswaldo Cruz Fundation (IGM/FIOCRUZ-BA)-
Descrição: dc.descriptionFaculty of Sciences and Letters - Araraquara Campus São Paulo State University (UNESP)-
Idioma: dc.languageen-
Relação: dc.relationJournal of Molecular Structure-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subject7,7-dimethylaporphine alkaloids-
Palavras-chave: dc.subjectCytotoxicity-
Palavras-chave: dc.subjectDFT-
Palavras-chave: dc.subjectDocking-
Palavras-chave: dc.subjectHepG2-
Palavras-chave: dc.subjectMolecular dynamics-
Título: dc.titleExperimental and theoretical study on spectral features, reactivity, solvation, topoisomerase I inhibition and in vitro cytotoxicity in human HepG2 cells of guadiscine and guadiscidine aporphine alkaloids-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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