Theoretical and experimental study by DFT, molecular docking calculations and cytotoxicity assay of 7,7-dimethylaporphine alkaloids type isolated from Guatteria friesiana (Annonaceae)

dc.creatorBranches, Adjane Dalvana Sampaio
dc.creatorCosta, Renyer Alves
dc.creatorAraujo Junior, Earle Silva
dc.creatorBezerra, Daniel Pereira
dc.creatorSoares, Milena Botelho Pereira
dc.creatorCosta, Emmanoel Vilaça
dc.creatorOliveira, Kelson Mota Teixeira de
dc.date2019-02-14T13:52:54Z
dc.date2019-02-14T13:52:54Z
dc.date2019
dc.date.accessioned2023-09-26T22:03:56Z
dc.date.available2023-09-26T22:03:56Z
dc.identifierBRANCHES, A. D. S. et al. Theoretical and experimental study by DFT, molecular docking calculations and cytotoxicity assay of 7,7-dimethylaporphine alkaloids type isolated from Guatteria friesiana (Annonaceae). Journal of Molecular Structure, v. 1177, p. 347-362, 2019.
dc.identifier0022-2860
dc.identifierhttps://www.arca.fiocruz.br/handle/icict/31642
dc.identifier10.1016/j.molstruc.2018.09.060
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8874546
dc.descriptionCAPES, CNPq, FAPEAM and FINEP for the financial support, and Gabriel G. Gato for helping in organizing the IR tables.
dc.descriptionA combined experimental and theoretical DFT study of the structural, vibrational and electronic properties of 9-methoxyguatterfriesine (I), (R)-6,6a-dihydro-9-methoxyguatterfriesine (II) and 4,5-dehydro- 9-methoxyguatterfriesine (III) is presented using B3LYP exchange-correlation functional with 6-311G (2d, p) basis set. The theoretical geometry optimization data were compared with the X-ray data for ( )-N-acetylanonaine, showing close values. In addition, molecular electrostatic potential surface (MEPS) calculation, HOMO-LUMO energy gap, natural bond orbitals (NBOs) and first and second order hyperpolarizabilities were also performed with the same calculation level. Transitions for UV spectrum for the three structures were assigned and the calculated bands showed good agreement with the measured experimental data. The comparative IR studies showed intermolecular hydrogen bonds that stabilize dimeric forms proposed for the three molecules and also revealed several characteristic vibrations for the structures. Molecular docking studies with DNA Topoisomerase II-DNA complex showed binding free energies of 7.6, 7.5 and 8.7 kcal/mol, for I, II and III respectively, which indicate III as a better potential inhibitor for this enzyme. In vitro cytotoxicity assay revealed an expressive antitumor activity of III against HepG2 cell line.
dc.formatapplication/pdf
dc.languageeng
dc.publisherElsevier
dc.rightsrestricted access
dc.subjectAlcaldes de 7,7-dimetilaporfina
dc.subjectDFT
dc.subjectAncoragem molecular
dc.subjectFT-IR
dc.subjectAnálise NBO / NLO
dc.subjectAnticâncer
dc.subject7,7-Dimethylaporphine alkaloids
dc.subjectDFT
dc.subjectMolecular docking
dc.subjectFT-IR
dc.subjectNBO/NLO analysis
dc.subjectAnti-cancer
dc.titleTheoretical and experimental study by DFT, molecular docking calculations and cytotoxicity assay of 7,7-dimethylaporphine alkaloids type isolated from Guatteria friesiana (Annonaceae)
dc.typeArticle


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