Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2018 |
| Outros Autores: | , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/31266 |
Resumo: | Capes and Finep for the financial support. |
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Costa, Renyer AlvesAraujo Junior, Earle SilvaLopes, Guilherme Braule PintoPinheiro, Maria Lucia BelémCosta, Emmanoel VilaçaBezerra, Daniel PereiraOliveira, Kelson2019-01-23T17:25:07Z2019-01-23T17:25:07Z2018COSTA, R. A. et al. Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach. Journal of Molecular Structure, v. 1171, p. 682-695, 2018.0022-2860https://www.arca.fiocruz.br/handle/icict/3126610.1016/j.molstruc.2018.06.054Capes and Finep for the financial support.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brasil.Federal Institute of Science and Technology of Amazonas. Manaus, AM, Brasil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brasil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brasil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brasil.A theoretical and experimental DFT study of the vibrational, structural and quantum properties of annomontine (1) and N-hydroxyannomontine (2) alkaloids using the B3LYP exchange-correlation functional with 6-311G (2d, p) basis set is presented. The theoretical geometry optimization data of the two structures were compared with the X-ray data of (1) in the associated literature and a conformational study is presented for both molecules, providing a good comprehension of the conformational stability. In addition, natural bond orbitals (NBOs), HOMO-LUMO energy gap and mapped molecular electrostatic potential surface (MEPS) calculations were also performed at the same calculation approach. The calculated UV spectra agreed well with the measured experimental data, with transitions assigned. The comparative IR studies confirmed the intramolecular hydrogen bonds of the conformations and the intermolecular hydrogen bonds of dimeric forms and also revealed several characteristic vibrations for the structures. Molecular docking studies with DNA Topoisomerase II-DNA complex showed binding free energies of 11.5 and 10.6 kcal/mol for 2 and 1 respectively, while for amsacrine, used for the treatment of leukemia, and doxorubicin, used for the treatment of breast cancer, bladder cancer, Kaposi's sarcoma, and acute lymphocytic leukemia, the presented binding free energies values are 10.0 and 9.9 kcal/mol respectively, revealing good bind affinities of the tested alkaloids with the complex. In vitro cytotoxicity assay revealed an expressive antitumor activity of N-hydroxyannomontine against human hepatocellular carcinoma cell line HepG2.engElsevierAnomontinaN-hidroxianomontinaUVeVisDFTAncoragem molecularAnticâncerAnnomontineN-hydroxyannomontine;UVeVisDFTMolecular dockingAnti-cancerStructural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approachinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/31266/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALCOSTA, R.A. Structural, vibrational...2018.pdfCOSTA, R.A. Structural, vibrational...2018.pdfapplication/pdf2936054https://www.arca.fiocruz.br/bitstream/icict/31266/2/COSTA%2c%20R.A.%20Structural%2c%20vibrational...2018.pdf2d4f8460eccd92e0c97e746bf8b04debMD52TEXTCOSTA, R.A. Structural, vibrational...2018.pdf.txtCOSTA, R.A. Structural, vibrational...2018.pdf.txtExtracted texttext/plain61817https://www.arca.fiocruz.br/bitstream/icict/31266/3/COSTA%2c%20R.A.%20Structural%2c%20vibrational...2018.pdf.txt33a74841a0f6604065424f436c71a45fMD53icict/312662023-03-15 14:34:17.437oai:www.arca.fiocruz.br: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ório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-03-15T17:34:17Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach |
| title |
Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach |
| spellingShingle |
Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach Costa, Renyer Alves Anomontina N-hidroxianomontina UVeVis DFT Ancoragem molecular Anticâncer Annomontine N-hydroxyannomontine; UVeVis DFT Molecular docking Anti-cancer |
| title_short |
Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach |
| title_full |
Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach |
| title_fullStr |
Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach |
| title_full_unstemmed |
Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach |
| title_sort |
Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach |
| author |
Costa, Renyer Alves |
| author_facet |
Costa, Renyer Alves Araujo Junior, Earle Silva Lopes, Guilherme Braule Pinto Pinheiro, Maria Lucia Belém Costa, Emmanoel Vilaça Bezerra, Daniel Pereira Oliveira, Kelson |
| author_role |
author |
| author2 |
Araujo Junior, Earle Silva Lopes, Guilherme Braule Pinto Pinheiro, Maria Lucia Belém Costa, Emmanoel Vilaça Bezerra, Daniel Pereira Oliveira, Kelson |
| author2_role |
author author author author author author |
| dc.contributor.author.fl_str_mv |
Costa, Renyer Alves Araujo Junior, Earle Silva Lopes, Guilherme Braule Pinto Pinheiro, Maria Lucia Belém Costa, Emmanoel Vilaça Bezerra, Daniel Pereira Oliveira, Kelson |
| dc.subject.other.pt_BR.fl_str_mv |
Anomontina N-hidroxianomontina UVeVis DFT Ancoragem molecular Anticâncer |
| topic |
Anomontina N-hidroxianomontina UVeVis DFT Ancoragem molecular Anticâncer Annomontine N-hydroxyannomontine; UVeVis DFT Molecular docking Anti-cancer |
| dc.subject.en.pt_BR.fl_str_mv |
Annomontine N-hydroxyannomontine; UVeVis DFT Molecular docking Anti-cancer |
| description |
Capes and Finep for the financial support. |
| publishDate |
2018 |
| dc.date.issued.fl_str_mv |
2018 |
| dc.date.accessioned.fl_str_mv |
2019-01-23T17:25:07Z |
| dc.date.available.fl_str_mv |
2019-01-23T17:25:07Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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| dc.identifier.citation.fl_str_mv |
COSTA, R. A. et al. Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach. Journal of Molecular Structure, v. 1171, p. 682-695, 2018. |
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https://www.arca.fiocruz.br/handle/icict/31266 |
| dc.identifier.issn.pt_BR.fl_str_mv |
0022-2860 |
| dc.identifier.doi.pt_BR.fl_str_mv |
10.1016/j.molstruc.2018.06.054 |
| identifier_str_mv |
COSTA, R. A. et al. Structural, vibrational, UVevis, quantum-chemical properties, molecular docking and anti-cancer activity study of annomontine and N-hydroxyannomontine b-carboline alkaloids: A combined experimental and DFT approach. Journal of Molecular Structure, v. 1171, p. 682-695, 2018. 0022-2860 10.1016/j.molstruc.2018.06.054 |
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Elsevier |
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Elsevier |
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