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
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| 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/47978 |
Resumo: | Conselho Nacional de Desenvolvi- mento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoa- mento de Pessoal de Nível Superior (CAPES) - Code 001, Finan- ciadora de Estudos e Projetos (FINEP), Fundação de Amparo àPesquisa do Estado da Bahia (FAPESB), and Federal University of Amazonas (UFAM) for financial support and fellowship |
| id |
CRUZ_8cddcf3544187af8fd4522659a311bc3 |
|---|---|
| oai_identifier_str |
oai:www.arca.fiocruz.br:icict/47978 |
| network_acronym_str |
CRUZ |
| network_name_str |
Repositório Institucional da FIOCRUZ (ARCA) |
| repository_id_str |
2135 |
| spelling |
Costa, Renyer A.Barros, Gabriel de A.Silva, Jonathas N. daOliveira, Kelson M.Bezerra, Daniel PereiraSoares, Milena Botelho PereiraCosta, Emmanoel Vilaça2021-07-05T14:01:42Z2021-07-05T14:01:42Z2021COSTA, Renyer A. et al. 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. Journal of Molecular Structure, v . 1229, 2021.0022-2860https://www.arca.fiocruz.br/handle/icict/4797810.1016/j.molstruc.2020.129844Conselho Nacional de Desenvolvi- mento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoa- mento de Pessoal de Nível Superior (CAPES) - Code 001, Finan- ciadora de Estudos e Projetos (FINEP), Fundação de Amparo àPesquisa do Estado da Bahia (FAPESB), and Federal University of Amazonas (UFAM) for financial support and fellowshipFederal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.University of Campinas. Chemistry institute. Campinas, SP, Brazil.São Paulo State University. Faculty of Sciences and Letters. São Paulo, SP, Brazil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.In 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 geom- etry 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 vi- brations that characterize the 7,7 dimethylaporphine skeleton, besides enabling the observation of inter- molecular 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.engElsevierDFTTécnicas In VitroGuatteriaDinâmica molecularCitotoxicidadeDNADFT7,7-dimethylaporphine alkaloidsDockingMolecular dynamicsCytotoxicityHepG2Experimental and theoretical study on spectral features, reactivity, solvation, topoisomerase I inhibition and in vitro cytotoxicity in human HepG2 cells of guadiscine and guadiscidine aporphine alkaloidsinfo: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-83097https://www.arca.fiocruz.br/bitstream/icict/47978/1/license.txt36b51ef91c52b5338d9d29ba0cc807bcMD51ORIGINALCosta, Renyer A. Experimental....pdfCosta, Renyer A. Experimental....pdfapplication/pdf3637507https://www.arca.fiocruz.br/bitstream/icict/47978/2/Costa%2c%20Renyer%20A.%20Experimental....pdffe081a03472bbf55d699b4fb7328c9a5MD52TEXTCosta, Renyer A. Experimental....pdf.txtCosta, Renyer A. Experimental....pdf.txtExtracted texttext/plain65627https://www.arca.fiocruz.br/bitstream/icict/47978/3/Costa%2c%20Renyer%20A.%20Experimental....pdf.txtfd7f5685a447806e76e176b8eb8780c2MD53icict/479782023-03-15 14:34:29.236oai:www.arca.fiocruz.br:icict/47978Q0VTU8ODTyBOw4NPIEVYQ0xVU0lWQSBERSBESVJFSVRPUyBBVVRPUkFJUw0KDQpBbmEgTWFyaWEgRmlzY2luYSBTYW1wYWlvLCBDUEY6IDA2NS40MzEuMDM1LTE1LCB2aW5jdWxhZG8gYSBDUHFHTSAtIENlbnRybyBkZSBQZXNxdWlzYXMgR29uw6dhbG8gTW9uaXoKCkFvIGFjZWl0YXIgb3MgVEVSTU9TIGUgQ09OREnDh8OVRVMgZGVzdGEgQ0VTU8ODTywgbyBBVVRPUiBlL291IFRJVFVMQVIgZGUgZGlyZWl0b3MKYXV0b3JhaXMgc29icmUgYSBPQlJBIGRlIHF1ZSB0cmF0YSBlc3RlIGRvY3VtZW50bzoKCigxKSBDRURFIGUgVFJBTlNGRVJFLCB0b3RhbCBlIGdyYXR1aXRhbWVudGUsIMOgIEZJT0NSVVogLSBGVU5EQcOHw4NPIE9TV0FMRE8gQ1JVWiwgZW0KY2Fyw6F0ZXIgcGVybWFuZW50ZSwgaXJyZXZvZ8OhdmVsIGUgTsODTyBFWENMVVNJVk8sIHRvZG9zIG9zIGRpcmVpdG9zIHBhdHJpbW9uaWFpcyBOw4NPCkNPTUVSQ0lBSVMgZGUgdXRpbGl6YcOnw6NvIGRhIE9CUkEgYXJ0w61zdGljYSBlL291IGNpZW50w61maWNhIGluZGljYWRhIGFjaW1hLCBpbmNsdXNpdmUgb3MgZGlyZWl0b3MKZGUgdm96IGUgaW1hZ2VtIHZpbmN1bGFkb3Mgw6AgT0JSQSwgZHVyYW50ZSB0b2RvIG8gcHJhem8gZGUgZHVyYcOnw6NvIGRvcyBkaXJlaXRvcyBhdXRvcmFpcywgZW0KcXVhbHF1ZXIgaWRpb21hIGUgZW0gdG9kb3Mgb3MgcGHDrXNlczsKCigyKSBBQ0VJVEEgcXVlIGEgY2Vzc8OjbyB0b3RhbCBuw6NvIGV4Y2x1c2l2YSwgcGVybWFuZW50ZSBlIGlycmV2b2fDoXZlbCBkb3MgZGlyZWl0b3MgYXV0b3JhaXMKcGF0cmltb25pYWlzIG7Do28gY29tZXJjaWFpcyBkZSB1dGlsaXphw6fDo28gZGUgcXVlIHRyYXRhIGVzdGUgZG9jdW1lbnRvIGluY2x1aSwgZXhlbXBsaWZpY2F0aXZhbWVudGUsCm9zIGRpcmVpdG9zIGRlIGRpc3BvbmliaWxpemHDp8OjbyBlIGNvbXVuaWNhw6fDo28gcMO6YmxpY2EgZGEgT0JSQSwgZW0gcXVhbHF1ZXIgbWVpbyBvdSB2ZcOtY3VsbywKaW5jbHVzaXZlIGVtIFJlcG9zaXTDs3Jpb3MgRGlnaXRhaXMsIGJlbSBjb21vIG9zIGRpcmVpdG9zIGRlIHJlcHJvZHXDp8OjbywgZXhpYmnDp8OjbywgZXhlY3XDp8OjbywKZGVjbGFtYcOnw6NvLCByZWNpdGHDp8OjbywgZXhwb3Npw6fDo28sIGFycXVpdmFtZW50bywgaW5jbHVzw6NvIGVtIGJhbmNvIGRlIGRhZG9zLCBwcmVzZXJ2YcOnw6NvLCBkaWZ1c8OjbywKZGlzdHJpYnVpw6fDo28sIGRpdnVsZ2HDp8OjbywgZW1wcsOpc3RpbW8sIHRyYWR1w6fDo28sIGR1YmxhZ2VtLCBsZWdlbmRhZ2VtLCBpbmNsdXPDo28gZW0gbm92YXMgb2JyYXMgb3UKY29sZXTDom5lYXMsIHJldXRpbGl6YcOnw6NvLCBlZGnDp8OjbywgcHJvZHXDp8OjbyBkZSBtYXRlcmlhbCBkaWTDoXRpY28gZSBjdXJzb3Mgb3UgcXVhbHF1ZXIgZm9ybWEgZGUKdXRpbGl6YcOnw6NvIG7Do28gY29tZXJjaWFsOwoKKDMpIFJFQ09OSEVDRSBxdWUgYSBjZXNzw6NvIGFxdWkgZXNwZWNpZmljYWRhIGNvbmNlZGUgw6AgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETwpDUlVaIG8gZGlyZWl0byBkZSBhdXRvcml6YXIgcXVhbHF1ZXIgcGVzc29hIOKAkyBmw61zaWNhIG91IGp1csOtZGljYSwgcMO6YmxpY2Egb3UgcHJpdmFkYSwgbmFjaW9uYWwgb3UKZXN0cmFuZ2VpcmEg4oCTIGEgYWNlc3NhciBlIHV0aWxpemFyIGFtcGxhbWVudGUgYSBPQlJBLCBzZW0gZXhjbHVzaXZpZGFkZSwgcGFyYSBxdWFpc3F1ZXIKZmluYWxpZGFkZXMgbsOjbyBjb21lcmNpYWlzOwoKKDQpIERFQ0xBUkEgcXVlIGEgb2JyYSDDqSBjcmlhw6fDo28gb3JpZ2luYWwgZSBxdWUgw6kgbyB0aXR1bGFyIGRvcyBkaXJlaXRvcyBhcXVpIGNlZGlkb3MgZSBhdXRvcml6YWRvcywKcmVzcG9uc2FiaWxpemFuZG8tc2UgaW50ZWdyYWxtZW50ZSBwZWxvIGNvbnRlw7pkbyBlIG91dHJvcyBlbGVtZW50b3MgcXVlIGZhemVtIHBhcnRlIGRhIE9CUkEsCmluY2x1c2l2ZSBvcyBkaXJlaXRvcyBkZSB2b3ogZSBpbWFnZW0gdmluY3VsYWRvcyDDoCBPQlJBLCBvYnJpZ2FuZG8tc2UgYSBpbmRlbml6YXIgdGVyY2Vpcm9zIHBvcgpkYW5vcywgYmVtIGNvbW8gaW5kZW5pemFyIGUgcmVzc2FyY2lyIGEgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETyBDUlVaIGRlCmV2ZW50dWFpcyBkZXNwZXNhcyBxdWUgdmllcmVtIGEgc3Vwb3J0YXIsIGVtIHJhesOjbyBkZSBxdWFscXVlciBvZmVuc2EgYSBkaXJlaXRvcyBhdXRvcmFpcyBvdQpkaXJlaXRvcyBkZSB2b3ogb3UgaW1hZ2VtLCBwcmluY2lwYWxtZW50ZSBubyBxdWUgZGl6IHJlc3BlaXRvIGEgcGzDoWdpbyBlIHZpb2xhw6fDtWVzIGRlIGRpcmVpdG9zOwoKKDUpIEFGSVJNQSBxdWUgY29uaGVjZSBhIFBvbMOtdGljYSBJbnN0aXR1Y2lvbmFsIGRlIEFjZXNzbyBBYmVydG8gZGEgRklPQ1JVWiAtIEZVTkRBw4fDg08KT1NXQUxETyBDUlVaIGUgYXMgZGlyZXRyaXplcyBwYXJhIG8gZnVuY2lvbmFtZW50byBkbyByZXBvc2l0w7NyaW8gaW5zdGl0dWNpb25hbCBBUkNBLgoKQSBQb2zDrXRpY2EgSW5zdGl0dWNpb25hbCBkZSBBY2Vzc28gQWJlcnRvIGRhIEZJT0NSVVogLSBGVU5EQcOHw4NPIE9TV0FMRE8gQ1JVWiByZXNlcnZhCmV4Y2x1c2l2YW1lbnRlIGFvIEFVVE9SIG9zIGRpcmVpdG9zIG1vcmFpcyBlIG9zIHVzb3MgY29tZXJjaWFpcyBzb2JyZSBhcyBvYnJhcyBkZSBzdWEgYXV0b3JpYQplL291IHRpdHVsYXJpZGFkZSwgc2VuZG8gb3MgdGVyY2Vpcm9zIHVzdcOhcmlvcyByZXNwb25zw6F2ZWlzIHBlbGEgYXRyaWJ1acOnw6NvIGRlIGF1dG9yaWEgZSBtYW51dGVuw6fDo28KZGEgaW50ZWdyaWRhZGUgZGEgT0JSQSBlbSBxdWFscXVlciB1dGlsaXphw6fDo28uCgpBIFBvbMOtdGljYSBJbnN0aXR1Y2lvbmFsIGRlIEFjZXNzbyBBYmVydG8gZGEgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETyBDUlVaCnJlc3BlaXRhIG9zIGNvbnRyYXRvcyBlIGFjb3Jkb3MgcHJlZXhpc3RlbnRlcyBkb3MgQXV0b3JlcyBjb20gdGVyY2Vpcm9zLCBjYWJlbmRvIGFvcyBBdXRvcmVzCmluZm9ybWFyIMOgIEluc3RpdHVpw6fDo28gYXMgY29uZGnDp8O1ZXMgZSBvdXRyYXMgcmVzdHJpw6fDtWVzIGltcG9zdGFzIHBvciBlc3RlcyBpbnN0cnVtZW50b3MuCg==Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-03-15T17:34:29Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
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 |
| title |
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 |
| spellingShingle |
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 Costa, Renyer A. DFT Técnicas In Vitro Guatteria Dinâmica molecular Citotoxicidade DNA DFT 7,7-dimethylaporphine alkaloids Docking Molecular dynamics Cytotoxicity HepG2 |
| title_short |
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 |
| title_full |
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 |
| title_fullStr |
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 |
| title_full_unstemmed |
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 |
| title_sort |
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 |
| author |
Costa, Renyer A. |
| author_facet |
Costa, Renyer A. Barros, Gabriel de A. Silva, Jonathas N. da Oliveira, Kelson M. Bezerra, Daniel Pereira Soares, Milena Botelho Pereira Costa, Emmanoel Vilaça |
| author_role |
author |
| author2 |
Barros, Gabriel de A. Silva, Jonathas N. da Oliveira, Kelson M. Bezerra, Daniel Pereira Soares, Milena Botelho Pereira Costa, Emmanoel Vilaça |
| author2_role |
author author author author author author |
| dc.contributor.author.fl_str_mv |
Costa, Renyer A. Barros, Gabriel de A. Silva, Jonathas N. da Oliveira, Kelson M. Bezerra, Daniel Pereira Soares, Milena Botelho Pereira Costa, Emmanoel Vilaça |
| dc.subject.other.pt_BR.fl_str_mv |
DFT Técnicas In Vitro Guatteria Dinâmica molecular Citotoxicidade DNA |
| topic |
DFT Técnicas In Vitro Guatteria Dinâmica molecular Citotoxicidade DNA DFT 7,7-dimethylaporphine alkaloids Docking Molecular dynamics Cytotoxicity HepG2 |
| dc.subject.en.pt_BR.fl_str_mv |
DFT 7,7-dimethylaporphine alkaloids Docking Molecular dynamics Cytotoxicity HepG2 |
| description |
Conselho Nacional de Desenvolvi- mento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoa- mento de Pessoal de Nível Superior (CAPES) - Code 001, Finan- ciadora de Estudos e Projetos (FINEP), Fundação de Amparo àPesquisa do Estado da Bahia (FAPESB), and Federal University of Amazonas (UFAM) for financial support and fellowship |
| publishDate |
2021 |
| dc.date.accessioned.fl_str_mv |
2021-07-05T14:01:42Z |
| dc.date.available.fl_str_mv |
2021-07-05T14:01:42Z |
| dc.date.issued.fl_str_mv |
2021 |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.citation.fl_str_mv |
COSTA, Renyer A. et al. 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. Journal of Molecular Structure, v . 1229, 2021. |
| dc.identifier.uri.fl_str_mv |
https://www.arca.fiocruz.br/handle/icict/47978 |
| dc.identifier.issn.pt_BR.fl_str_mv |
0022-2860 |
| dc.identifier.doi.none.fl_str_mv |
10.1016/j.molstruc.2020.129844 |
| identifier_str_mv |
COSTA, Renyer A. et al. 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. Journal of Molecular Structure, v . 1229, 2021. 0022-2860 10.1016/j.molstruc.2020.129844 |
| url |
https://www.arca.fiocruz.br/handle/icict/47978 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
| eu_rights_str_mv |
openAccess |
| dc.publisher.none.fl_str_mv |
Elsevier |
| publisher.none.fl_str_mv |
Elsevier |
| dc.source.none.fl_str_mv |
reponame:Repositório Institucional da FIOCRUZ (ARCA) instname:Fundação Oswaldo Cruz (FIOCRUZ) instacron:FIOCRUZ |
| instname_str |
Fundação Oswaldo Cruz (FIOCRUZ) |
| instacron_str |
FIOCRUZ |
| institution |
FIOCRUZ |
| reponame_str |
Repositório Institucional da FIOCRUZ (ARCA) |
| collection |
Repositório Institucional da FIOCRUZ (ARCA) |
| bitstream.url.fl_str_mv |
https://www.arca.fiocruz.br/bitstream/icict/47978/1/license.txt https://www.arca.fiocruz.br/bitstream/icict/47978/2/Costa%2c%20Renyer%20A.%20Experimental....pdf https://www.arca.fiocruz.br/bitstream/icict/47978/3/Costa%2c%20Renyer%20A.%20Experimental....pdf.txt |
| bitstream.checksum.fl_str_mv |
36b51ef91c52b5338d9d29ba0cc807bc fe081a03472bbf55d699b4fb7328c9a5 fd7f5685a447806e76e176b8eb8780c2 |
| bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
| repository.name.fl_str_mv |
Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ) |
| repository.mail.fl_str_mv |
repositorio.arca@fiocruz.br |
| _version_ |
1813009255306887168 |