Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities
Autor(a) principal: | |
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Data de Publicação: | 2010 |
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/30311 |
Resumo: | DFT calculations using the B3LYP and PBE1PBE functionals with the standard 6-31G(d) and 6-311+G(2d,p) basis sets were carried out for the 3-(2-phenylhydrazone)-naphthalene-1,2,4-trione system in solution (dmso) and in the gas phase, and showed the keto-hydrazone forms (rotamers Ia and Ib) to be more stable than the enol-azo forms (rotamers IIa and IIb, by about 14 kcal mol-1) and III (by approximately 6 kcal mol-1), independently of the nature of the substituent in the phenylene ring. These results were confirmed by spectroscopic data on the derivatives HL1-HL13, obtained from 2-hydroxy-1,4-naphthoquinone and arylamines (R = 4-OMe, 4-N2-C6H5, 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO2, 3-NO2, 2-NO2). The in vitro antitumor (against SF-295, HCT-8, MDAMB-435 and HL-60 cancer cell lines) and antibacterial activities (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa) of compounds HL1-HL13 and of their respective copper(II) complexes, [Cu(L1-13)2], were tested. In general, these compounds exhibited low antibacterial activity, except for HL5 (R = 3-I), more active than the control; however, the corresponding complex was inactive. In contrast, increased cytotoxicity was observed upon complexation. Complex [Cu(L13)2] (R = 3-NO2) presented moderate cytotoxicity against human leukemia (HL-60). |
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Francisco, Acácio I.Vargas, Maria D.Fragoso, Thaís P.Carneiro, J. Walkimar de M.Casellato, AnneliseSilva, Fernando de C. daFerreira, Vitor F.Barbosa, Jussara P.Pessoa, ClaudiaLotufo, Letícia V. CostaMarinho Filho, José D. B.Moraes, Manoel O. deMangrich, Antonio S.2018-11-29T13:12:59Z2018-11-29T13:12:59Z2010FRANCISCO, Acácio I. et al. Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities. J. Bras. Chem. Soc., v.21, n.7, p.1293-1302, 2010.0103 - 5053https://www.arca.fiocruz.br/handle/icict/303111678-4790engSociedade Brasileira de QuímicaNaftoquinonasatividade antibacterianatautomerismocompostos de hidrazonaatividade antibacterianaatividade antitumoralnaphthoquinonescopper(II) complexestautomerismhydrazone compoundsantibacterial activityantitumor activityNaftoquinonasTheoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleDFT calculations using the B3LYP and PBE1PBE functionals with the standard 6-31G(d) and 6-311+G(2d,p) basis sets were carried out for the 3-(2-phenylhydrazone)-naphthalene-1,2,4-trione system in solution (dmso) and in the gas phase, and showed the keto-hydrazone forms (rotamers Ia and Ib) to be more stable than the enol-azo forms (rotamers IIa and IIb, by about 14 kcal mol-1) and III (by approximately 6 kcal mol-1), independently of the nature of the substituent in the phenylene ring. These results were confirmed by spectroscopic data on the derivatives HL1-HL13, obtained from 2-hydroxy-1,4-naphthoquinone and arylamines (R = 4-OMe, 4-N2-C6H5, 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO2, 3-NO2, 2-NO2). The in vitro antitumor (against SF-295, HCT-8, MDAMB-435 and HL-60 cancer cell lines) and antibacterial activities (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa) of compounds HL1-HL13 and of their respective copper(II) complexes, [Cu(L1-13)2], were tested. In general, these compounds exhibited low antibacterial activity, except for HL5 (R = 3-I), more active than the control; however, the corresponding complex was inactive. In contrast, increased cytotoxicity was observed upon complexation. Complex [Cu(L13)2] (R = 3-NO2) presented moderate cytotoxicity against human leukemia (HL-60).Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil.Universidade Federal do Ceará. Depto de Fisiologia e Farmacologia. Campus do Porangabussu, Fortaleza, CE, Brasil.Universidade Federal do Ceará. Depto de Fisiologia e Farmacologia. Campus do Porangabussu, Fortaleza, CE, Brasil.Universidade Federal do Ceará. Depto de Fisiologia e Farmacologia. Campus do Porangabussu, Fortaleza, CE, Brasil.Universidade Federal do Ceará. Depto de Fisiologia e Farmacologia. Campus do Porangabussu, Fortaleza, CE, Brasil.Universidade Federal do Paraná. Departamento de Química. Curitiba, PR, Brasil.Cálculos teóricos utilizando os funcionais B3LYP e PBE1PBE e as bases 6-31G(d) e 6-311+G(2d,p) para o sistema 3-(2-fenil-hidrazona)-naftaleno-1,2,4-triona, em solução (dmso) e em fase gasosa, evidenciaram, em ambos os casos, a maior estabilidade da forma ceto-hidrazona (rotâmeros Ia e Ib) comparada às formas enol-azo (rotâmeros IIa/IIb, por volta de 14 kcal mol-1) e III (aproximadamente 6 kcal mol-1). A natureza do substituinte no grupo fenil não influenciou a estabilidade relativa dos tautômeros. Estes resultados foram confirmados por dados espectroscópicos dos derivados HL1-HL13, sintetizados a partir da 2-hidroxi-1,4-naftoquinona e arilaminas (R = 4-OMe, 4-N2-C6H5, 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO2, 3-NO2, 2-NO2). A avaliação da atividade anticâncer in vitro (contra linhagens de células cancerosas SF-295, HCT‑8, MDAMB-435 e HL-60) e bactericida (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia e Pseudomonas aeruginosa) dos compostos HL1-HL13 e dos seus respectivos complexos de cobre(II), [Cu(L1-13)2], foi avaliada. Em geral a atividade bactericida foi baixa, exceto para o derivado HL5 (R = 3-I), mais ativo do que o controle; entretanto, seu complexo não foi ativo. Por outro lado, a complexação levou, em geral, ao aumento da atividade antitumoral dos pré-ligantes. O complexo [Cu(L13)2] (R = 3-NO2) apresentou moderada citotoxicidade contra leucemia humana (HL-60).info: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/30311/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALjussarap_barbosa_etal_IOC_2010.pdfjussarap_barbosa_etal_IOC_2010.pdfapplication/pdf1564535https://www.arca.fiocruz.br/bitstream/icict/30311/2/jussarap_barbosa_etal_IOC_2010.pdfb114a73b75a02eda0887520d01d69d53MD52TEXTjussarap_barbosa_etal_IOC_2010.pdf.txtjussarap_barbosa_etal_IOC_2010.pdf.txtExtracted texttext/plain74670https://www.arca.fiocruz.br/bitstream/icict/30311/3/jussarap_barbosa_etal_IOC_2010.pdf.txtc323f23342361aae07bb7f34673108c4MD53icict/303112018-11-30 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dc.title.pt_BR.fl_str_mv |
Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities |
title |
Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities |
spellingShingle |
Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities Francisco, Acácio I. Naftoquinonas atividade antibacteriana tautomerismo compostos de hidrazona atividade antibacteriana atividade antitumoral naphthoquinones copper(II) complexes tautomerism hydrazone compounds antibacterial activity antitumor activity Naftoquinonas |
title_short |
Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities |
title_full |
Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities |
title_fullStr |
Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities |
title_full_unstemmed |
Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities |
title_sort |
Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities |
author |
Francisco, Acácio I. |
author_facet |
Francisco, Acácio I. Vargas, Maria D. Fragoso, Thaís P. Carneiro, J. Walkimar de M. Casellato, Annelise Silva, Fernando de C. da Ferreira, Vitor F. Barbosa, Jussara P. Pessoa, Claudia Lotufo, Letícia V. Costa Marinho Filho, José D. B. Moraes, Manoel O. de Mangrich, Antonio S. |
author_role |
author |
author2 |
Vargas, Maria D. Fragoso, Thaís P. Carneiro, J. Walkimar de M. Casellato, Annelise Silva, Fernando de C. da Ferreira, Vitor F. Barbosa, Jussara P. Pessoa, Claudia Lotufo, Letícia V. Costa Marinho Filho, José D. B. Moraes, Manoel O. de Mangrich, Antonio S. |
author2_role |
author author author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Francisco, Acácio I. Vargas, Maria D. Fragoso, Thaís P. Carneiro, J. Walkimar de M. Casellato, Annelise Silva, Fernando de C. da Ferreira, Vitor F. Barbosa, Jussara P. Pessoa, Claudia Lotufo, Letícia V. Costa Marinho Filho, José D. B. Moraes, Manoel O. de Mangrich, Antonio S. |
dc.subject.other.pt_BR.fl_str_mv |
Naftoquinonas atividade antibacteriana tautomerismo compostos de hidrazona atividade antibacteriana atividade antitumoral |
topic |
Naftoquinonas atividade antibacteriana tautomerismo compostos de hidrazona atividade antibacteriana atividade antitumoral naphthoquinones copper(II) complexes tautomerism hydrazone compounds antibacterial activity antitumor activity Naftoquinonas |
dc.subject.en.pt_BR.fl_str_mv |
naphthoquinones copper(II) complexes tautomerism hydrazone compounds antibacterial activity antitumor activity |
dc.subject.decs.pt_BR.fl_str_mv |
Naftoquinonas |
description |
DFT calculations using the B3LYP and PBE1PBE functionals with the standard 6-31G(d) and 6-311+G(2d,p) basis sets were carried out for the 3-(2-phenylhydrazone)-naphthalene-1,2,4-trione system in solution (dmso) and in the gas phase, and showed the keto-hydrazone forms (rotamers Ia and Ib) to be more stable than the enol-azo forms (rotamers IIa and IIb, by about 14 kcal mol-1) and III (by approximately 6 kcal mol-1), independently of the nature of the substituent in the phenylene ring. These results were confirmed by spectroscopic data on the derivatives HL1-HL13, obtained from 2-hydroxy-1,4-naphthoquinone and arylamines (R = 4-OMe, 4-N2-C6H5, 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO2, 3-NO2, 2-NO2). The in vitro antitumor (against SF-295, HCT-8, MDAMB-435 and HL-60 cancer cell lines) and antibacterial activities (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa) of compounds HL1-HL13 and of their respective copper(II) complexes, [Cu(L1-13)2], were tested. In general, these compounds exhibited low antibacterial activity, except for HL5 (R = 3-I), more active than the control; however, the corresponding complex was inactive. In contrast, increased cytotoxicity was observed upon complexation. Complex [Cu(L13)2] (R = 3-NO2) presented moderate cytotoxicity against human leukemia (HL-60). |
publishDate |
2010 |
dc.date.issued.fl_str_mv |
2010 |
dc.date.accessioned.fl_str_mv |
2018-11-29T13:12:59Z |
dc.date.available.fl_str_mv |
2018-11-29T13:12:59Z |
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 |
FRANCISCO, Acácio I. et al. Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities. J. Bras. Chem. Soc., v.21, n.7, p.1293-1302, 2010. |
dc.identifier.uri.fl_str_mv |
https://www.arca.fiocruz.br/handle/icict/30311 |
dc.identifier.issn.pt_BR.fl_str_mv |
0103 - 5053 |
dc.identifier.eissn.none.fl_str_mv |
1678-4790 |
identifier_str_mv |
FRANCISCO, Acácio I. et al. Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities. J. Bras. Chem. Soc., v.21, n.7, p.1293-1302, 2010. 0103 - 5053 1678-4790 |
url |
https://www.arca.fiocruz.br/handle/icict/30311 |
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 |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
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/30311/1/license.txt https://www.arca.fiocruz.br/bitstream/icict/30311/2/jussarap_barbosa_etal_IOC_2010.pdf https://www.arca.fiocruz.br/bitstream/icict/30311/3/jussarap_barbosa_etal_IOC_2010.pdf.txt |
bitstream.checksum.fl_str_mv |
5a560609d32a3863062d77ff32785d58 b114a73b75a02eda0887520d01d69d53 c323f23342361aae07bb7f34673108c4 |
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_ |
1813008861658873856 |