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

Detalhes bibliográficos
Autor(a) principal: Francisco, Acácio I.
Data de Publicação: 2010
Outros Autores: 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.
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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spelling 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
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repository.mail.fl_str_mv repositorio.arca@fiocruz.br
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