Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona
Autor(a) principal: | |
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Data de Publicação: | 2008 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações do UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/11087 |
Resumo: | Oximes are chemical compounds used to reactivate the inhibited acetylcholinesterase (AChE) enzyme by organophosphates (OPs). The OPs, besides classically recognized as AChE irreversible inhibitors, are also involved in the generation of oxidative stress conditions. However, researches focusing on the possible antioxidant properties of oximes are lacking in the literature. The aim of this study was to investigate the potential antioxidant and toxic properties of 3-(phenylhydrazono)butan-2-one oxime and butane-2,3-dionethiosemicarbazone oxime in mice, and to understand the mechanism(s) by which they act. Firstly, we investigated the existence and the mechanism(s) by which 3- (phenylhydrazono)butan-2-one oxime exert its antioxidant properties (Manuscript 1). The obtained results show that in vitro hydrogen peroxide (H2O2), malonate, or ferrous ions (Fe2+)-induced lipid peroxidation was decreased by low concentrations of the oxime. Oxime treatment did not modify the basal peroxidation level nor prevented the induced lipid peroxidation determined ex vivo. The obtained results suggest that 3-(phenylhydrazono)butan-2-one oxime could be employed as a satisfactory antioxidant compound. The absence of toxicity signs after in vivo administration of 3-(phenylhydrazono)butan-2-one oxime to mice may indicate that it could be a safe drug for further studies. The other objective of this study was to investigate the existence and the mechanism(s) by which butane-2,3-dionethiosemicarbazone oxime exert its antioxidant properties (Manuscript 2). The obtained results indicate a significant H2O2, nitric oxide (NO) and 1,1-diphenyl-2-picrylhydrazyl (DPPH●) scavenging activity at low oxime concentrations. Besides, the butane-2,3-dionethiosemicarbazone oxime significantly diminished the deoxyribose degradation induced by Fe2+ or Fe2+ + H2O2, and also the benzoate hydroxylation induced by ferric ions (Fe3+) + H2O2 reaction. Besides, the oxime showed a significant inhibitory effect on s-phenantroline reaction with Fe2+. A significant decrease in the basal and pro-oxidants induced lipid peroxidation in brain, liver, and kidney of mice was observed both in vitro and ex vivo. In addition, in our ex vivo experiments the butane-2,3- dionethiosemicarbazone oxime did not determine significant changes in thiol (-SH) levels of liver, kidney and brain, as well as did not modify the delta-aminolevulinate dehydratase (δ- ALA-D) activity in these tissues of mice. The obtained results indicate that the oximes tested depicted significant antioxidant properties, and that further studies are necessary to improve our knowledge regarding the exact antioxidant action mechanism of these oximes. |
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2017-04-242017-04-242008-05-12PUNTEL, Gustavo Orione. Analysis of the antioxidant properties of the 3-(phenyl hydrazone) butane-2-one and butane-2,3-Dionethiosemicarbazone oximes. 2008. 94 f. Dissertação (Mestrado em Bioquímica) - Universidade Federal de Santa Maria, Santa Maria, 2008.http://repositorio.ufsm.br/handle/1/11087Oximes are chemical compounds used to reactivate the inhibited acetylcholinesterase (AChE) enzyme by organophosphates (OPs). The OPs, besides classically recognized as AChE irreversible inhibitors, are also involved in the generation of oxidative stress conditions. However, researches focusing on the possible antioxidant properties of oximes are lacking in the literature. The aim of this study was to investigate the potential antioxidant and toxic properties of 3-(phenylhydrazono)butan-2-one oxime and butane-2,3-dionethiosemicarbazone oxime in mice, and to understand the mechanism(s) by which they act. Firstly, we investigated the existence and the mechanism(s) by which 3- (phenylhydrazono)butan-2-one oxime exert its antioxidant properties (Manuscript 1). The obtained results show that in vitro hydrogen peroxide (H2O2), malonate, or ferrous ions (Fe2+)-induced lipid peroxidation was decreased by low concentrations of the oxime. Oxime treatment did not modify the basal peroxidation level nor prevented the induced lipid peroxidation determined ex vivo. The obtained results suggest that 3-(phenylhydrazono)butan-2-one oxime could be employed as a satisfactory antioxidant compound. The absence of toxicity signs after in vivo administration of 3-(phenylhydrazono)butan-2-one oxime to mice may indicate that it could be a safe drug for further studies. The other objective of this study was to investigate the existence and the mechanism(s) by which butane-2,3-dionethiosemicarbazone oxime exert its antioxidant properties (Manuscript 2). The obtained results indicate a significant H2O2, nitric oxide (NO) and 1,1-diphenyl-2-picrylhydrazyl (DPPH●) scavenging activity at low oxime concentrations. Besides, the butane-2,3-dionethiosemicarbazone oxime significantly diminished the deoxyribose degradation induced by Fe2+ or Fe2+ + H2O2, and also the benzoate hydroxylation induced by ferric ions (Fe3+) + H2O2 reaction. Besides, the oxime showed a significant inhibitory effect on s-phenantroline reaction with Fe2+. A significant decrease in the basal and pro-oxidants induced lipid peroxidation in brain, liver, and kidney of mice was observed both in vitro and ex vivo. In addition, in our ex vivo experiments the butane-2,3- dionethiosemicarbazone oxime did not determine significant changes in thiol (-SH) levels of liver, kidney and brain, as well as did not modify the delta-aminolevulinate dehydratase (δ- ALA-D) activity in these tissues of mice. The obtained results indicate that the oximes tested depicted significant antioxidant properties, and that further studies are necessary to improve our knowledge regarding the exact antioxidant action mechanism of these oximes.As oximas são compostos químicos utilizados para reativar a enzima actilcolinesterase (AChE) inibida por organofosforados (OPs). Os OPs, além de serem classicamente reconhecidos como inibidores da AChE, também estão envolvidos em situações que geram estresse oxidativo. Contudo, pesquisas enfocando as possíveis propriedades antioxidantes das oximas são escassas na literatura. O objetivo deste estudo foi investigar o potencial antioxidante e as propriedades tóxicas das oximas 3-(fenil hidrazona) butano-2-ona e butana- 2,3-dionatiosemicarbazona em camundongos, e entender o(s) possível(is) mecanismo(s) pelo(s) qual(is) elas atuam. Inicialmente investigamos a existência, e o(s) mecanismo(s) pelo(s) qual(is) a oxima 3-(fenil hidrazona) butano-2-ona exerce suas propriedades antioxidantes (Manuscrito 1). Os resultados obtidos mostram que a peroxidação lipídica induzida por peróxido de hidrogênio (H2O2), por malonato, e por íons ferrosos (Fe2+) foi diminuída em baixas concentrações da oxima. O tratamento dos camundongos com a oxima não alterou os níveis basais de peroxidação lipídica, nem preveniu a peroxidação lipídica induzida em experimentos ex vivo. Os resultados obtidos sugerem que a oxima 3-(fenil hidrazona) butano-2-ona pode ser empregada como um satisfatório composto antioxidante. A ausência de sinais de toxicidade após a administração in vivo da oxima 3-(fenil hidrazona) butano-2-ona em camundongos indica que esta pode ser uma droga segura para futuros estudos. O outro objetivo deste estudo foi investigar a existência e o(s) mecanismo(s) pelo(s) qual(is) a oxima butana-2,3-dionatiosemicarbazona exerce suas propriedades antioxidantes (Manuscrito 2). Os resultados obtidos indicam uma significativa atividade da oxima em neutralizar H2O2, o radical 1,1-difenil-2-picrilhidrazil (DPPH●), e a formação de óxido nítrico (NO), em baixas concentrações. Além disso, a oxima butana-2,3-dionatiosemicarbazona diminuiu significativamente a degradação da desoxirribose induzida por Fe2+ e pela reação Fe2+ + H2O2, e também a hidroxilação do benzoato induzida pela reação íons férricos (Fe3+) + H2O2. Além disso, a oxima apresentou um efeito inibitório significativo na reação da s- fenantrolina com Fe2+ Uma diminuição significativa na peroxidação lipídica basal e na peroxidação lipídica induzida por agentes pro-oxidantes no cérebro, fígado e rim de camundongos foi observada tanto in vitro quanto ex vivo. A oxima butana-2,3- dionatiosemicarbazona não determinou mudanças nos níveis de tióis (-SH) no fígado, rim e cérebro, bem como não modificou a atividade da enzima delta-aminolevulinato desidratase (δ-ALA-D) nestes tecidos de camundongos em experimentos ex vivo. Os resultados obtidos indicam que as oximas testadas apresentaram propriedades antioxidantes significativas, e que futuros estudos são necessários para aumentar o conhecimento a respeito do exato mecanismo de ação antioxidante destas oximas.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em Ciências Biológicas: Bioquímica ToxicológicaUFSMBRBioquímicaOxima 3-(fenil hidrazona) butano-2-onaOxima butana-2,3- dionatiosemicarbazonaAntioxidanteEspécies reativas3-(phenylhydrazono)butan-2-one oximeButane-2,3-dionethiosemicarbazone oximeAntioxidantReactive speciesCNPQ::CIENCIAS BIOLOGICAS::BIOQUIMICAAnálise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazonaAnalysis of the antioxidant properties of the 3-(phenyl hydrazone) butane-2-one and butane-2,3-Dionethiosemicarbazone oximesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisSoares, Félix Alexandre Antuneshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4769181A8Rocha, João Batista Teixeira dahttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782281H2Schetinger, Maria Rosa ChitolinaBarbosa, Nilda Berenice de Vargashttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4795127P7http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4755342Y6Puntel, Gustavo Orione2008000000024005005005005005003aef53b7-b173-4c56-a944-bed2de5e5ddab48de824-6671-434b-8706-76fa82d016f4e8eeabe9-81ea-43be-9587-51ffc22e820c93acb9e6-39fa-412c-84a4-a90a4863b53e0198eecb-263d-4159-82c5-3698b0253f4finfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALGUSTAVOPUNTEL.pdfapplication/pdf596775http://repositorio.ufsm.br/bitstream/1/11087/1/GUSTAVOPUNTEL.pdfeeae574d15d15b6b69a23cc29a22be70MD51TEXTGUSTAVOPUNTEL.pdf.txtGUSTAVOPUNTEL.pdf.txtExtracted texttext/plain152413http://repositorio.ufsm.br/bitstream/1/11087/2/GUSTAVOPUNTEL.pdf.txt3cd3ca3f6e6b80bbea9de0f6f83c9657MD52THUMBNAILGUSTAVOPUNTEL.pdf.jpgGUSTAVOPUNTEL.pdf.jpgIM Thumbnailimage/jpeg5708http://repositorio.ufsm.br/bitstream/1/11087/3/GUSTAVOPUNTEL.pdf.jpg1d39983d6b0e1af32a4e4243a7be6ebbMD531/110872017-07-25 12:09:26.488oai:repositorio.ufsm.br:1/11087Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2017-07-25T15:09:26Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona |
dc.title.alternative.eng.fl_str_mv |
Analysis of the antioxidant properties of the 3-(phenyl hydrazone) butane-2-one and butane-2,3-Dionethiosemicarbazone oximes |
title |
Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona |
spellingShingle |
Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona Puntel, Gustavo Orione Oxima 3-(fenil hidrazona) butano-2-ona Oxima butana-2,3- dionatiosemicarbazona Antioxidante Espécies reativas 3-(phenylhydrazono)butan-2-one oxime Butane-2,3-dionethiosemicarbazone oxime Antioxidant Reactive species CNPQ::CIENCIAS BIOLOGICAS::BIOQUIMICA |
title_short |
Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona |
title_full |
Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona |
title_fullStr |
Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona |
title_full_unstemmed |
Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona |
title_sort |
Análise das propriedades antioxidantes das oximas 3-(fenil hidrazona) butano-2-ona e butano-2,3-dionatiosemicarbazona |
author |
Puntel, Gustavo Orione |
author_facet |
Puntel, Gustavo Orione |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Soares, Félix Alexandre Antunes |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4769181A8 |
dc.contributor.referee1.fl_str_mv |
Rocha, João Batista Teixeira da |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782281H2 |
dc.contributor.referee2.fl_str_mv |
Schetinger, Maria Rosa Chitolina |
dc.contributor.referee3.fl_str_mv |
Barbosa, Nilda Berenice de Vargas |
dc.contributor.referee3Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4795127P7 |
dc.contributor.authorLattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4755342Y6 |
dc.contributor.author.fl_str_mv |
Puntel, Gustavo Orione |
contributor_str_mv |
Soares, Félix Alexandre Antunes Rocha, João Batista Teixeira da Schetinger, Maria Rosa Chitolina Barbosa, Nilda Berenice de Vargas |
dc.subject.por.fl_str_mv |
Oxima 3-(fenil hidrazona) butano-2-ona Oxima butana-2,3- dionatiosemicarbazona Antioxidante Espécies reativas |
topic |
Oxima 3-(fenil hidrazona) butano-2-ona Oxima butana-2,3- dionatiosemicarbazona Antioxidante Espécies reativas 3-(phenylhydrazono)butan-2-one oxime Butane-2,3-dionethiosemicarbazone oxime Antioxidant Reactive species CNPQ::CIENCIAS BIOLOGICAS::BIOQUIMICA |
dc.subject.eng.fl_str_mv |
3-(phenylhydrazono)butan-2-one oxime Butane-2,3-dionethiosemicarbazone oxime Antioxidant Reactive species |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS BIOLOGICAS::BIOQUIMICA |
description |
Oximes are chemical compounds used to reactivate the inhibited acetylcholinesterase (AChE) enzyme by organophosphates (OPs). The OPs, besides classically recognized as AChE irreversible inhibitors, are also involved in the generation of oxidative stress conditions. However, researches focusing on the possible antioxidant properties of oximes are lacking in the literature. The aim of this study was to investigate the potential antioxidant and toxic properties of 3-(phenylhydrazono)butan-2-one oxime and butane-2,3-dionethiosemicarbazone oxime in mice, and to understand the mechanism(s) by which they act. Firstly, we investigated the existence and the mechanism(s) by which 3- (phenylhydrazono)butan-2-one oxime exert its antioxidant properties (Manuscript 1). The obtained results show that in vitro hydrogen peroxide (H2O2), malonate, or ferrous ions (Fe2+)-induced lipid peroxidation was decreased by low concentrations of the oxime. Oxime treatment did not modify the basal peroxidation level nor prevented the induced lipid peroxidation determined ex vivo. The obtained results suggest that 3-(phenylhydrazono)butan-2-one oxime could be employed as a satisfactory antioxidant compound. The absence of toxicity signs after in vivo administration of 3-(phenylhydrazono)butan-2-one oxime to mice may indicate that it could be a safe drug for further studies. The other objective of this study was to investigate the existence and the mechanism(s) by which butane-2,3-dionethiosemicarbazone oxime exert its antioxidant properties (Manuscript 2). The obtained results indicate a significant H2O2, nitric oxide (NO) and 1,1-diphenyl-2-picrylhydrazyl (DPPH●) scavenging activity at low oxime concentrations. Besides, the butane-2,3-dionethiosemicarbazone oxime significantly diminished the deoxyribose degradation induced by Fe2+ or Fe2+ + H2O2, and also the benzoate hydroxylation induced by ferric ions (Fe3+) + H2O2 reaction. Besides, the oxime showed a significant inhibitory effect on s-phenantroline reaction with Fe2+. A significant decrease in the basal and pro-oxidants induced lipid peroxidation in brain, liver, and kidney of mice was observed both in vitro and ex vivo. In addition, in our ex vivo experiments the butane-2,3- dionethiosemicarbazone oxime did not determine significant changes in thiol (-SH) levels of liver, kidney and brain, as well as did not modify the delta-aminolevulinate dehydratase (δ- ALA-D) activity in these tissues of mice. The obtained results indicate that the oximes tested depicted significant antioxidant properties, and that further studies are necessary to improve our knowledge regarding the exact antioxidant action mechanism of these oximes. |
publishDate |
2008 |
dc.date.issued.fl_str_mv |
2008-05-12 |
dc.date.accessioned.fl_str_mv |
2017-04-24 |
dc.date.available.fl_str_mv |
2017-04-24 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
PUNTEL, Gustavo Orione. Analysis of the antioxidant properties of the 3-(phenyl hydrazone) butane-2-one and butane-2,3-Dionethiosemicarbazone oximes. 2008. 94 f. Dissertação (Mestrado em Bioquímica) - Universidade Federal de Santa Maria, Santa Maria, 2008. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/11087 |
identifier_str_mv |
PUNTEL, Gustavo Orione. Analysis of the antioxidant properties of the 3-(phenyl hydrazone) butane-2-one and butane-2,3-Dionethiosemicarbazone oximes. 2008. 94 f. Dissertação (Mestrado em Bioquímica) - Universidade Federal de Santa Maria, Santa Maria, 2008. |
url |
http://repositorio.ufsm.br/handle/1/11087 |
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UFSM |
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Bioquímica |
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Universidade Federal de Santa Maria |
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