Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/6287 |
Resumo: | This thesis focus on the synthesis, characterization and evaluation of the biological properties of three series of phosphinic ruthenium complexes containing bioligands of purine and pyrimidine derivatives. Series 1: [RuCl(alo)(dppb)(bipy)]PF6, [RuCl(alo)(dppb)(bipy)] Cl, [RuCl(alo)(dppb)(4mebipy)]PF6, [RuCl(alo)(dppb)(5mebipy)]PF6, [RuCl(Im) (dppb)(bipy)]PF6, [RuCl(Bzm)(dppb)(bipy)]PF6, [RuCl2(alo)2(dppb)], [RuCl2(alo)2 (PPh3)2] and [RuCl3(alo)(dppb)], where alo = allopurinol, Im = imidazole, benzimidazole Bzm =, bipy = 2,2'-bipyridine, 4mebipy = 4,4'-dimethyl-2,2 '-bipyridine, 5mebipy = 5,5'-dimethyl-2, 2'- bipyridine, PPh3 = triphenylphosphine and dppb = 1,4-bis (diphenylphosphino)butane. Series 2: [Ru(tim)(dppb)(bipy)]PF6 and [Ru(cit)(dppb)(bipy)]ClO4, trans- [Ru(PPh3)2(5FU)(bipy)]PF6, trans-[Ru(PPh3)2(tim) (bipy)]PF6 and trans- [Ru(PPh3)2(CTD)(bipy)]ClO4, where tim = thymine, cit = cytosine, 5-FU = 5-fluorouracil, CTD = cytidine . Series 3: cis-[Ru(PPh3)2(2TU)2], cis-[Ru(PPh3)2(6m2TU)2], [Ru(2TU)2(dppb)] and [Ru(6m2TU)2(dppb )], trans-[Ru(PPh3)2(2TU)(bipy)]PF6 and trans- [Ru(PPh3)2(6m2TU)(bipy)]PF6, [Ru(2MT)(dppb) (bipy)]PF6, cis-[Ru(PPh3)2(2MT)2] and trans-[Ru(PPh3)2(2MT)(bipy)]PF6. (2TU = 2-thiouracil; 6m2TU = 6-methyl-2-thiouracil, 2MT = mercaptothiazoline). These compounds were characterized by 31P{1H} 13C and 1H nuclear magnetic resonance and by cyclic voltammetry and differential pulse, conductometry, absorption spectroscopy in the infrared region, elemental analysis, mass spectrometry and Xray diffraction, and absorption spectroscopy in the UV/Vis which has assisted the spectroscopic study of DNA interactions. The interaction constants (Kb) values are in the range of 103-104 M-1, suggesting a weak interaction between the complex and DNA (noncovalent). Cationic compounds with regions suitable to be involved hydrogen bonding present greater interaction constant (104 M-1) than the neutral complexes and with less possibility of intermolecular bonds. The complexes were also evaluated, in vitro, against breast cancer cells (MDA-MB-231 and MCF-7), as well as fibroblasts cells (L-929). It was observed that the compounds of the series 1 and 2 are more selective against tumor cells than the complexes of series 3. In addition, the compounds of series 1 were also tested against xanthine oxidase, an enzyme which is directly involved in the gout disease. The complexes RuCl(alo)(dppb)(bipy)]PF6 (IC50 = 2.2 μM), [RuCl(alo)(dppb)(4mebipy)]PF6 (IC50 = 2.8 μM) and [RuCl(alo)(dppb)(5mebipy)]PF6 (IC50 = 0.75 μM) are more active than free allopurinol (IC50 = 4.2 μM), showing that the coordination of allopurinol enhances the effect of the drug. Also, series 1 and compounds with 2MT were evaluated against the T. cruzi parasite (trypomastigote) in order to screening their potential against Chagas' disease. The [RuCl(alo)(dppb)(4mebipy)]PF6 (IC50 = 1.87 μM), [Ru(2MT)(dppb)(bipy)]PF6 (IC50 = 0.16 μM) and trans-[Ru(PPh3)2(2MT)(bipy)]PF6 (IC50 = 0.011 μM) complexes were the most active ones, in which the last one is 1000-fold better than the benznidazole drug (IC50 = 10.6 μM). |
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Corrêa, Rodrigo de SouzaBatista, Alzir Azevedohttp://lattes.cnpq.br/6469642481998660http://lattes.cnpq.br/974771897074317525a92c1a-26c3-49eb-9e17-b1992fadcbac2016-06-02T20:34:48Z2013-12-112016-06-02T20:34:48Z2013-09-20CORRÊA, Rodrigo de Souza. Ruthenium complexes with ligands of biological interest: Chemical and Structural aspects and evaluation of their Biological Activities. 2013. 1 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2013.https://repositorio.ufscar.br/handle/ufscar/6287This thesis focus on the synthesis, characterization and evaluation of the biological properties of three series of phosphinic ruthenium complexes containing bioligands of purine and pyrimidine derivatives. Series 1: [RuCl(alo)(dppb)(bipy)]PF6, [RuCl(alo)(dppb)(bipy)] Cl, [RuCl(alo)(dppb)(4mebipy)]PF6, [RuCl(alo)(dppb)(5mebipy)]PF6, [RuCl(Im) (dppb)(bipy)]PF6, [RuCl(Bzm)(dppb)(bipy)]PF6, [RuCl2(alo)2(dppb)], [RuCl2(alo)2 (PPh3)2] and [RuCl3(alo)(dppb)], where alo = allopurinol, Im = imidazole, benzimidazole Bzm =, bipy = 2,2'-bipyridine, 4mebipy = 4,4'-dimethyl-2,2 '-bipyridine, 5mebipy = 5,5'-dimethyl-2, 2'- bipyridine, PPh3 = triphenylphosphine and dppb = 1,4-bis (diphenylphosphino)butane. Series 2: [Ru(tim)(dppb)(bipy)]PF6 and [Ru(cit)(dppb)(bipy)]ClO4, trans- [Ru(PPh3)2(5FU)(bipy)]PF6, trans-[Ru(PPh3)2(tim) (bipy)]PF6 and trans- [Ru(PPh3)2(CTD)(bipy)]ClO4, where tim = thymine, cit = cytosine, 5-FU = 5-fluorouracil, CTD = cytidine . Series 3: cis-[Ru(PPh3)2(2TU)2], cis-[Ru(PPh3)2(6m2TU)2], [Ru(2TU)2(dppb)] and [Ru(6m2TU)2(dppb )], trans-[Ru(PPh3)2(2TU)(bipy)]PF6 and trans- [Ru(PPh3)2(6m2TU)(bipy)]PF6, [Ru(2MT)(dppb) (bipy)]PF6, cis-[Ru(PPh3)2(2MT)2] and trans-[Ru(PPh3)2(2MT)(bipy)]PF6. (2TU = 2-thiouracil; 6m2TU = 6-methyl-2-thiouracil, 2MT = mercaptothiazoline). These compounds were characterized by 31P{1H} 13C and 1H nuclear magnetic resonance and by cyclic voltammetry and differential pulse, conductometry, absorption spectroscopy in the infrared region, elemental analysis, mass spectrometry and Xray diffraction, and absorption spectroscopy in the UV/Vis which has assisted the spectroscopic study of DNA interactions. The interaction constants (Kb) values are in the range of 103-104 M-1, suggesting a weak interaction between the complex and DNA (noncovalent). Cationic compounds with regions suitable to be involved hydrogen bonding present greater interaction constant (104 M-1) than the neutral complexes and with less possibility of intermolecular bonds. The complexes were also evaluated, in vitro, against breast cancer cells (MDA-MB-231 and MCF-7), as well as fibroblasts cells (L-929). It was observed that the compounds of the series 1 and 2 are more selective against tumor cells than the complexes of series 3. In addition, the compounds of series 1 were also tested against xanthine oxidase, an enzyme which is directly involved in the gout disease. The complexes RuCl(alo)(dppb)(bipy)]PF6 (IC50 = 2.2 μM), [RuCl(alo)(dppb)(4mebipy)]PF6 (IC50 = 2.8 μM) and [RuCl(alo)(dppb)(5mebipy)]PF6 (IC50 = 0.75 μM) are more active than free allopurinol (IC50 = 4.2 μM), showing that the coordination of allopurinol enhances the effect of the drug. Also, series 1 and compounds with 2MT were evaluated against the T. cruzi parasite (trypomastigote) in order to screening their potential against Chagas' disease. The [RuCl(alo)(dppb)(4mebipy)]PF6 (IC50 = 1.87 μM), [Ru(2MT)(dppb)(bipy)]PF6 (IC50 = 0.16 μM) and trans-[Ru(PPh3)2(2MT)(bipy)]PF6 (IC50 = 0.011 μM) complexes were the most active ones, in which the last one is 1000-fold better than the benznidazole drug (IC50 = 10.6 μM).A presente tese tem como foco principal a síntese, caracterização e avaliação das propriedades biológicas de três séries de complexos fosfínicos de rutênio contendo bioligantes derivados de purina e pirimidina. Série 1: [RuCl(alo)(dppb)(bipy)]PF6, [RuCl(alo)(dppb)(bipy)]Cl, [RuCl(alo)(dppb)(4mebipy)]PF6, [RuCl(alo)(dppb)(5mebipy)]PF6, [RuCl(Im)(dppb)(bipy)]PF6, [RuCl(Bzm)(dppb)(bipy)]PF6, [RuCl2(alo)2(dppb)], [RuCl2(alo)2(PPh3)2] e [RuCl3(alo)(dppb)], onde alo = alopurinol, Im = imidazol, Bzm = benzoimidazol, bipy = 2,2 -bipiridina, 4mebipy = 4,4 -dimetil-2,2 - bipiridina, 5mebipy = 5,5 -dimetil-2,2 -bipiridina, PPh3 = trifenilfosfina e dppb =1,4 bis(difenilfosfina)butano. Série 2: [Ru(tim)(dppb)(bipy)]PF6 e [Ru(cit)(dppb)(bipy)]ClO4, trans-[Ru(PPh3)2(5FU)(bipy)]PF6, trans-[Ru(PPh3)2(tim)(bipy)]PF6 e trans- [Ru(PPh3)2(CTD)(bipy)]ClO4, onde tim = timina, cit = citosina, 5FU = 5-fluorouracil, CTD = citidina. Série 3: cis-[Ru(PPh3)2(2TU)2], cis-[Ru(PPh3)2(6m2TU)2], [Ru(2TU)2(dppb)] e [Ru(6m2TU)2(dppb)]; trans-[Ru(PPh3)2(2TU)(bipy)]PF6 e trans- [Ru(PPh3)2(6m2TU)(bipy)]PF6; [Ru(2MT)(dppb)(bipy)]PF6, cis-[Ru(PPh3)2(2MT)2] e trans- [Ru(PPh3)2(2MT)(bipy)]PF6. (2TU = 2-tiouracil; 6m2TU = 6-metil-2-tiouracil; 2MT = 2- mercaptotiazolina). Estes complexos foram caracterizados por várias técnicas analíticas, que incluem espectroscopia de ressonância magnética nuclear de 31P{1H}, 13C e 1H, por técnicas de voltametria cíclica e de pulso diferencial, condutimetria, espectroscopia de absorção na região do infravermelho, análise elementar, espectrometria de massa e difração de raios X por monocristal, além de espectroscopia de absorção na região do UV/Vis que auxiliou no estudo de interações espectroscópicas com o DNA. Os valores das constantes de interação (Kb) dos complexos com o DNA estão em uma faixa de 103 104 M-1, o que indicam uma interação fraca com o DNA (não covalente). Observa-se que os compostos que apresentam mais regiões para realizar ligações de hidrogênio, bem como a presença de carga positiva, apresentam valores de constantes de interações com o DNA mais elevadas (104 M-1) do que os complexos neutros e com menos possibilidade de realizar ligações intermoleculares. Os complexos sintetizados também foram avaliados, in vitro, como agentes antitumorais contra a linhagens de células de câncer de mama MDA-MB-231 (compostos da série 1 e da série 3 exceto com 2MT) e MCF-7 (compostos da série 2 e da série 3 contendo 2MT). Também foram realizados ensaios contra células de fibroblastos (L-929) para avaliar a toxicidade em células sadias. Observou-se que os compostos das séries 1 e 2 apresentam maior seletividade para células tumorais de câncer de mama do que os complexos da série 3. Em adição, os compostos da série 1 foram testados também contra xantina oxidase, enzima que está diretamente ligada à doença de gota. Os testes mostraram que os complexos RuCl(alo)(dppb)(bipy)]PF6 (IC50 = 2,2 μM), [RuCl(alo)(dppb)(4mebipy)]PF6 (IC50 = 2,8 μM) e [RuCl(alo)(dppb)(5mebipy)]PF6 (IC50 = 0,75 μM) apresentaram inibição enzimática superior a do fármaco alopurinol (IC50 = 4,2 μM), mostrando que a sua coordenação potencializa o efeito do fármaco. Também, para a série 1 e os complexos com 2MT (série 3), realizou-se ensaios contra o parasita T. cruzi (forma tripomastigota) para avaliar o potencial contra doença de Chagas. Os complexos mais ativos foram o [RuCl(alo)(dppb)(4mebipy)]PF6 (IC50 = 1,87 μM), [Ru(2MT)(dppb)(bipy)]PF6 (IC50 = 0,16 μM) e trans-[Ru(PPh3)2(2MT)(bipy)]PF6 (IC50 = 0,011 μM), no qual o último apresentou ser 1000 vezes mais ativo do que o fármaco de referencia benznidazol (IC50 = 10,6 μM).Universidade Federal de Minas Geraisapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRQuímica inorgânicaComplexos de rutênioBioligantesAgentes antineoplásicosAgentes antigotaCIENCIAS EXATAS E DA TERRA::QUIMICAComplexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicasRuthenium complexes with ligands of biological interest: Chemical and Structural aspects and evaluation of their Biological Activitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesis-1-1e62fb48f-fa23-4158-8d60-0b17f006946cinfo:eu-repo/semantics/embargoedAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALRetido.pdfapplication/pdf19733https://repositorio.ufscar.br/bitstream/ufscar/6287/1/Retido.pdf6aad255badc436a06364517de2344ab6MD51THUMBNAILRetido.pdf.jpgRetido.pdf.jpgIM Thumbnailimage/jpeg2920https://repositorio.ufscar.br/bitstream/ufscar/6287/2/Retido.pdf.jpg89c8556201035bdad03e5b132aaeba68MD52ufscar/62872023-09-18 18:31:10.651oai:repositorio.ufscar.br:ufscar/6287Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:10Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas |
dc.title.alternative.eng.fl_str_mv |
Ruthenium complexes with ligands of biological interest: Chemical and Structural aspects and evaluation of their Biological Activities |
title |
Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas |
spellingShingle |
Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas Corrêa, Rodrigo de Souza Química inorgânica Complexos de rutênio Bioligantes Agentes antineoplásicos Agentes antigota CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas |
title_full |
Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas |
title_fullStr |
Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas |
title_full_unstemmed |
Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas |
title_sort |
Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas atividades biológicas |
author |
Corrêa, Rodrigo de Souza |
author_facet |
Corrêa, Rodrigo de Souza |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/9747718970743175 |
dc.contributor.author.fl_str_mv |
Corrêa, Rodrigo de Souza |
dc.contributor.advisor1.fl_str_mv |
Batista, Alzir Azevedo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6469642481998660 |
dc.contributor.authorID.fl_str_mv |
25a92c1a-26c3-49eb-9e17-b1992fadcbac |
contributor_str_mv |
Batista, Alzir Azevedo |
dc.subject.por.fl_str_mv |
Química inorgânica Complexos de rutênio Bioligantes Agentes antineoplásicos Agentes antigota |
topic |
Química inorgânica Complexos de rutênio Bioligantes Agentes antineoplásicos Agentes antigota CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This thesis focus on the synthesis, characterization and evaluation of the biological properties of three series of phosphinic ruthenium complexes containing bioligands of purine and pyrimidine derivatives. Series 1: [RuCl(alo)(dppb)(bipy)]PF6, [RuCl(alo)(dppb)(bipy)] Cl, [RuCl(alo)(dppb)(4mebipy)]PF6, [RuCl(alo)(dppb)(5mebipy)]PF6, [RuCl(Im) (dppb)(bipy)]PF6, [RuCl(Bzm)(dppb)(bipy)]PF6, [RuCl2(alo)2(dppb)], [RuCl2(alo)2 (PPh3)2] and [RuCl3(alo)(dppb)], where alo = allopurinol, Im = imidazole, benzimidazole Bzm =, bipy = 2,2'-bipyridine, 4mebipy = 4,4'-dimethyl-2,2 '-bipyridine, 5mebipy = 5,5'-dimethyl-2, 2'- bipyridine, PPh3 = triphenylphosphine and dppb = 1,4-bis (diphenylphosphino)butane. Series 2: [Ru(tim)(dppb)(bipy)]PF6 and [Ru(cit)(dppb)(bipy)]ClO4, trans- [Ru(PPh3)2(5FU)(bipy)]PF6, trans-[Ru(PPh3)2(tim) (bipy)]PF6 and trans- [Ru(PPh3)2(CTD)(bipy)]ClO4, where tim = thymine, cit = cytosine, 5-FU = 5-fluorouracil, CTD = cytidine . Series 3: cis-[Ru(PPh3)2(2TU)2], cis-[Ru(PPh3)2(6m2TU)2], [Ru(2TU)2(dppb)] and [Ru(6m2TU)2(dppb )], trans-[Ru(PPh3)2(2TU)(bipy)]PF6 and trans- [Ru(PPh3)2(6m2TU)(bipy)]PF6, [Ru(2MT)(dppb) (bipy)]PF6, cis-[Ru(PPh3)2(2MT)2] and trans-[Ru(PPh3)2(2MT)(bipy)]PF6. (2TU = 2-thiouracil; 6m2TU = 6-methyl-2-thiouracil, 2MT = mercaptothiazoline). These compounds were characterized by 31P{1H} 13C and 1H nuclear magnetic resonance and by cyclic voltammetry and differential pulse, conductometry, absorption spectroscopy in the infrared region, elemental analysis, mass spectrometry and Xray diffraction, and absorption spectroscopy in the UV/Vis which has assisted the spectroscopic study of DNA interactions. The interaction constants (Kb) values are in the range of 103-104 M-1, suggesting a weak interaction between the complex and DNA (noncovalent). Cationic compounds with regions suitable to be involved hydrogen bonding present greater interaction constant (104 M-1) than the neutral complexes and with less possibility of intermolecular bonds. The complexes were also evaluated, in vitro, against breast cancer cells (MDA-MB-231 and MCF-7), as well as fibroblasts cells (L-929). It was observed that the compounds of the series 1 and 2 are more selective against tumor cells than the complexes of series 3. In addition, the compounds of series 1 were also tested against xanthine oxidase, an enzyme which is directly involved in the gout disease. The complexes RuCl(alo)(dppb)(bipy)]PF6 (IC50 = 2.2 μM), [RuCl(alo)(dppb)(4mebipy)]PF6 (IC50 = 2.8 μM) and [RuCl(alo)(dppb)(5mebipy)]PF6 (IC50 = 0.75 μM) are more active than free allopurinol (IC50 = 4.2 μM), showing that the coordination of allopurinol enhances the effect of the drug. Also, series 1 and compounds with 2MT were evaluated against the T. cruzi parasite (trypomastigote) in order to screening their potential against Chagas' disease. The [RuCl(alo)(dppb)(4mebipy)]PF6 (IC50 = 1.87 μM), [Ru(2MT)(dppb)(bipy)]PF6 (IC50 = 0.16 μM) and trans-[Ru(PPh3)2(2MT)(bipy)]PF6 (IC50 = 0.011 μM) complexes were the most active ones, in which the last one is 1000-fold better than the benznidazole drug (IC50 = 10.6 μM). |
publishDate |
2013 |
dc.date.available.fl_str_mv |
2013-12-11 2016-06-02T20:34:48Z |
dc.date.issued.fl_str_mv |
2013-09-20 |
dc.date.accessioned.fl_str_mv |
2016-06-02T20:34:48Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/doctoralThesis |
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doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
CORRÊA, Rodrigo de Souza. Ruthenium complexes with ligands of biological interest: Chemical and Structural aspects and evaluation of their Biological Activities. 2013. 1 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2013. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/6287 |
identifier_str_mv |
CORRÊA, Rodrigo de Souza. Ruthenium complexes with ligands of biological interest: Chemical and Structural aspects and evaluation of their Biological Activities. 2013. 1 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2013. |
url |
https://repositorio.ufscar.br/handle/ufscar/6287 |
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por |
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por |
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Universidade Federal de São Carlos |
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Programa de Pós-Graduação em Química - PPGQ |
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UFSCar |
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BR |
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Universidade Federal de São Carlos |
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