Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos
| Ano de defesa: | 2016 |
|---|---|
| Autor(a) principal: | |
| Orientador(a): | |
| Banca de defesa: | , |
| Tipo de documento: | Dissertação |
| Tipo de acesso: | Acesso aberto |
| Idioma: | por |
| Instituição de defesa: |
Universidade Federal de Alfenas
|
| Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
| Departamento: |
Instituto de Química
|
| País: |
Brasil
|
| Palavras-chave em Português: | |
| Área do conhecimento CNPq: | |
| Link de acesso: | https://repositorio.unifal-mg.edu.br/handle/123456789/890 |
Resumo: | For some time, transition metal complexes, especially cisplatin, have been investigated due to their antineoplastic and trypanocidal activities. There are several studies in literature that seek to exploit the properties of palladium complexes, such as cancer cells anti-proliferative activity, anti-inflammatory activity, bactericidal activity and applications in catalytic processes. As a study material, we have palladium(II) compounds, containing iminic ligands. The N,N'-bis(3,4-dimethoxybenzaldehyde)ethane-1,2-diamine (3,4dm-1,2am) and N-(p-dimethylamino)benzylidine-(p-dimethylamino)aniline ( 4dm-1,4fen) ligand is a Schiff Base and has its synthesis and characterization reported in literature. The compounds were characterized by elemental and thermogravimetric analyses, as well as nuclear magnetic resonance spectroscopies ¹H and ¹³C, ultravioleta-visible and infrared (IR) spectroscopies. The results of NMR indicate the formation of N,N-chelated products ([Pd(Cl)2(3,4dm-1,2am)], [PdBrCl(3,4dm-1,2am)], [Pd(N3)2(3,4dm-1,2am)], [Pd(NCO)2(3,4dm-1,2am)]). Regarding the vibrational spectroscopy in the ultraviolet -visible, there was the shift of the absorption bands of the complexes indicating coordination of the ligand and the substitution of groups chlorides. This technique confirmed that the azide and cyanate groups are preferably coordinated N-terminal. The analysis of NMR ¹H and ¹³C, UV-Vis and IR spectra of ligand nitrogen (4dm-1,4fen) and complexes cyclopalladated ([Pd(μ-Cl)(4dm-1,4fen)]2) showed the presence of signs consistent with the proposed. The TG/DTA curves showed that the thermal decomposition of the palladium(II) complexes occurred in steps that involve the removal of both inorganic and organic ligand, and palladium oxidation steps forming palladium oxide followed by the reduction of palladium oxide into palladium(0), this being the constituent of the residual mass observed at the end of the TG curves, which have values consistent with the expected ones. The synthesized compounds were tested in biological assays against Leishmania where in vitro experiments with L. amazonensis promastigote cells were performed, and the compounds [Pd(N3)2(3,4dm-1,2am)] and [Pd(μ-Cl)(4dm-1,4fen)]2 showed IC50 near the Amphotericin B. |
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Xavier, Tatiana Teodorohttp://lattes.cnpq.br/6402668883583711Marques, Marcos JoséPissetti, Fábio LuizSilva, Roberto Santana DaAlmeida, Eduardo Tonon Dehttp://lattes.cnpq.br/67623587572583932017-01-03T17:40:39Z2016-10-31XAVIER, Tatiana Teodoro. Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos. 2016. 121 f. Dissertação (Mestrado em Química) - Universidade Federal de Alfenas, Alfenas, MG, 2016.https://repositorio.unifal-mg.edu.br/handle/123456789/890For some time, transition metal complexes, especially cisplatin, have been investigated due to their antineoplastic and trypanocidal activities. There are several studies in literature that seek to exploit the properties of palladium complexes, such as cancer cells anti-proliferative activity, anti-inflammatory activity, bactericidal activity and applications in catalytic processes. As a study material, we have palladium(II) compounds, containing iminic ligands. The N,N'-bis(3,4-dimethoxybenzaldehyde)ethane-1,2-diamine (3,4dm-1,2am) and N-(p-dimethylamino)benzylidine-(p-dimethylamino)aniline ( 4dm-1,4fen) ligand is a Schiff Base and has its synthesis and characterization reported in literature. The compounds were characterized by elemental and thermogravimetric analyses, as well as nuclear magnetic resonance spectroscopies ¹H and ¹³C, ultravioleta-visible and infrared (IR) spectroscopies. The results of NMR indicate the formation of N,N-chelated products ([Pd(Cl)2(3,4dm-1,2am)], [PdBrCl(3,4dm-1,2am)], [Pd(N3)2(3,4dm-1,2am)], [Pd(NCO)2(3,4dm-1,2am)]). Regarding the vibrational spectroscopy in the ultraviolet -visible, there was the shift of the absorption bands of the complexes indicating coordination of the ligand and the substitution of groups chlorides. This technique confirmed that the azide and cyanate groups are preferably coordinated N-terminal. The analysis of NMR ¹H and ¹³C, UV-Vis and IR spectra of ligand nitrogen (4dm-1,4fen) and complexes cyclopalladated ([Pd(μ-Cl)(4dm-1,4fen)]2) showed the presence of signs consistent with the proposed. The TG/DTA curves showed that the thermal decomposition of the palladium(II) complexes occurred in steps that involve the removal of both inorganic and organic ligand, and palladium oxidation steps forming palladium oxide followed by the reduction of palladium oxide into palladium(0), this being the constituent of the residual mass observed at the end of the TG curves, which have values consistent with the expected ones. The synthesized compounds were tested in biological assays against Leishmania where in vitro experiments with L. amazonensis promastigote cells were performed, and the compounds [Pd(N3)2(3,4dm-1,2am)] and [Pd(μ-Cl)(4dm-1,4fen)]2 showed IC50 near the Amphotericin B.Nas últimas décadas, os complexos de metais de transição vêm sendo investigados devido as suas atividades antineoplásica e tripanossomicida. Há diversos trabalhos na literatura que buscam explorar as propriedades de complexos de paládio, entre elas podemos citar: avaliação de atividade como anti-proliferativo de células cancerosas, avaliação de atividade anti-inflamátoria, avaliação de atividade bactericida e aplicações em processos catalíticos. Nosso material de estudo foram compostos de paládio(II) contendo ligantes imínicos. Os Ligantes N,N’-bis(3,4-dimetoxibenzaldeído)etano-1,2-diamina (3,4dm-1,2am) e N-(p-dimetilamino)benzilideno-(p-dimetilamino)anilina (4dm-1,4fen) são bases de Shiff já relatadas na literatura. Os compostos foram caracterizados por análise elementar, análise termogravimétrica, espectroscopia de ressonância magnética nuclear (RMN) de ¹H e ¹³C, espectroscopia de ultravioleta-visível (UV-Vis) e de infravermelho (IV). Os resultados de RMN sugerem a formação de complexos N,N-quelato ([Pd(Cl)2(3,4dm-1,2am)], [PdBrCl(3,4dm-1,2am)], [Pd(N3)2(3,4dm-1,2am)], [Pd(NCO)2(3,4dm-1,2am)]). As espectroscopias vibracionais e na região do ultravioleta-visível mostraram o deslocamento das bandas de absorção dos complexos indicando a coordenação do ligante, bem como a substituição regioespecífica dos cloretos. Esta técnica confirmou que os grupos azida e cianato estão coordenados preferencialmente de modo N-terminal. A análise dos espectros de RMN de ¹H e ¹³C, UV-Vis e IV do ligante nitrogenado (4dm-1,4fen) e do complexo ciclopaladado ([Pd(μ-Cl)(4dm-1,4fen)]2) mostrou a presença de sinais compatíveis com as estruturas propostas. As curvas TG/DTA mostraram que a termodecomposição dos complexos de paládio(II) ocorreram em etapas que envolvem a eliminação dos ligantes orgânicos e inorgânicos, e etapas de oxidação do paládio formando óxido de paládio e em seguida a redução de óxido de paládio em paládio(0), sendo este o constituinte da massa residual observada ao final das curvas TG, as quais possuem valores concordantes com os valores esperados. Empregou-se estes compostos em ensaios biológicos frente à Leishmania, onde foram realizados experimentos in vitro de células promastigotas L. amazonensis onde os compostos [Pd(N3)2(3,4dm-1,2am)] e [Pd(μ-Cl)(4dm-1,4fen)]2 apresentaram IC50 próximo ao da Anfotericina B.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESapplication/pdfporUniversidade Federal de AlfenasPrograma de Pós-Graduação em QuímicaUNIFAL-MGBrasilInstituto de Químicainfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-nd/4.0/Complexos de paládio(II)Base de SchiffQUIMICA::QUIMICA INORGANICASíntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicosinfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/publishedVersion132825307882678230660060060031391270652389310962075167498588264571reponame:Biblioteca Digital de Teses e Dissertações da UNIFALinstname:Universidade Federal de Alfenas (UNIFAL)instacron:UNIFALXavier, Tatiana TeodoroLICENSElicense.txtlicense.txttext/plain; charset=utf-81987https://repositorio.unifal-mg.edu.br/bitstreams/db0af50b-9ccb-403c-abe5-55b0a9fe01e0/download31555718c4fc75849dd08f27935d4f6bMD51CC-LICENSElicense_urllicense_urltext/plain; charset=utf-849https://repositorio.unifal-mg.edu.br/bitstreams/5c47b6e3-c22c-4897-87c3-08d42419ee72/download4afdbb8c545fd630ea7db775da747b2fMD52license_textlicense_texttext/html; charset=utf-80https://repositorio.unifal-mg.edu.br/bitstreams/f1051c52-d3b6-424b-b045-71591fd9e393/downloadd41d8cd98f00b204e9800998ecf8427eMD53license_rdflicense_rdfapplication/rdf+xml; charset=utf-80https://repositorio.unifal-mg.edu.br/bitstreams/8ee67619-6566-4171-9f48-6ef91231ed96/downloadd41d8cd98f00b204e9800998ecf8427eMD54ORIGINALDissertação de TatianaTeodoro Xavier.pdfDissertação de TatianaTeodoro Xavier.pdfapplication/pdf9867774https://repositorio.unifal-mg.edu.br/bitstreams/ccf97573-0283-4590-97b6-8a859153bd8c/downloada4b08978c92ea74a6cbb5c80ac0b6e8eMD55TEXTDissertação de TatianaTeodoro Xavier.pdf.txtDissertação de TatianaTeodoro Xavier.pdf.txtExtracted texttext/plain103010https://repositorio.unifal-mg.edu.br/bitstreams/b10ec994-5d50-4e36-a938-bfa08a26aac9/download9164b6b83b3f843e6254b132fea889c9MD56THUMBNAILDissertação de TatianaTeodoro Xavier.pdf.jpgDissertação de TatianaTeodoro Xavier.pdf.jpgGenerated Thumbnailimage/jpeg2588https://repositorio.unifal-mg.edu.br/bitstreams/6592c218-288f-4321-9406-a50491da7c4e/download0d5730d271be5ed13da563f2fe5fbf17MD57123456789/8902025-04-14 17:38:47.764http://creativecommons.org/licenses/by-nc-nd/4.0/open.accessoai:repositorio.unifal-mg.edu.br:123456789/890https://repositorio.unifal-mg.edu.brBiblioteca Digital de Teses e DissertaçõesPUBhttps://bdtd.unifal-mg.edu.br:8443/oai/requestbdtd@unifal-mg.edu.br || bdtd@unifal-mg.edu.bropendoar:2025-04-14T20:38:47Biblioteca Digital de Teses e Dissertações da UNIFAL - Universidade Federal de Alfenas (UNIFAL)falseTElDRU7Dh0EgREUgRElTVFJJQlVJw4fDg08gTsODTy1FWENMVVNJVkEKCkNvbSBhIGFwcmVzZW50YcOnw6NvIGRlc3RhIGxpY2Vuw6dhLCBvIGF1dG9yIG91IG8gdGl0dWxhciBkb3MgZGlyZWl0b3MgZGUgYXV0b3IgY29uY2VkZSDDoCBVbml2ZXJzaWRhZGUgCkZlZGVyYWwgZGUgQWxmZW5hcyAgKFVOSUZBTC1NRykgbyBkaXJlaXRvIG7Do28tZXhjbHVzaXZvIGRlIHJlcHJvZHV6aXIsICB0cmFkdXppciAoY29uZm9ybWUgZGVmaW5pZG8gYWJhaXhvKSwgZS9vdSAKZGlzdHJpYnVpciBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gKGluY2x1aW5kbyBvIHJlc3VtbykgcG9yIHRvZG8gbyBtdW5kbyBubyBmb3JtYXRvIGltcHJlc3NvIGUgZWxldHLDtG5pY28gZSAKZW0gcXVhbHF1ZXIgbWVpbywgaW5jbHVpbmRvIG9zIGZvcm1hdG9zIMOhdWRpbyBvdSB2w61kZW8uCgpWb2PDqiBjb25jb3JkYSBxdWUgYSBVTklGQUwtTUcgcG9kZSwgc2VtIGFsdGVyYXIgbyBjb250ZcO6ZG8sIHRyYW5zcG9yIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyAKcGFyYSBxdWFscXVlciBtZWlvIG91IGZvcm1hdG8gcGFyYSBmaW5zIGRlIHByZXNlcnZhw6fDo28uCgpWb2PDqiB0YW1iw6ltIGNvbmNvcmRhIHF1ZSBhICBVTklGQUwtTUcgcG9kZSBtYW50ZXIgbWFpcyBkZSB1bWEgY8OzcGlhIGRlIHN1YSB0ZXNlIG91IApkaXNzZXJ0YcOnw6NvIHBhcmEgZmlucyBkZSBzZWd1cmFuw6dhLCBiYWNrLXVwIGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIGRlY2xhcmEgcXVlIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyDDqSBvcmlnaW5hbCBlIHF1ZSB2b2PDqiB0ZW0gbyBwb2RlciBkZSBjb25jZWRlciBvcyBkaXJlaXRvcyBjb250aWRvcyAKbmVzdGEgbGljZW7Dp2EuIFZvY8OqIHRhbWLDqW0gZGVjbGFyYSBxdWUgbyBkZXDDs3NpdG8gZGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyBuw6NvLCBxdWUgc2VqYSBkZSBzZXUgCmNvbmhlY2ltZW50bywgaW5mcmluZ2UgZGlyZWl0b3MgYXV0b3JhaXMgZGUgbmluZ3XDqW0uCgpDYXNvIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyBjb250ZW5oYSBtYXRlcmlhbCBxdWUgdm9jw6ogbsOjbyBwb3NzdWkgYSB0aXR1bGFyaWRhZGUgZG9zIGRpcmVpdG9zIGF1dG9yYWlzLCB2b2PDqiAKZGVjbGFyYSBxdWUgb2J0ZXZlIGEgcGVybWlzc8OjbyBpcnJlc3RyaXRhIGRvIGRldGVudG9yIGRvcyBkaXJlaXRvcyBhdXRvcmFpcyBwYXJhIGNvbmNlZGVyIMOgICBVTklGQUwtTUcgCm9zIGRpcmVpdG9zIGFwcmVzZW50YWRvcyBuZXN0YSBsaWNlbsOnYSwgZSBxdWUgZXNzZSBtYXRlcmlhbCBkZSBwcm9wcmllZGFkZSBkZSB0ZXJjZWlyb3MgZXN0w6EgY2xhcmFtZW50ZSAKaWRlbnRpZmljYWRvIGUgcmVjb25oZWNpZG8gbm8gdGV4dG8gb3Ugbm8gY29udGXDumRvIGRhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyBvcmEgZGVwb3NpdGFkYS4KCkNBU08gQSBURVNFIE9VIERJU1NFUlRBw4fDg08gT1JBIERFUE9TSVRBREEgVEVOSEEgU0lETyBSRVNVTFRBRE8gREUgVU0gUEFUUk9Dw41OSU8gT1UgCkFQT0lPIERFIFVNQSBBR8OKTkNJQSBERSBGT01FTlRPIE9VIE9VVFJPIE9SR0FOSVNNTyBRVUUgTsODTyBTRUpBIEEgIFVOSUZBTC1NRywgClZPQ8OKIERFQ0xBUkEgUVVFIFJFU1BFSVRPVSBUT0RPUyBFIFFVQUlTUVVFUiBESVJFSVRPUyBERSBSRVZJU8ODTyBDT01PIApUQU1Cw4lNIEFTIERFTUFJUyBPQlJJR0HDh8OVRVMgRVhJR0lEQVMgUE9SIENPTlRSQVRPIE9VIEFDT1JETy4KCkEgVU5JRkFMLU1HIHNlIGNvbXByb21ldGUgYSBpZGVudGlmaWNhciBjbGFyYW1lbnRlIG8gc2V1IG5vbWUgKHMpIG91IG8ocykgbm9tZShzKSBkbyhzKSAKZGV0ZW50b3IoZXMpIGRvcyBkaXJlaXRvcyBhdXRvcmFpcyBkYSB0ZXNlIG91IGRpc3NlcnRhw6fDo28sIGUgbsOjbyBmYXLDoSBxdWFscXVlciBhbHRlcmHDp8OjbywgYWzDqW0gZGFxdWVsYXMgCmNvbmNlZGlkYXMgcG9yIGVzdGEgbGljZW7Dp2EuCg== |
| dc.title.pt-BR.fl_str_mv |
Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos |
| title |
Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos |
| spellingShingle |
Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos Xavier, Tatiana Teodoro Complexos de paládio(II) Base de Schiff QUIMICA::QUIMICA INORGANICA |
| title_short |
Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos |
| title_full |
Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos |
| title_fullStr |
Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos |
| title_full_unstemmed |
Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos |
| title_sort |
Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos |
| author |
Xavier, Tatiana Teodoro |
| author_facet |
Xavier, Tatiana Teodoro |
| author_role |
author |
| dc.contributor.author.fl_str_mv |
Xavier, Tatiana Teodoro |
| dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6402668883583711 |
| dc.contributor.advisor-co1.fl_str_mv |
Marques, Marcos José |
| dc.contributor.referee1.fl_str_mv |
Pissetti, Fábio Luiz |
| dc.contributor.referee2.fl_str_mv |
Silva, Roberto Santana Da |
| dc.contributor.advisor1.fl_str_mv |
Almeida, Eduardo Tonon De |
| dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/6762358757258393 |
| contributor_str_mv |
Marques, Marcos José Pissetti, Fábio Luiz Silva, Roberto Santana Da Almeida, Eduardo Tonon De |
| dc.subject.por.fl_str_mv |
Complexos de paládio(II) Base de Schiff |
| topic |
Complexos de paládio(II) Base de Schiff QUIMICA::QUIMICA INORGANICA |
| dc.subject.cnpq.fl_str_mv |
QUIMICA::QUIMICA INORGANICA |
| description |
For some time, transition metal complexes, especially cisplatin, have been investigated due to their antineoplastic and trypanocidal activities. There are several studies in literature that seek to exploit the properties of palladium complexes, such as cancer cells anti-proliferative activity, anti-inflammatory activity, bactericidal activity and applications in catalytic processes. As a study material, we have palladium(II) compounds, containing iminic ligands. The N,N'-bis(3,4-dimethoxybenzaldehyde)ethane-1,2-diamine (3,4dm-1,2am) and N-(p-dimethylamino)benzylidine-(p-dimethylamino)aniline ( 4dm-1,4fen) ligand is a Schiff Base and has its synthesis and characterization reported in literature. The compounds were characterized by elemental and thermogravimetric analyses, as well as nuclear magnetic resonance spectroscopies ¹H and ¹³C, ultravioleta-visible and infrared (IR) spectroscopies. The results of NMR indicate the formation of N,N-chelated products ([Pd(Cl)2(3,4dm-1,2am)], [PdBrCl(3,4dm-1,2am)], [Pd(N3)2(3,4dm-1,2am)], [Pd(NCO)2(3,4dm-1,2am)]). Regarding the vibrational spectroscopy in the ultraviolet -visible, there was the shift of the absorption bands of the complexes indicating coordination of the ligand and the substitution of groups chlorides. This technique confirmed that the azide and cyanate groups are preferably coordinated N-terminal. The analysis of NMR ¹H and ¹³C, UV-Vis and IR spectra of ligand nitrogen (4dm-1,4fen) and complexes cyclopalladated ([Pd(μ-Cl)(4dm-1,4fen)]2) showed the presence of signs consistent with the proposed. The TG/DTA curves showed that the thermal decomposition of the palladium(II) complexes occurred in steps that involve the removal of both inorganic and organic ligand, and palladium oxidation steps forming palladium oxide followed by the reduction of palladium oxide into palladium(0), this being the constituent of the residual mass observed at the end of the TG curves, which have values consistent with the expected ones. The synthesized compounds were tested in biological assays against Leishmania where in vitro experiments with L. amazonensis promastigote cells were performed, and the compounds [Pd(N3)2(3,4dm-1,2am)] and [Pd(μ-Cl)(4dm-1,4fen)]2 showed IC50 near the Amphotericin B. |
| publishDate |
2016 |
| dc.date.issued.fl_str_mv |
2016-10-31 |
| dc.date.accessioned.fl_str_mv |
2017-01-03T17:40:39Z |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
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masterThesis |
| status_str |
publishedVersion |
| dc.identifier.citation.fl_str_mv |
XAVIER, Tatiana Teodoro. Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos. 2016. 121 f. Dissertação (Mestrado em Química) - Universidade Federal de Alfenas, Alfenas, MG, 2016. |
| dc.identifier.uri.fl_str_mv |
https://repositorio.unifal-mg.edu.br/handle/123456789/890 |
| identifier_str_mv |
XAVIER, Tatiana Teodoro. Síntese, caracterização e avaliação da atividade anti-leishmania de complexos de Paládio(II) contendo ligantes imínicos. 2016. 121 f. Dissertação (Mestrado em Química) - Universidade Federal de Alfenas, Alfenas, MG, 2016. |
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https://repositorio.unifal-mg.edu.br/handle/123456789/890 |
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por |
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por |
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1328253078826782306 |
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600 600 600 |
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3139127065238931096 |
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2075167498588264571 |
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info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by-nc-nd/4.0/ |
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openAccess |
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http://creativecommons.org/licenses/by-nc-nd/4.0/ |
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application/pdf |
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Universidade Federal de Alfenas |
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Programa de Pós-Graduação em Química |
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UNIFAL-MG |
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Brasil |
| dc.publisher.department.fl_str_mv |
Instituto de Química |
| publisher.none.fl_str_mv |
Universidade Federal de Alfenas |
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Biblioteca Digital de Teses e Dissertações da UNIFAL |
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Biblioteca Digital de Teses e Dissertações da UNIFAL - Universidade Federal de Alfenas (UNIFAL) |
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bdtd@unifal-mg.edu.br || bdtd@unifal-mg.edu.br |
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1850508409533628416 |