Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas
Ano de defesa: | 2011 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/27281 |
Resumo: | This thesis describes the synthesis of a series of peptides precursors of cyclopeptide alkaloids Condaline-A, Scutianine-M, Scutianine-L e Adouetine-Y. Their antimicrobial activity was evaluated to conduct a study of their structure-activity relationships (SAR). In addition, we can evaluate their action against some enzymes involved in degenerative diseases of the central nervous system (CNS), as well as the antioxidant activity of these precursors. For the synthesis of these peptides, the non-proteinogenic amino acid b-Phenylserine was obtained in its diastereoisomeric forms (D, L-threo and D, L-erythro) and separated by recrystallization. The general strategy of synthesis employed the classical techniques of protection and deprotection of the amino acids with the usual coupling reagents to the peptide synthesis in solution, what enabled the construction of di-, tri-and tetrapeptides in pure forms. This strategy enabled the achievement of the tripeptides with the N-terminal, protected, free, N, N-dimethyl and N-methylated, with their structures confirmed by NMR experiments, and also for the dipeptide Z-L-Phe-L-threo-Pheser-OMe, and the tripeptide and N, N-(Me)2-LPhe- D-threo-Pheser-L-Ile-OMe, it was possible to obtain crystals that were analyzed by X-ray diffraction, in order to achieve structural confirmation and support in determining the stereochemistry. To study the SAR, the natural peptides and metabolites were subjected to analysis of their antimicrobial activity through the micro-dilution method using different microorganisms: two Gram-positive bacteria [Staphylococcus aureus, Staphylococcus epidermidis], three Gram-negative bacteria [Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae] and two fungi [Saccharomyces cerevisiae, Candida albicans]. Additionally, a screening was conducted with these compounds to identify some possible inhibitors of acetylcholinesterase (AChE), prolyl-oligopeptidase (POP) and dipeptidilpeptidase-IV (DPP-IV), as well as some compound capable of capture free radicals (antioxidant activity). |
id |
UFSM_1c7875922d2946551c3ec0c219b1027b |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/27281 |
network_acronym_str |
UFSM |
network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
spelling |
2022-12-07T16:39:36Z2022-12-07T16:39:36Z2011-07-10http://repositorio.ufsm.br/handle/1/27281This thesis describes the synthesis of a series of peptides precursors of cyclopeptide alkaloids Condaline-A, Scutianine-M, Scutianine-L e Adouetine-Y. Their antimicrobial activity was evaluated to conduct a study of their structure-activity relationships (SAR). In addition, we can evaluate their action against some enzymes involved in degenerative diseases of the central nervous system (CNS), as well as the antioxidant activity of these precursors. For the synthesis of these peptides, the non-proteinogenic amino acid b-Phenylserine was obtained in its diastereoisomeric forms (D, L-threo and D, L-erythro) and separated by recrystallization. The general strategy of synthesis employed the classical techniques of protection and deprotection of the amino acids with the usual coupling reagents to the peptide synthesis in solution, what enabled the construction of di-, tri-and tetrapeptides in pure forms. This strategy enabled the achievement of the tripeptides with the N-terminal, protected, free, N, N-dimethyl and N-methylated, with their structures confirmed by NMR experiments, and also for the dipeptide Z-L-Phe-L-threo-Pheser-OMe, and the tripeptide and N, N-(Me)2-LPhe- D-threo-Pheser-L-Ile-OMe, it was possible to obtain crystals that were analyzed by X-ray diffraction, in order to achieve structural confirmation and support in determining the stereochemistry. To study the SAR, the natural peptides and metabolites were subjected to analysis of their antimicrobial activity through the micro-dilution method using different microorganisms: two Gram-positive bacteria [Staphylococcus aureus, Staphylococcus epidermidis], three Gram-negative bacteria [Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae] and two fungi [Saccharomyces cerevisiae, Candida albicans]. Additionally, a screening was conducted with these compounds to identify some possible inhibitors of acetylcholinesterase (AChE), prolyl-oligopeptidase (POP) and dipeptidilpeptidase-IV (DPP-IV), as well as some compound capable of capture free radicals (antioxidant activity).O presente trabalho de tese descreve a síntese de uma série de peptídeos precursores dos alcalóides ciclopeptídicos Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y. Além disso, a atividade antimicrobiana foi avaliada a fim de se realizar um estudo das relações estrutura-atividade (REA). Ainda foi avaliada sua ação frente a algumas enzimas envolvidas em doenças degenerativas do Sistema Nervoso Central (SNC), bem como a atividade antioxidante destes precursores. Para a síntese destes peptídeos, o aminoácido não proteinogênico b-fenilserina foi obtido nas suas formas diastereoisomérica (D,L-treo e D,L-eritro) e separados por recristalização. A estratégia geral de síntese empregou técnicas clássicas de proteção e desproteção dos aminoácidos com reagentes de acoplamento usuais à síntese peptídica em solução, o que possibilitou a construção de di-, tri- e tetrapeptídeos de forma pura. Esta estratégia possibilitou ainda a obtenção dos tripeptídeos com a extremidade N-terminal protegida, livre, N,N-dimetilada e N-metilada, com suas estruturas confirmadas por experimentos de RMN, e ainda para o dipeptídeo Z-L-Phe-L-treo-Pheser-OMe e o tripeptídeo N,N-(Me)2-L-Phe-Dtreo- Pheser-L-Ile-OMe, sendo possível obter cristais que foram submetidos à análise por difração de raios-X, com a finalidade de confirmação estrutural e suporte na determinação das estereoquímicas. Para o estudo de REA, os peptídeos e os metabólitos naturais foram submetidos à análise das possíveis atividades antimicrobianas pelo método da micro-diluição, empregando diferentes microrganismos: duas bactérias Gram-positivas [Staphylococcus aureus, Staphylococcus epidermidis], três bactérias Gram-negativas [Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae] e dois fungos [Sacharomyces cerevisae, Candida albicans]. Adicionalmente, foi realizada uma triagem com estes compostos a fim de identificar alguns possíveis inibidores das enzimas acetilcolinesterase (AChE), prolil-oligopeptidase (POP) e dipeptidilpeptidase-IV (DPP-IV), bem como algum composto com a capacidade de capturar radicais livres (atividade antioxidante).Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessSíntesePeptídeos lineares precursoresAlcalóidesCondalina-AScutianina-MScutianina-LAdouetina-YCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicasinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMorel, Ademir Fariashttp://lattes.cnpq.br/3554994385525333Dornelles, LucianoCaro, Miguel Soriano BalpardaDalcol, Ionara IronMostardeiro, Marco Auréliohttp://lattes.cnpq.br/3882671719676564Ilha, Vinicius1006000000006006006006006006006008c99befa-f1b3-4afb-98b8-7fab46c3d493ab2e5d3f-d49d-4c2e-8e54-30d13c7581547dfea8f7-fe97-4100-9d09-8f5a40fe23163209cb7e-bf46-45b7-9ec0-d81b856e6a07ed64cd73-8b80-4162-bf54-b2cc4cb07228bdd40376-c7b0-4451-8b43-4ebfeada90fcreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUÍMICA_2011_ILHA_VINICIUS.pdfTES_PPGQUÍMICA_2011_ILHA_VINICIUS.pdfTese de doutoradoapplication/pdf21275390http://repositorio.ufsm.br/bitstream/1/27281/1/TES_PPGQU%c3%8dMICA_2011_ILHA_VINICIUS.pdf7fd073dc9379ee9b9815239f10a50058MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/27281/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/27281/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/272812022-12-07 13:39:39.55oai:repositorio.ufsm.br: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 Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-12-07T16:39:39Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas |
title |
Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas |
spellingShingle |
Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas Ilha, Vinicius Síntese Peptídeos lineares precursores Alcalóides Condalina-A Scutianina-M Scutianina-L Adouetina-Y CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas |
title_full |
Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas |
title_fullStr |
Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas |
title_full_unstemmed |
Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas |
title_sort |
Síntese de peptídeos lineares precursores dos alcalóides Condalina-A, Scutianina-M, Scutianina-L e Adouetina-Y: estudos estruturais e suas atividades biológicas |
author |
Ilha, Vinicius |
author_facet |
Ilha, Vinicius |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Morel, Ademir Farias |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/3554994385525333 |
dc.contributor.referee1.fl_str_mv |
Dornelles, Luciano |
dc.contributor.referee2.fl_str_mv |
Caro, Miguel Soriano Balparda |
dc.contributor.referee3.fl_str_mv |
Dalcol, Ionara Iron |
dc.contributor.referee4.fl_str_mv |
Mostardeiro, Marco Aurélio |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3882671719676564 |
dc.contributor.author.fl_str_mv |
Ilha, Vinicius |
contributor_str_mv |
Morel, Ademir Farias Dornelles, Luciano Caro, Miguel Soriano Balparda Dalcol, Ionara Iron Mostardeiro, Marco Aurélio |
dc.subject.por.fl_str_mv |
Síntese Peptídeos lineares precursores Alcalóides Condalina-A Scutianina-M Scutianina-L Adouetina-Y |
topic |
Síntese Peptídeos lineares precursores Alcalóides Condalina-A Scutianina-M Scutianina-L Adouetina-Y CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This thesis describes the synthesis of a series of peptides precursors of cyclopeptide alkaloids Condaline-A, Scutianine-M, Scutianine-L e Adouetine-Y. Their antimicrobial activity was evaluated to conduct a study of their structure-activity relationships (SAR). In addition, we can evaluate their action against some enzymes involved in degenerative diseases of the central nervous system (CNS), as well as the antioxidant activity of these precursors. For the synthesis of these peptides, the non-proteinogenic amino acid b-Phenylserine was obtained in its diastereoisomeric forms (D, L-threo and D, L-erythro) and separated by recrystallization. The general strategy of synthesis employed the classical techniques of protection and deprotection of the amino acids with the usual coupling reagents to the peptide synthesis in solution, what enabled the construction of di-, tri-and tetrapeptides in pure forms. This strategy enabled the achievement of the tripeptides with the N-terminal, protected, free, N, N-dimethyl and N-methylated, with their structures confirmed by NMR experiments, and also for the dipeptide Z-L-Phe-L-threo-Pheser-OMe, and the tripeptide and N, N-(Me)2-LPhe- D-threo-Pheser-L-Ile-OMe, it was possible to obtain crystals that were analyzed by X-ray diffraction, in order to achieve structural confirmation and support in determining the stereochemistry. To study the SAR, the natural peptides and metabolites were subjected to analysis of their antimicrobial activity through the micro-dilution method using different microorganisms: two Gram-positive bacteria [Staphylococcus aureus, Staphylococcus epidermidis], three Gram-negative bacteria [Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae] and two fungi [Saccharomyces cerevisiae, Candida albicans]. Additionally, a screening was conducted with these compounds to identify some possible inhibitors of acetylcholinesterase (AChE), prolyl-oligopeptidase (POP) and dipeptidilpeptidase-IV (DPP-IV), as well as some compound capable of capture free radicals (antioxidant activity). |
publishDate |
2011 |
dc.date.issued.fl_str_mv |
2011-07-10 |
dc.date.accessioned.fl_str_mv |
2022-12-07T16:39:36Z |
dc.date.available.fl_str_mv |
2022-12-07T16:39:36Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/27281 |
url |
http://repositorio.ufsm.br/handle/1/27281 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 |
dc.relation.authority.fl_str_mv |
8c99befa-f1b3-4afb-98b8-7fab46c3d493 ab2e5d3f-d49d-4c2e-8e54-30d13c758154 7dfea8f7-fe97-4100-9d09-8f5a40fe2316 3209cb7e-bf46-45b7-9ec0-d81b856e6a07 ed64cd73-8b80-4162-bf54-b2cc4cb07228 bdd40376-c7b0-4451-8b43-4ebfeada90fc |
dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/27281/1/TES_PPGQU%c3%8dMICA_2011_ILHA_VINICIUS.pdf http://repositorio.ufsm.br/bitstream/1/27281/2/license_rdf http://repositorio.ufsm.br/bitstream/1/27281/3/license.txt |
bitstream.checksum.fl_str_mv |
7fd073dc9379ee9b9815239f10a50058 4460e5956bc1d1639be9ae6146a50347 2f0571ecee68693bd5cd3f17c1e075df |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1793240009328820224 |