Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol

Detalhes bibliográficos
Autor(a) principal: Santos, C
Data de Publicação: 2005
Outros Autores: Mateus, ML, dos Santos, AP, Moreira, R, de Oliveira, E, Gomes, P
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/10216/82058
Resumo: Dipeptide esters of paracetamol were prepared in high yields. These compounds are quantitatively hydrolyzed to paracetamol and corresponding 2,5-diketopiperazines at pH 7.4 and 37 degrees C. The reactivity is increased in sarcosine and proline peptides and decreased by bulky side chains at both the N- and C-terminal residues of the dipeptide carrier. Moreover, dipeptide esters of paracetamol did not affect the levels of hepatic glutathione. Thus, dipeptides seem promising candidates as carriers for cyclization-activated prodrugs.
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spelling Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamolQuímicaChemical sciencesDipeptide esters of paracetamol were prepared in high yields. These compounds are quantitatively hydrolyzed to paracetamol and corresponding 2,5-diketopiperazines at pH 7.4 and 37 degrees C. The reactivity is increased in sarcosine and proline peptides and decreased by bulky side chains at both the N- and C-terminal residues of the dipeptide carrier. Moreover, dipeptide esters of paracetamol did not affect the levels of hepatic glutathione. Thus, dipeptides seem promising candidates as carriers for cyclization-activated prodrugs.20052005-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10216/82058eng0960-894X10.1016/j.bmcl.2005.01.065Santos, CMateus, MLdos Santos, APMoreira, Rde Oliveira, EGomes, Pinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-11-29T15:17:42Zoai:repositorio-aberto.up.pt:10216/82058Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T00:19:56.096776Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol
title Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol
spellingShingle Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol
Santos, C
Química
Chemical sciences
title_short Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol
title_full Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol
title_fullStr Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol
title_full_unstemmed Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol
title_sort Cyclization-activated prodrugs. Synthesis, reactivity and toxicity of dipeptide esters of paracetamol
author Santos, C
author_facet Santos, C
Mateus, ML
dos Santos, AP
Moreira, R
de Oliveira, E
Gomes, P
author_role author
author2 Mateus, ML
dos Santos, AP
Moreira, R
de Oliveira, E
Gomes, P
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Santos, C
Mateus, ML
dos Santos, AP
Moreira, R
de Oliveira, E
Gomes, P
dc.subject.por.fl_str_mv Química
Chemical sciences
topic Química
Chemical sciences
description Dipeptide esters of paracetamol were prepared in high yields. These compounds are quantitatively hydrolyzed to paracetamol and corresponding 2,5-diketopiperazines at pH 7.4 and 37 degrees C. The reactivity is increased in sarcosine and proline peptides and decreased by bulky side chains at both the N- and C-terminal residues of the dipeptide carrier. Moreover, dipeptide esters of paracetamol did not affect the levels of hepatic glutathione. Thus, dipeptides seem promising candidates as carriers for cyclization-activated prodrugs.
publishDate 2005
dc.date.none.fl_str_mv 2005
2005-01-01T00:00:00Z
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.uri.fl_str_mv https://hdl.handle.net/10216/82058
url https://hdl.handle.net/10216/82058
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0960-894X
10.1016/j.bmcl.2005.01.065
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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