Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors

Detalhes bibliográficos
Autor(a) principal: Piovan, Leandro
Data de Publicação: 2010
Outros Autores: Alves, Marcio Fernando [UNIFESP], Juliano, Luiz [UNIFESP], Brömme, Dieter, Cunha, Rodrigo Luiz Oliveira Rodrigues [UNIFESP], Andrade, Leandro H
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNIFESP
Texto Completo: http://dx.doi.org/10.1590/S0103-50532010001100012
http://repositorio.unifesp.br/handle/11600/5540
Resumo: A series of organoselenium dihalides (organoselenanes) was synthesized from organoselenides using a chemoenzymatic approach. The organoselenanes have variations in their stereochemistry and in the halogen atom bonded to the selenium atom. Because of the unique selenium-thiol chemistry displayed by several organoselenium compounds, the organoselenanes were evaluated as new potential inhibitors of cysteine proteases (cathepsins S and V). By the analysis of the second-order rate constants of the inhibition of cathepsin S and V, it was possible to conclude that organoselenanes inhibited the cathepsin S faster than cathepsin V. It was observed higher inhibitory potencies for the dibromo organoselenanes derivatives than the dichloro analogues. In addition, the present data suggest the use of hypervalent selenium compounds as novel motifs for cysteine proteases inhibitors.
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spelling Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitorsseleniumcathepsininhibitorsbiocatalysisA series of organoselenium dihalides (organoselenanes) was synthesized from organoselenides using a chemoenzymatic approach. The organoselenanes have variations in their stereochemistry and in the halogen atom bonded to the selenium atom. Because of the unique selenium-thiol chemistry displayed by several organoselenium compounds, the organoselenanes were evaluated as new potential inhibitors of cysteine proteases (cathepsins S and V). By the analysis of the second-order rate constants of the inhibition of cathepsin S and V, it was possible to conclude that organoselenanes inhibited the cathepsin S faster than cathepsin V. It was observed higher inhibitory potencies for the dibromo organoselenanes derivatives than the dichloro analogues. In addition, the present data suggest the use of hypervalent selenium compounds as novel motifs for cysteine proteases inhibitors.Uma série de organosselenanas foi sintetizada utilizando-se uma metodologia quimio-enzimática. Estas organosselenanas apresentam variações na estereoquímica e no halogênio ligado ao átomo de selênio. Devido à reação característica envolvendo compostos de selênio e tióis, estas organosselenanas foram avaliadas como inibidores de cisteíno proteases (catepsinas V e S). As constantes de inibição de segunda-ordem mostraram que a catepsina S é inibida mais rapidamente do que a catepsina V. Pode-se observar que as organosselenanas dibromadas são inibidores mais potentes do que as dicloradas. Desta forma, os resultados obtidos mostram que compostos hipervalentes de selênio podem ser aplicados como inibidores de cisteíno proteases.Universidade de São Paulo Instituto de QuímicaUniversidade Federal de São Paulo (UNIFESP) Escola Paulista de Medicina Departamento de BiofísicaUniversity of British Columbia Faculty of Dentistry Department of Dentistry Center for Blood ResearchUniversidade Federal do ABC Centro de Ciências Naturais e HumanasUNIFESP, EPM, Depto. de BiofísicaSciELOFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Sociedade Brasileira de QuímicaUniversidade de São Paulo (USP)Universidade Federal de São Paulo (UNIFESP)University of British Columbia Faculty of Dentistry Department of Dentistry Center for Blood ResearchUniversidade Federal do ABC Centro de Ciências Naturais e HumanasPiovan, LeandroAlves, Marcio Fernando [UNIFESP]Juliano, Luiz [UNIFESP]Brömme, DieterCunha, Rodrigo Luiz Oliveira Rodrigues [UNIFESP]Andrade, Leandro H2015-06-14T13:41:28Z2015-06-14T13:41:28Z2010-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion2108-2118application/pdfhttp://dx.doi.org/10.1590/S0103-50532010001100012Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 21, n. 11, p. 2108-2118, 2010.10.1590/S0103-50532010001100012S0103-50532010001100012.pdf0103-5053S0103-50532010001100012http://repositorio.unifesp.br/handle/11600/5540WOS:000284094500013engJournal of the Brazilian Chemical Societyinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESP2024-07-29T21:14:42Zoai:repositorio.unifesp.br/:11600/5540Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestbiblioteca.csp@unifesp.bropendoar:34652024-07-29T21:14:42Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false
dc.title.none.fl_str_mv Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors
title Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors
spellingShingle Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors
Piovan, Leandro
selenium
cathepsin
inhibitors
biocatalysis
title_short Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors
title_full Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors
title_fullStr Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors
title_full_unstemmed Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors
title_sort Chemoenzymatic synthesis of organoselenium(IV) compounds and their evaluation as cysteine protease inhibitors
author Piovan, Leandro
author_facet Piovan, Leandro
Alves, Marcio Fernando [UNIFESP]
Juliano, Luiz [UNIFESP]
Brömme, Dieter
Cunha, Rodrigo Luiz Oliveira Rodrigues [UNIFESP]
Andrade, Leandro H
author_role author
author2 Alves, Marcio Fernando [UNIFESP]
Juliano, Luiz [UNIFESP]
Brömme, Dieter
Cunha, Rodrigo Luiz Oliveira Rodrigues [UNIFESP]
Andrade, Leandro H
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade de São Paulo (USP)
Universidade Federal de São Paulo (UNIFESP)
University of British Columbia Faculty of Dentistry Department of Dentistry Center for Blood Research
Universidade Federal do ABC Centro de Ciências Naturais e Humanas
dc.contributor.author.fl_str_mv Piovan, Leandro
Alves, Marcio Fernando [UNIFESP]
Juliano, Luiz [UNIFESP]
Brömme, Dieter
Cunha, Rodrigo Luiz Oliveira Rodrigues [UNIFESP]
Andrade, Leandro H
dc.subject.por.fl_str_mv selenium
cathepsin
inhibitors
biocatalysis
topic selenium
cathepsin
inhibitors
biocatalysis
description A series of organoselenium dihalides (organoselenanes) was synthesized from organoselenides using a chemoenzymatic approach. The organoselenanes have variations in their stereochemistry and in the halogen atom bonded to the selenium atom. Because of the unique selenium-thiol chemistry displayed by several organoselenium compounds, the organoselenanes were evaluated as new potential inhibitors of cysteine proteases (cathepsins S and V). By the analysis of the second-order rate constants of the inhibition of cathepsin S and V, it was possible to conclude that organoselenanes inhibited the cathepsin S faster than cathepsin V. It was observed higher inhibitory potencies for the dibromo organoselenanes derivatives than the dichloro analogues. In addition, the present data suggest the use of hypervalent selenium compounds as novel motifs for cysteine proteases inhibitors.
publishDate 2010
dc.date.none.fl_str_mv 2010-01-01
2015-06-14T13:41:28Z
2015-06-14T13:41:28Z
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.1590/S0103-50532010001100012
Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 21, n. 11, p. 2108-2118, 2010.
10.1590/S0103-50532010001100012
S0103-50532010001100012.pdf
0103-5053
S0103-50532010001100012
http://repositorio.unifesp.br/handle/11600/5540
WOS:000284094500013
url http://dx.doi.org/10.1590/S0103-50532010001100012
http://repositorio.unifesp.br/handle/11600/5540
identifier_str_mv Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 21, n. 11, p. 2108-2118, 2010.
10.1590/S0103-50532010001100012
S0103-50532010001100012.pdf
0103-5053
S0103-50532010001100012
WOS:000284094500013
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Journal of the Brazilian Chemical Society
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 2108-2118
application/pdf
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da UNIFESP
instname:Universidade Federal de São Paulo (UNIFESP)
instacron:UNIFESP
instname_str Universidade Federal de São Paulo (UNIFESP)
instacron_str UNIFESP
institution UNIFESP
reponame_str Repositório Institucional da UNIFESP
collection Repositório Institucional da UNIFESP
repository.name.fl_str_mv Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)
repository.mail.fl_str_mv biblioteca.csp@unifesp.br
_version_ 1814268278576513024

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