Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes
Autor(a) principal: | |
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Data de Publicação: | 2010 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000700013 |
Resumo: | The influence of the nucleobase (uracyl, U; cytosine, C; adenine, A; guanine, G) on the physicochemical characteristics and in vitro biological activities of SbV-ribonucleoside complexes has been investigated. The 1:1 Sb-U and Sb-C complexes were characterized by NMR and ESI-MS spectroscopies and elemental analysis. The stability constant and the apparent association and dissociation rate constants of 1:1 SbV-U, SbV-C and SbV-A complexes were determined. Although SbV most probably binds via oxygen atoms to the same 2' and 3' positions in the different nucleosides, the ribose conformational changes and the physicochemical characteristics of the complex depend on the nucleobase. The nucleobase had a strong influence on the cytotoxicity against macrophages and the antileishmanial activity of the SbV-ribonucleoside complexes. The SbV-purine complexes were more cytotoxic and more effective against Leishmania chagasi than the SbV-pyrimidine complexes, supporting the model that the interaction of SbV with purine nucleosides may mediate the antileishmanial activity of pentavalent antimonial drugs. |
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Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexesantimonykineticsnucleosidescytotoxicityleishmaniasisThe influence of the nucleobase (uracyl, U; cytosine, C; adenine, A; guanine, G) on the physicochemical characteristics and in vitro biological activities of SbV-ribonucleoside complexes has been investigated. The 1:1 Sb-U and Sb-C complexes were characterized by NMR and ESI-MS spectroscopies and elemental analysis. The stability constant and the apparent association and dissociation rate constants of 1:1 SbV-U, SbV-C and SbV-A complexes were determined. Although SbV most probably binds via oxygen atoms to the same 2' and 3' positions in the different nucleosides, the ribose conformational changes and the physicochemical characteristics of the complex depend on the nucleobase. The nucleobase had a strong influence on the cytotoxicity against macrophages and the antileishmanial activity of the SbV-ribonucleoside complexes. The SbV-purine complexes were more cytotoxic and more effective against Leishmania chagasi than the SbV-pyrimidine complexes, supporting the model that the interaction of SbV with purine nucleosides may mediate the antileishmanial activity of pentavalent antimonial drugs.Sociedade Brasileira de Química2010-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000700013Journal of the Brazilian Chemical Society v.21 n.7 2010reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532010000700013info:eu-repo/semantics/openAccessFerreira,Cláudio S.Rocha,Iara C. M. daM. Neto,Rubens L.Melo,Maria N.Frézard,FrédéricDemicheli,Cynthiaeng2010-07-30T00:00:00Zoai:scielo:S0103-50532010000700013Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2010-07-30T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes |
title |
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes |
spellingShingle |
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes Ferreira,Cláudio S. antimony kinetics nucleosides cytotoxicity leishmaniasis |
title_short |
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes |
title_full |
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes |
title_fullStr |
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes |
title_full_unstemmed |
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes |
title_sort |
Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes |
author |
Ferreira,Cláudio S. |
author_facet |
Ferreira,Cláudio S. Rocha,Iara C. M. da M. Neto,Rubens L. Melo,Maria N. Frézard,Frédéric Demicheli,Cynthia |
author_role |
author |
author2 |
Rocha,Iara C. M. da M. Neto,Rubens L. Melo,Maria N. Frézard,Frédéric Demicheli,Cynthia |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Ferreira,Cláudio S. Rocha,Iara C. M. da M. Neto,Rubens L. Melo,Maria N. Frézard,Frédéric Demicheli,Cynthia |
dc.subject.por.fl_str_mv |
antimony kinetics nucleosides cytotoxicity leishmaniasis |
topic |
antimony kinetics nucleosides cytotoxicity leishmaniasis |
description |
The influence of the nucleobase (uracyl, U; cytosine, C; adenine, A; guanine, G) on the physicochemical characteristics and in vitro biological activities of SbV-ribonucleoside complexes has been investigated. The 1:1 Sb-U and Sb-C complexes were characterized by NMR and ESI-MS spectroscopies and elemental analysis. The stability constant and the apparent association and dissociation rate constants of 1:1 SbV-U, SbV-C and SbV-A complexes were determined. Although SbV most probably binds via oxygen atoms to the same 2' and 3' positions in the different nucleosides, the ribose conformational changes and the physicochemical characteristics of the complex depend on the nucleobase. The nucleobase had a strong influence on the cytotoxicity against macrophages and the antileishmanial activity of the SbV-ribonucleoside complexes. The SbV-purine complexes were more cytotoxic and more effective against Leishmania chagasi than the SbV-pyrimidine complexes, supporting the model that the interaction of SbV with purine nucleosides may mediate the antileishmanial activity of pentavalent antimonial drugs. |
publishDate |
2010 |
dc.date.none.fl_str_mv |
2010-01-01 |
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://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000700013 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000700013 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532010000700013 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
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 |
Journal of the Brazilian Chemical Society v.21 n.7 2010 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318171075641344 |