Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study
Autor(a) principal: | |
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Data de Publicação: | 2008 |
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=S0103-50532008000800002 |
Resumo: | This paper describes a theoretical analysis of the interaction between 5a,6-anhydrotetracycline platinum(II) complex (AHTC-Pt) and some biological nucleophiles; adenine (A), guanine (G), cysteine (Cys) and methionine (Met). The aquated species [Pt(AHTC)Cl(H2O)]+ was taken as reagent for the processes studied here. For DNA bases (A and G), the calculated values for ΔGa,aq at the B3LYP/6-311+G(2d,p) level were 21.7 and 20.7 kcal mol-1 for interaction with A and G, respectively, which are in accordance with the expected behavior of faster process involving G. These values are higher than the experimental activation energy for the parent compound cisplatin (18.5 kcal mol-1 for interaction with G). For the process involving the amino-acids, the barriers were 17.6 (Cys) and 18.5 kcal mol-1 (Met), which are lower than the observed values for cisplatin (20.5 and 20.2 kcal mol-1, respectively). These outcomes show that AHTC-Pt hybrid complex may be considered a promising lead compound in the development of novel anticancer drugs based on platinum complex. |
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Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical studycisplatin analoguestetracyclinesab initio calculationsThis paper describes a theoretical analysis of the interaction between 5a,6-anhydrotetracycline platinum(II) complex (AHTC-Pt) and some biological nucleophiles; adenine (A), guanine (G), cysteine (Cys) and methionine (Met). The aquated species [Pt(AHTC)Cl(H2O)]+ was taken as reagent for the processes studied here. For DNA bases (A and G), the calculated values for ΔGa,aq at the B3LYP/6-311+G(2d,p) level were 21.7 and 20.7 kcal mol-1 for interaction with A and G, respectively, which are in accordance with the expected behavior of faster process involving G. These values are higher than the experimental activation energy for the parent compound cisplatin (18.5 kcal mol-1 for interaction with G). For the process involving the amino-acids, the barriers were 17.6 (Cys) and 18.5 kcal mol-1 (Met), which are lower than the observed values for cisplatin (20.5 and 20.2 kcal mol-1, respectively). These outcomes show that AHTC-Pt hybrid complex may be considered a promising lead compound in the development of novel anticancer drugs based on platinum complex.Sociedade Brasileira de Química2008-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000800002Journal of the Brazilian Chemical Society v.19 n.8 2008reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532008000800002info:eu-repo/semantics/openAccessMarcial,Bruna L.Costa,Luiz Antônio S.De Almeida,Wagner B.Dos Santos,Hélio F.eng2008-12-09T00:00:00Zoai:scielo:S0103-50532008000800002Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2008-12-09T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study |
title |
Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study |
spellingShingle |
Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study Marcial,Bruna L. cisplatin analogues tetracyclines ab initio calculations |
title_short |
Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study |
title_full |
Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study |
title_fullStr |
Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study |
title_full_unstemmed |
Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study |
title_sort |
Reactivity of 5a,6-anhydrotetracycline platinum(II) complex with biological nucleophiles: a theoretical study |
author |
Marcial,Bruna L. |
author_facet |
Marcial,Bruna L. Costa,Luiz Antônio S. De Almeida,Wagner B. Dos Santos,Hélio F. |
author_role |
author |
author2 |
Costa,Luiz Antônio S. De Almeida,Wagner B. Dos Santos,Hélio F. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Marcial,Bruna L. Costa,Luiz Antônio S. De Almeida,Wagner B. Dos Santos,Hélio F. |
dc.subject.por.fl_str_mv |
cisplatin analogues tetracyclines ab initio calculations |
topic |
cisplatin analogues tetracyclines ab initio calculations |
description |
This paper describes a theoretical analysis of the interaction between 5a,6-anhydrotetracycline platinum(II) complex (AHTC-Pt) and some biological nucleophiles; adenine (A), guanine (G), cysteine (Cys) and methionine (Met). The aquated species [Pt(AHTC)Cl(H2O)]+ was taken as reagent for the processes studied here. For DNA bases (A and G), the calculated values for ΔGa,aq at the B3LYP/6-311+G(2d,p) level were 21.7 and 20.7 kcal mol-1 for interaction with A and G, respectively, which are in accordance with the expected behavior of faster process involving G. These values are higher than the experimental activation energy for the parent compound cisplatin (18.5 kcal mol-1 for interaction with G). For the process involving the amino-acids, the barriers were 17.6 (Cys) and 18.5 kcal mol-1 (Met), which are lower than the observed values for cisplatin (20.5 and 20.2 kcal mol-1, respectively). These outcomes show that AHTC-Pt hybrid complex may be considered a promising lead compound in the development of novel anticancer drugs based on platinum complex. |
publishDate |
2008 |
dc.date.none.fl_str_mv |
2008-01-01 |
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=S0103-50532008000800002 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000800002 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532008000800002 |
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.19 n.8 2008 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 |
_version_ |
1750318169377996800 |