Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]

Mono(nucleobase) complexes of the general composition cis-PtCl2(NH3)L] with L=1-methylcytosine, 1-MeC (1 a) and L=1-ethyl-5-methylcytosine, as well as trans-PtX2(NH3)(1-MeC)] with X=I (5 a) and X=Br (5 b) have been isolated and were characterized by X-ray crystallography. The Pt coordination occurs...

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Autores: Siebel, S., Dammann, C., Sanz Miguel, P. J., Drewello, T., Kampf, G., Teubner, N., Bednarski, P. J., Freisinger, E., Lippert, B.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2015
País:España
Institución:Universidad de Zaragoza
Repositorio:Zaguán. Repositorio Digital de la Universidad de Zaragoza
OAI Identifier:oai:zaguan.unizar.es:61427
Acceso en línea:http://zaguan.unizar.es/record/61427
Access Level:acceso abierto
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spelling Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]Siebel, S.Dammann, C.Sanz Miguel, P. J.Drewello, T.Kampf, G.Teubner, N.Bednarski, P. J.Freisinger, E.Lippert, B.Mono(nucleobase) complexes of the general composition cis-PtCl2(NH3)L] with L=1-methylcytosine, 1-MeC (1 a) and L=1-ethyl-5-methylcytosine, as well as trans-PtX2(NH3)(1-MeC)] with X=I (5 a) and X=Br (5 b) have been isolated and were characterized by X-ray crystallography. The Pt coordination occurs through the N3 atom of the cytosine in all cases. The diaqua complexes of compounds 1 a and 5 a, cis-Pt(H2O)2(NH3)(1-MeC)]2+ and trans-Pt(H2O)2(NH3)(1-MeC)]2+, display a rich chemistry in aqueous solution, which is dominated by extensive condensation reactions leading to µ-OH- and µ-(1-MeC--N3, N4)-bridged species and ready oxidation of Pt to mixed-valence state complexes as well as diplatinum(III) compounds, one of which was characterized by X-ray crystallography: h, t-{Pt(NH3)2(OH)(1-MeC--N3, N4)}2](NO3)2.2 NH4](NO3).2 H2O. A combination of 1H NMR spectroscopy and ESI mass spectrometry was applied to identify some of the various species present in solution and the gas phase, respectively. As it turned out, mass spectrometry did not permit an unambiguous assignment of the structures of +1 cations due to the possibilities of realizing multiple bridging patterns in isomeric species, the occurrence of different tautomers, and uncertainties regarding the Pt oxidation states. Additionally, compound 1 a was found to have selective and moderate antiproliferative activity for a human cervix cancer line (SISO) compared to six other human cancer cell lines.2015info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://zaguan.unizar.es/record/61427reponame:Zaguán. Repositorio Digital de la Universidad de Zaragozainstname:Universidad de ZaragozaInglésinfo:eu-repo/semantics/openAccessoai:zaguan.unizar.es:614272026-05-29T13:59:51Z
dc.title.none.fl_str_mv Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
title Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
spellingShingle Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
Siebel, S.
title_short Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
title_full Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
title_fullStr Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
title_full_unstemmed Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
title_sort Analogues of Cis- and Transplatin with a Rich Solution Chemistry: Cis-[PtCl2(NH3)(1-MeC-N3)] and trans-[PtI2(NH3)(1-MeC-N3)]
dc.creator.none.fl_str_mv Siebel, S.
Dammann, C.
Sanz Miguel, P. J.
Drewello, T.
Kampf, G.
Teubner, N.
Bednarski, P. J.
Freisinger, E.
Lippert, B.
author Siebel, S.
author_facet Siebel, S.
Dammann, C.
Sanz Miguel, P. J.
Drewello, T.
Kampf, G.
Teubner, N.
Bednarski, P. J.
Freisinger, E.
Lippert, B.
author_role author
author2 Dammann, C.
Sanz Miguel, P. J.
Drewello, T.
Kampf, G.
Teubner, N.
Bednarski, P. J.
Freisinger, E.
Lippert, B.
author2_role author
author
author
author
author
author
author
author
description Mono(nucleobase) complexes of the general composition cis-PtCl2(NH3)L] with L=1-methylcytosine, 1-MeC (1 a) and L=1-ethyl-5-methylcytosine, as well as trans-PtX2(NH3)(1-MeC)] with X=I (5 a) and X=Br (5 b) have been isolated and were characterized by X-ray crystallography. The Pt coordination occurs through the N3 atom of the cytosine in all cases. The diaqua complexes of compounds 1 a and 5 a, cis-Pt(H2O)2(NH3)(1-MeC)]2+ and trans-Pt(H2O)2(NH3)(1-MeC)]2+, display a rich chemistry in aqueous solution, which is dominated by extensive condensation reactions leading to µ-OH- and µ-(1-MeC--N3, N4)-bridged species and ready oxidation of Pt to mixed-valence state complexes as well as diplatinum(III) compounds, one of which was characterized by X-ray crystallography: h, t-{Pt(NH3)2(OH)(1-MeC--N3, N4)}2](NO3)2.2 NH4](NO3).2 H2O. A combination of 1H NMR spectroscopy and ESI mass spectrometry was applied to identify some of the various species present in solution and the gas phase, respectively. As it turned out, mass spectrometry did not permit an unambiguous assignment of the structures of +1 cations due to the possibilities of realizing multiple bridging patterns in isomeric species, the occurrence of different tautomers, and uncertainties regarding the Pt oxidation states. Additionally, compound 1 a was found to have selective and moderate antiproliferative activity for a human cervix cancer line (SISO) compared to six other human cancer cell lines.
publishDate 2015
dc.date.none.fl_str_mv 2015
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://zaguan.unizar.es/record/61427
url http://zaguan.unizar.es/record/61427
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv
publisher.none.fl_str_mv
dc.source.none.fl_str_mv reponame:Zaguán. Repositorio Digital de la Universidad de Zaragoza
instname:Universidad de Zaragoza
instname_str Universidad de Zaragoza
reponame_str Zaguán. Repositorio Digital de la Universidad de Zaragoza
collection Zaguán. Repositorio Digital de la Universidad de Zaragoza
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