Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues

G-quadruplexes and i-motifs are tetraplex structures present in telomeres and the promoter regions of oncogenes. The possibility of producing nanodevices with pH-sensitive functions has triggered interest in modified oligonucleotides with improved structural properties. We synthesized C-rich oligonu...

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Autores: Aviñó, Anna, Dellafiore, María A., Gargallo, Raimundo, Bustamante González, Carlos Alberto, Iribarren, A.M, Montserrat, Javier M., Eritja Casadellà, Ramón
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/152495
Acceso en línea:http://hdl.handle.net/10261/152495
Access Level:acceso abierto
Palabra clave:Circular dichroism
deoxymethylcytidine
i-motifs
NMR spectroscopy
telomeres
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spelling Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine ResiduesAviñó, AnnaDellafiore, María A.Gargallo, RaimundoBustamante González, Carlos AlbertoIribarren, A.MMontserrat, Javier M.Eritja Casadellà, RamónCircular dichroismdeoxymethylcytidinei-motifsNMR spectroscopytelomeresG-quadruplexes and i-motifs are tetraplex structures present in telomeres and the promoter regions of oncogenes. The possibility of producing nanodevices with pH-sensitive functions has triggered interest in modified oligonucleotides with improved structural properties. We synthesized C-rich oligonucleotides carrying conformationally restricted (2′S)-2′-deoxy-2′-C-methyl-cytidine units. The effect of this modified nucleoside on the stability of intramolecular i-motifs from the vertebrate telomere was investigated by UV, CD, and NMR spectroscopy. The replacement of selected positions of the C-core with C-modified residues induced the formation of stable intercalated tetraplexes at near-neutral pH. This study demonstrates the possibility of enhancing the stability of the i-motif by chemical modification. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimThis work was supported by the Spanish Ministry of Economy and Competitiveness (grants CTQ2014-52588-R, CTQ2012-38616-C02-02, BFU2014- 52864-R and CTQ2015-66254-C2-2-P), and the Generalitat de Catalunya (grant 2014 SGR 1106; 2014 SGR 187). CIBER-BBN is an initiative funded by the VI National R&D&I Plan 2008–2011, Iniciativa Ingenio 2010, Consolider Program, CIBER Actions and are financed by the Instituto de Salud Carlos III with assistance from the European Regional Development Fund. MD was recipient of an EMBO short term fellowship (ASTF 515-2015).Peer reviewedWiley-VCHMinisterio de Economía y Competitividad (España)Generalitat de CatalunyaEuropean CommissionConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201720172017info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/152495reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52588-Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/BFU2014-52864-Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-66254-C2-2-Phttp://doi.org/10.1002/cbic.201700112Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1524952026-05-22T06:33:51Z
dc.title.none.fl_str_mv Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues
title Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues
spellingShingle Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues
Aviñó, Anna
Circular dichroism
deoxymethylcytidine
i-motifs
NMR spectroscopy
telomeres
title_short Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues
title_full Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues
title_fullStr Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues
title_full_unstemmed Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues
title_sort Stabilization of Telomeric I-Motif Structures by (2′S)-2′-Deoxy-2′-C-Methylcytidine Residues
dc.creator.none.fl_str_mv Aviñó, Anna
Dellafiore, María A.
Gargallo, Raimundo
Bustamante González, Carlos Alberto
Iribarren, A.M
Montserrat, Javier M.
Eritja Casadellà, Ramón
author Aviñó, Anna
author_facet Aviñó, Anna
Dellafiore, María A.
Gargallo, Raimundo
Bustamante González, Carlos Alberto
Iribarren, A.M
Montserrat, Javier M.
Eritja Casadellà, Ramón
author_role author
author2 Dellafiore, María A.
Gargallo, Raimundo
Bustamante González, Carlos Alberto
Iribarren, A.M
Montserrat, Javier M.
Eritja Casadellà, Ramón
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Generalitat de Catalunya
European Commission
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Circular dichroism
deoxymethylcytidine
i-motifs
NMR spectroscopy
telomeres
topic Circular dichroism
deoxymethylcytidine
i-motifs
NMR spectroscopy
telomeres
description G-quadruplexes and i-motifs are tetraplex structures present in telomeres and the promoter regions of oncogenes. The possibility of producing nanodevices with pH-sensitive functions has triggered interest in modified oligonucleotides with improved structural properties. We synthesized C-rich oligonucleotides carrying conformationally restricted (2′S)-2′-deoxy-2′-C-methyl-cytidine units. The effect of this modified nucleoside on the stability of intramolecular i-motifs from the vertebrate telomere was investigated by UV, CD, and NMR spectroscopy. The replacement of selected positions of the C-core with C-modified residues induced the formation of stable intercalated tetraplexes at near-neutral pH. This study demonstrates the possibility of enhancing the stability of the i-motif by chemical modification. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
publishDate 2017
dc.date.none.fl_str_mv 2017
2017
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/152495
url http://hdl.handle.net/10261/152495
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52588-R
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/BFU2014-52864-R
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-66254-C2-2-P
http://doi.org/10.1002/cbic.201700112
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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