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dc.contributor.authorBordello Malde, Jorge
dc.contributor.authorSánchez López, Mateo Isidro
dc.contributor.authorVázquez Sentís, Marco Eugenio
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorAl-Soufi, Wajih
dc.contributor.authorNovo Rodríguez, María de la Merced
dc.date.accessioned2015-02-12T11:59:05Z
dc.date.available2017-08-29T01:00:16Z
dc.date.issued2014-11-21
dc.identifier.citationBordello, J., Sánchez, M. I., Vázquez, M. E., Mascareñas, J. L., Al-Soufi, W. and Novo, M. (2015), Fluorescence-Labeled Bis-benzamidines as Fluorogenic DNA Minor-Groove Binders: Photophysics and Binding Dynamics. Chem. Eur. J., 21: 1609–1619. doi: 10.1002/chem.201404926
dc.identifier.issn0947-6539
dc.identifier.otherE-ISSN 1521-3765
dc.identifier.urihttp://hdl.handle.net/10347/12290
dc.descriptionNOTICE: This is the peer reviewed version of the following article: Bordello, J., Sánchez, M. I., Vázquez, M. E., Mascareñas, J. L., Al-Soufi, W. and Novo, M. (2015), Fluorescence-Labeled Bis-benzamidines as Fluorogenic DNA Minor-Groove Binders: Photophysics and Binding Dynamics. Chem. Eur. J., 21: 1609–1619 [doi: 10.1002/chem.201404926]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving.
dc.description.abstractIn recent decades there has been great interest in the design of highly sensitive sequence-specific DNA binders. The eligibility of the binder depends on the magnitude of the fluorescence increase upon binding, related to its photophysics, and on its affinity and specificity, which is, in turn, determined by the dynamics of the binding process. Therefore, progress in the design of DNA binders requires both thorough photophysical studies and precise determination of the association and dissociation rate constants involved. We have studied two bis-benzamidine (BBA) derivatives labeled by linkers of various lengths with the dye Oregon Green (OG). These fluorogenic binders show a dramatic fluorescence enhancement upon binding to the minor groove of double-stranded (ds) DNA, as well as significant improvement in their sequence specificity versus the parent BBA, although with decreased affinity constants. Detailed photophysical analysis shows that static and dynamic quenching of the OG fluorescence by BBA through photoinduced electron transfer is suppressed upon insertion of BBA into the minor groove of DNA. Fluorescence correlation spectroscopy yields precise dynamic rate constants that prove that the association process of these fluorogenic binders to dsDNA is very similar to that of BBA alone and that their lower affinity is mainly a consequence of their weaker attachment to the minor groove and the resultant faster dissociation process. The conclusions of this study will allow us to go one step further in the design of new DNA binders with tunable fluorescence and binding properties
dc.description.sponsorshipJ.B. and M.I.S thank the Spanish MCINN for their research scholarships. The authors are thankful for financial support from Spanish grants (CTQ2010-21369, SAF2013-41943-R and CTQ2012-31341), the Xunta de Galicia (GPC2013/052, GRC2013-041, CN 2012/314), the ERDF, and the European Research Council (Advanced Grant Nº 340055). Support of COST Actions CM1105 and CM1306 and the orfeo-cinqa network is also kindly acknowledged
dc.language.isoeng
dc.publisherWILEY-VCH Verlag GmbH
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/340055
dc.relationinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2013-41943-R/ES/HERRAMIENTAS SINTETICAS EN QUIMICA BIOLOGICA. NUEVAS ESTRATEGIAS MOLECULARES PARA EL TRATAMIENTO Y DIAGNOSTICO DE CANCERES
dc.rights© WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.subjectDNA minor-groove binder
dc.subjectDNA recognition
dc.subjectFluorescence correlation spectroscopy
dc.subjectPhotophysics
dc.subjectReaction dynamics
dc.subject.classificationMaterias::Investigación::23 Química
dc.titleFluorescence-Labeled Bis-benzamidines as Fluorogenic DNA Minor-Groove Binders: Photophysics and Binding Dynamics
dc.typeinfo:eu-repo/semantics/article
dc.identifier.DOI10.1002/chem.201404926
dc.relation.publisherversionhttp://dx.doi.org/10.1002/chem.201404926
dc.type.versioninfo:eu-repo/semantics/acceptedVersion
dc.rights.accessrightsinfo:eu-repo/semantics/openAccess
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Física
dc.description.peerreviewedSI


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