Carbohydrate-DNA interactions at G-quadruplexes: Folding and stability changes by attaching sugars at the 5′-End

Quadruplex DNA structures are attracting an enormous interest in many areas of chemistry, ranging from chemical biology, supramolecular chemistry to nanoscience. We have prepared carbohydrate-DNA conjugates containing the oligonucleotide sequences of G-quadruplexes (thrombin binding aptamer (TBA) an...

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Detalles Bibliográficos
Autores: Gómez-Pinto, Irene, Vengut-Climent, Empar, Lucas, Ricardo, Aviñó, Anna, Eritja Casadellà, Ramón, Bustamante González, Carlos Alberto, Morales, Juan Carlos
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2013
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/136311
Acceso en línea:http://hdl.handle.net/10261/136311
Access Level:acceso abierto
Palabra clave:carbohydrates
DNA
G-quadruplexes
Hydrogen bonds
molecular interactions
Stacking
Descripción
Sumario:Quadruplex DNA structures are attracting an enormous interest in many areas of chemistry, ranging from chemical biology, supramolecular chemistry to nanoscience. We have prepared carbohydrate-DNA conjugates containing the oligonucleotide sequences of G-quadruplexes (thrombin binding aptamer (TBA) and human telomere (TEL)), measured their thermal stability and studied their structure in solution by using NMR and molecular dynamics. The solution structure of a fucose-TBA conjugate shows stacking interactions between the carbohydrate and the DNA G-tetrad in addition to hydrogen bonding and hydrophobic contacts. We have also shown that attaching carbohydrates at the 5′-end of a quadruplex telomeric sequence can alter its folding topology. These results suggest the possibility of modulating the folding of the G-quadruplex by linking carbohydrates and have clear implications in molecular recognition and the design of new G-quadruplex ligands. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.