Effects of 8-methylguanine on structure, stability and kinetics of formation of tetramolecular quadruplexes |
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Authors: | Tran Phong Lan Thao Virgilio Antonella Esposito Veronica Citarella Giuseppe Mergny Jean-Louis Galeone Aldo |
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Institution: | a INSERM, U869, European Institute of Chemistry and Biology, Bordeaux University, 2 rue Robert Escarpit, Pessac F-33607, France b Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, via D. Montesano, 49, I-80131 Napoli, Italy c INSERM, U565, Acides Nucléiques: Dynamique, Ciblage et Fonctions Biologiques, Muséum National d’Histoire Naturelle (MNHN) USM503, CNRS, UMR5153, Département de “Régulations, Développement et Diversité Moléculaire”, 43 rue Cuvier, CP26, Paris Cedex 5, F-75231 France |
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Abstract: | Tetramolecular G-quadruplexes result from the association of four guanine-rich strands. Modification of the backbone strand or the guanine bases of the oligonucleotide may improve stability or introduce new functionalities. In this regard, the 8 position of a guanosine is particularly suitable for introduction of modifications since as it is positioned in the groove of the quadruplex structure. Modifications at this position should not interfere with structural assembly as would changes at Watson-Crick and Hoogsteen sites. In this study, we investigated the effect of an 8-methyl-2′-deoxyguanosine residue (M) on the structure and stability of tetramolecular parallel G-quadruplexes. In some cases, the presence of this residue resulted in the formation of unusual quadruplex structures containing all-syn tetrads. Furthermore, the modified nucleoside M at the 5′-end of the sequence accelerated quadruplex formation by 15-fold or more relative to the unmodified oligonucleotide, which makes this nucleobase an attractive replacement for guanine in the context of tetramolecular parallel quadruplexes. |
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Keywords: | Parallel G-quadruplex 8-Methyl-2&prime -deoxyguanosine Glycosidic conformation |
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