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Chembiochem. 2017 Jun 19;18(12):1123-1128. doi: 10.1002/cbic.201700112. Epub 2017 May 15.

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

Author information

1
Institute for Advanced Chemistry of Catalonia (IQAC), Spanish Council for Scientific Research (CSIC), Jordi Girona 18-26, 08034, Barcelona, Spain.
2
Networking Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN).
3
INGEBI (CONICET), Vuelta de Obligado 2490-(1428), Buenos Aires, Argentina.
4
Department of Chemical Engineering and Analytical Chemistry, University of Barcelona, Martí i Franquès, 1-11, 08028, Barcelona, Spain.
5
BIOESTRAN, Associated Unit UB-CSIC.
6
Institute of Physical Chemistry Rocasolano (IQFR), Spanish Council for Scientific Research (CSIC), Serrano 119, 28006, Madrid, Spain.
7
CONICET. Laboratorio de Biotransformaciones, Universidad Nacional de Quilmes, Roque Saenz Peña 352 (1876) Bernal, Prov. de Buenos Aires, Argentina.
8
CONICET. Universidad Nacional de General Sarmiento, J. M. Gutiérrez 1150, 1613, Los Polvorines, Buenos Aires, Argentina.

Abstract

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.

KEYWORDS:

NMR spectroscopy; circular dichroism; deoxymethylcytidine; i-motifs; telomeres

PMID:
28407336
DOI:
10.1002/cbic.201700112
[Indexed for MEDLINE]
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