Efficient RNA-targeting by the introduction of aromatic stacking in the duplex major groove via 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridines

Nicolai Krog Andersen; Navneet Chandak; Lucie Brulíková; Pawan Kumar; Michael Dalager Jensen; Frank Jensen; Pawan K Sharma; Poul Nielsen

doi:10.1016/j.bmc.2010.05.019

Efficient RNA-targeting by the introduction of aromatic stacking in the duplex major groove via 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridines

Bioorg Med Chem. 2010 Jul 1;18(13):4702-10. doi: 10.1016/j.bmc.2010.05.019. Epub 2010 May 12.

Authors

Nicolai Krog Andersen¹, Navneet Chandak, Lucie Brulíková, Pawan Kumar, Michael Dalager Jensen, Frank Jensen, Pawan K Sharma, Poul Nielsen

Affiliation

¹ Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.

PMID: 20570158
DOI: 10.1016/j.bmc.2010.05.019

Abstract

Three pyrimidine nucleosides with differently substituted phenyltriazoles attached to the 5-position were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) and incorporated into oligonucleotides. Efficient π-π-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA:RNA duplex significantly. The best stacking, and most stable duplex, was obtained by a sulfonamide substituted derivative.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry
Azides / chemistry
Catalysis
Circular Dichroism
Copper / chemistry
DNA / chemistry
Deoxyuridine / chemical synthesis
Deoxyuridine / chemistry*
Deoxyuridine / pharmacology
Models, Molecular
Nucleic Acid Hybridization
RNA / chemistry*

Substances

Alkynes
Azides
RNA
Copper
DNA
Deoxyuridine