5-Propynylamino alpha-deoxyuridine promotes DNA duplex stabilization of anionic and neutral but not cationic alpha-oligonucleotides

Gaëlle Deglane; François Morvan; Françoise Debart; Jean-Jacques Vasseur

doi:10.1016/j.bmcl.2006.11.052

5-Propynylamino alpha-deoxyuridine promotes DNA duplex stabilization of anionic and neutral but not cationic alpha-oligonucleotides

Bioorg Med Chem Lett. 2007 Feb 15;17(4):951-4. doi: 10.1016/j.bmcl.2006.11.052. Epub 2006 Nov 18.

Authors

Gaëlle Deglane¹, François Morvan, Françoise Debart, Jean-Jacques Vasseur

Affiliation

¹ LCOBS, UMR 5625 CNRS-UM II, Université Montpellier II, 34095 Montpellier, France.

PMID: 17157020
DOI: 10.1016/j.bmcl.2006.11.052

Abstract

Incorporation of 5-propynylamino and 5-propynyl alpha-2'-deoxyuridine into alpha-oligonucleotides (alpha-ON) allows high-affinity targeting of complementary DNA for alpha-ON with anionic and neutral backbone but not for cationic alpha-ON, revealing clues on the role of the amino group of the propynylamino on the formation of DNA duplexes.

MeSH terms

Anions
Cations
Chemical Phenomena
Chemistry, Physical
DNA / chemistry*
DNA / drug effects*
Deoxyuridine / analogs & derivatives*
Deoxyuridine / pharmacology
Nucleic Acid Denaturation
Oligonucleotides / chemistry*
Oligonucleotides, Antisense / chemistry
Ultraviolet Rays

Substances

5-Propynylamino alpha-deoxyuridine
Anions
Cations
Oligonucleotides
Oligonucleotides, Antisense
DNA
Deoxyuridine