Effects of pendant groups at phosphorus on binding properties of d-ApA analogues.

Abstract:

:The interaction of several synthetic analogues of d-ApA with Poly U and Poly dT was examined to explore the effects of substituents at phosphorus on binding properties of oligonucleotides. These analogues contained a bulky, lipophilic group (2,2,2-trichloroethoxy or 2,2,2-trichloro-1,1-dimethylethoxy) a small, uncharged hydrogen-bonding group (amido), or a cationic phosphoramidate (2-aminoethylamido, protonated in neutral aqueous media) in place of the anionic oxygen of the internucleotide phosphate. As determined by "melting curves" each formed a complex with Poly U more stable than the Poly U.d-ApA complex. Binding to Poly dT was comparable or in some cases stronger. Checks on composition (mixing curves) revealed the expected stoichiometry of ldA:2U (or 2dT). Stereochemistry at phosphorus influenced stability of the complexes, but the effect was not a major one. These results suggest that oligonucleotides containing large, lipophilic groups, as well as small non-ionic groups (e.g., the methyl phosphonates) or polar groups, could be useful as probes in hybridization experiments.

journal_name

Nucleic Acids Res

journal_title

Nucleic acids research

authors

Letsinger RL,Bach SA,Eadie JS

doi

10.1093/nar/14.8.3487

subject

Has Abstract

pub_date

1986-04-25 00:00:00

pages

3487-99

issue

8

eissn

0305-1048

issn

1362-4962

journal_volume

14

pub_type

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