Bioreductive deprotection of 4-nitrobenzyl group on thymine base in oligonucleotides for the activation of duplex formation

[Display omitted] Oligonucleotides containing 4-O-(4-NO2-benzyl)thymine residues were synthesized to assess potential prodrug-type action against hypoxic cells. These modified oligonucleotides were incapable of stable duplex formation under non-hypoxic conditions. However, following deprotection of...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2015-12, Vol.25 (23), p.5632-5635
Main Authors: Saneyoshi, Hisao, Hiyoshi, Yuki, Iketani, Koichi, Kondo, Kazuhiko, Ono, Akira
Format: Article
Language:English
Subjects:
Chromatography, High Pressure Liquid
Hybridization
Hypoxia
Molecular Structure
Nitrophenols - chemistry
Nucleic acid-based therapeutics
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Oxidation-Reduction
Prodrug
Protecting group
Thymine - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] Oligonucleotides containing 4-O-(4-NO2-benzyl)thymine residues were synthesized to assess potential prodrug-type action against hypoxic cells. These modified oligonucleotides were incapable of stable duplex formation under non-hypoxic conditions. However, following deprotection of the thymine residues under bioreductive conditions, the deprotected oligonucleotides were able to form stable duplexes with target oligonucleotides.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2015.10.025