title: Bioreductive deprotection of 4-nitrobenzyl group on thymine base in oligonucleotides for the activation of duplex formation.
abstract: 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.
authors.affiliation: Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan. Electronic address: saneyoshih@kanagawa-u.ac.jp.
authors.forename: Hisao
authors.initials: H
authors.lastname: Saneyoshi
authors.affiliation: Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Hiyoshi
authors.affiliation: Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Iketani
authors.affiliation: Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan.
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Kondo
authors.affiliation: Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan. Electronic address: akiraono@kanagawa-u.ac.jp.
authors.forename: Akira
authors.initials: A
authors.lastname: Ono
mesh_terms: D002851:Chromatography, High Pressure Liquid; D000860:Hypoxia; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D013941:Thymine / Q000737:chemistry*
chemical_list: D009596:Nitrophenols; D009841:Oligonucleotides; D013941:Thymine
keywords: Hybridization; Hypoxia; Nucleic acid-based therapeutics; Prodrug; Protecting group