title: Modulated drug release from the stem-and-loop structured oligodeoxynucleotide upon UV-A irradiation in the presence of target DNA.
abstract: o-Nitrobenzyl photochemistry as induced by UV-A irradiation was applied to a photoactivated drug releasing system based on a molecular beacon strategy. A stem-and-loop structured oligodeoxynucleotide (ODN) possessing a photoreactive o-nitrobenzyl chromophore at the 3'-end and 1-aminonaphthalene quencher at the 5'-end underwent conformational change into a conventional double strand structure by hybridization with a specified target DNA. The intrinsic stem-and-loop structure suppressed photoactivated release of benzoic acid as a phantom drug from the o-nitrobenzyl chromophore because of intramolecular quenching by the 1-aminonaphthalene unit in close proximity to the chromophore. Formation of the double strand structure in the presence of perfectly matched target DNA minimized occurrence of intramolecular quenching and thereby enhanced the photoactivated drug release.
authors.affiliation: Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, 615-8510, Japan. tanabeka@scl.kyoto-u.ac.jp
authors.forename: Kazuhito
authors.initials: K
authors.lastname: Tanabe
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Nakata
authors.forename: Shin
authors.initials: S
authors.lastname: Mukai
authors.forename: Sei-ichi
authors.initials: S
authors.lastname: Nishimoto
mesh_terms: D004247:DNA; D016503:Drug Delivery Systems / Q000379:methods*; D009690:Nucleic Acid Conformation / Q000528:radiation effects; D009693:Nucleic Acid Hybridization; D009838:Oligodeoxyribonucleotides / Q000737:chemistry* / Q000627:therapeutic use*; D015345:Oligonucleotide Probes; D010777:Photochemistry; D014466:Ultraviolet Rays
chemical_list: D009838:Oligodeoxyribonucleotides; D015345:Oligonucleotide Probes; D004247:DNA