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Issue 21, 2005
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Modulated drug release from the stem-and-loop structured oligodeoxynucleotide upon UV-A irradiation in the presence of target DNA

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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.

Graphical abstract: Modulated drug release from the stem-and-loop structured oligodeoxynucleotide upon UV-A irradiation in the presence of target DNA

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Article information


Submitted
26 Jul 2005
Accepted
31 Aug 2005
First published
26 Sep 2005

Org. Biomol. Chem., 2005,3, 3893-3897
Article type
Paper

Modulated drug release from the stem-and-loop structured oligodeoxynucleotide upon UV-A irradiation in the presence of target DNA

K. Tanabe, H. Nakata, S. Mukai and S. Nishimoto, Org. Biomol. Chem., 2005, 3, 3893 DOI: 10.1039/B510608G

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