Reduction-Responsive Guanine Incorporated into G-Quadruplex-Forming DNA

Masato Ikeda; Masahiro Kamimura; Yukiko Hayakawa; Aya Shibata; Yukio Kitade

doi:10.1002/cbic.201600164

Reduction-Responsive Guanine Incorporated into G-Quadruplex-Forming DNA

Chembiochem. 2016 Jul 15;17(14):1304-7. doi: 10.1002/cbic.201600164. Epub 2016 May 24.

Authors

Masato Ikeda^{1

2

3}, Masahiro Kamimura⁴, Yukiko Hayakawa⁴, Aya Shibata^{5

4}, Yukio Kitade^{6

7

8}

Affiliations

¹ Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1, Yanagido, Gifu, 501-1193, Japan. m_ikeda@gifu-u.ac.jp.
² Department of Biomolecular Science, Graduate School of Engineering, Gifu University, 1-1, Yanagido, Gifu, 501-1193, Japan. m_ikeda@gifu-u.ac.jp.
³ United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University, 1-1, Yanagido, Gifu, 501-1193, Japan. m_ikeda@gifu-u.ac.jp.
⁴ Department of Biomolecular Science, Graduate School of Engineering, Gifu University, 1-1, Yanagido, Gifu, 501-1193, Japan.
⁵ Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1, Yanagido, Gifu, 501-1193, Japan.
⁶ Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1, Yanagido, Gifu, 501-1193, Japan. ykkitade@gifu-u.ac.jp.
⁷ Department of Biomolecular Science, Graduate School of Engineering, Gifu University, 1-1, Yanagido, Gifu, 501-1193, Japan. ykkitade@gifu-u.ac.jp.
⁸ United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University, 1-1, Yanagido, Gifu, 501-1193, Japan. ykkitade@gifu-u.ac.jp.

PMID: 27124306
DOI: 10.1002/cbic.201600164

Abstract

Stimulus-responsive biomolecules are attractive targets to understand biomolecule behaviour as well as to explore their therapeutic and diagnostic applications. We demonstrate that a reduction-responsive cleavable group (chemically caged unit) introduced into the guanine ring enables modulation of the secondary structure transition of an oligonucleotide in a reduction-responsive and traceless manner leaving the unmodified oligonucleotide of interest. This simple but robust strategy could yield a variety of stimuli-responsive oligonucleotides.

Keywords: DNA structures; G-quadruplexes; cleavage reactions; conjugation; stimuli-responsive.

Publication types

Review

MeSH terms

DNA / chemistry
G-Quadruplexes*
Guanine / chemistry*
Nucleic Acid Conformation
Oligonucleotides / chemistry*
Oxidation-Reduction

Substances

Oligonucleotides
Guanine
DNA