Construction of a Reduction-responsive DNA Microsphere using a Reduction-cleavable Spacer based on a Nitrobenzene Scaffold

Sayuri L Higashi; Ayaka Isogami; Junko Takahashi; Aya Shibata; Koichiro M Hirosawa; Kenichi G N Suzuki; Shunsuke Sawada; Shinya Tsukiji; Kazunori Matsuura; Masato Ikeda

doi:10.1002/asia.202200142

Construction of a Reduction-responsive DNA Microsphere using a Reduction-cleavable Spacer based on a Nitrobenzene Scaffold

Chem Asian J. 2022 May 16;17(10):e202200142. doi: 10.1002/asia.202200142. Epub 2022 Apr 5.

Authors

Sayuri L Higashi¹, Ayaka Isogami², Junko Takahashi², Aya Shibata², Koichiro M Hirosawa³, Kenichi G N Suzuki³, Shunsuke Sawada⁴, Shinya Tsukiji^{4

5}, Kazunori Matsuura^{6

7}, Masato Ikeda^{1

2

3

8}

Affiliations

¹ United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan.
² Department of Life Science and Chemistry, Graduate School of Natural Science and Technology, Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan.
³ Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan.
⁴ Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology Gokiso-cho, Showa-ku, Nagoya, 466-8555, Japan.
⁵ Department of Life Science and Applied Chemistry, Nagoya Institute of Technology Gokiso-cho, Showa-ku, Nagoya, 466-8555, Japan.
⁶ Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Tottori, 680-8552, Japan.
⁷ Centre for Research on Green Sustainable Chemistry, Tottori University, Tottori, 680-8552, Japan.
⁸ Institute of Nano-Life-Systems, Institutes of Innovation for Future Society, Nagoya University Furo-cho, Chikusa-ku, Nagoya, 464-8603, Japan.

PMID: 35338588
DOI: 10.1002/asia.202200142

Abstract

Here, we describe the design and synthesis of a new reduction-cleavable spacer (RCS) based on a nitrobenzene scaffold for constructing reduction-responsive oligonucleotides according to standard phosphoramidite chemistry. In addition, we demonstrate that the introduction of the RCS in the middle of an oligonucleotide (30 nt) enables the construction of a self-assembled microsphere capable of exhibiting a reduction-responsive disassembly.

Keywords: DNA structures; cleavage reaction; reduction; self-assembly.

MeSH terms

DNA*
Microspheres
Nitrobenzenes
Oligonucleotides*

Substances

Nitrobenzenes
Oligonucleotides
DNA

Abstract

MeSH terms

Substances

Grants and funding