Azobenzene-modified DNA aptamers evolved by capillary electrophoresis (CE)-SELEX method

Kunihiko Morihiro; Osamu Hasegawa; Yuuya Kasahara; Shohei Mori; Tatsuro Kasai; Masayasu Kuwahara; Satoshi Obika

doi:10.1016/j.bmcl.2020.127607

Azobenzene-modified DNA aptamers evolved by capillary electrophoresis (CE)-SELEX method

Bioorg Med Chem Lett. 2021 Jan 1:31:127607. doi: 10.1016/j.bmcl.2020.127607. Epub 2020 Oct 8.

Authors

Kunihiko Morihiro¹, Osamu Hasegawa², Yuuya Kasahara³, Shohei Mori², Tatsuro Kasai⁴, Masayasu Kuwahara⁵, Satoshi Obika⁶

Affiliations

¹ National Institutes of Biomedical Innovation, Health and Nutrition (NIBIOHN), 7-6-8 Saito-Asagi, Ibaraki, Osaka 567-0085, Japan; Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. Electronic address: morihiro@bioorg.rcast.u-tokyo.ac.jp.
² Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
³ National Institutes of Biomedical Innovation, Health and Nutrition (NIBIOHN), 7-6-8 Saito-Asagi, Ibaraki, Osaka 567-0085, Japan; Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
⁴ Graduate School of Science and Technology, Gunma University, 1-5-1 Tenjin-Cho, Kiryu, Gunma 376-8515, Japan.
⁵ Graduate School of Science and Technology, Gunma University, 1-5-1 Tenjin-Cho, Kiryu, Gunma 376-8515, Japan; Graduate School of Integrated Basic Sciences, Nihon University, 3-25-40 Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan.
⁶ National Institutes of Biomedical Innovation, Health and Nutrition (NIBIOHN), 7-6-8 Saito-Asagi, Ibaraki, Osaka 567-0085, Japan; Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. Electronic address: obika@phs.osaka-u.ac.jp.

PMID: 33039563
DOI: 10.1016/j.bmcl.2020.127607

Abstract

Chemically modified aptamers have recently emerged as important materials for nucleic acid based therapeutics and diagnostic tools. Here, we report in vitro evolution of azobenzene-modified DNA aptamers by capillary electrophoresis (CE)-SELEX method. Azobenzene has been considered to be a fascinating functional group due to its trans-cis photo-isomerization property. We harnessed C5-azobenzene-modified 2'-deoxyuridine (dU^Az) as a azobenzene-tethered unit and subjected it to CE-SELEX with human thrombin. The obtained dU^Az-modified aptamer showed strong binding affinity toward human thrombin and could be reversibly photo-isomerized by different wavelengths of light. This work demonstrates that CE-SELEX is a powerful method to obtain chemically modified aptamers and dU^Az is an excellent photo-responsive nucleoside for nucleic acid photo-switches.

Keywords: 5′-Triphosphate; Azobenzene; CE-SELEX; DNA aptamer; DNA polymerase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aptamers, Nucleotide / chemistry*
Azo Compounds / chemistry*
Electrophoresis, Capillary
Humans
Molecular Structure
SELEX Aptamer Technique*

Substances

Aptamers, Nucleotide
Azo Compounds
azobenzene