Vinylnaphthalene-bearing hexaoxazole as a fluorescence turn-on type G-quadruplex ligand

Yue Ma; Yuki Wakabayashi; Naruyuki Watatani; Ryota Saito; Takatsugu Hirokawa; Masayuki Tera; Kazuo Nagasawa

doi:10.1039/D1OB01500A

Vinylnaphthalene-bearing hexaoxazole as a fluorescence turn-on type G-quadruplex ligand†

Yue Ma,*^a Yuki Wakabayashi,^b Naruyuki Watatani,^b Ryota Saito,

^c Takatsugu Hirokawa,^def Masayuki Tera

^b and Kazuo Nagasawa

*^b

Author affiliations

* Corresponding authors

^a Institute of Global Innovation Research, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, To-kyo 184-8588, Japan
E-mail: yue-ma@m2.tuat.ac.jp

^b Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Ko-ganei, Tokyo 184-8588, Japan
E-mail: knaga@cc.tuat.ac.jp

^c Department of Chemistry Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan

^d Transborder Medical Research center, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Japan

^e Division of Biomedical Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Japan

^f Molecular Profiling Research Center for Drug Discovery, National Institute of Advanced Industrial Science and Technology, 2-4-7 Aomi, Koto-ward, Tokyo 135-0064, Japan

Abstract

Oxazole-type fluorophores show an increase of fluorescence intensity upon interaction with nucleic acids, and therefore can be used as tools for nucleic acid-sensing and fluorescence imaging. Here, we developed a novel stilbene-type fluorophore, MO-VN (1), consisting of a mono oxazole bearing a vinyl naphthalene moiety. This compound (1) was embedded in a trioxazole 2 and a cyclic hexaoxazole 3a. The fluorescence properties of 1, 2, and 3a were evaluated in the presence of various nucleic acid sequences. Compound 3 showed significant fluorescent enhancement upon interacting with G-quadruplex (G4) structure, which plays critical roles in various biological phenomena. Further structural development focusing on the vinyl naphthalene moiety of 3a afforded a turn-on type G4 ligand 3e that shows G4-specific fluorescence. Measurement of the fluorescence of 3e during titration of a telomeric DNA, telo24, with its C-rich complementary sequence, which unwinds the G4 structure, allowed us to monitor the dynamics of G4.

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DOI: https://doi.org/10.1039/D1OB01500A
Article type: Communication
Submitted: 31 Jul 2021
Accepted: 02 Sep 2021
First published: 03 Sep 2021

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Org. Biomol. Chem., 2021,19, 8035-8040

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Vinylnaphthalene-bearing hexaoxazole as a fluorescence turn-on type G-quadruplex ligand

Y. Ma, Y. Wakabayashi, N. Watatani, R. Saito, T. Hirokawa, M. Tera and K. Nagasawa, Org. Biomol. Chem., 2021, 19, 8035 DOI: 10.1039/D1OB01500A

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Organic & Biomolecular Chemistry

Vinylnaphthalene-bearing hexaoxazole as a fluorescence turn-on type G-quadruplex ligand†

Abstract

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Vinylnaphthalene-bearing hexaoxazole as a fluorescence turn-on type G-quadruplex ligand

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