Development of Water Solubility of 2-Phenylsulfanylhydroquinone Dimer Dye

Akio Kamimura; Haruka Umemoto; Takuji Kawamoto; Takeshi Honda

doi:10.1021/acsomega.1c00703

Development of Water Solubility of 2-Phenylsulfanylhydroquinone Dimer Dye

ACS Omega. 2021 Mar 23;6(13):9254-9262. doi: 10.1021/acsomega.1c00703. eCollection 2021 Apr 6.

Authors

Akio Kamimura¹, Haruka Umemoto¹, Takuji Kawamoto¹, Takeshi Honda²

Affiliations

¹ Department of Applied Chemistry, Yamaguchi University, Ube 755-8611, Japan.
² Department of Pharmacology, School of Medicine, Yamaguchi University, Ube 755-8505, Japan.

Abstract

With the aim of developing a new fluorescence dye with enhanced photophysical properties, this study describes the modification of the 2-phenylsulfanylhydroquinone dimer to realize a new bioimaging molecule. The characteristics of the dimer were advanced by introducing tetraethylene glycol side chains to provide sufficient water solubility and a tether consisting of an N-hydroxysuccinimide-terminated C6-carbon chain to attach bioactive molecules. Two derivatives containing two or three tetraethylene glycol side chains were designed and prepared, and the latter showed sufficient water solubility for biochemical applications. Both compounds exhibited similar photophysical properties and blue fluorescence under UV light irradiation. The dye containing three tetraethylene glycol units reacted with bovine serum albumin in water to give fluorescent derivatives.