A New Boron–Rhodamine-Containing Carboxylic Acid as a Sugar Chemosensor

Komori, Yuta; Sugimoto, Shun; Sato, Toranosuke; Okawara, Honoka; Watanabe, Ryo; Takano, Yuki; Kitaoka, Satoshi; Egawa, Yuya

doi:10.3390/s23031528

Open AccessArticle

A New Boron–Rhodamine-Containing Carboxylic Acid as a Sugar Chemosensor

by

Yuta Komori

,

Shun Sugimoto

,

Toranosuke Sato

,

Honoka Okawara

,

Ryo Watanabe

,

Yuki Takano

,

Satoshi Kitaoka

and

Yuya Egawa

^*

Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado 350-0295, Saitama, Japan

^*

Author to whom correspondence should be addressed.

Sensors 2023, 23(3), 1528; https://doi.org/10.3390/s23031528

Submission received: 18 December 2022 / Revised: 18 January 2023 / Accepted: 21 January 2023 / Published: 30 January 2023

(This article belongs to the Special Issue Chemical Sensors in Analytical Chemistry)

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Abstract

We propose a boron–rhodamine-containing carboxylic acid (BRhoC) substance as a new sugar chemosensor. BRhoC was obtained by the Friedel–Crafts reaction of 4-formylbenzoic acid and N,N-dimethylphenylboronic acid, followed by chloranil oxidation. In an aqueous buffer solution at pH 7.4, BRhoC exhibited an absorption maximum (Abs_max) at 621 nm. Its molar absorption coefficient at Abs_max was calculated to be 1.4 × 10⁵ M⁻¹ cm⁻¹, and it exhibited an emission maximum (Em_max) at 644 nm for the excitation at 621 nm. The quantum yield of BRhoC in CH₃OH was calculated to be 0.16. The borinate group of BRhoC reacted with a diol moiety of sugar to form a cyclic ester, which induced a change in the absorbance and fluorescence spectra. An increase in the D-fructose (Fru) concentration resulted in the red shift of the Abs_max (621 nm without sugar and 637 nm with 100 mM Fru) and Em_max (644 nm without sugar and 658 nm with 100 mM Fru) peaks. From the curve fitting of the plots of the fluorescence intensity ratio at 644 nm and 658 nm, the binding constants (K) were determined to be 2.3 × 10² M⁻¹ and 3.1 M⁻¹ for Fru and D-glucose, respectively. The sugar-binding ability and presence of a carboxyl group render BRhoC a suitable building block for the fabrication of highly advanced chemosensors.

Keywords: borinic acid; borinate; boron; rhodamine; sensor; glucose; diabetes

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MDPI and ACS Style

Komori, Y.; Sugimoto, S.; Sato, T.; Okawara, H.; Watanabe, R.; Takano, Y.; Kitaoka, S.; Egawa, Y. A New Boron–Rhodamine-Containing Carboxylic Acid as a Sugar Chemosensor. Sensors 2023, 23, 1528. https://doi.org/10.3390/s23031528

AMA Style

Komori Y, Sugimoto S, Sato T, Okawara H, Watanabe R, Takano Y, Kitaoka S, Egawa Y. A New Boron–Rhodamine-Containing Carboxylic Acid as a Sugar Chemosensor. Sensors. 2023; 23(3):1528. https://doi.org/10.3390/s23031528

Chicago/Turabian Style

Komori, Yuta, Shun Sugimoto, Toranosuke Sato, Honoka Okawara, Ryo Watanabe, Yuki Takano, Satoshi Kitaoka, and Yuya Egawa. 2023. "A New Boron–Rhodamine-Containing Carboxylic Acid as a Sugar Chemosensor" Sensors 23, no. 3: 1528. https://doi.org/10.3390/s23031528

APA Style

Komori, Y., Sugimoto, S., Sato, T., Okawara, H., Watanabe, R., Takano, Y., Kitaoka, S., & Egawa, Y. (2023). A New Boron–Rhodamine-Containing Carboxylic Acid as a Sugar Chemosensor. Sensors, 23(3), 1528. https://doi.org/10.3390/s23031528

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A New Boron–Rhodamine-Containing Carboxylic Acid as a Sugar Chemosensor

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