Benzothiazole-Pyimidine-Based BF2 Complex for Selective Detection of Cysteine

Qingsong Liu; Changli Zhang; Xiaoqing Wang; Shuwen Gong; Weijiang He; Zhipeng Liu

doi:10.1002/asia.201501013

Benzothiazole-Pyimidine-Based BF2 Complex for Selective Detection of Cysteine

Chem Asian J. 2016 Jan;11(2):202-6. doi: 10.1002/asia.201501013. Epub 2015 Nov 17.

Authors

Qingsong Liu¹, Changli Zhang², Xiaoqing Wang³, Shuwen Gong⁴, Weijiang He⁵, Zhipeng Liu^{6

7}

Affiliations

¹ School of Chemistry and Chemical Engineering & School of Material Science and Engineering, Liaocheng University, No.1 Hunan Road, Liaocheng, 252000, P. R. China.
² Department of chemistry, Nanjing Xiaozhuang College, 3601 Hongjing Road, Nanjing, 211171, P. R. China.
³ School of Chemistry and Chemical Engineering & School of Material Science and Engineering, Liaocheng University, No.1 Hunan Road, Liaocheng, 252000, P. R. China. wangxiaoqing@lcu.edu.cn.
⁴ School of Chemistry and Chemical Engineering & School of Material Science and Engineering, Liaocheng University, No.1 Hunan Road, Liaocheng, 252000, P. R. China. gongshw@lcu.edu.cn.
⁵ State Key Laboratory of Coordination Chemistry, Coordination Chemistry Institute, School of Chemistry and Chemical Engineering, Nanjing University, Hankou Road No. 22, Nanjing, 210093, P. R. China.
⁶ School of Chemistry and Chemical Engineering & School of Material Science and Engineering, Liaocheng University, No.1 Hunan Road, Liaocheng, 252000, P. R. China. iamzpliu@njtech.edu.cn.
⁷ Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University (Nanjing Tech), 30 South Puzhu Road, Nanjing, 211816, P. R. China. iamzpliu@njtech.edu.cn.

PMID: 26530080
DOI: 10.1002/asia.201501013

Abstract

Due to the similar structure and reactivity of cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), the simultaneous discrimination of Cys over Hcy and GSH by a single fluorescent sensor is still a great challenge. In this work, a benzothiazole-pyimidine-based boron difluoride complex (BPB) was developed as a new fluorescent sensor for Cys. The sensor exhibits a highly selective "turn-on" response to cysteine over Hcy, GSH and other amino acids in aqueous solution at physiological pH. The observed pseudo-first-order rate constant for the reaction of BPB with Cys was calculated to be about 0.062 min(-1) . The detection limit of this sensor for Cys was determined to be 332 nm, and bioimaging of exogenous Cys by this sensor was successfully applied in living cells, thus indicating that this sensor holds great potential for biological applications.

Keywords: BODIPY; cysteine; fluorescent sensing; fluorescent sensors; selectivity.

Publication types

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

MeSH terms

Benzothiazoles / chemistry*
Biosensing Techniques
Cysteine / chemistry*
Fluorescence
Fluorescent Dyes / chemistry*
Glutathione / chemistry
HeLa Cells
Homocysteine / chemistry
Humans
Microscopy, Confocal
Molecular Structure
Pyrimidines / chemistry*

Substances

Benzothiazoles
Fluorescent Dyes
Pyrimidines
Homocysteine
benzothiazole
Glutathione
Cysteine