A bifunctional fluorescent probe based on PET & ICT for simultaneously recognizing Cys and H2S in living cells

Huawei Niu; Yuhan Duan; Yuanyuan Zhang; Xinting Hua; Chuan Xu; Zhaozhou Li; Jinliang Ma; Fangyuan Qin; Yaping Zhai; Yong Ye; Yufen Zhao

doi:10.1016/j.jphotobiol.2022.112441

A bifunctional fluorescent probe based on PET & ICT for simultaneously recognizing Cys and H₂S in living cells

J Photochem Photobiol B. 2022 May:230:112441. doi: 10.1016/j.jphotobiol.2022.112441. Epub 2022 Apr 4.

Authors

Huawei Niu¹, Yuhan Duan¹, Yuanyuan Zhang¹, Xinting Hua¹, Chuan Xu¹, Zhaozhou Li², Jinliang Ma¹, Fangyuan Qin³, Yaping Zhai⁴, Yong Ye⁵, Yufen Zhao⁶

Affiliations

¹ National Demonstration Center for Experimental Food Processing and Safety Education, College of Food and Bioengineering, Henan University of Science and Technology, Luoyang, 471000, China.
² National Demonstration Center for Experimental Food Processing and Safety Education, College of Food and Bioengineering, Henan University of Science and Technology, Luoyang, 471000, China. Electronic address: ilizhaozhou@126.com.
³ Institute of Ophthalmology, Henan Provincial People's Hospital, Zhengzhou 450003, China.
⁴ Institute of Ophthalmology, Henan Provincial People's Hospital, Zhengzhou 450003, China. Electronic address: zhaiyaping@sina.com.
⁵ Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, China. Electronic address: yeyong03@tsinghua.org.cn.
⁶ Institute of Drug Discovery Technology, Ningbo University, Ningbo 450052, China.

PMID: 35397303
DOI: 10.1016/j.jphotobiol.2022.112441

Abstract

Most reported probes that respond to Cysteine (Cys) and Hydrogen sulfide (H₂S) can only identify one analyte, or they were interfered with homocysteine (Hcy) and glutathione (GSH) when recognizing Cys and H₂S. In addition, nitrobenzoxadiazole (NBD) ether, as one of thiols recognition sites, inevitably encounters the situation that Cys, GSH and H₂S cannot be distinguished on the same channel at the cellular level. In this work, by introducing NBD ether and NBD amine, we constructed a bifunctional fluorescent probe NJB for dual-site response to Cys and H₂S via PET & ICT processes. NJB has wonderful selectivity for identifying Cys and HS^-, with limits of detection as low as 58.4 nM and 81.1 nM, respectively. Interestingly, NJB has been successfully applied to detect Cys and HS^- in MCF-7 cells. Therefore, the probe that serves as a great tool for inquiring the physiological and pathological functions of Cys and H₂S in living cells is promising.

Keywords: Bifunctional; Cysteine; Dual-site; Fluorescence probe; Hydrogen sulfide.

MeSH terms

Cysteine*
Ethers
Fluorescent Dyes*
Glutathione
Humans
Oxadiazoles
Positron-Emission Tomography

Substances

Ethers
Fluorescent Dyes
Oxadiazoles
Glutathione
Cysteine