A long-wavelength-emitting fluorescent probe for simultaneous discrimination of H2S/Cys/GSH and its bio-imaging applications

Huawei Niu; Bowen Ni; Keke Chen; Xiaopeng Yang; Wenbo Cao; Yong Ye; Yufen Zhao

doi:10.1016/j.talanta.2018.12.031

A long-wavelength-emitting fluorescent probe for simultaneous discrimination of H₂S/Cys/GSH and its bio-imaging applications

Talanta. 2019 May 1:196:145-152. doi: 10.1016/j.talanta.2018.12.031. Epub 2018 Dec 15.

Authors

Huawei Niu¹, Bowen Ni¹, Keke Chen¹, Xiaopeng Yang¹, Wenbo Cao², Yong Ye³, Yufen Zhao⁴

Affiliations

¹ Phosphorus Chemical Engineering Research Center of Henan Province, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China.
² School of Basic Medical Science, Zhengzhou University, Zhengzhou 450001, China. Electronic address: caowenbo@zzu.edu.cn.
³ Phosphorus Chemical Engineering Research Center of Henan Province, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China; The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, China. Electronic address: yeyong03@tsinghua.org.cn.
⁴ Phosphorus Chemical Engineering Research Center of Henan Province, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China; The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, China.

PMID: 30683344
DOI: 10.1016/j.talanta.2018.12.031

Abstract

A long-wavelength fluorescent probe NR-CY was developed for simultaneous identification of cysteine/glutathione and sulphide by combining the derivative of Nile red with 7-nitrobenzofurazan. The response of NR-CY to thiols is regulated by intramolecular charge transfer and photoinduced electron transfer mechanisms. For sulphide at 560 nm, cysteine at 475 nm and glutathione at 425 nm, different absorbance increases can be observed. NR-CY can detect cysteine at fluorescence emission 543 nm and distinguish sulphide from other analytes by kinetic experiments at 636 nm. The probe showed a rapid response to these thiols (cysteine was 90 s and sulphide was 30 s). In addition, NR-CY has been successfully applied to live MCF-7 cell imaging.

Keywords: Biothiols; Cell imaging; Fluorescent probe; Long-wavelength-emitting.

MeSH terms

4-Chloro-7-nitrobenzofurazan / chemistry*
Cysteine / analysis*
Cysteine / chemistry
Fluorescent Dyes / chemistry*
Glutathione / analysis*
Glutathione / chemistry
Homocysteine / analysis*
Homocysteine / chemistry
Humans
MCF-7 Cells
Oxazines / chemistry*

Substances

Fluorescent Dyes
Oxazines
Homocysteine
4-Chloro-7-nitrobenzofurazan
Glutathione
Cysteine
nile red