Novel near-infrared fluorescent probe with large stokes shift for detection of cysteine in food sample and living cells

Min Zhou; Chunyan Liu; Yanfei Lin; Tianwen Bai; Tianqing Ye; Zhaosheng Qian; Lei Li; Longhua Guo; Haiying Liu; Jianbo Wang

doi:10.1016/j.foodchem.2024.141755

Novel near-infrared fluorescent probe with large stokes shift for detection of cysteine in food sample and living cells

Food Chem. 2024 Oct 28;464(Pt 2):141755. doi: 10.1016/j.foodchem.2024.141755. Online ahead of print.

Authors

Min Zhou¹, Chunyan Liu², Yanfei Lin³, Tianwen Bai⁴, Tianqing Ye⁴, Zhaosheng Qian², Lei Li⁴, Longhua Guo⁴, Haiying Liu⁵, Jianbo Wang⁶

Affiliations

¹ Jiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China; College of Chemistry and Material Sciences, Zhejiang Normal University, Jinhua 321004, China.
² College of Chemistry and Material Sciences, Zhejiang Normal University, Jinhua 321004, China.
³ Jiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China. Electronic address: [email protected].
⁴ Jiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China.
⁵ Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA. Electronic address: [email protected].
⁶ Jiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China. Electronic address: [email protected].

PMID: 39471557
DOI: 10.1016/j.foodchem.2024.141755

Abstract

Cysteine (Cys) plays a pivotal role in numerous physiological processes and holds significant importance in food analysis. In this study, we designed a novel near-infrared (NIR) fluorescent probe TF for specifically detecting Cys, derived from benzo[e]indole-conjugated tetrahydro-acridine salt. Leveraging the electron-withdrawing properties of the 3,5-bis(trifluoromethyl)benzenethiol group, the probe exhibits a distinctive colorimetric response and a notable enhancement in NIR emission, featuring a substantial Stokes shift of 135 nm, facilitating precise Cys detection. The detection mechanism was elucidated through comprehensive analyses including NMR, MS spectral, and quantum theory calculations. Moreover, the probe demonstrates exceptional attributes such as rapid response (8 min), exceptional selectivity, and sensitivity (with a detection limit as low as 74 nM). The probe's NIR fluorescent response, coupled with its large Stokes shift, enables accurate quantification of Cys in real food samples and facilitates imaging for monitoring both exogenous and endogenous Cys levels in living cells.

Keywords: Cysteine; Fluorescent probe; Food samples; Large stokes shift; Near-infrared.