ICT-modulated NIR water-soluble fluorescent probe with large Stokes shift for selective detection of cysteine in living cells and zebrafish

Xufeng Hou; Zhensheng Li; Yunqiang Li; Qihang Zhou; Chunhui Liu; Dang Fan; Jinjin Wang; Ruijie Xu; Zhihong Xu

doi:10.1016/j.saa.2020.119030

ICT-modulated NIR water-soluble fluorescent probe with large Stokes shift for selective detection of cysteine in living cells and zebrafish

Spectrochim Acta A Mol Biomol Spectrosc. 2021 Feb 5:246:119030. doi: 10.1016/j.saa.2020.119030. Epub 2020 Oct 5.

Authors

Xufeng Hou¹, Zhensheng Li¹, Yunqiang Li¹, Qihang Zhou², Chunhui Liu¹, Dang Fan¹, Jinjin Wang¹, Ruijie Xu¹, Zhihong Xu³

Affiliations

¹ Key Laboratory of Chemo/Biosensing and Detection, College of Chemical and Materials Engineering, Xuchang University, Henan 461000, PR China.
² Key Laboratory of Chemo/Biosensing and Detection, College of Chemical and Materials Engineering, Xuchang University, Henan 461000, PR China; Department of Chemistry, Zhengzhou University, Zhengzhou, 450052, PR China.
³ Key Laboratory of Chemo/Biosensing and Detection, College of Chemical and Materials Engineering, Xuchang University, Henan 461000, PR China; Department of Chemistry, Zhengzhou University, Zhengzhou, 450052, PR China. Electronic address: xuzhihong1980@yahoo.com.

PMID: 33049474
DOI: 10.1016/j.saa.2020.119030

Abstract

The fluorescent probes with good water-solubility, long-wavelength emission and large Stokes shift are greatly desirable for in vivo detection. Herein, we designed a novel 1,8-naphthalimide-based near-infrared (NIR) optical and fluorescent probe (NTC) for sensing cysteine (Cys). Using acrylate as the recognition site, the probe demonstrated high selectivity and sensitivity for Cys with a low detection limit (0.093 μM) in aqueous buffer solution due to the excellent water-solubility. Upon the reaction with Cys, the recovery of intramolecular charge transfer (ICT) in the probe led to about 40-fold fluorescence enhancement. Furthermore, the reaction result was investigated by ¹H NMR, and HRMS analyses, and the sensing mechanism was validated by quantum calculations. Finally, NTC was applied to image exogenous and endogenous Cys in HeLa cells and zebrafish selectively, implying that the probe possessed great potential application in biological fluorescence sensing.

Keywords: Cysteine; Fluorescent probe; In vivo imaging; Naphthalimide; Water-soluble.

MeSH terms

Animals
Cysteine*
Fluorescent Dyes*
HeLa Cells
Humans
Limit of Detection
Water
Zebrafish

Substances

Fluorescent Dyes
Water
Cysteine