3-Hydroxyflavone-Based Excited State Intramolecular Proton Transfer Probe for Detection of Biothiols

doi:10.19894/j.issn.1000-0518.240161

Chinese Journal of Applied Chemistry ›› 2024, Vol. 41 ›› Issue (10): 1502-1510.DOI: 10.19894/j.issn.1000-0518.240161

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3-Hydroxyflavone-Based Excited State Intramolecular Proton Transfer Probe for Detection of Biothiols

Yong-Mei ZHAO¹, Pei-Xuan CHENG², Jing-Jiao XIE², Wen LUO²()

^1.Pharmaceutical Engineering Department，Henan Technical Institute，Kaifeng 475004，China
^2.Henan Key Laboratory of Natural Medicine Innovation and Transformation，Henan University，Kaifeng 475004，China

Received:2024-05-20 Accepted:2024-08-27 Published:2024-10-01 Online:2024-10-29
Contact: Wen LUO
About author:luowen83@163.com
Supported by:
Science and Technology Planning Project of Henan Province(242102310427);Science and Technology Planning Project of Kaifeng City(2303062)

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Abstract

Abstract:

Biothiols play an important role in cell growth and differentiation， metabolism and redox balance. In this paper， a new “off-on” fluorescent probe， HF-DBS， was designed and synthesized from the starting material 4-dimethylaminobenzaldehyde. The probe can be selectively hydrolyzed by biothiols to produce the 3-hydroxyflavone fluorophore （HF） with strong fluorescence emission， which has the property of excited state intramolecular proton transfer （ESIPT） and therefore has a large Stokes shift. In addition， the probe has high selectivity， high sensitivity， good biocompatibility and anti-interference ability， it can be used under physiological conditions. Thus， this probe has been successfully applied to intracellular biothiols detection and live cell imaging. In addition， the probe can be made into test paper for rapid cysteine detection.

Key words: Flavone, Excited state intramolecular proton transfer, Fluorescence probe, Biothiols

CLC Number:

O657.3

Yong-Mei ZHAO, Pei-Xuan CHENG, Jing-Jiao XIE, Wen LUO. 3-Hydroxyflavone-Based Excited State Intramolecular Proton Transfer Probe for Detection of Biothiols[J]. Chinese Journal of Applied Chemistry, 2024, 41(10): 1502-1510.

Figures/Tables 10

Fig.1 Chemical structures of some reported flavonoid probes （A-E）［10-16］

Fig.2 Synthetic route of probe HF-DBS

Fig.3 Absorption （A） and fluorescent spectra （λex=400 nm）（B） of probe （10 μmol/L） with or without different biothiols （50 μmol/L）

Fig.4 Fluorescence intensity （546 nm） of the probe （10 μmol/L） with Cys （50 μmol/L） and the interference of coexisting various small molecules （50 μmol/L）

Fig.5 Time-dependent （A） and pH （B） effect on fluorescence response of the probe for biothiols at room temperature

Fig.6 The titration experiment of probe for Cys （A） and the relationship of fluorescence intensity difference of probe with the concentration of Cys （B）， Hcy （C） or GSH （D） at 546 nm

Fig.7 The recognition mechanism of probe HF-DBS for biothiols

Fig. 8 Effect of probe HF-DBS on the viability of HepG2 cells

Fig.9 Fluorescence images of Cys in HepG2 cells with different treatments

Fig.10 Rapid detection of Cys by test paper loaded HF-DBS

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3-Hydroxyflavone-Based Excited State Intramolecular Proton Transfer Probe for Detection of Biothiols

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