Citation: Zheng Li, Xiaofeng Xia, Yu You, Cuifen Lu, Guichun Yang, Chao Ma, Junqi Nie, Qi Sun, Shuilin Wu, Jun Ren, Feiyi Wang. Fast-response fluorescent probe with favorable water solubility for highly sensitive imaging of endogenous tyrosinase in living cells and zebrafish model[J]. Chinese Chemical Letters, ;2021, 32(5): 1785-1789. doi: 10.1016/j.cclet.2020.12.053 shu

Fast-response fluorescent probe with favorable water solubility for highly sensitive imaging of endogenous tyrosinase in living cells and zebrafish model

Zheng Li ^a ,
Xiaofeng Xia ^a ,
Yu You ^a ,
Cuifen Lu ^{a, *,} ,
Guichun Yang ^a ,
Chao Ma ^a ,
Junqi Nie ^a ,
Qi Sun ^{b, *,} ,
Shuilin Wu ^a ,
Jun Ren ^a ,
Feiyi Wang ^{a, *,}

a.
Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials & Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules & State Key Laboratory of Biocatalysis and Enzyme Engineering, Hubei University, Wuhan 430062, China
b.
Key Laboratory for Green Chemical Process of Ministry of Education and School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, China

Received Date: 5 November 2020
Revised Date: 28 December 2020
Accepted Date: 29 December 2020
Available Online: 5 January 2021

Figures(5)

Tyrosinase (TYR) is an important polyphenolic oxidase enzyme and usually regards as a biomarker of melanoma cancer. Highly effective tracking TYR activity in vivo will help to study the mechanism of TYR in living organisms and forecasts related diseases. In this study, we present a novel TYR-activatable fluorescent probe (CHMC-DOPA) for tracking TYR activity in vitro and in vivo. CHMC-DOPA is constructed by incorporating dopamine (DOPA) moiety into a fluorescent chloro-hydroxyl-merocyanine (CHMC) scaffold. Upon exposure to TYR, the dopamine unit in CHMC-DOPA is oxidized to a dopaquinone derivative, and an intramolecular photo-induced electron transfer (PET) process between CHMC fluorophore and o-dopaquinone will take place, the fluorescence of CHMC-DOPA is quenched rapidly. Therefore, the evaluation of TYR activity is established in terms of the relationship between fluorescence quenching efficiency and TYR activity. In our experiments, CHMC-DOPA shows various advantages, such as fast response (8 min), low concentration of TYR activation (0.5 U/mL), good water-solubility, as well as the lowest detection limit (0.003 U/mL) compared with previously reported works. Furthermore, CHMC-DOPA also exhibits excellent cell membrane permeability and low cytotoxicity, which is successfully used to monitor endogenous TYR activity in living cancer cells and zebrafish models. CHMC-DOPA performs well, and we anticipate that this newly designed novel platform will provide an alternative for high effective monitoring TYR activity in biosystems.
- Fast-response,
- Fluorescent probe,
- Tyrosinase,
- Good biocompatibility,
- Fluorescence imaging
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