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Compounds for detecting tyrosinase as well as preparation method and application of compounds

A technology of tyrosinase and compounds, which is applied in the field of fluorescent probes for detecting intracellular tyrosinase (Tyr) and its preparation, can solve the problems of unsuitability for real-time imaging and low sensitivity, and achieve strong anti-interference ability, Effect of high sensitivity and excellent signal-to-noise ratio

Active Publication Date: 2019-04-12
HUBEI UNIV
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Problems solved by technology

However, these methods suffer from low sensitivity and are not suitable for real-time imaging in living samples

Method used

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  • Compounds for detecting tyrosinase as well as preparation method and application of compounds
  • Compounds for detecting tyrosinase as well as preparation method and application of compounds
  • Compounds for detecting tyrosinase as well as preparation method and application of compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0059] Example: Preparation method of near-infrared fluorescent molecular probe FL-O-T.

[0060] 0.3mmol FT-OH (R 1 , R 2 , R 3 for hydrogen) was dissolved in 20 mL of anhydrous DMF, and then 0.9 mmol K was added 2 CO 3 , stirred at 60 °C for 10 min under an argon atmosphere. Afterwards, 5 mL of anhydrous DMF solution with a concentration of 1.2 mmol / 5 mL m-hydroxybenzyl bromide was added dropwise. Stirring was continued at 60° C. for 5 hours under argon atmosphere. The progress of the reaction was monitored by TLC. After the reaction, add water, adjust the pH value to 5-6 with dilute hydrochloric acid, extract with EA, and wash with water. The organic solution was washed with anhydrous Na 2 SO 4 Dry and evaporate in vacuo. The residue was purified by column chromatography using EA / PE to afford the target FL-O-T.

[0061] The hydrogen spectrum of the compound FL-O-T (such as Figure 5 ), the deuterated reagent is d 6 -DMSO.

[0062] 1 H NMR (400 MHz, (CD 3 )...

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Abstract

The invention belongs to the field of biochemical industry, and particularly relates to a preparation method and application of compounds FL-O-T for detecting tyrosinase. The compounds FL-O-T have a structural general formula shown in the description, wherein R1, R2 and R3 are hydrogen, alkyl or other common substituent groups. The compounds FL-O-T can be used as a fluorescent probe for detectingthe tyrosinase, and the compounds FL-O-T are synthesized by a nucleophilic substitution reaction of a fluorescein derivative and m-hydroxybenzyl bromide. The compounds FL-O-T provided by the inventionare synthesized by the nucleophilic substitution reaction of the fluorescein derivative FT-OH and the m-hydroxybenzyl bromide; and the target compounds have high chemoselectivity, can track and detect the tyrosinase in vitro and in vivo, and successfully monitor activity of the tyrosinase in cancer cells and zebrafish.

Description

technical field [0001] The invention belongs to the field of biochemical industry, relates to constructing a fluorescent probe for detecting intracellular tyrosinase (Tyr), in particular to a fluorescent probe for detecting intracellular tyrosinase (Tyr) and a preparation method thereof and biological applications. Background technique [0002] Tyrosinase (Tyr) is an important copper-containing oxidase that widely exists in plants, animal tissues and fungi. Tyrosinase also plays an important role in the synthesis of melanin, which determines skin color, and protects the DNA in skin cells from UV radiation. In addition, abnormally expressed tyrosinase in biological systems is thought to be involved in many diseases, such as skin diseases and melanoma. In addition, tyrosinase may also induce neurodegeneration, which is the cause of Parkinson's disease. Therefore, developing a sensitive and selective method to evaluate this biomarker is of great value for understanding its...

Claims

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Application Information

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IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06C09K2211/1007C09K2211/1088G01N21/6428
Inventor 王飞翼杨桂春胡思思陈祖兴卢翠芬聂俊琦马超
Owner HUBEI UNIV
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