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Compound for detecting tyrosinase and application thereof

A technology of tyrosinase and compounds, applied in the field of fluorescent probes, can solve the problems of poor biocompatibility and achieve good stability

Active Publication Date: 2021-01-22
ANYANG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, the method of detecting Tyr with reactive fluorescent probes has been developed rapidly, and has attracted continuous attention because of its high specificity, high sensitivity, and easy operation. Molecules, but most of them are chemically modified based on chemical dyes such as BODIPY, Cyanine and imide, or inorganic nanomaterials, and their biocompatibility is not superior

Method used

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  • Compound for detecting tyrosinase and application thereof
  • Compound for detecting tyrosinase and application thereof
  • Compound for detecting tyrosinase and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Synthesis of FluotyLu1

[0046]

[0047] Compound 4 (154 mg, 0.748 mmol) and 6-amino-2-cyanobenzothiazole (compound 7, 131 mg, 0.748 mmol) were dissolved in MeCN (8 ml). AcOH (400 μl) and NaBH were added sequentially 3 CN (100 mg, 1.59 mmol). The mixture was stirred at room temperature. Add NaHCO after 10 minutes 3 Aqueous solution (30ml), all extracted with ethyl acetate (200ml). Combine the organic layers with H 2 O and brine wash. The organic layer was washed with Na 2 SO 4 Dry and evaporate the solvent. The residue was purified by flash silica gel column chromatography with a mixed solvent of ethyl acetate and n-hexane to obtain compound 9.

[0048] 1 H NMR (500MHz, CDCl 3 )δ=7.88(d,1H),6.84-6.80(m,2H),6.64(d,1H),6.59-6.57(m,2H),4.151(s,1H,NH),,3.19(t,2H) ), 2.65(t, 2H), 1.94(quintet, 2H), 1.66(s, 6H).

[0049] 13CNMR (500MHz, DMSO-d6), δ=150.51, 147.22, 145.37, 139.35, 135.30, 128.02, 125.23, 120.98, 117.94, 117.75, 114.86, 109.01, 108.28...

Embodiment 2

[0055] Example 2 Synthesis of FluotyLu 2

[0056]

[0057] 2-Cyano-6-hydroxybenzothiazole (compound 6, commercially available, 150 mg, 0.85 mmol) was placed in DMF and K as the base 2 CO 3 (352.4 mg, 2.55 mol) was added to the reaction solution. After the mixture was stirred at room temperature for 15 minutes, compound 11 (1.15 g, 4.26 mmol) was added, and the temperature of the mixture was heated to 70°C overnight. When the reaction was completed under TLC monitoring, the reaction mixture was cooled, diluted with ethyl acetate, and washed 3 times with saturated brine. The organic phase was dried over anhydrous magnesium sulfate, then the solvent was removed under reduced pressure, and the crude solid product was purified by flash silica gel column chromatography with a mixed solvent of ethyl acetate and petroleum ether to obtain compound 12.

[0058] Compound 12 (0.10 mmol) was added to 10 ml of degassed CH in a 50 ml round bottom flask equipped with a stir bar under ar...

Embodiment 3

[0059] Example 3 Performance of FluotyLu1

[0060] figure 1 The time-dependent fluorescence spectra of FluotyLu1 solutions at different pH values ​​for Tyr detection activity were determined. The results showed that the detection activity of FluotyLu1 was severely inhibited under the condition of pH=5.8; the detection was slightly inhibited under the condition of pH=8.0, and the detection activity of FluotyLu1 in PBS with pH value of 6.8 was exhibited.

[0061] figure 2 It was determined that the maximum emission peak of FluotyLu1 was located at 535nm, showing a characteristic green fluorescence (the left cuvette in the fluorescence snapshot); after the addition of Tyr, its fluorescence decreased rapidly within 2min and finally disappeared (the right color in the fluorescence snapshot). dish). It can be speculated that there is a photoinduced electron transfer (PET) process between the ortho-diphenol hydroxyl group (electron donating group) and the fluorescein structure. ...

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Abstract

According to the invention, a compound for detecting tyrosinase is designed by utilizing catalytic oxidation characteristics of luminescent substance firefly Luciferrin with good stability and excellent biocompatibility in a biological system and tyrosinase in a firefly body, a firefly luciferin derivative is used as a parent structure and o-diphenolic hydroxyl is used as a response group, and thetwo are covalently bonded through an alkyl chain. The compound has good biocompatibility and fluorescence performance, the maximum emission peak is located at 535 nm, and after Tyr is dropwise added,fluorescence is rapidly reduced within 2 min. An action mechanism is that a photo-induced electron transfer process (PET) exists between a o-diphenolic hydroxyl group and a fluorescein structure, after the Tyr is added into the system, the o-diphenolic hydroxyl is oxidized into a quinone structure, the photo-induced electron transfer process is inhibited after electron cloud arrangement in the system is changed, and fluorescence is quenched. A detection limit of 0.06087 M (PBS) is calculated according to a dose-dependent fluorescence spectrum change of FluotyLu. The compound is found to havethe value of detecting Fe<3+> in the interference capacity of metal ions to FluotyLu for detecting Tyr.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, relates to a compound for detecting tyrosinase and its application, in particular to a tyrosinase fluorescent probe molecular compound based on firefly luciferin. Background technique [0002] Tyrosinase (EC 1.14.18.1, tyrosinase, Tyr) is a copper-containing oxidoreductase, widely present in microorganisms, animals, plants and mammals, especially in human tissues, can promote the production of melanin, make skin and hair. Displays normal black. At the same time, dysregulation of Tyr activity is closely related to malignant melanoma, type I oculocutaneous albinism, Parkinson's disease and other neurodegenerative-related diseases. Studies have also shown that the content of Tyr is also an important factor affecting the nutritional value of fruits and vegetables. Therefore, the detection of Tyr can not only provide a wealth of medical diagnostic information, but also provide a guarantee...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64C07D277/64C09K11/06
CPCG01N21/64G01N21/6428G01N21/643C07D277/64C09K11/06G01N2021/6417G01N2021/6432C09K2211/1037
Inventor 王建广辛卫丽王芳魏静静李保利陈雨涵翟国壮张苗苗孙茹侯绍刚牛永生
Owner ANYANG INST OF TECH
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