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A kind of fluorescent probe and its preparation method, application

A fluorescent probe and reaction technology, applied in the field of chemistry, can solve the problems of poor water solubility of fluorescent groups, high price, complicated synthesis, etc., and achieve good water solubility, good water solubility and fluorescence detection effect, and molecular volume. small effect

Inactive Publication Date: 2016-11-23
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A big problem with these fluorescent probes is that the synthesis is complicated and requires a huge cost, so the price remains high
Another problem is that the water solubility of the fluorophore is too poor, and it is difficult to dissolve in normal cell physiological environment

Method used

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  • A kind of fluorescent probe and its preparation method, application
  • A kind of fluorescent probe and its preparation method, application
  • A kind of fluorescent probe and its preparation method, application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1 Preparation of fluorescent detection probe for β-galactosidase

[0073] The first step: dissolve 1g (2.43mmol) tetraacetyl-α-D-bromogalactose and 0.35g (2.43mmol) 6-hydroxyquinoline in 15ml dimethyl diamide, add 1g (3.07mmol) cesium carbonate, the reaction was complete after stirring at 15°C for 10 hours. The reaction solution was poured into 200ml 0.1M HCl solution, extracted with ethyl acetate, and the solvent was spin-dried in vacuo, and then purified by silica gel column chromatography using ethyl acetate and dichloromethane (1:1) as the eluent. A white powdery solid (0.3 g) was obtained. 1 HNMR (400MHz, Methanol-d 4 ), δ(TMS,ppm):8.75(dd,J=4.4,1.7Hz,1H),8.35–8.26(m,1H),7.99(d,J=9.0Hz,1H),7.58–7.43(m, 3H),5.56–5.39(m,3H),5.31(dd,J=10.3,3.5Hz,1H),4.41(ddd,J=7.3,6.1,1.2Hz,1H),4.22(dd,J=6.5, 2.2Hz,2H),2.19(s,3H),2.07(s,3H),2.03(s,3H),1.99(s,3H).Mass Spec HRMS(ESI+):calcd for[M+H] + , 476.1512; found, 476.1545. The reaction structure is as follows:

[00...

Embodiment 2

[0077] Example 2 Preparation of fluorescent detection probe for β-galactosidase

[0078] The first step: dissolve 1g (2.43mmol) tetraacetyl-α-D-bromogalactose and 0.55g (3.65mmol) 6-hydroxyquinoline in 15ml dimethyl diamide, add 1g (3.07mmol) cesium carbonate, the reaction was complete after stirring at 25°C for 14 hours. The reaction solution was poured into 200ml 0.1M HCl solution, extracted with ethyl acetate, and the solvent was spin-dried in vacuo, and then purified by silica gel column chromatography using ethyl acetate and dichloromethane (1:1) as the eluent. A white powdery solid (0.3 g) was obtained. 1 HNMR (400MHz, Methanol-d 4 ), δ(TMS,ppm):8.75(dd,J=4.4,1.7Hz,1H),8.35–8.26(m,1H),7.99(d,J=9.0Hz,1H),7.58–7.43(m, 3H),5.56–5.39(m,3H),5.31(dd,J=10.3,3.5Hz,1H),4.41(ddd,J=7.3,6.1,1.2Hz,1H),4.22(dd,J=6.5, 2.2Hz,2H),2.19(s,3H),2.07(s,3H),2.03(s,3H),1.99(s,3H).Mass Spec HRMS(ESI+):calcd for[M+H] + , 476.1512; found, 476.1545.

[0079] Step 2: Dissolve 0.2 g (0.42 mmol)...

Embodiment 3

[0080] Example 3 Preparation of fluorescent detection probe for β-galactosidase

[0081] The first step: dissolve 1g (2.43mmol) tetraacetyl-α-D-bromogalactose and 0.47g (3.04mmol) 6-hydroxyquinoline in 15ml dimethyl diamide, add 1g (3.07mmol) cesium carbonate, the reaction was complete after stirring at 35°C for 12 hours. The reaction solution was poured into 200ml 0.1M HCl solution, extracted with ethyl acetate, and the solvent was spin-dried in vacuo, and then purified by silica gel column chromatography using ethyl acetate and dichloromethane (1:1) as the eluent. A white powdery solid (0.33 g) was obtained. 1 HNMR (400MHz, Methanol-d 4 ), δ(TMS,ppm):8.75(dd,J=4.4,1.7Hz,1H),8.35–8.26(m,1H),7.99(d,J=9.0Hz,1H),7.58–7.43(m, 3H),5.56–5.39(m,3H),5.31(dd,J=10.3,3.5Hz,1H),4.41(ddd,J=7.3,6.1,1.2Hz,1H),4.22(dd,J=6.5, 2.2Hz,2H),2.19(s,3H),2.07(s,3H),2.03(s,3H),1.99(s,3H).Mass Spec HRMS(ESI+):calcd for[M+H] + , 476.1512; found, 476.1545.

[0082] The second step: Dissolve 0.2 g (...

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Abstract

The invention relates to the field of chemistry and especially relates to fluorescent probes and their preparation method and use. The 6-hydroxyquinoline salt-based beta-galactosidase fluorescent probe is synthesized by three steps and the 6-hydroxyquinoline salt-based lipase fluorescent probe is synthesized by two steps so that a production cost is greatly reduced and good water solubility and good fluorescence detection effects are obtained.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a fluorescent probe and its preparation method and application. Background technique [0002] β-galactosidase is an enzyme that can catalyze the hydrolysis of lactose into galactose and glucose, and its content is relatively high in renal proximal tubule epithelial cells. Medically, the activity of β-galactosidase in urine can reflect the early injury of renal parenchyma, especially renal tubules. In laboratory research, the β-galactosidase gene (lacZ) is often used as a reporter gene to monitor the expression of the target gene by detecting the expression level of β-galactosidase. Therefore, the detection of β-galactosidase is of great significance. [0003] At present, the relatively mature method is to detect by photometry. The chromogenic substrates detected by it include p-nitrophenyl-β-D-galactoside (Biochemical, 1960, 209), 4-methylfanyl-β-D-galactoside (J Organ Chem, 1962, 27...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/20C07H17/02G01N21/64C09K11/06
Inventor 王攀张国庆毕国强许向川陈伟
Owner UNIV OF SCI & TECH OF CHINA