A compound, a product containing the compound and applications in detection of gamma-glutamyl transpeptidase

A glutamyl transpeptidase and compound technology, applied in the field of fluorescence detection, can solve the problems of low fluorescence ratio change times, slow response speed of fluorescent probes, detection of difficult tissue sample content, etc.

Active Publication Date: 2019-09-06
FUDAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on fluorescent probes for ratiometric detection of GGT, and these fluorescent probes have slow response speeds and low folds of fluorescence ratio changes, so these probes are difficult to use for the detection of content in tissue samples

Method used

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  • A compound, a product containing the compound and applications in detection of gamma-glutamyl transpeptidase
  • A compound, a product containing the compound and applications in detection of gamma-glutamyl transpeptidase
  • A compound, a product containing the compound and applications in detection of gamma-glutamyl transpeptidase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0165] Example 1, Preparation of γ-glutamyl transpeptidase-responsive fluorescent probe C3

[0166]

[0167]Compound A3 (0.5 g) was dissolved in 20 ml of methanol solution, and an aqueous solution (10 ml) of B1 (0.35 g) was added thereto at room temperature, and the reaction was continued for 12 hours at room temperature. After the reaction, the solvent was removed by rotary evaporation, and the crude product was separated and purified by high performance liquid chromatography (acetonitrile / water=2 / 1) to obtain compound C1 (0.21 g, yield 28%). The structure is confirmed as follows: 1 H NMR (400MHz,D 2 O, δ) 7.77(d, J=9.6Hz, 2H), 6.87(dd, J=9.6Hz, J=2Hz, 2H), 6.46(d, J=2Hz, 2H), 4.31(dd, J=8Hz , J=4.8 Hz, 1H), 3.6-3.2(m, 12H), 2.3-2.05(m, 3H), 1.9-1.8(m, 12H).

Embodiment 2

[0168] Example 2, Preparation of γ-glutamyl transpeptidase-responsive fluorescent probe C5

[0169]

[0170] Compound A5 (0.46 g) was dissolved in 20 ml of methanol solution, and an aqueous solution (12 ml) of B1 (0.35 g) was added thereto at room temperature, and the reaction was continued for 12 hours at room temperature. After the reaction, the solvent was removed by rotary evaporation, and the crude product was separated and purified by high performance liquid chromatography (acetonitrile / water=3 / 2) to obtain compound C5 (0.1 g, yield 29%). The structure is confirmed as follows: 1 H NMR (400MHz,D 2 O,δ)8.37(d,J=9.0Hz,1H), 8.29(d,J=15Hz,1H),8.26(d,J=9.0Hz,1H),8.06(d,J=15Hz,1H), 7.84 (t, J = 8.3Hz, 1H), 7.76 (m, 2H), 6.95 (dd, J1 = 2.4Hz, J2 = 9.6Hz, 1H), 6.69 (d, J = 2.2 Hz, 1H), 4.22 ( s, 3H), 4.03(m, 1H), 3.6-3.2(m, 9H), 2.06(t, 2H), 1.9-1.7(m, 2H), 1.32(d, J=7.2Hz, 3H).

Embodiment 3

[0171] Example 3, Preparation of γ-glutamyl transpeptidase-responsive fluorescent probe C7

[0172]

[0173] Compound A7 (0.4 g) was dissolved in 20 ml of methanol solution, and an aqueous solution (8 ml) of B1 (0.45 g) was added thereto at room temperature, and the reaction was continued for 24 hours at room temperature. After the reaction, the solvent was removed by rotary evaporation, and the crude product was separated and purified by high performance liquid chromatography (acetonitrile / water=4 / 1) to obtain compound C7 (0.1 g, yield 23%). The structure is confirmed as follows: 1 H NMR (400MHz,D 2 O,δ)7.28(d,J=9.6Hz,1H), 6.77(d,J=9.6Hz,1H),4.04(m,1H),3.6-3.2(m,3H),2.05(t,2H) ,1.9-1.8(m,2H), 1.32(d,J=7.2Hz,3H).

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PUM

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Abstract

The invention relates to a compound having a structure which is represented by a formula (1) shown in the description, a product containing the compound, preparation methods of the compound and the product and applications in the detection of gamma-glutamyl transpeptidase.

Description

technical field [0001] The invention belongs to the field of fluorescence detection. Specifically, the present invention relates to a compound, products containing the compound, their preparation method and application in the detection of γ-glutamyl transpeptidase. Background technique [0002] In the process of clinical tumor resection, accurate positioning and resection of the tumor site is conducive to ensuring the quality of life and relatively good prognosis of patients after surgery. In clinical medical diagnosis and basic biomedical research, tissue section analysis is widely used to determine the position of resection margin and postoperative pathological analysis. Frozen section has high accuracy and is currently the most widely used slice analysis method in clinical practice. However, this method is time-consuming and labor-intensive, and it is difficult to apply to intraoperative tumor localization. Fluorescence imaging technology has fast imaging speed and high...

Claims

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Application Information

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IPC IPC(8): C07D209/10C07D271/12C07D311/84C07D417/06C07F9/572C09K11/06G01N21/31G01N21/64
CPCC07D311/84C07D417/06C07D271/12C07D209/10C07F9/5728C09K11/06G01N21/6458G01N21/6428G01N21/3151G01N2021/3155C09K2211/1088C09K2211/1037C09K2211/1048C09K2211/1029
Inventor 李富友周晓波吴勇
Owner FUDAN UNIV
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