Photoaffinity labeling marker probe molecule for marking serum glycogen phosphorylase concentration level as well as preparation method and medical application of photoaffinity labeling marker probe molecule

A technology for probe molecules and labeled probes, which is applied in the field of photoaffinity-labeled probe molecules, and can solve problems such as temperature sensitivity and poor stability of antibodies

Inactive Publication Date: 2014-05-28
CHENGDE MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method utilizes the specific molecular recognition mechanism between antibody and antigen, and has disadvantages such as poor stability of the antibody itself and sensitivity to temperature, which restricts its clinical application to a certain extent (Clin.Chem.1996, 42, S129)

Method used

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  • Photoaffinity labeling marker probe molecule for marking serum glycogen phosphorylase concentration level as well as preparation method and medical application of photoaffinity labeling marker probe molecule
  • Photoaffinity labeling marker probe molecule for marking serum glycogen phosphorylase concentration level as well as preparation method and medical application of photoaffinity labeling marker probe molecule
  • Photoaffinity labeling marker probe molecule for marking serum glycogen phosphorylase concentration level as well as preparation method and medical application of photoaffinity labeling marker probe molecule

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Experimental program
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Effect test

Embodiment 1

[0042]

[0043] 2-(2-{2-[2-(2-Methanesulfonyloxyethoxy)ethoxy]ethoxy}ethoxy)-tetrahydro-2H-pyran (2)

[0044] Tetraethylene glycol (8.90mL, 0.052mmol) and triethylamine (16.70mL, 0.12mol) were dissolved in 50mL of dichloromethane, and methanesulfonyl chloride (8.05mL, 0.104mol) was slowly added dropwise under cooling in an ice-water bath. After stirring at room temperature for 4h. The solvent was evaporated to dryness under reduced pressure, the residue was diluted with ethyl acetate and then washed with water, 1N hydrochloric acid, saturated NaHCO 3 solution and saturated brine, anhydrous Na 2 SO 4 After drying, the solvent was evaporated, and concentrated under reduced pressure to obtain 2-{2-[2-(2-methanesulfonyloxyethoxy)ethoxy]ethoxy}ethanol (8.70g, 62.1%), the product did not need further Purification was used directly in the next reaction. The above 2-{2-[2-(2-methanesulfonyloxyethoxy)ethoxy]ethoxy}ethanol (8.70 g, 31.97 mmol) was dissolved in anhydrous dichlorom...

Embodiment 2

[0091]

[0092] (S)-2-propynyl 6-(2-chloroacetylamino)-2-(4-benzoylbenzamido)hexanoate (14)

[0093] The above crude (S)-6-amino-2-(4-benzoylbenzamido)hexanoic acid-2-endynyl ester (5.00 g, 12.75 mmol) was dissolved in dry dichloromethane (300 mL) , added triethylamine (12.44 mL, 89.25 mmol), cooled to 0°C. Under ice-cooling, chloroacetyl chloride (5.76 mL, 76.49 mmol) was slowly added dropwise to the solution within 30 min, and then stirred at room temperature for 12 hours. The solvent was evaporated under reduced pressure, and the residue was diluted with dichloromethane, washed successively with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. Flash column chromatography (petroleum ether / ethyl acetate: 8 / 1, V / V) gave a white solid (5.10 g, 86%).

[0094] ESI-MS m / z: 491.1 (M+Na) + .

[0095] 1 H-NMR (400MHz, CDCl 3 ): 1.49-1.66(m, 4H), 1.85-2.05(m, 2H), 2.54(t, J=2.4Hz, 1H), 3.32-3.38(m,...

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Abstract

The invention relates to the field of medicinal chemistry, in particular to a photoaffinity labeling marker probe molecule as well as a preparation method and medical application thereof. The probe molecule can be used for selectively marking glycogen phosphorylase in serum, and then the glycogen phosphorylase can be qualitatively and quantitatively detected, so that the probe molecule can be applied to marking detection on a biochemistry marker, namely, glycogen phosphorylase when diseases such as myocardial infarction, angina, arrhythmia, ischemic sudden cardiac arrest and coronary heart disease occur.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a kind of photoaffinity labeled probe molecule, its preparation method and medical application. The probe molecules involved in the present invention can selectively label glycogen phosphorylase in serum, so that glycogen phosphorylase can be detected qualitatively and quantitatively, so it can be used for myocardial infarction, angina pectoris, arrhythmia, ischemic cardiac Stop, marker detection of biochemical marker glycogen phosphorylase in the onset of coronary heart disease. Background technique [0002] Glycogen phosphorylase is the key enzyme for the breakdown of glycogen. There are three isoenzymes, brain isoenzyme (GPBB), muscle isoenzyme (GPMM) and liver isoenzyme (GPLL). GPBB is the isozyme predominant in human brain and myocardium. GPBB was first detected in the laboratory due to myocardial ischemia. At present, GPBB has become the most potential biomarker of myo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D493/10C07D401/14C12Q1/48G01N33/52
CPCC07D401/14C09K11/06C09K2211/1029C12Q1/48C12Y204/01001G01N33/582G01N2800/324G01N2800/325G01N2800/326
Inventor 张丽颖
Owner CHENGDE MEDICAL UNIV
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