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Trimetazidine hapten and artificial antigen, and preparation methods and applications thereof

A technology of trimetazidine and artificial antigen, which is applied in the biological field and can solve the problems of difficulty in realizing the immunodetection of trimetazidine and the like

Inactive Publication Date: 2018-11-13
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to overcome the shortcoming that trimetazidine immunodetection is difficult to realize in the prior art, and a kind of trimetazidine hapten is provided

Method used

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  • Trimetazidine hapten and artificial antigen, and preparation methods and applications thereof
  • Trimetazidine hapten and artificial antigen, and preparation methods and applications thereof
  • Trimetazidine hapten and artificial antigen, and preparation methods and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] This example provides a trimetazidine hapten with a structural formula such as formula (I), n=1:

[0048]

[0049] The preparation method is as follows (such as figure 2 ):

[0050] 1 part of trimetazidine (structural formula such as figure 1 ) was mixed with 10 parts of succinic anhydride, dissolved in 30 parts of 1,4-dioxane, and then 5 drops of triethylamine were added dropwise, and the reaction was carried out under closed stirring at 40°C for 12h. After the reaction, the reaction solution was poured into water, extracted 3 times with 100 parts of ethyl acetate, the extracts were combined, dried with anhydrous Na2SO4, concentrated to obtain a solid, and recrystallized from 75% ethanol to obtain a solid product that was trimetazidine hapten.

[0051]The structure of the obtained product is characterized by: 1H NMR (400MHz, DMSO) δ6.93(d, J=7.6Hz, 1H), 6.50(d, J=7.3Hz, 1H), 3.98(s, J=4.1Hz, 3H ), 3.80(s, J=4.2Hz, 3H), 3.69(s, J=4.1Hz2H), 3.62(s, J=4.4Hz, 3H), ...

Embodiment 2

[0061] This embodiment provides a trimetazidine hapten, the structural formula is as formula (I), and n is 2.

[0062] The preparation method is as follows:

[0063] After mixing 1 part of trimetazidine with 10 parts of glutaric anhydride, the subsequent steps are the same as in Example 1.

[0064] The structure of the obtained product is characterized by: 1H NMR (400MHz, DMSO) δ6.96(d, J=7.8Hz, 1H), 6.45(d, J=8.1Hz, 1H), 3.94(s, J=4.4Hz, 3H ),3.85(s,J=4.3Hz,3H),3.76(s,J=4.1Hz,2H),3.65(s,J=4.4Hz,3H),3.40(t,J=3.0Hz,4H), 2.42(t, J=2.8Hz, 4H), 2.37(t, J=3.5Hz, 2H), 2.30(t, J=3.6Hz, 2H), 2.02(m, J=4.7Hz, 2H).

[0065] The corresponding artificial antigen can be prepared by using the hapten, and the preparation method is consistent with Example 1.

Embodiment 3

[0067] This embodiment provides a trimetazidine hapten, the structural formula is as formula (I), and n is 3.

[0068] The preparation method is as follows:

[0069] After mixing 1 part of trimetazidine with 10 parts of adipic anhydride, the subsequent steps are the same as in Example 1.

[0070] The structure of the obtained product is characterized by: 1H NMR (400MHz, DMSO) δ6.90(d, J=8.6Hz, 1H), 6.52(d, J=7.8Hz, 1H), 3.87(s, J=5.0Hz, 3H ), 3.76(s, J=4.2Hz, 3H), 3.69(s, J=4.1Hz, 2H), 3.64(s, J=4.4Hz, 3H), 3.43(t, J=3.1Hz, 4H) ,2.50(t,J=3.3Hz,4H),2.31(t,J=3.5Hz,2H),2.18(t,J=3.4Hz,2H),1.54(m,2.7Hz,2H),1.52(m ,.J=4.9Hz, 2H).

[0071] The corresponding artificial antigen can be prepared by using the hapten, and the preparation method is consistent with Example 1.

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Abstract

The invention relates to a trimetazidine hapten and an artificial antigen, and preparation methods and applications thereof. The hapten has a structure represented by the formula (I) or formula (II) defined in the specification, wherein n is 1-3 and m is 1-3; the hapten provided by the invention is introduced with an arm connecting structure and an active group for coupling macromolecules on the basis of reserving a basic structure of trimetazidine, not only facilitates coupling of macromolecules, but also fully exposes a self molecular structure and the basic structure of trimetazidine with small molecular weight after coupling, and prevents the hapten from being masked by the macromolecules and prevents influence of animal body identification. The artificial antigen is prepared by coupling the hapten with a protein by an active esterification method, the coupling ratio can reach 14.2, and the artificial antigen can be used for immunological detection of trimetazidine.

Description

technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to a trimetazidine hapten, an artificial antigen, a preparation method and application thereof. Background technique [0002] Trimetazidine, also known as 1-[(2,3,4-trimethoxyphenyl)methyl]piperazine, has a molecular formula of C14H22N2O3, a molecular weight of 266.34, and a CAS number of 5011-34-7. Trimetazidine is a stronger antianginal drug, its onset is slower than that of nitroglycerin, but its duration of action is longer. It has anti-epinephrine, norepinephrine and vasopressin effects, can reduce vascular resistance, increase coronary blood flow and peripheral blood flow, and promote myocardial metabolism and myocardial energy production. At the same time, it can reduce the workload of the heart, reduce the consumption of myocardial oxygen and myocardial energy, thereby improving the balance of supply and demand of myocardial oxygen, and can also increase the toleran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185C07K14/765C07K14/77G01N33/53
CPCC07D295/185C07K14/765C07K14/77G01N33/53
Inventor 黄玄贺卢宇靖蔡森源李莹龙威张焜黄宝华
Owner GUANGDONG UNIV OF TECH
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