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Preparation method for trace tritiated deoxynivalenol

A deoxynivalenol and labeling technology, which is applied in the direction of organic chemistry, can solve the problems of not being able to determine the number of 14C, not conforming to the trace research of such compounds, and the qualitative and quantitative tests cannot be carried out, etc., to achieve the reaction The conditions are easy to control, the synthesis conditions are suitable, and the cost is low

Inactive Publication Date: 2013-12-04
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] 2) Since the whole synthesis is completed under the action of fungi, this synthesis method cannot determine the site of the marker, nor can it determine the upper part of the marker. 14 The number of C makes it impossible to carry out subsequent qualitative and quantitative tests
[0007] 3) The existing synthesis operation time is long, the steps are cumbersome, the yield is low, and the amount of radioactive waste is large
[0008] 4) The existing marker position is unreasonable and does not meet the tracer research of this type of compound in animals
[0009] 5) The existing product configuration is not single, and it is difficult to separate and purify
[0010] In view of the fact that there is no radioactive synthesis method of deoxynivalenol suitable for animal tracer studies so far, and there is no 3α,7α,15-trihydroxy-12,13-epoxytrichothecene- The tritium labeling method of 9-anthracene-8-one has been reported in patents and non-patent literature, so it is necessary to develop a new synthesis method so that the synthetic product meets the requirements of carrying out isotope tracer research related experiments

Method used

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  • Preparation method for trace tritiated deoxynivalenol
  • Preparation method for trace tritiated deoxynivalenol
  • Preparation method for trace tritiated deoxynivalenol

Examples

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Embodiment 1

[0039] Take 400mg of deoxynivalenol (content 70%, purity >90%), 300mg of phenylboronic acid, and appropriate amount of activated molecular sieve (4A). After adding anhydrous acetone, stopper and seal to isolate the air. After reacting for 4 h, the molecular sieves were removed by filtration under reduced pressure. Crystallization with acetone:petroleum ether (v / v 4:1) gave PBA-DON as a white needle-like solid.

[0040] Dissolve 20mg of PBA-DON in 1mL of anhydrous dichloromethane, seal, dry, and set aside (1); dissolve 30μL of oxalyl chloride in 2mL of anhydrous dichloromethane, pre-cool to -60°C, and set aside (2) ; Dissolve 50 μL of anhydrous dimethyl sulfoxide (DMSO) in 2 mL of anhydrous dichloromethane for use in (3); slowly add (3) to (2) dropwise, and stir for 30 minutes while adding at -78°C. A white solid (4) can be observed; slowly add (1) to (4), stir at -78°C for 30 min or 2 h, then add 200 μL of triethylamine, continue stirring for 5 min, add 10 mL of water to ter...

Embodiment 2

[0043] The operation method is the same as in Example 1, wherein: no activated molecular sieve is added to the phenylboronic acid protection reaction.

Embodiment 3

[0045] The protection reaction of phenylboronic acid is the same as in Examples 1 and 2. Oxidation reactions employ trifluoroacetic anhydride and DMSO as oxidants. The operation method is as follows.

[0046] Dissolve 50mg of PBA-DON in 6mL of anhydrous dichloromethane, seal, dry and set aside (1). Dissolve 30 μL of trifluoroacetic anhydride in 2 mL of anhydrous dichloromethane, pre-cool to -60 °C, and set aside (2). Dissolve 50 μL of anhydrous DMSO in 2 mL of anhydrous dichloromethane for use (3). (3) was slowly added dropwise to (2), and stirred at -60°C for 15 minutes, and a white solid (4) could be observed to form. Slowly add (1) to (4), stir at -60°C for 30 minutes, add 200 μL triethylamine, continue stirring for 5 minutes, add 10 mL water to terminate the reaction, extract the organic layer with ethyl acetate three times, combine the ethyl acetate layers, Wash with water first, then with saturated NaCl, and then dry with anhydrous sodium sulfate overnight. The next...

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Abstract

The invention relates to a preparation method for trace tritiated biotoxin deoxynivalenol. The method comprises the following steps: using the deoxynivalenol as a raw materials, and phenylboronic acid to protect 7 alpha-position and 15-position hydroxies, and oxidizing 3-position hydroxyl through Swern Oxidation; using isopropyl alcohol as a resolvent, and adopting tritiated sodium boro-hydride to selectively reduce the 3-position carboxide, so as to obtain tritiated deoxynivalenol. The method has the advantages that the raw materials are easy to obtain, the reaction condition is mild, the operation is easy, and the obtained tritiated compound is clear in labeling position and stable; the chemical purity and the radiochemical purity of the product are not less than 98 percent, and the specific activity is 2.52 Ci / mmol. The method provides an important material foundation for carrying out poison mechanism and food safety evaluation of the deoxynivalenol in a deep-going way.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a biotoxin tritium-labeled deoxynivalenol (3α,7α,15-trihydroxy-12,13-epoxytrichothecene-9-anthracene-8- Ketone, deoxynivalenol, DON) chemical synthesis method. The parent ring structure of a mycotoxin deoxynivalenol is prepared with positioning markers, which can trace the absorption, distribution, metabolism and excretion of deoxynivalenol in animals. Background technique [0002] Isotope tracer technology is an important scientific research method in contemporary life science research, and has been widely used in various fields of life science research. Isotope tracer technology can be used to study various processes of compound transformation in vivo, such as metabolic pathway, absorption and elimination speed, tissue distribution, and quantification of important metabolites. The chemical and biological properties of the radionuclides and their compounds used in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10
Inventor 袁宗辉万丹潘源虎黄玲利王玉莲陈冬梅陶燕飞谢书宇王旭戴梦红彭大鹏郝海红程古月刘振利
Owner HUAZHONG AGRI UNIV
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