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Deuteration-3-nitrobenzene boric acid and preparation method and application thereof

A technology of nitrophenylboronic acid and phenylboronic acid, which is applied in the field of analysis and detection, can solve problems such as easy loss of structural information, reduced sensitivity, and complexity, so as to improve specificity and identification accuracy, high mass spectrometry detection sensitivity, and increase mass spectrometry response Effect

Active Publication Date: 2018-12-28
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is time-consuming and the pretreatment process is complicated, which is easy to cause sample loss
At the same time, the mass spectrometry detection of monoglycerides as a whole is limited by the ionization properties of the hydroxyl groups in the monoglycerides structure, and can only be detected in negative ion mode, which reduces the sensitivity of the detection and is easy to lose the structure in the secondary mass spectrometry. information
In addition, the quantification of monoglycerides is limited by factors such as the lack of suitable internal standards or the difficulty of obtaining deuterated monoglycerides, which increases the difficulty of detection, identification and quantification in complex biological samples

Method used

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  • Deuteration-3-nitrobenzene boric acid and preparation method and application thereof
  • Deuteration-3-nitrobenzene boric acid and preparation method and application thereof
  • Deuteration-3-nitrobenzene boric acid and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] [embodiment 1] the preparation of deuterium-3-nitro-phenylboronic acid

[0035] Deuterated-3-nitroaniline (50mg, 0.36mmol) was dissolved in water (1mL), and 5% hydrochloric acid solution (0.6mL, 0.90mmol) was added, and stirred at room temperature for 1 minute to obtain a mixed solution. Sodium nitrite (30mg, 0.43mmol) was dissolved in water (0.5mL), added dropwise to the above mixed solution, stirred at 0°C for 15 minutes, added B 2 (OH) 4 (64.9mg, 0.72mmol), sodium acetate (59.36mg, 0.72mmol) and water (6mL), stirred at room temperature for 20 minutes, added ethyl acetate (25mL), and adjusted the pH value to 8 with saturated potassium carbonate. After the mixture was separated, the organic layer was extracted with saturated potassium carbonate (10mL×4), the combined aqueous phase was adjusted to pH 6 with 5% hydrochloric acid solution, extracted with ethyl acetate (10mL×3), the combined organic phase was washed with water (10mL × 2) washing, then washed with saturat...

Embodiment 2

[0036] [Example 2] Derivatization of standard monoglycerides and detection by ultra-high performance liquid chromatography-mass spectrometry (UPLC-MS)

[0037] 1. Accurately weigh palmitic acid monoglyceride (PG), oleic acid monoglyceride (OG), arachidonic acid monoglyceride (AG), linoleic acid monoglyceride (LG), stearic acid monoglyceride (SG) Five standard substances were dissolved in methanol to prepare a mixed standard solution with a concentration of 100 μM.

[0038] 2. Precise weighing d 0 -NPB and d 4 - NPB solid, dissolved in methanol, prepared as 10 mM stock solution.

[0039] 3. Take 100 μL of the mixed standard solution and add the prepared 10 mM d 0 -NPB solution and d 4 - Each 10 μL of the NPB solution was subjected to a derivatization reaction, and the reaction conditions were 37° C., 400 rpm, and the reaction was performed for 2 hours.

[0040] 4. After the derivatization reaction, centrifuge at 18,000 rpm for 10 minutes at 4°C, and take 50 μL of the superna...

Embodiment 3

[0042] [Example 3] Injecting samples after liver tissue derivatization to verify the effect of deuterated reagents

[0043] The liver of obese mice was used as the experimental group d 4 -NPB derivatized, normal mouse liver was used as control d 0 -NPB derivatization to verify the role of deuterated reagents.

[0044] The specific process is as follows:

[0045] 1. Weigh 60 mg each of obese mouse liver and normal mouse liver, add 400 μL methanol, 4000 rpm, homogenate for 1 minute, shake for 10 minutes, let stand at -20°C for 20 minutes, then centrifuge at 4°C, 18,000 rpm for 10 minutes Minutes remove the supernatant for later use.

[0046] 2. Precise weighing d 0 -NPB and d 4 - NPB solid, dissolved in methanol, prepared as 10 mM stock solution.

[0047] 3. Take 100 μL of the supernatant of the obesity group and add 10 μL of the prepared d 4 -NPB solution was derivatized, and 100 μL of the supernatant of the normal group was added to 10 μL of the prepared d 0 -The NPB s...

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Abstract

The invention disclose deuteration-3-nitrobenzene boric acid and a preparation method and application thereof. The compound is capable of improving the mass spectrum response of monoglyceride after being subjected to derivatization with monoglyceride; the special isotope distribution property of boron atoms is utilized to improve the specificity of monoglyceride detection and the identification accuracy; the deuteration-3-nitrobenzene boric can be used in match with a light marking agent in detection and relative quantitative analysis of monoglyceride in a complex biospecimen.

Description

technical field [0001] The invention belongs to the field of analysis and detection, and in particular relates to deuterium-3-nitrophenylboronic acid and its preparation method and application. Background technique [0002] Monoglyceride (MAG) is a class of active substances involved in various physiological processes in the body. Studies have shown that monoglycerides are closely related to various diseases, such as diabetes, obesity, cancer, etc. At present, indirect detection methods are often used to identify monoglyceride mixtures in complex biological samples, that is, monoglycerides are degraded into glycerol and corresponding free fatty acids, and the free fatty acids are separated by thin-layer chromatography. Methods The obtained free fatty acid mixture was separated and identified. This method is time-consuming and the pretreatment process is complicated, which is easy to cause sample loss. At the same time, the mass spectrometry detection of monoglycerides as ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07B59/00G01N30/02
CPCC07B59/004C07B2200/05C07F5/025G01N30/02
Inventor 郝海平徐小为郑秋凌朱梦乐韩佳玲
Owner CHINA PHARM UNIV
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