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2,3,4,5,-tetra(3',4'-dihydroxyl phenyl)thiophene and application thereof as MALDI (matrix assisted laser desorption ionization) matrix in analyzing small molecules

A matrix and matrix-assisted laser technology, which is applied in the analysis of materials, material analysis by electromagnetic means, and measurement devices, can solve the problems of long time consumption, cumbersome preparation, and decline in analysis results, and achieve reduction requirements and good sample compatibility. Effect

Active Publication Date: 2012-07-25
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
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Problems solved by technology

[0004] However, there are problems such as tedious preparation, high cost, and low sensitivity when using inorganic substances and carbon material matrices, which cannot fully reflect the rapid and high-sensitivity characteristics of MALDI-TOF MS analysis samples.
When desorption / ionization occurs on the porous silicon surface, the surface of the silicon crystal must first be etched to produce a nanostructured surface. Although peptides and antiviral drugs can be directly analyzed on such a surface, the repeated use of this surface is not effective. OK, so repeated treatments on the same nanostructured surface are required to get a reusable surface
In addition, it takes a long time to chemically modify the surface of porous silicon, and the analysis effect will be greatly reduced when the modified porous silicon is reused.
Proton sponge as an organic matrix does not interfere in the low molecular weight range, but it can only analyze organic acids

Method used

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  • 2,3,4,5,-tetra(3',4'-dihydroxyl phenyl)thiophene and application thereof as MALDI (matrix assisted laser desorption ionization) matrix in analyzing small molecules
  • 2,3,4,5,-tetra(3',4'-dihydroxyl phenyl)thiophene and application thereof as MALDI (matrix assisted laser desorption ionization) matrix in analyzing small molecules
  • 2,3,4,5,-tetra(3',4'-dihydroxyl phenyl)thiophene and application thereof as MALDI (matrix assisted laser desorption ionization) matrix in analyzing small molecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1, synthesis 2,3,4,5-tetra(3 ', 4'-dihydroxyphenyl) thiophene

[0054] Add Pd(PPh 3 ) 4 (0.07g, 6mol%), after stirring at room temperature for 30 minutes, add 3,4-dimethoxyphenylboronic acid (2,5.0mmol), K 3 PO 4 (4.0 mmol) and 1 mL of water. The mixture was stirred at 90°C for 12 hours, and after cooling to room temperature, it was successively diluted with ethyl acetate, dried over anhydrous sodium sulfate, and then filtered. After the solution was removed from the solvent by a rotary evaporator, the residue was separated by silica gel column chromatography (ethyl acetate:petroleum ether=1:50, v / v) to obtain the intermediate product 2,3,4,5-tetra(3', 4'-Dimethoxyphenyl)thiophene solid (3, 0.56g, 0.9mmol), yield 90%. 3 (0.56 g, 0.9 mmol) was dissolved in 5 mL of dichloromethane, then cooled to -78 °C. Under these conditions, 2.5 mL of a dichloromethane solution of boron tribromide (0.68 mL, 7.2 mmol) was added dropwise, stirred for 2 hours, returned to...

Embodiment 2

[0057] Example 2. Analysis of various small molecules (including β-stimulants, amino acids, vitamins, caffeine, urea, dopamine, melamine, anilines, purines, pyrimidines and other amines)

[0058] Various prepared sample solutions (concentration: 1mM) and matrix solution (concentration: 20mM) were mixed uniformly at a volume ratio of 1:1, and then 1 μL of the mixed sample was added to the MALDI target plate, dried in the air and then subjected to mass spectrometry analysis. The mass spectrometry conditions are: voltage: accelerating voltage: 19.000kv; delayed extraction voltage: 14.920kv; reflector voltage: 20.000kv; lens voltage: 7.000kv; frequency: 1.000Hz; laser energy: 75-80%; accumulation times: 90 times ; Positive ion mode.

[0059] In the MALDI ionization mode, the matrix can transfer protons to the analyte compound, making the analyte compound positively charged and thus detected by mass spectrometry. Experiments have shown that the matrix is ​​effective for the above ...

Embodiment 3

[0060] Embodiment 3, small molecule analysis in urine sample

[0061] Take 2 mL of fresh urine from healthy male volunteers, centrifuge to remove precipitates and insoluble matter, then take 1 μL and mix it with 1 μL matrix solution (concentration: 20 mM), and finally take 1 μL of the mixed solution and add it to the MALDI target plate, dry it in the air and enter the mass spectrometer analyze. The mass spectrometry conditions are: voltage: accelerating voltage: 19.000kv; delayed extraction voltage: 14.920kv; reflector voltage: 20.000kv; lens voltage: 7.000kv; frequency: 1.000Hz; laser energy: 75-80%; accumulation times: 90 times ; Positive ion mode.

[0062] From Figure 8 It can be seen from the figure that more signal peaks are generated in the small molecule region, indicating that many small molecules in the urine sample are ionized to generate mass spectrometry signals. Therefore, this matrix can be used for the analysis of small molecule metabolites in urine samples....

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Abstract

The invention discloses 2,3,4,5,-tetra(3',4'-dihydroxyl phenyl)thiophene and application of 2,3,4,5,-tetra(3',4'-dihydroxyl phenyl)thiophene as an MALDI (matrix assisted laser desorption ionization) matrix in analyzing small molecules. The analysis method using 2,3,4,5,-tetra(3',4'-dihydroxyl phenyl)thiophene as the MALDI matrix is suitable for performing mass spectrum analysis on the small molecules with m / z being less than 1000. And adaptive molecule varieties comprise amine matters such as amino acids, vitamins, excitants, caffeine, urea, dopamine, melamine, aniline, purines and pyrimidines, etc., wherein background interference is not produced because of only a few fixed background peaks when the method is used for detecting the molecules with m / z being less than 1000. The method for preparing 2,3,4,5,-tetra(3',4'-dihydroxyl phenyl)thiophene provided by the invention can be effectively applied to fields such as the organic and biological mass spectrum, the mass spectrum imaging, the protein spectroscopy, the metabonomics, the biomarker discovery, the environment analysis and the like.

Description

technical field [0001] The invention relates to a kind of 2,3,4,5-tetrakis(3',4'-dihydroxyphenyl)thiophene and its application as a MALDI matrix for analyzing small molecules. Background technique [0002] Since Karas et al. and Tanaka et al. reported in 1988 that matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) technology can be used for effective mass spectrometry analysis of biological macromolecules, MALDI-TOF MS technology has been favored by researchers from various countries. of favor. However, due to the commonly used matrices of MALDI-TOF MS technology, such as α-cyano-4-hydroxycinnamic acid (CHCA), 2,5-dihydroxybenzoic acid (DHB), sinapinic acid (SA), 3-hydroxy-2- Picolinic acid (3-HPA), anthracenol (DI) and 3-aminoquinoline (3-AQ) will be fragmented during the analysis process and the association between molecules will be in the range of m / z<500 Severe matrix background interference occurs in the matrix, therefore, s...

Claims

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Application Information

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IPC IPC(8): C07D333/16G01N27/62G01N27/626
Inventor 聂宗秀陈素明陈力陈芮王佳宁侯剑
Owner INST OF CHEM CHINESE ACAD OF SCI
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