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Sulfhydrylated folic acid and preparation method thereof

A technology for sulfhydrylation and folic acid, which is applied in the field of sulfhydrylation folic acid and its preparation, and achieves the effects of convenient use, simple preparation process and broad application prospect.

Inactive Publication Date: 2014-07-02
QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, there is no sulfhydryl derivative product of folic acid as a modification reagent, so that it can be directly used for the modification of nano-metal particles

Method used

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  • Sulfhydrylated folic acid and preparation method thereof
  • Sulfhydrylated folic acid and preparation method thereof
  • Sulfhydrylated folic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of Disulfides by Oxidative Coupling of 3-Mercaptopropanol

[0046] Add 9.216 g (0.100 mol, 2.50 mol / L) of 3-mercaptopropanol ethanol solution into a 100 mL Erlenmeyer flask equipped with a magnet and constant pressure funnel, and add 30% hydrogen peroxide 11.337 g (0.100 mol), put the Erlenmeyer flask into the ice-water mixture, add hydrogen peroxide dropwise to the solution in the Erlenmeyer flask, and stir for 2 hours. After the reaction, put the flask containing the mixed solution into the rotary evaporator, set the temperature at 80 °C, stop the rotary evaporation until the solution no longer produces bubbles, and the remaining liquid is the prepared disulfide 3,3'-dimercapto dipropanol. Use infrared spectroscopy to test and characterize 3-mercaptopropanol and product 3,3'-dimercaptodipropanol, see the attached figure 1 , figure 2 . It can be seen from the infrared spectrum of the product that the characteristic infrared absorption peak of the sulfh...

Embodiment 2

[0048] Preparation of Disulfides by Oxidative Coupling of 2-Mercapto-3-Butanol

[0049] Add 7.433 g (0.070 mol, 2.30 mol / L) butanone solution of 2-mercapto-3-butanol into a 100 mL Erlenmeyer flask equipped with a magnet and a constant pressure funnel, and add a concentration of 30 % hydrogen peroxide 3.968 g (0.035 mol), put the Erlenmeyer flask into a low-temperature thermostat, control the reaction temperature at 10°C, add hydrogen peroxide dropwise to the solution in the Erlenmeyer flask, and stir for 4 hours. After the reaction was completed, 1.988 g (0.014 mol) of anhydrous sodium sulfate was added, the anhydrous sodium sulfate absorbed water and crystallized, and the filtrate was collected by filtration to obtain the disulfide 2,2’-dimercaptodi-3-butanol. Using infrared spectroscopy to test and characterize 2-mercapto-3-butanol and the product 2,2'-dimercaptodi-3-butanol, it can be seen from the infrared spectrum of the product that the characteristic infrared absorptio...

Embodiment 3

[0051] Preparation of Disulfides by Oxidative Coupling of 3-Mercaptohexanol

[0052] Add 6.712 g (0.050 mol, 2.20 mol / L) of 3-mercaptohexanol in acetone solution into a 100 mL Erlenmeyer flask equipped with a magnet and constant pressure funnel, and add 30% hydrogen peroxide 11.337 g (0.100 mol), the Erlenmeyer flask was placed in a low-temperature thermostat, and the reaction temperature was controlled at 10°C. Hydrogen peroxide was added dropwise to the solution in the Erlenmeyer flask, and the reaction was stirred for 6 hours. After the reaction was completed, the mixed solution was distilled under reduced pressure, and then rotary evaporated at a temperature of 80°C until the solution in the flask stopped bubbling to obtain the disulfide 3,3'-dimercaptodihexanol. Using infrared spectroscopy to test and characterize 3-mercaptohexanol and the product 3,3’-dimercaptodihexanol, it can be seen from the infrared spectrum of the product that the characteristic infrared absorption...

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Abstract

The invention relates to a sulfhydrylated folic acid and a preparation method thereof, and belongs to the field of organic synthesis technology. The preparation method comprises a step of oxidizing a sulfhydryl group in a sulfhydryl compound comprising two functional groups (a hydroxy group and a sulfhydryl group) into a disulphur bond to obtain a multifunctional disulphur compound; a step of subjecting the disulphur compound and folic acid (FA) to an esterification reaction; and a step of breaking the disulphur bond by using a reductant to prepare a folic acid derivative containing a free sulfhydryl group. The folic acid derivative can be combined with metal nanoparticles by forming a firm sulphur-metal bond (S-Me), and therefore surface modification of the folic acid to the metal nanoparticles is produced. The sulfhydrylated folic acid and the preparation method have advantages of simple preparation technology and low cost. The structural formula of the sulfhydrylated folic acid is shown as the following formula.

Description

Technical field [0001] The invention relates to a thiol folic acid and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] Improving the drug efficiency of disease treatment is an eternal theme in the medical field. After most drugs enter the human body, they reach various organs and tissues of the human body along with the blood circulation, and the part that actually reaches the target lesion tissue is extremely small, and most of the drugs accumulate in healthy human tissues, failing to achieve therapeutic effects. At the same time, drugs are toxic to a certain extent and have negative effects on healthy cells. In recent years, the nano-loading and targeted delivery of drugs has been extensively studied, which has greatly improved the utilization rate of drugs and the therapeutic effect of diseases. The targeting of nano-loading and targeted delivery of drugs is provided by targeting agents combined with the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D475/04
Inventor 刘继宪孙燕唐建国王瑶黄震黄林军武鹏
Owner QINGDAO UNIV
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