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Preparation method of artificial phospholipid DSPG

A technology of artificial phospholipids and stearyl phosphatidylglycerol, which is applied in the field of medicine and chemical industry, can solve the problems of being unsuitable for industrial production and cumbersome reaction steps, and achieve the effects of facilitating industrial application, simplifying reaction steps, and mild reaction conditions

Inactive Publication Date: 2014-06-18
苏州东南药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses glycerol as a raw material, and it is necessary to protect and deprotect the dihydroxyl and monohydroxyl groups of the glycerol skeleton, and the reaction steps are cumbersome.
Not suitable for industrial production
And, this method produces racemic distearoylphosphatidylglycerol, and there is no literature report on the preparation method of a single optical isomer of distearoylphosphatidylglycerol

Method used

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  • Preparation method of artificial phospholipid DSPG
  • Preparation method of artificial phospholipid DSPG

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation of embodiment 1 (S)-1,2-diol-3-iodopropane

[0035] Add 0.08 g (0.1 mmol) of hydroquinidine 1,4-(2,3-naphthyridine) diether (DHQD) into a round bottom reaction flask 2 PHAL, 0.018g (0.05mmol)K 2 OSo 2 (OH) 4 , 9.8 g (30 mmol) K 3 Fe(CN) 6 , 4.2 g (30 mmol) K 2 CO 3 , 2.5 g (30 mmol) NaHCO 3 , 0.95g (10mmol) and 100mL of an aqueous solution of tert-butanol (tert-butanol: water = 1:1), stirred well at 0°C, then added 1.7g (10mmol) of 3-iodopropene to react for 6 hours, and added 10g Na 2 S 2 o 4 And continue stirring for 30 minutes to stop the reaction. The aqueous layer was separated and extracted with ethyl acetate, and the combined organic layers were washed with 1N KOH, dilute hydrochloric acid and saturated brine, respectively. Dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. Recrystallized from a mixed solvent of petroleum ether and methanol to obtain 1.58 g of (S)-1,2-diol-3-iodopropane with a yield of 78...

Embodiment 2

[0036] The preparation of embodiment 2 (R)-1,2-distearoyl-3-iodopropane

[0037] Stearic anhydride (0.8g, 1.5mmol), (S)-1,2-diol-3-iodopropane (0.2g, 1mmol) was added to 50mL of dichloromethane, stirred and refluxed at 40°C under nitrogen protection for 3 Hours, stop heating, after cooling to room temperature, pour 50mL of anhydrous diethyl ether. The organic layer was washed with 10 mL of 5% aqueous sodium bicarbonate solution and 10 mL of saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product that was recrystallized with ethanol to obtain 0.61 g of (S)-1,2-diol-3 - iodopropane, yield 83%.

Embodiment 3

[0038] The preparation of embodiment 3 (R)-1,2-distearoyl-3-(3,4-dimethoxybenzyloxy) phosphate propane

[0039](R)-1,2-Distearoyl-3-iodopropane (0.6g, 0.8mmol) and 3,4-dimethoxybenzyl silver phosphate (1.3g, 2.5mmol) were added under dark conditions into 50 mL of toluene, reflux for 6 h to stop the reaction, cool to room temperature, filter, wash with dichloromethane, combine the organic layers and concentrate under reduced pressure, and recrystallize the obtained crude product with ethanol to obtain 0.52 g of a white solid, with a yield of 65%.

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Abstract

The invention provides a preparation method of artificial phospholipid DSPG. The preparation method comprises the following steps: oxidizing 3-halogenated propylene serving as a raw material so as to obtain (S)-1, 2-diol-3-halogenated propane, then carrying out addition reaction between (S)-1, 2-diol-3-halogenated propane and stearic anhydride or stearoyl halide, introducing phosphate groups with protecting groups, and removing the protecting groups so as to obtain (R)-1, 2-glycerin distearate-glycerin-3-phosphatidic acid; finally carrying out addition reaction between (R)-1, 2-glycerin distearate-glycerin-3-phosphatidic acid and 2, 2-dimentyl-4-methyl alcohol-1, 3-dioxolame in anhydrous pyridine so as to obtain (R)-1, 2-distearoyl phosphatidyl glycerol. The preparation method is simple in steps, mild in reaction and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a preparation method of artificial phospholipid (R)-1,2-distearoylphosphatidylglycerol (DSPG). Background technique [0002] Phospholipids are an important part of biological membranes. The polar end containing phosphate is hydrophilic, and the non-polar ends of the two longer hydrocarbon chains are lipophilic. This unique physical and chemical property enables it to spontaneously dissolve in water. A closed bilayer is formed in the medium, which becomes a biomembrane skeleton and can be used as a liposome material in the pharmaceutical industry. However, as liposome materials, natural phospholipids have disadvantages such as short lifespan, easy oxidation, and poor stability, which limit their application. [0003] Distearoylphosphatidylglycerol (DSPG) is an important synthetic phospholipid, which is mainly used in the preparation of liposomes. It is an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/10
CPCY02P20/55
Inventor 吉民蔡进陈峻青李锐
Owner 苏州东南药业股份有限公司
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