Thioctic acid-glucan conjugate, preparation method and usage thereof

A technology of glucan and lipoic acid, applied in the field of pharmacy, can solve the problems of unstable raw material quality and low encapsulation rate, and achieve the effect of increasing lipophilic performance

Inactive Publication Date: 2010-03-17
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the limitation of the quality and stability of the main excipient of liposomes—medicinal phospholipids, after more than 30 years of full research, problems such as unstable raw material quality, low encapsulation efficiency, and rapid elimination in the body have been overcome. Obtained marketing authorization from FDA in 1995

Method used

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  • Thioctic acid-glucan conjugate, preparation method and usage thereof
  • Thioctic acid-glucan conjugate, preparation method and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 1.0g (6.17mmol anhydrous glucose unit) dextran (molecular weight is 70,000) is dissolved in 20ml mixed solvent (formamide: dimethylformamide: dichloromethane=10:10:1 (v / v / v) ), heat at 30°C for 2 hours, add 0.64g (6.17mmol) of lipoic acid, dissolve and add 75mg (0.61mmol) of DMAP, stir to dissolve, add 0.65g (6.17mmol) of dicyclohexylcarbodiimide, and stir , 30 ℃ heat preservation reaction for 24 hours. The generated dicyclohexyl urea was removed by filtration, and the filtrate was poured into 160ml of methanol:ether (3:1, V / V) mixture, a solid precipitated, collected by filtration, washed with 50ml of ether and 50ml of acetone in turn. Dry in the presence of phosphorus pentoxide and store in a desiccator. The yield is 52.4%, the molecular weight of the obtained product is 89,000, and the substitution degree of lipoic acid on dextran is 20.1% by weight.

[0046] The product was confirmed by UV. at 1720cm -1 There are characteristic absorption peaks of ester bonds ne...

Embodiment 2

[0048] By the method of embodiment 1, increase the ratio of raw material lipoic acid and dextran.

[0049] 1.0g dextran (molecular weight: 40,000) was dissolved in 40ml mixed solvent (formamide: dimethylformamide: dichloromethane = 6:6:1 (v / v / v)), and kept at 40°C for 1 hour , add lipoic acid 1.28g (12.3mmol), after dissolving, add 100mg (0.82mmol) DMAP, stir to dissolve, add dicyclohexylcarbodiimide 1.30g (12.3mmol), under stirring, 40 ℃ insulation reaction for 20 hours. The generated dicyclohexylurea was removed by filtration, and the filtrate was poured into 200ml of methanol:water (1:3, V / V) mixture, a solid was precipitated, collected by filtration, washed with 50ml of methanol and 50ml of water successively. Dry in the presence of phosphorus pentoxide and store in a desiccator. The yield is 40.8%, the molecular weight of the obtained product is 74,000, and the substitution degree of lipoic acid on dextran is 45.5% by weight.

[0050] The product was confirmed by UV. a...

Embodiment 3

[0052] 1.0g (6.17mmol) of carbonyldiimidazole was dissolved in 20ml of tetrahydrofuran, at room temperature, 0.64g (6.17mmol) of lipoic acid was added, stirred for 2 hours, THF was evaporated under reduced pressure, the solid was dissolved by adding 5ml of DMSO, and then dissolved in 1.0 g (6.17 mmol of anhydrous glucose unit) dextran (70,000 molecular weight) in DMSO solution 15 ml and 0.62 g of triethylamine were stirred and reacted at 30° C. for 24 hours. The reaction solution was poured into 200ml of methanol:ether (3:1, V / V) mixture, and a solid precipitated out, which was collected by filtration and washed successively with 50ml of ether and 50ml of acetone. Dry in the presence of phosphorus pentoxide and store in a desiccator. The yield is 35.5%, the molecular weight of the obtained product is 87,000, and the substitution degree of lipoic acid on dextran is 19.5% by weight.

[0053] The product was confirmed by UV. at 1720cm -1 There are characteristic absorption pea...

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Abstract

The invention relates to a thioctic acid-glucan conjugate, a preparation method and the usage thereof. The functional thioctic acid-glucan conjugate is designed and synthesized by taking glucan as rawmaterial, and the degree of substitution of thioctic acid on the glucan is 0.1-50% based on the weight percent. The active carboxyl contained by the thioctic acid and the hydroxy on the glucan can bedirectly esterified, and the thioctic acid-glucan conjugate can be prepared. By controlling different degrees of substitution of the thioctic acid, glucan derivatives having different properties canbe obtained. The thioctic acid-glucan conjugate can be taken as thioctic acid polymer drug and novel pharmaceutic adjuvant.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to a novel drug lipoic acid-dextran conjugate and its preparation method and application. Background technique [0002] The new drug delivery system can enter the body through various routes of administration, so that the carried drugs have targeted and sustained release effects, accumulate in lesion sites, tissues and cells and release slowly, thereby enhancing the efficacy of drugs. In terms of dosage forms, the new drug delivery system mainly refers to nano-drugs, including liposomes, nanoparticles, microspheres, vesicles, microemulsions, micelles, gels, self-emulsification, transfersomes, inclusion complexes, macromolecular couples, etc. joint things, etc. At present, nano-medicines have been industrialized, mainly including liposome preparations (doxorubicin, amphotericin, daumycin, daunorubicin and gentamicin, etc.), nanoparticles, microemulsions (cyclosporin A microemuls...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/36A61K47/22A61K31/385A61P3/10A61P25/00A61P39/06A61P1/16A61P3/06
Inventor 郝爱军陈长兰陈立江
Owner LIAONING UNIVERSITY
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