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Low molecular weight carboxyl-reduced derivatives of fucosylated glycosaminoglycans and preparation method and applications of low molecular weight carboxyl-reduced derivatives

A glycated sugar amine, low molecular weight technology, applied in the field of medicine, can solve the problems of non-response to treatment, no low molecular weight derivatives of FGAG carboxyl group, toxic and side effects, etc.

Inactive Publication Date: 2012-07-11
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Over the past two decades, great progress has been made in the basic research related to HIV virus and its infection, as well as in the applied basic research and clinical practice of drug treatment of AIDS (such as HIV reverse transcriptase / protease inhibitors), but the clinical treatment of AIDS There are still problems such as intractability, non-response to treatment, drug resistance and serious side effects
However, there is no public report on the structural modification of FGAG carboxyl to obtain its low molecular weight derivatives and its application in anti-HIV

Method used

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  • Low molecular weight carboxyl-reduced derivatives of fucosylated glycosaminoglycans and preparation method and applications of low molecular weight carboxyl-reduced derivatives
  • Low molecular weight carboxyl-reduced derivatives of fucosylated glycosaminoglycans and preparation method and applications of low molecular weight carboxyl-reduced derivatives
  • Low molecular weight carboxyl-reduced derivatives of fucosylated glycosaminoglycans and preparation method and applications of low molecular weight carboxyl-reduced derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] [Example 1] Carboxyl Reduction of Fucosylated Glycosaminoglycans

[0074] 1.1 Materials

[0075] FGAG: FGAG derived from Meihua ginseng, sea cucumber and yuzu sea cucumber, extracted and prepared according to the literature method (J. Biol. Chem., 1991, 266(21): 13530-13536). The purity was greater than 98% (HPGPC, area normalization method).

[0076] 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 1-phenyl-3-methyl-5-pyrazolone (PMP), HCl, NaBH 4 , NaCl and other reagents used: all commercially available analytical reagents; 4-chondroitin sulfate, glucose (Glc), glucuronic acid (GlcUA), acetamidogalactose (GalNAc) and fucose (Fuc) and other monosaccharides The reference substances are all products of sigma company; DCl and D 2 O is a product of Norell Company.

[0077] 1.2 Method

[0078] Weigh 300mg of FGAG and dissolve them in 48ml of water, adjust the pH to 4.75 with 0.1M HCl. 905 mg of solid EDC was added over the course of approximately 5 min and the pH...

Embodiment 2

[0085] [Example 2] Preparation of low molecular weight products by peroxide depolymerization

[0086] 2.1 Materials

[0087] CRG-1: FGAG carboxyl reduction product derived from plum flower ginseng, prepared according to the method of [Example 1]. Purity 98% (HPGPC, area normalization method), weight average molecular weight (Mw), 68,840.

[0088] h 2 o 2 , CH 3 COONa·3H 2 O, NaCl, NaOH, Cu(CH 3 COO) 2 ·H 2 Reagents used in O, etc.: All commercially available analytical reagents.

[0089] 2.2 Method

[0090] Preparation of oligomeric carboxyl reduction products: Dissolve 5.0 g of ginseng CRG-1 in 180 ml of aqueous solution in a round-bottomed flask, keep warm in a water bath at 35° C. and continue to stir evenly, then add copper chloride (Cu 2+ ) solution, and then drop 15% H at a rate of 10ml / h within 2 hours 2 o 2 , During the reaction process, 1N NaOH solution was used to control the pH value range from 7.2 to 7.8. After continuously stirring and reacting for 4 ...

Embodiment 3

[0103] [Example 3] Anti-HIV activity of low molecular weight fucosylated glycosaminoglycan carboxyl reduction product LCRG-1

[0104] 3.1 Materials

[0105] (1) Test sample: LCRG-1 (Mw12930Da) prepared in [Example 2] was dissolved in water for injection, prepared as a storage solution with a concentration of 25 mg / ml, and stored at 4°C.

[0106](2) Reagents: MTT (3-(4,5)-dimethylthiahiazo-2-y1)-2,5-diphenyltetrazoliumbromide), SDS (SodiumDodecylSulfate), DMSO (Dimethylsulfoxide) and other reagents are commercially available and analytically pure. Coagulation quality control plasma, activated partial thromboplastin time (APTT) assay kit, thrombin time (TT) assay kit, prothrombin time assay kit (PT-dry powder), all produced by TECO GmbH in Germany; all others Reagents were commercially available analytically pure.

[0107] Instrument: MC-4000 Hemagglutination Analyzer (Metron, Germany); ELx800ELISAReader Microplate Reader (Bote, USA)

[0108] (3) Cells and viruses: C8166, HIV...

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Abstract

The invention discloses low molecular weight carboxyl-reduced derivatives of fucosylated glycosaminoglycans (LCRG). The extent of carboxyl reduction is not less than 20%. Weight-average molecular weight of the LCRG is about 3000-20000Da, and monosaccharides comprise acetyl galactosamine (GalNAc), glucose (Glc) or glucuronic acid (GlcUA) and fucose (Fuc) or sulfates of fucose (shown as -OSO3-). The mole ratio of GalNAc, Glc (containing GlcUA), Fuc and -OSO3- is about 1: (1+-0.3): (1+-0.3): (3.0+-1.0). The LCRG is a potent human immunodeficiency virus (HIV) Type 1 entry inhibitor which acts on conserved regions and has the advantages of high activity against HIV Type 1, high therapeutic index and no-drug-resistance, and the LCRG can be used for preventing or curing HIV. The invention further provides a preparation method of the LCRG. The carboxyl-reduced derivatives of fucosylated glycosaminoglycans and medicinal compositions of the carboxyl-reduced derivatives can be prepared into injection agents, lyophilized powder or suppository and the like.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a low molecular weight carboxyl-reduced derivatives offucosylated glycosaminoglycans (LCRG) and a preparation method thereof, and a low molecular weight fucosylated glycosaminoglycan A pharmaceutical composition of carboxyl-reduced derivatives of polysaccharides and its application in the preparation of medicaments for preventing or treating AIDS. Background technique [0002] Acquired immunodeficiency syndrome (AIDS) caused by human immunodeficiency virus (humanimmunodeficiencyvirus, HIV) infection is a major disease that seriously endangers human life and health. Over the past two decades, great progress has been made in the basic research related to HIV virus and its infection, as well as in the applied basic research and clinical practice of drug treatment of AIDS (such as HIV reverse transcriptase / protease inhibitors), but the clinical treatment of AIDS There a...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K31/737A61P31/18
Inventor 刘吉开郑永唐赵金华吴明一黄宁李姿高娜文丹丹连武何江波
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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