Low molecular weight glycosylated chondroitin sulfate and its purpose in preparation of anti-HIV-1 medicament

A chondroitin sulfate and low-molecular-weight sugar technology, which is used in medical preparations, antiviral agents, and pharmaceutical formulations containing active ingredients, can solve problems such as significant toxic and side effects, drug resistance, and non-response to treatment. Separation and purification, stable depolymerization speed, and the effect of avoiding drug resistance

Inactive Publication Date: 2011-11-23
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

Although great progress has been made in the treatment of AIDS, there are still defects such as difficult to cure, non-response to treatment, emergence of drug resistance, and significant side effects
At present, HAART treatment is ineffective for about 30% of AIDS patients due to reasons such as treatment non-response or drug resistance

Method used

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  • Low molecular weight glycosylated chondroitin sulfate and its purpose in preparation of anti-HIV-1 medicament
  • Low molecular weight glycosylated chondroitin sulfate and its purpose in preparation of anti-HIV-1 medicament
  • Low molecular weight glycosylated chondroitin sulfate and its purpose in preparation of anti-HIV-1 medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] [Example 1] Preparation of low molecular weight glycosylated chondroitin sulfate (LGC)

[0067] 1.1 Materials:

[0068] Plum ginseng (Thelenota ananas Jaeger), commercially available, gutted and dried body wall;

[0069] H 2 O 2 , CH 3 COONa 3H 2 O, NaCl, NaOH, Cu(CH 3 COO) 2 ·H 2 The reagents used in O etc. are all commercially available analytically pure reagents.

[0070]1.2 Method:

[0071] (1) Preparation of Glycosylated Chondroitin Sulfate (GCs): Take the dried body wall of Echinoderm Prunus chinensis, and prepare GCs according to the literature method (J Biol Chem, 1991, 266(21): 13530-6), with a yield of 0.75% , purity 98% (HPGPC, area normalization method), weight average molecular weight (Mw), 65,820.

[0072] (2) Preparation of low-molecular-weight glycosylated chondroitin sulfate (LGC): 5.0 g of GCs obtained in step (1) was added to a round-bottomed flask, 180 ml of distilled water was added to dissolve it, the temperature was kept in a water bath ...

Embodiment 2

[0090] [Example 2] Preparation of a series of molecular weight LGC-1

[0091] 2.1 Materials:

[0092] The GCs derived from Plum ginseng were prepared by the method described in Example 1.

[0093] H 2 O 2 , CH 3 COONa 3H 2 O, NaCl, NaOH, Cu(CH 3 COO) 2 ·H 2 The reagents used in O etc. are all commercially available analytically pure reagents.

[0094] 2.2 Method:

[0095] (1) Preparation of LGC-1 samples with a series of molecular weights: Four GCs derived from Plum ginseng, 5 g each, were depolymerized by the method described in step (2) of Example 1, but the time points for terminating the reaction were 90, 120, 360, and 420 min, respectively. . The LGC-1 products thus prepared are respectively numbered: LGC-1B, LGC-1C, LGC-1D and LGC-1E. The yields of the depolymerization reactions were all greater than 70%.

[0096] (2) LGC-1 product detection: HPGPC detection of molecular weight and distribution; conductivity detection-OSO 3 - / -COO - Molar ratio; optical r...

Embodiment 3

[0103] [Example 3] Terminal reductive amination of LGC-1A

[0104] 3.1 Materials:

[0105] LGC-1A: Example 1 Preparation of depolymerized GCs product.

[0106] Tyramine hydrochloride and sodium cyanoborohydride: both are commercially available analytical reagents.

[0107] 3.2 Method:

[0108] (1) Terminal reductive amination of LGC-1A: 1000 mg of GCs depolymerization product LGC-1A was dissolved in 35 ml of 0.2 mM phosphate buffer (PBS, pH 8.0), and an excess of 800 mg of tyramide and 300 mg of cyanoboron were added during stirring. Sodium hydride was reacted in a constant temperature water bath at 35°C for about 100hr. After the reaction is completed, add 105 ml of 95% ethanol, and centrifuge to obtain a precipitate. After the obtained precipitate is washed twice with 30 ml of 95% ethanol, the obtained precipitate is redissolved with 35 ml of 0.1% NaCl, centrifuged to remove insoluble matter, and the supernatant is placed on Seph adex. TM G-100 column, eluted with 0.1% ...

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Abstract

The invention discloses a low molecular weight glycosylated chondroitin sulfate, whose weight average molecular weight is 3000-15000Da. The monosaccharide composition comprises acetyl galactosamine (D-GalNAc), glucuronic acid (D-GlcUA), fucose (L-Fuc), or its sulfuric ester (expressed in -OS03<->), wherein the mole ratio of D-GalNAc to D-GlcUA to L-Fuc to -OS03<-> is 1: (1+/-0.3): (1+/-0.3): (3.5+/-0.5). The low molecular weight glycosylated chondroitin sulfate has a strong anti-HIV-1 virus activity, is a gp120 entry inhibitor, and can be used for preventing and/or treating AIDS. The invention also provides a method for preparing the low molecular weight glycosylated chondroitin sulfate and its composition preparation. Glycosylated chondroitin sulfate is depolymerized by the peroxide method to obtain a low molecular weight product, and then low molecular and/or high-molecular impurities of the product are removed by gel separation or ultrafiltration method. The low molecular weight glycosylated chondroitin sulfate and its medicinal composition can be prepared in the form of an injection, a lyophilized powder or a suppository.

Description

technical field [0001] The invention relates to a low molecular weight glycosylated chondroitin sulfate (LGC) and a preparation method thereof, a medicinal composition containing LGC and its use in the preparation of medicines for preventing and / or treating AIDS. Background technique [0002] Acquired immunodeficiency syndrome (AIDS) caused by human immunodeficiency virus (HIV-1) infection is a major disease that seriously endangers human life and health. According to a report released by UNAIDS on November 23, 2010, an estimated 33.3 million people worldwide are living with HIV and 25 million people have died since AIDS was first identified in June 1981. In China, as of the end of 2009, an estimated 740,000 adults and children were living with HIV, and 48,000 were new infections in 2009. Of these patients, an estimated 105,000 had AIDS cases and 26,000 died of AIDS-related causes in 2009. In addition to complication treatment, anti-infection treatment, and immunomodulator...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/737A61P31/18C08B37/08
Inventor 赵金华刘吉开郑永唐吴明一黄宁李姿何江波
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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