Hyaluronic acid oligosaccharide fractions and drugs containing the same

A technology of hyaluronic acid and oligosaccharides, applied in the direction of medical preparations containing active ingredients, sugar derivatives, sugar derivatives, etc., can solve problems such as no description or hint

Inactive Publication Date: 2003-09-03
SEIKAGAKU KOGYO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this publication, it is described that the average molecular weight of HA is preferably 100,000 or more, but there is no description or hint about HA oligosaccharides and their excellent effects.

Method used

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  • Hyaluronic acid oligosaccharide fractions and drugs containing the same
  • Hyaluronic acid oligosaccharide fractions and drugs containing the same
  • Hyaluronic acid oligosaccharide fractions and drugs containing the same

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0207] Preparation and physicochemical properties of oligosaccharides of the present invention and fractions of the present invention

[0208] 1. The preparation of oligosaccharide of the present invention and fraction of the present invention

[0209] The oligosaccharide of the present invention and the fraction of the present invention were prepared using the sodium salt of HA isolated and purified from cockscomb as a raw material by the following method. In addition, the sodium salt of HA as a raw material showed a single band by electrophoresis using a cellulose acetate membrane (electrophoresis buffer: pyridine-formic acid buffer, current: 15 mA, electrophoresis time: 30 minutes), and HA was not detected Other mucopolysaccharides (chondroitin, 4-chondroitin sulfate, 6-chondroitin sulfate, chondroitin sulfate E, chondroitin sulfate D, heparin, heparan sulfate, dermatan sulfate). (Preparation Example 1) Decomposition by Hyaluronidase

preparation example 1

[0209] The oligosaccharide of the present invention and the fraction of the present invention were prepared using the sodium salt of HA isolated and purified from cockscomb as a raw material by the following method. In addition, the sodium salt of HA as a raw material showed a single band by electrophoresis using a cellulose acetate membrane (electrophoresis buffer: pyridine-formic acid buffer, current: 15 mA, electrophoresis time: 30 minutes), and HA was not detected Other mucopolysaccharides (chondroitin, 4-chondroitin sulfate, 6-chondroitin sulfate, chondroitin sulfate E, chondroitin sulfate D, heparin, heparan sulfate, dermatan sulfate). (Preparation Example 1) Decomposition by Hyaluronidase

[0210] Dissolve 25 g of sodium salt of HA in 1.IL of 0.1 M phosphate buffer (pH 5.3) containing 0.15 M NaCl. To the obtained solution, 200 mg of hyaluronidase (5.342 units / mg; manufactured by Seikagaku Kogyo Co., Ltd.) derived from bovine testis was added and reacted at 37° C. for 9...

preparation example 2

[0213] HA4(330mg), HA6(1210mg), HA8(305mg), HA10(1625mg), HA12(685mg), HA14(620mg), HA16(430mg), HA18(210mg), HA20(202mg), HA22(819mg), HA24(197mg), HA26(187mg), HA28(159mg), HA30(137mg), HA32(122mg), HA34(102mg), HA36(91mg), HA38(89mg), HA40(65mg), HA42(76mg), HA44 (61 mg), HA46 (58 mg), HA48 (46 mg), HA50 (48 mg), HA52 (21 mg). (Preparation Example 2) Decomposition of ACI by Chondroitinase

[0214] Dissolve 8 g of sodium salt of HA in 500 ml of 0.1 M acetic acid buffer (pH6.0) containing 0.1% bovine serum albumin.

[0215] To the obtained solution, 32 units of chondroitinase ACI (manufactured by Seikagaku Kogyo Co., Ltd.) was added and reacted at 37° C. for 6 hours.

[0216] After the reaction, the supernatant was collected by centrifugation at 10,000 rpm for 30 minutes. The recovered supernatant was loaded onto a Dowex 1×2 (100-200 mesh) (manufactured by Dow chemical) ion-exchange column (φ4.5×123 cm), and eluted by a linear concentration gradient (0.01M-0.50M) of NaCl ...

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Abstract

The invention provides hyaluronic acid oligosaccharides having a size selected from sizes of 4 to 60 saccharides, fractions containing the hyaluronic acid oligosaccharides and having particular physicochemical properties, and drugs containing the same. The hyaluronic acid oligosaccharides of the present invention are extremely useful, because they exert superior pharmaceutical effects as active ingredients of a heat shock protein expression promoter, cell death inhibitor, cell injury inhibitor and cell and tissue protecting agent (e.g., organ preservation agent, antiulcer agent, antihepatopathic agent, IL-10 production promoter or IL-8 production inhibitor) and exhibit high safety.

Description

technical field [0001] The present invention relates to hyaluronic acid oligosaccharides (hereinafter referred to as "HA oligosaccharides") and novel fractions thereof. [0002] And the present invention also relates to medicines (especially for heat shock protein expression enhancers, cell death inhibitors, cell barrier inhibitors, or cell and tissue protection agents (especially for organ preservation) using this HA oligosaccharide as an active ingredient. agent, ulcer treatment agent, and liver disorder treatment agent, IL-10 production accelerator, or IL-8 production inhibitor). Background technique [0003] As for hyaluronic acid (hereinafter referred to as "HA"), it is known that its activity or function varies with its molecular size. For example, HA with a molecular weight of 1.2 million can inactivate NF-κb and inhibit angiogenesis [High molecular weight hyaluronic acid inhibits advanced glycation endproduct-induced NF-kappaB activation and cytokine expression. Neu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/702A61K31/728A61P1/04A61P1/16A61P43/00C07H7/033C08B37/08
CPCA61K31/702A61K31/728C07H7/033C08B37/0072A61P1/04A61P1/16A61P43/00
Inventor 浅利晃栗原仁柴田知己宫崎由佳山之口裕子多和田明政孝浩松崎祐二
Owner SEIKAGAKU KOGYO CO LTD
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