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Photoreactive polysaccharide, photocrosslinking polysaccharide product, preparation method thereof and medical material prepared from the crosslinking polysaccharide

By combining glycidyl esters with photoreactive polysaccharides and cross-linking them with light irradiation, the problem of difficulty in balancing the barrier effect and degradation performance of existing polysaccharide products in the body is solved, and photo-cross-linked polysaccharide products with high strength and excellent degradation performance are achieved. , suitable for pharmaceutical applications such as anti-adhesive agents and drug sustained release.

Inactive Publication Date: 2007-08-15
SEIKAGAKU KOGYO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is a recurring paradox caused by conventional photocrosslinked polysaccharides used as anti-sticking agents
Especially if the barrier properties are made high, the retention of the product in the body becomes undesirably long, however, if suitable degradation properties are imparted, a sufficient barrier effect cannot be obtained
For example, when sponges or sheets made of traditional photo-crosslinked polysaccharide gels with high barrier effect are used as anti-adhesive agents, undesirable side effects may occur because the gels remain in the organism due to delayed metabolism. too long

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0137] Preparation of glycidyl cinnamate-introduced hyaluronic acid (hereinafter sometimes referred to as GLCN-HA) and cross-linked products thereof

[0138] 1-(1). Synthesis of GLCN-HA (reverse precipitation method)

[0139] 50 ml of water for injection and 75 ml of 1,4-dioxane were added to 100 ml of 1 wt % hyaluronic acid aqueous solution (weight average molecular weight: 800,000), and 3 ml of glycidyl cinnamate (epoxy equivalent: 240.3) was added thereto , followed by stirring for 24 hours in a thermostatic vessel at 50°C.

[0140] Sodium chloride (1 g) was added to the above solution, followed by stirring, and the mixture was poured into 800 ml of ethanol to obtain a cottony precipitate. The precipitate was washed well with ethanol and dried to obtain 1.1 g of GLCN-HA. The degree of substitution of glycidyl cinnamate was 2.9%.

[0141] 1-(2). Synthesis of GLCN-HA (general precipitation method).

[0142] Sodium chloride (1 g) was added to the solution prepared in the s...

Embodiment 2

[0166] Preparation of hyaluronic acid (hereinafter referred to as GLTA-HA) and its cross-linked product by introducing glycidyl thiophene acrylate

[0167] Synthesis of Hyaluronic Acid (GLTA-HA) Introducing Glycidyl Thiophene Acrylate:

[0168] Add 50 ml of water for injection and 75 ml of 1,4-dioxane to 100 ml of 1 wt % hyaluronic acid aqueous solution (weight average molecular weight: 800,000), and add 3 ml of glycidylthiophene acrylate (epoxy equivalent: 596.8) thereto , followed by stirring for 24 hours in a thermostatic vessel at 50°C.

[0169] Sodium chloride (1 g) was added to the resulting solution, followed by stirring, and the mixture was poured into 800 ml of ethanol to obtain a cottony precipitate. The resulting precipitate was washed well with ethanol and dried to obtain 1.1 g of GLTA-HA. The measured degree of substitution of glycidylthiophene acrylate was 1.4%.

[0170] Preparation of Photocrosslinked Hyaluronic Acid Gels.

[0171] A gel-like product was pre...

Embodiment 3

[0182] Preparation of hyaluronic acid (hereinafter referred to as GLCdN-HA) with glycidyl cinnamylidene acetate and its cross-linked products

[0183] Synthesis of hyaluronic acid (GLCdN-HA) introducing glycidyl cinnamylidene acetate:

[0184] Add 50 ml of water for injection and 75 ml of 1,4-dioxane in 100 ml of 1 wt % hyaluronic acid aqueous solution (weight average molecular weight: 800,000), and add 3 ml of glycidyl cinnamylidene acetate (epoxy equivalent : 444.3), followed by stirring in a constant temperature container at 50°C for 24 hours. Sodium chloride (1 g) was added to the solution, followed by stirring, and the mixture was poured into 800 ml of ethanol to give a cottony precipitate. The resulting precipitate was washed well with ethanol and dried to obtain 1.1 g of GLCdN-HA. The measured degree of substitution of glycidyl cinnamylidene acetate was 3.1%.

[0185] Preparation of Photocrosslinked Hyaluronic Acid Gels.

[0186] A gel-like product was prepared in t...

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Abstract

A photoreactive polysaccharide which comprises a polysaccharide bound to a glycidyl ester via a covalent bond, a photocrosslinked-polysaccharide prepared by using the photoreactive polysaccharide, and medical products comprising the photocrosslinked-polysaccharide.

Description

technical field [0001] The present invention relates to a photoreactive polysaccharide, a photocrosslinked polysaccharide product obtained by photocrosslinking the photoreactive polysaccharide, and a pharmaceutical product manufactured from the crosslinked compound. In particular, the present invention relates to a polysaccharide bonded to a glycidyl ester having a carboxyl group and an unsaturated carbon double bond that promotes photoreactivity and crosslinking, a photocrosslinked polysaccharide produced by irradiating the polysaccharide with light. Polysaccharide products, and pharmaceutical products comprising the photocrosslinked polysaccharides. Background technique [0002] Since polysaccharide is a safe polymer derived from living organisms, modified materials of polysaccharide have been attempted to be applied to various medical materials. [0003] An example of such a medicinal product is disclosed in Eur.J.Pharm.Sci., 2002 Mar;15(2):139-48, wherein polysaccharide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/00C08J9/28
CPCC08B37/0006C08L1/286A61K31/738C08B37/0039C08J2201/0484C08B37/003C08B37/0042A61K31/74C08J2305/08C08B37/0063A61L31/042C08B37/0036C08B37/0045C08L5/10C08B37/0069C08B37/0009C08B11/12C08L5/08C08B37/0075C08J3/075A61L27/20C08B37/0072C08L5/04C08B37/006C08B37/0084C08B37/00A61K47/36
Owner SEIKAGAKU KOGYO CO LTD