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Polysaccharide pseudo-sponge

A polysaccharide and sponge technology, applied in the field of polysaccharide pseudosponge, can solve problems such as easy cracking of gel sheets, and achieve the effects of high barrier effect, high strength and excellent biodegradability

Inactive Publication Date: 2006-10-18
SEIKAGAKU KOGYO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Also, the problem of brittle gel sheets tends to be exacerbated by their high swelling properties, especially when used as anti-adhesion materials in living tissues

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0096] Hereinafter, the present invention is described in more detail through examples, but the examples are only for illustration and are not intended to limit the scope of the present invention. Meanwhile, technical terms and measurement methods used in the Examples are defined as follows.

[0097] (1) Degree of substitution of photoreactive groups

[0098] In the case of introducing a photoreactive group to the carboxyl group of a glycosaminoglycan as a polysaccharide, the degree of substitution of the photoreactive group refers to the number of photoreactive groups introduced per disaccharide repeating unit. percentage. The amount of glycosaminoglycan required to calculate the degree of substitution of photoreactive groups was measured by the carbazole method using its calibration curve. When using cinnamic acid or substituted cinnamic acid as the photoreactive substance, the amount of cinnamic acid was measured by absorbing The measurement method (measurement wavelength...

manufacture Embodiment 1

[0101] Production Example 1 (production of photoreactive hyaluronic acid):

[0102] A mixed solution containing 250 mL of water and 375 mL of dioxane was added to 500 g of 1 wt% sodium hyaluronate (comb-derived product, manufactured by Seikagaku Co., Ltd.; weight-average molecular weight: 900,000) under stirring. in aqueous solution. The resulting mixed solution was mixed successively with the following solutions at room temperature and stirred for 2.5 hours: a solution prepared by dissolving 860 mg of N-hydroxysuccinimide in 2 mL of water (0.6 equivalents / hyaluronic acid disaccharide unit (mol / mol) ), a solution prepared by dissolving 717mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCl / HCl) in 2mL of water (0.3 equivalents / hyaluronic acid disaccharide unit (mol / mol)) and 903mg aminopropyl cinnamate hydrochloride (HCl·H 2 N(CH 2 ) 3 A solution prepared by dissolving OCO-CH=CH-Ph, wherein Ph represents phenyl) in 2 mL of water (0.3 equivalents / disacch...

manufacture Embodiment 2

[0103] Manufacturing example 2 (manufacture of cross-linked hyaluronic acid gel):

[0104] (1) The cinnamic acid-introduced hyaluronic acid obtained in Production Example 1 was dissolved in water for injection to prepare a 4 wt% aqueous solution thereof. The resulting solution was poured into a tempered glass plate mold with a cavity of 6cm x 2.5cm x 1mm (thickness), and then irradiated with ultraviolet light on each surface for 15 minutes under water-cooling conditions using a 3kW metal halide lamp to obtain a transparent Sheet gel (water content: 96wt%). The cross-linking ratio of the obtained gel was determined to be 30%.

[0105] (2) The same procedure as defined in (1) above was carried out, except that cinnamic acid-introduced hyaluronic acid having a degree of substitution of 4.6% was produced using the same method as defined in Production Example 1, thereby obtaining a transparent sheet-like gel . The cross-linking ratio of the resulting gel was determined to be 13....

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Abstract

There is provided a photocrosslinked polysaccharide exhibiting a low swelling property and a high degradation ability in vivo while retaining a suitable strength. The polysaccharide pseudo-sponge is produced by a crosslinking reaction of a photoreactive polysaccharide obtained by introducing a photoreactive group into a polysaccharide, and exhibits a low swelling property and a blue dextran-low dyeaffinity which satisfy the following properties (I) and (II), respectively: (I) a swelling ratio of not more than 125% as calculated from the values measured by immersing a test specimen having a thickness of 1 mm, a length of 10 mm and a width of 10 mm, and a solvent content of 96% by weight, in water for injection at room temperature for 1 hour, according to the following formula: Swelling€ƒratio = { ( S 2 - S 1 ) / S 1 } × 100 wherein S1 represents an area of the test specimen before the immersion, and S2 is an area of the test specimen after the immersion, in which the area is calculated from the length and width of the test specimen; and (II) an absorbance of not more than 0.15 at a wavelength of 620 nm as measured with respect to an aqueous solution containing 0.67% by weight of a polysaccharide which is prepared by immersing a test specimen having a thickness of 1 mm, a length of 20 mm and a width of 10 mm, and a solvent content of 96% by weight, in an aqueous solution containing 0.5 g / mL of blue dextran having a weight-average molecular weight of 2,000,000, and then subjecting the test specimen to water-washing and hydrolysis.

Description

technical field [0001] The present invention relates to polysaccharide pseudosponges, and more particularly to polysaccharide pseudosponges combining sponge and gel properties, which are manufactured by cross-linking reactions of photoreactive polysaccharides obtained by introducing photoreactive groups into polysaccharides . Background technique [0002] Conventionally, there have been known photoreactive polysaccharides obtained by introducing photoreactive groups into polysaccharides, and crosslinked polysaccharides obtained by crosslinking photoreactive polysaccharides by irradiation of light such as ultraviolet rays (for example, Japanese Patent Application Publication (KOKAI) Nos. 6-73102(1994), 8-143604(1996), 9-87236(1997) and 2002-249501). In addition, gels (polysaccharide gels) or sponges (polysaccharide sponges) made of these crosslinked polysaccharides are also known. [0003] Polysaccharide gels have been produced by irradiating photoreactive polysaccharide so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K9/16A61K47/36A61L31/00C08B11/12C08B37/00C08B37/04
CPCA61K9/1652A61K47/36C08B37/0045C08B37/0084C08B37/00
Inventor 佐藤伦也
Owner SEIKAGAKU KOGYO CO LTD
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