WO2003085001A1 - Polysaccharide contenant un groupe phosphorylcholine et procede de production correspondant - Google Patents
Polysaccharide contenant un groupe phosphorylcholine et procede de production correspondant Download PDFInfo
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- WO2003085001A1 WO2003085001A1 PCT/JP2003/004430 JP0304430W WO03085001A1 WO 2003085001 A1 WO2003085001 A1 WO 2003085001A1 JP 0304430 W JP0304430 W JP 0304430W WO 03085001 A1 WO03085001 A1 WO 03085001A1
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- polysaccharide
- phosphorylcholine
- group
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- structural formula
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/20—Post-etherification treatments of chemical or physical type, e.g. mixed etherification in two steps, including purification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0018—Pullulan, i.e. (alpha-1,4)(alpha-1,6)-D-glucan; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
Definitions
- the present invention relates to a polysaccharide having a phosphorylcholine group and a production method.
- the phosphorylcholine group-containing polysaccharide of the present invention is excellent in biocompatibility and moisture retention, and is useful as a medical polymer material. Specifically, it is used, for example, as a coating agent for artificial organs, biological membranes, and medical devices, drug delivery, and cosmetic ingredients. Background art
- Polymers having phosphorylcholine groups have been developed as biocompatible materials.
- a method for synthesizing a polymer having a phosphorylcholine group an acrylic monomer mainly having a hydroxyl group is reacted with 2-chloro-1,3-, 2-dioxaphosphorane-12-oxide, and trimethyl chloride is further reacted.
- a method of synthesizing a monomer having a phosphorylcholine structure by converting it into a quaternary ammonium with an amine and polymerizing the monomer has been adopted.
- the conventional production method of polymerizing a monomer having phosphorylcholine in a side chain has a problem that the polymerization yield is reduced or a desired polymer cannot be obtained due to steric hindrance of the phosphorylcholine group.
- the present inventors have conducted intensive studies on a method for producing a phosphorylcholine group-containing polymer, and as a result, reacted a phosphorylcholine group-containing compound with a polysaccharide having a functional group reactive with the compound. Then, the present inventors have found that a polysaccharide having a phosphorylcholine structure can be obtained easily and with high versatility by a polymer reaction in a side chain of the polymer, thereby completing the present invention. Disclosure of the invention
- the present invention provides a polysaccharide having a phosphorylcholine group represented by the following general formula (1).
- the present invention provides a polysaccharide having a phosphorylcholine group represented by the following general formulas (2) to (10).
- n is :! Integers of ⁇ 22, m :! An integer of 220, S UG AR represents a polysaccharide.
- R1, R2, and R5 represent 0, NH, or tertiary amine.
- R 3 and R 4 each represent a linear or branched alkylene having 1 to 22 carbon atoms or ethylene oxide having a repeating unit of 1 to 20.
- R 6 represents an aromatic-containing hydrocarbon or a perfluoroalkylene group having 1 to 22 carbon atoms.
- k is an integer of 0 to 6
- n, m, q are positive integers
- sugar further c represents a polysaccharide
- the present invention is an aldehyde-containing compound obtained by the oxidative cleavage reaction of glycerin port phosphorylcholine down To a polysaccharide having a phosphorylcholine group, which is characterized by adding It is.
- FIG. 1 is a scheme for preparing a monofunctional aldehyde containing a phosphorylcholine group.
- FIG. 2 is a production scheme of the polysaccharide represented by the general formula (2).
- FIG. 3 shows a structural formula and an NMR spectrum of Synthesis Example 1.
- FIG. 4 is a structural formula of Synthesis Example 2.
- FIG. 5 shows the structural formula and NMR spectrum of Synthesis Example 3.
- FIG. 6 shows the structural formula and NMR spectrum of Synthesis Example 4.
- FIG. 7 is a structural formula of Synthesis Example 5.
- FIG. 8 is a structural formula of Synthesis Example 6.
- FIG. 9 is a structural formula of Synthesis Example 7.
- FIG. 10 shows the structural formula and NMR spectrum of Synthesis Example 8.
- FIG. 11 is a structural formula of Synthesis Example 9.
- FIG. 12 shows the structural formula and NMR spectrum of Synthesis Example 10.
- FIG. 13 is a structural formula of Synthesis Example 11
- FIG. 14 is a structural formula of Synthesis Example 12.
- FIG. 15 is a structural formula of Synthesis Example 13.
- FIG. 16 is a structural formula of Synthesis Example 14.
- FIG. 17 is a structural formula of Synthesis Example 15.
- FIG. 18 is a structural formula of Synthesis Example 16.
- FIG. 19 is a structural formula of Synthesis Example 17.
- FIG. 20 is a structural formula of Synthesis Example 18.
- FIG. 21 is a structural formula of Synthesis Example 19.
- FIG. 22 is a structural formula of Synthesis Example 20.
- FIG. 23 is a structural formula of Synthesis Example 21.
- FIG. 24 is a graph showing the results of the hemolysis test. BEST MODE FOR CARRYING OUT THE INVENTION
- the method for producing the polysaccharide having a phosphorylcholine group of the present invention is as follows.
- the production method of the present invention by the reaction (1) has a great advantage that the introduction yield is high and the introduction rate can be easily controlled.
- the desired functions of the functional polymer material can be obtained by imparting the necessary functions to the sugar chain by a hydrophobic group or the like without being affected by the phosphorylcholine group, and then adding an arbitrary amount of the phosphorylcholine group. Can be easily obtained.
- a polymer in which phosphorylcholine is introduced into the main chain of a polysaccharide and a polymer in which phosphorylcholine is introduced into the main chain of a polymer introduced into the polysaccharide can be synthesized, and can be used properly depending on the application.
- oxidative cleavage of glycerol phosphorylcholine The aldehyde-containing compound obtained by the reaction is a very simple step, which oxidatively cleaves a known glycerol phosphorylcholine group by a known method.
- 1,2-diol is oxidized with periodate or periodate to cleave the bond, and two aldehydes are obtained. Generates aldehyde and formaldehyde.
- the reaction is usually performed in water or an organic solvent containing water. The reaction temperature ranges from 0 ° C to room temperature. The aldehyde may undergo hydration through equilibrium reaction in water, but does not affect the subsequent reaction with amine.
- the polysaccharide having an amino group is not particularly limited. It is only necessary that the side chain of the polysaccharide has an amino group capable of reacting with an aldehyde obtained by oxidative cleavage of glycerol phosphorylcholine.
- Known polysaccharides can be used.
- An amino group can be introduced into a known polysaccharide by a known method to design a polysaccharide suitable for the intended use.
- Polysaccharides include, for example, dextran, cellulose, hyaluronic acid, plurane, darcomannan, chondroitin sulfate, agarose, pectin, chitin, chitosan, gum arabic, carrageenan, juran, guar gum, arginic acid, xanthan gum, amylose , Leozan and the like.
- a carboxylic acid is introduced by a carboxymethylation reaction, followed by an amidation reaction with diamine.
- a polysaccharide having an amino group such as chitosan can be directly subjected to a phosphorylcholine introduction reaction.
- the phosphorylcholine group content of the final product can be designed based on the amino group content.
- an ordinary polysaccharide having a reducing end and a polymer having an amino group such as polylysine or polyethyleneimine can be coupled by reductive amination to obtain an amino group-containing polysaccharide.
- the reductive amination reaction in which the aldehyde (or hydrate polymer) obtained by oxidative cleavage of glycerol phosphorylcholine is bonded to the amino group of the polymer, is easily performed by stirring both in a solvent. You can do it.
- both are dissolved in water or alcohol (the organic solvent of the third component may be mixed) to form an imine, which is then reduced with a reducing agent to obtain a secondary amine.
- a mild reducing agent such as sodium cyanoboronate is preferable.
- other reducing agents can be used.
- the c reaction is usually performed at 0 ° C. to room temperature. May be heated. According to the above-mentioned production method, a polysaccharide containing a phosphorylcholine group in a hydrophilic portion in an arbitrary amount can be easily obtained.
- a polymer containing a structure of a biomembrane component such as phosphatidylethanolamine, phosphatidinoreserin, phosphatidylinositol ⁇ /, diphosphatidylglycerol can be designed.
- the hydrophilic part of the polysaccharide contains a carboxylic acid group, a hydroxyl group, a primary to tertiary amino group, a sulfonate group, a phosphate group, a polyoxyethylene group, an ammonium group, an amide, a carboxybetaine, a saccharide, etc.
- the function can be designed with these types and contents.
- hydrophobic portion of the polysaccharide examples include a linear or branched alkyl having 1 to 22 carbon atoms, a cyclic alkyl such as cholesterol, an alkyl group having an unsaturated bond such as oleyl, a benzene ring, a naphthalene ring, and pyrene.
- Hydrophobic groups such as hydrocarbon-based aromatics, pyridine rings, heteroaromatics such as imidazole, thiazol and indole, and hydrophobic groups such as perfluoroalkyl and polyalkylsiloxane are introduced according to the intended use. Can be designed.
- the bonding form of the hydrophobic group may be directly bonded to the main chain by an ester, ether, amide, urethane, urea bond, or the like, or may be bonded to the main chain via a spacer.
- the spacer include hydrophilic polyethylene oxide, hydrophobic polypropylene oxide, and linear alkyl (2 to 22 carbon atoms).
- the polysaccharide of the present invention represented by the general formulas (1) to (10) can be easily produced.
- the polysaccharides represented by the general formulas (2) to (10) are characterized in that the polysaccharide and phosphorylcholine are bonded via a secondary amine.
- the binding site of phosphorylcholine is directly linked to the polymer main chain via secondary amine.
- a polysaccharide and phosphorylcholine can be bound via a secondary amine, or a polymer in which an acryl-based polymer or the like is bound to a sugar chain terminal in a block-like manner. It is also possible to bind phosphorylcholine via a secondary amine.
- the polysaccharide having a phosphorylcholine group of the present invention is a polysaccharide polymer material excellent in hydrophilicity and moisture retention.
- “sugar” representing a polysaccharide is a straight-chain or branched alkyl group having 1 to 22 carbon atoms, a perfluoroalkyl group, an aromatic group, or a heterocyclic group. It may contain an aromatic group.
- the polysaccharides of the general formulas (8) to (10) are polymers obtained by adding a phosphorylcholine group and a polysaccharide to the main chain of the polymer.
- a repeating unit in which a polysaccharide and a phosphorylcholine group are added is polymerized randomly.
- m, n, and q are positive integers, and represent a group in the polymer of a repeating unit to which a polysaccharide and a phosphorylcholine group are respectively added. Can be expressed.
- a repeating unit in which a polysaccharide and a phosphorylcholine group are added to a polymer having an amino group to produce the polymer by a high-molecular reaction may be.
- the polysaccharide in the general formulas (2) to (7) is not particularly limited, and any polysaccharide can be used as long as it has a hydroxyl group and is soluble in a reaction solvent.
- the polysaccharide in the general formulas (8) to (10) has a reducing terminal, and any polysaccharide can be used as long as it is soluble in the reaction solvent.
- the polysaccharide having a phosphorylcholine group represented by any one of the general formulas (2) to (10) is produced from the polysaccharide having an amino group represented by the following general formulas (11) to (19). Can be manufactured more easily.
- a sugar having an amino group such as chitosan
- a sugar having an amino group can be used.
- n is an integer of 1 to 22
- m is an integer of 1 to 20
- SUGAR represents a polysaccharide
- R1, R2, and R5 represent O, NH, or a tertiary amine.
- R 3 and R 4 each represent a linear or branched alkylene having 1 to 22 carbon atoms, or ethylene oxide having a repeating unit of 1 to 20.
- R 6 represents an aromatic-containing hydrocarbon or a perfluoroalkylene group having 1 to 22 carbon atoms.
- k is an integer of 0 to 6
- n, m, q are positive integers
- sugar in c Figure 1 representing a polysaccharide
- schemes for preparing aldehydes of monofunctional containing phosphorylcholine group general formula 2
- the production scheme of the polysaccharide of (2) is shown.
- Polysaccharides of the general formulas (3) to (11) can be obtained in exactly the same manner.
- FIG. 6 shows the structural formula and the NMR spectrum.
- FIG. 10 shows the structural formula and NMR spectrum.
- FIG. 11 shows the structural formula.
- Figure 14 shows the structural formula. Synthesis Example 13 Synthesis of hydrophobized phosphorinolecollin cellulose
- Figure 15 shows the structural formula. Synthesis Example 14 Synthesis of hydrophobized phosphorylcholine hyaluronic acid
- FIG. 16 shows the structural formula.
- Synthesis Example 15 Synthesis of hydrophobized phosphorylcholine pullulan A solution of lauric acid (0.02 g) in DMF (15 ml) was added to the aqueous solution (15 ml) of aminopullulan (1 g) in Synthesis Example 7, and 1 ⁇ 3- (dimethylamino) propyl ⁇ 3-ethylcarbyl was added. Slowly add 1.5 g of posimid hydrochloride. After stirring at room temperature for 1 ⁇ , the reaction solution is dialyzed in water, 1 g of phosphorylcholine aldehyde of Synthesis Example 1 is added to the aqueous solution, and the mixture is stirred at room temperature for 5 hours. Add 500 mg of sodium hydrogen cyanoboronate, and stir with stirring. Purify by dialysis and freeze-drying to obtain 1.1 g of the desired product.
- Hyaluronic acid (1 g) and polylysine (1 g) are dissolved in 15 ml of distilled water and stirred at room temperature for 5 hours. Add 50 mg of sodium hydrogen cyanoboronate and stir overnight. Dialysis, and purified by freeze-drying, 1 to obtain the desired product 1.8 5 8: The structural formula in FIG 8. Synthesis Example 17 Synthesis of dextran-polyallylamine
- Dextran (1 g) and polyallylamine (1 g) are dissolved in 15 ml of distilled water and stirred at room temperature for 5 hours. Add 500 mg of sodium hydrogen cyanoboronate and stir overnight. Purification by dialysis and freeze-drying gives 1.6 g of the desired product.
- Hydroxicetinoresenorelose (lg) and Hydroxicetinoresenorelose Poly N-isopropylacrylamide-Poly N- (3-aminopropyl) meta Dissolve the acrylamide 1: 1 copolymer (1 g) in 15 ml of distilled water and stir at room temperature for 5 hours. Add 500 mg of sodium cyanoborohydride and stir overnight. Purify by dialysis and freeze-drying to obtain 1.5 g of the desired product.
- FIG. 21 shows the structural formula.
- Synthesis Example 20 Synthesis of dextran-phosphorylcholine polyallylamine 1 g of the phosphorylcholine aldehyde of Synthesis Example 1 was added to an aqueous solution (15 ml) of dextran-polyallylamine (1 g) of Synthesis Example 18; Stir at room temperature for hours. Add 50 mg of sodium hydrogen cyanoboronate and stir overnight. Purification by dialysis and lyophilization gives 1.2 g of the desired product.
- Degree of hemolysis (%) ⁇ (UV absorption of polymer-supplemented blood supernatant) 1 / (UV absorption of polymer-free supernatant) ⁇ / ⁇ (Complete hemolysis blood supernatant UV absorption)-(polymer-free supernatant) UV absorption) xl OO
- the degree of hemolysis (%) in the hemolysis test results is shown in Table 1 and Figure 24.
- the degree of hemolysis (%) of the polymers into which the phosphorine groups were introduced, produced in Synthesis Examples 8 to 15 was almost 0% so that they all overlapped the horizontal axis, indicating no hemolysis reaction. . Therefore, it can be seen that all of the polysaccharides (polymers) into which the phosphoryl group has been introduced according to the present invention have extremely high blood compatibility.
- the phosphorylcholine group-containing polysaccharide of the present invention has high biocompatibility and moisturizing properties, is a useful polymer material, and can be used for various components such as artificial organs, biological membranes, coating agents for medical devices, drug delivery, and cosmetic ingredients. There are application fields.
- the production method of the present invention has a great advantage that a phosphorylcholine group-containing polymer that is optimal for a specific application as a biocompatible polymer material or the like can be freely designed.
- the most suitable material for the intended use can be obtained by freely designing the polysaccharide to introduce a hydrophobic group without being affected by the phosphorylcholine group. Thereafter, an arbitrary amount of a phosphorylcholine group is added, and the desired functional polymer material can be easily obtained.
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Description
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP03715780A EP1493754B1 (en) | 2002-04-09 | 2003-04-08 | Polysaccharide containing phosphorylcholine group and process for producing the same |
KR1020047013002A KR100977788B1 (ko) | 2002-04-09 | 2003-04-08 | 포스포릴콜린기 함유 다당류 및 그 제조 방법 |
US10/506,771 US7348424B2 (en) | 2002-04-09 | 2003-04-08 | Polysaccharide containing phosphorylcholine group and process for producing the same |
DE60321778T DE60321778D1 (de) | 2002-04-09 | 2003-04-08 | Polysaccharid mit phosphorylcholingruppe und herstellungsverfahren dafür |
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JP2002-106356 | 2002-04-09 | ||
JP2002106356A JP4248189B2 (ja) | 2002-04-09 | 2002-04-09 | ホスホリルコリン基含有多糖類及びその製造方法 |
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WO2003085001A1 true WO2003085001A1 (fr) | 2003-10-16 |
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US (1) | US7348424B2 (ja) |
EP (1) | EP1493754B1 (ja) |
JP (1) | JP4248189B2 (ja) |
KR (1) | KR100977788B1 (ja) |
CA (1) | CA2484840C (ja) |
DE (1) | DE60321778D1 (ja) |
WO (1) | WO2003085001A1 (ja) |
Cited By (1)
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CN110804104A (zh) * | 2019-10-30 | 2020-02-18 | 暨南大学 | 一种细胞膜仿生表面改性细菌纤维素及其制备方法与应用 |
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JP4245336B2 (ja) * | 2002-11-25 | 2009-03-25 | 株式会社資生堂 | ホスホリルコリン基を有するポリシロキサン及びその製造方法 |
JP4530197B2 (ja) * | 2003-11-21 | 2010-08-25 | 株式会社資生堂 | フィルター材料 |
CN1886427B (zh) | 2003-11-28 | 2012-05-23 | 伊士曼化工公司 | 纤维素共聚体和氧化方法 |
JP4853994B2 (ja) * | 2004-03-31 | 2012-01-11 | 昭和電工株式会社 | 皮膚外用剤 |
JP4535490B2 (ja) * | 2004-04-09 | 2010-09-01 | 株式会社資生堂 | 蛋白質吸着防止方法 |
LT1988910T (lt) | 2006-02-28 | 2018-01-10 | Kodiak Sciences Inc. | Akriloiloksietilfosforilcholiną turintys polimero konjugatai ir jų gavimo būdas |
WO2007101243A1 (en) * | 2006-02-28 | 2007-09-07 | Novozymes Biopolymer A/S | Derivatives of hyaluronic acids |
JP5242921B2 (ja) * | 2007-02-06 | 2013-07-24 | 帝人株式会社 | ホスファチジルエタノールアミン結合多糖類の製造方法 |
JP2009114073A (ja) * | 2007-11-01 | 2009-05-28 | Shiseido Co Ltd | ヒアルロニダーゼ阻害剤 |
US8765432B2 (en) * | 2009-12-18 | 2014-07-01 | Oligasis, Llc | Targeted drug phosphorylcholine polymer conjugates |
FR2958646B1 (fr) | 2010-04-07 | 2012-05-18 | Adocia | Polysaccharides comportant des groupes fonctionnels carboxyles substitues par un derive d'acide hydrophobe. |
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- 2003-04-08 KR KR1020047013002A patent/KR100977788B1/ko not_active IP Right Cessation
- 2003-04-08 DE DE60321778T patent/DE60321778D1/de not_active Expired - Lifetime
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CN110804104A (zh) * | 2019-10-30 | 2020-02-18 | 暨南大学 | 一种细胞膜仿生表面改性细菌纤维素及其制备方法与应用 |
CN110804104B (zh) * | 2019-10-30 | 2021-12-07 | 暨南大学 | 一种细胞膜仿生表面改性细菌纤维素及其制备方法与应用 |
Also Published As
Publication number | Publication date |
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US20050222405A1 (en) | 2005-10-06 |
JP2003301001A (ja) | 2003-10-21 |
KR100977788B1 (ko) | 2010-08-24 |
US7348424B2 (en) | 2008-03-25 |
EP1493754A4 (en) | 2007-03-14 |
JP4248189B2 (ja) | 2009-04-02 |
KR20040094716A (ko) | 2004-11-10 |
EP1493754A1 (en) | 2005-01-05 |
EP1493754B1 (en) | 2008-06-25 |
DE60321778D1 (de) | 2008-08-07 |
CA2484840A1 (en) | 2006-04-15 |
CA2484840C (en) | 2012-05-08 |
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