JPS61154567A - 架橋グリコサミノグリカン複合体 - Google Patents
架橋グリコサミノグリカン複合体Info
- Publication number
- JPS61154567A JPS61154567A JP59273492A JP27349284A JPS61154567A JP S61154567 A JPS61154567 A JP S61154567A JP 59273492 A JP59273492 A JP 59273492A JP 27349284 A JP27349284 A JP 27349284A JP S61154567 A JPS61154567 A JP S61154567A
- Authority
- JP
- Japan
- Prior art keywords
- complex
- crosslinked
- water
- chs
- gag
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 title 1
- 229960002442 glucosamine Drugs 0.000 title 1
- -1 glucosamine glycan Chemical class 0.000 title 1
- 229920002683 Glycosaminoglycan Polymers 0.000 claims description 11
- 108010035532 Collagen Proteins 0.000 claims description 4
- 102000008186 Collagen Human genes 0.000 claims description 4
- 229920001436 collagen Polymers 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 3
- 229920000159 gelatin Polymers 0.000 claims description 3
- 239000008273 gelatin Substances 0.000 claims description 3
- 235000019322 gelatine Nutrition 0.000 claims description 3
- 235000011852 gelatine desserts Nutrition 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000002131 composite material Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000006228 supernatant Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000011084 recovery Methods 0.000 description 6
- 108010045569 atelocollagen Proteins 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 4
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 210000002808 connective tissue Anatomy 0.000 description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
- 229960000789 guanidine hydrochloride Drugs 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- FNEHAOQZWPHONV-UHFFFAOYSA-N 9h-carbazole;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C3=CC=CC=C3NC2=C1 FNEHAOQZWPHONV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- KXCLCNHUUKTANI-RBIYJLQWSA-N keratan Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H]([C@@H](COS(O)(=O)=O)O[C@@H](O)[C@@H]3O)O)[C@H](NC(C)=O)[C@H]2O)COS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@@H]1O KXCLCNHUUKTANI-RBIYJLQWSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 1
- 229920001287 Chondroitin sulfate Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229920002971 Heparan sulfate Polymers 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000288 Keratan sulfate Polymers 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229940059329 chondroitin sulfate Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005520 electrodynamics Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 238000012869 ethanol precipitation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- 210000004127 vitreous body Anatomy 0.000 description 1
Landscapes
- Materials For Medical Uses (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59273492A JPS61154567A (ja) | 1984-12-26 | 1984-12-26 | 架橋グリコサミノグリカン複合体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59273492A JPS61154567A (ja) | 1984-12-26 | 1984-12-26 | 架橋グリコサミノグリカン複合体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61154567A true JPS61154567A (ja) | 1986-07-14 |
| JPH0586234B2 JPH0586234B2 (cs) | 1993-12-10 |
Family
ID=17528654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59273492A Granted JPS61154567A (ja) | 1984-12-26 | 1984-12-26 | 架橋グリコサミノグリカン複合体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61154567A (cs) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2622104A1 (fr) * | 1987-10-22 | 1989-04-28 | Bioetica Sa | Procede de stabilisation de phases lamellaires lipidiques hydratees, par ex. de liposomes, composition de phases lamellaires lipidiques hydratees, par ex. des liposomes, stabilisees par un emploi d'un support stabilisant a base d'atelocollagene et de glycosaminoglycannes et utilisation en pharmacie ou en cosmetologie |
| WO1989008465A1 (fr) * | 1988-03-09 | 1989-09-21 | Terumo Kabushiki Kaisha | Substance medicale dans laquelle les cellules peuvent penetrer et peau artificielle |
| FR2645455A2 (fr) * | 1987-10-22 | 1990-10-12 | Bioetica Sa | Procede de stabilisation de phases lamellaires lipidiques hydratees, par exemple de liposomes, composition de phases lamellaires lipidiques hydratees, par exemple des liposomes, stabilisees et utilisation en pharmacie ou en cosmetologie sous forme de compositions pharmaceutiques ou cosmetiques |
| JP2679409B2 (ja) * | 1990-05-29 | 1997-11-19 | ストライカー・コーポレーション | 合成骨マトリックス |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58170721A (ja) * | 1982-03-17 | 1983-10-07 | アベ ウイドラ | 親水性バイオポリマ−コポリエレクトロライト |
-
1984
- 1984-12-26 JP JP59273492A patent/JPS61154567A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58170721A (ja) * | 1982-03-17 | 1983-10-07 | アベ ウイドラ | 親水性バイオポリマ−コポリエレクトロライト |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2622104A1 (fr) * | 1987-10-22 | 1989-04-28 | Bioetica Sa | Procede de stabilisation de phases lamellaires lipidiques hydratees, par ex. de liposomes, composition de phases lamellaires lipidiques hydratees, par ex. des liposomes, stabilisees par un emploi d'un support stabilisant a base d'atelocollagene et de glycosaminoglycannes et utilisation en pharmacie ou en cosmetologie |
| FR2645455A2 (fr) * | 1987-10-22 | 1990-10-12 | Bioetica Sa | Procede de stabilisation de phases lamellaires lipidiques hydratees, par exemple de liposomes, composition de phases lamellaires lipidiques hydratees, par exemple des liposomes, stabilisees et utilisation en pharmacie ou en cosmetologie sous forme de compositions pharmaceutiques ou cosmetiques |
| WO1989008465A1 (fr) * | 1988-03-09 | 1989-09-21 | Terumo Kabushiki Kaisha | Substance medicale dans laquelle les cellules peuvent penetrer et peau artificielle |
| JP2679409B2 (ja) * | 1990-05-29 | 1997-11-19 | ストライカー・コーポレーション | 合成骨マトリックス |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0586234B2 (cs) | 1993-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1276143C (en) | Chemically modified hyaluronic acid preparation and method of recovery thereof from animal tissues | |
| DE60029761T2 (de) | Verfahren zur vernetzung von hyaluronsäure mit polymeren | |
| CN111518289B (zh) | 一种力学性能可调的可注射自愈合水凝胶及其制备方法与应用 | |
| US5529986A (en) | Conjugate, its preparation and use and a substrate prepared with the conjugate | |
| JP4230135B2 (ja) | 多官能性架橋剤によって架橋したグリコサミノグリカン−コラーゲン複合体の製造法 | |
| Mathews | The interaction of collagen and acid mucopolysaccarides. A model for connective tissue | |
| US4350629A (en) | Procedures for preparing composite materials from collagen and glycosaminoglycan | |
| Bettelheim et al. | The hydration of proteoglycans of bovine cornea | |
| US4963666A (en) | Material of polysaccharides containing carboxyl groups, and a process for producing such polysaccharides | |
| Pal et al. | The separation of new forms of the proteinpolysaccharides of bovine nasal cartilage | |
| EP0167363A2 (en) | Crosslinked glycosaminoglycans and their use | |
| JPH0637575B2 (ja) | 架橋ヒアルロン酸ゲル組成物及び製造法 | |
| JPH0740932B2 (ja) | 細胞培養組成物およびその用途 | |
| JPH10502665A (ja) | 創傷治癒剤 | |
| CA1116087A (en) | Artificial medical material with anticoagulative activity | |
| CN113214476B (zh) | 一种仿生糖聚肽水凝胶及其制备方法和应用 | |
| CN106397846A (zh) | 一种交联透明质酸钠及其制备方法与应用 | |
| JPH04506971A (ja) | 人工生物膜 | |
| Tse Sum Bui et al. | Molecularly imprinted polymer hydrogel nanoparticles: synthetic antibodies for cancer diagnosis and therapy | |
| CH636628A5 (en) | Process for the preparation of biologically active compounds, and the use thereof | |
| Fried et al. | [22] Water-soluble nonionic polymers in protein purification | |
| EP4457266A1 (en) | Hyaluronic acid-collagen copolymer compositions and medical applications thereof | |
| JPS61154567A (ja) | 架橋グリコサミノグリカン複合体 | |
| Debbage et al. | Detection of receptors for sulfated polysaccharides in human placenta by biotinylated probes. | |
| Hunter et al. | Dupuytren's contracture I—Chemical pathology |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |