CN1325409A - 羧化多糖的交联方法 - Google Patents
羧化多糖的交联方法 Download PDFInfo
- Publication number
- CN1325409A CN1325409A CN99813144A CN99813144A CN1325409A CN 1325409 A CN1325409 A CN 1325409A CN 99813144 A CN99813144 A CN 99813144A CN 99813144 A CN99813144 A CN 99813144A CN 1325409 A CN1325409 A CN 1325409A
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- China
- Prior art keywords
- cross
- polysaccharide
- carboxyl
- reaction
- crosslinked
- Prior art date
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- Granted
Links
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- 239000005017 polysaccharide Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000004132 cross linking Methods 0.000 title claims abstract description 19
- 230000008569 process Effects 0.000 title claims abstract description 7
- 150000004676 glycans Chemical class 0.000 title abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 229920000768 polyamine Polymers 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 56
- 150000004804 polysaccharides Chemical class 0.000 claims description 29
- 229920002674 hyaluronan Polymers 0.000 claims description 19
- 229960003160 hyaluronic acid Drugs 0.000 claims description 19
- ZWGYXDVUKKAUQU-UHFFFAOYSA-N 3-(chloromethyl)-2-iodopyridine Chemical compound ClCc1cccnc1I ZWGYXDVUKKAUQU-UHFFFAOYSA-N 0.000 claims description 14
- -1 polyoxy Polymers 0.000 claims description 13
- 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 group 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 claims description 12
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 150000004781 alginic acids Chemical class 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 230000019635 sulfation Effects 0.000 claims description 6
- 238000005670 sulfation reaction Methods 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
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- JFOIBTLTZWOAIC-UHFFFAOYSA-N (4-nitrophenyl) 2,2,2-trifluoroacetate Chemical compound [O-][N+](=O)C1=CC=C(OC(=O)C(F)(F)F)C=C1 JFOIBTLTZWOAIC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 2
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 claims description 2
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- 239000001257 hydrogen Substances 0.000 claims description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
- HOGDNTQCSIKEEV-UHFFFAOYSA-N n'-hydroxybutanediamide Chemical compound NC(=O)CCC(=O)NO HOGDNTQCSIKEEV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- QJDRFICTELBSSO-UHFFFAOYSA-N triazol-4-ylidenemethanone Chemical compound O=C=C1C=NN=N1 QJDRFICTELBSSO-UHFFFAOYSA-N 0.000 claims description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 2
- 230000004913 activation Effects 0.000 abstract description 2
- 239000012467 final product Substances 0.000 abstract description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 5
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- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(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- Chemical compound [Na+].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 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 2
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- 210000002784 stomach Anatomy 0.000 description 2
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
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- 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
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- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- 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
-
- 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
-
- 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
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/005—Crosslinking of cellulose derivatives
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- C08B31/00—Preparation of derivatives of starch
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/003—Crosslinking of starch
- C08B31/006—Crosslinking of derivatives of starch
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- 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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- 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
- C08B37/0084—Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates
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Abstract
Description
实施例 | 交联剂(mol) | CMPJ(mol)的量(g) | 交联度 | SD | NMR(13)(ppm) | I.R.(膜)(cm-1) | 扫描电子显微镜检查(SEM) |
9 | 1,3-丙二胺(0.024) | 0.6g(1.210-3) | (100%) | 13.200 | 29.3/39.8(-CH2-CH2-CH2丙二胺链接);172.5(-CO-NH-CH2-CH2-CH2-) | 1630(-CO-NH-);1560(-CO-NH-); | 均匀,波浪形态 |
10 | 0,0’-1-二-(-2-二氨基丙基)PEG500(0.022) | 0.15g(6×10-4) | (50%) | 9.000 | 交替的光滑区域和孔,直径几微米的圆形突起 | ||
11 | 0,0’-二-(2-氨基丙基)PEG800(0.022) | 0.15g(6×10-4) | (50%) | 6.100 | 两种形态不同的区域,第一个区域波浪并且第二个区域具有孔状结构 | ||
12 | 1,6-二氨基己烷(0.023) | 0.15g(6×10-4) | (50%) | 8.000 | 169.46(-CO-NH-交联);74.04/76.80/83.17/80.41(-CH2-交联臂) | 1740(-COOH);1630(-CO-NH-);1610(-COO-);1560(-CO-NH-); | 光滑表面,具有几微米直径的突起 |
C-1 | C-2 | C-3 | C-4 | C-5 | x-C=0 | y-CH3 | |
103.5 | 57.3 | 85.4 | 71.3 | 78.7 | 178.0 | 25.3 | ppm |
C-1’ | C-2’ | C-3’ | C-4’ | C-5’ | 6-C=0 | ||
105.9 | 75.2 | 76.4 | 82.8 | 78.6 | 176.2 | ppm | |
1-CH2 | 2-CH2 | 3-CH2 | 6’-C=0 | 交联 | |||
39.8 | 29.3 | 39.8 | 172.5 | ppm |
交联聚合物(50%聚合度) | ΔHa[J/g] | Tg[℃] | ΔHb[J/g] | wt%水分 |
C.L.Hyal-1,3(实施例8) | 276 | 51 | 42 | 12 |
C.L.HyalS-1,3(实施例13) | 357 | 64 | 53 | 16 |
C.L.Hyal-1,6(实施例12) | 327 | 64 | 58 | 16 |
C.L.HyalS-1,6 | 465 | 64 | 65 | 20 |
5 C.L.Hyal-P500.2NH2(实施例10) | 239 | 45 | 72 | 10 |
6 C.L.HyalS-P500.2NH2 | 384 | 69 | 113 | 16 |
7 C.L.Hyal-P800.2NH2(实施例11) | 179 | 73 | 30 | 10 |
8 C.L.HyalS-P800.2NH2 | 206 | 76 | 52 | 10 |
Hyal ITBA | 164 | - | 130 | 5 |
Claims (11)
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IT1998MI002443A IT1303738B1 (it) | 1998-11-11 | 1998-11-11 | Processo di reticolazione di polisaccaridi carbossilati. |
ITMI98A002443 | 1998-11-11 |
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JPH09278803A (ja) * | 1996-04-09 | 1997-10-28 | Kuraray Co Ltd | 医療用手当材 |
JP3413062B2 (ja) * | 1996-06-19 | 2003-06-03 | キヤノン株式会社 | 糖鎖高分子化合物を含む高分子化合物及びその分解方法 |
FR2752843B1 (fr) * | 1996-08-30 | 1998-10-16 | Sod Conseils Rech Applic | Copolymeres reticules a base de polymeres polycarboxyliques et leur utilisation comme support de composition pharmaceutique |
ES2317657T3 (es) * | 1996-09-19 | 2009-04-16 | The Regents Of The University Of Michigan | Polimeros que contienen polisacaridos tales como alginatos o alginatos modificados. |
US6630457B1 (en) * | 1998-09-18 | 2003-10-07 | Orthogene Llc | Functionalized derivatives of hyaluronic acid, formation of hydrogels in situ using same, and methods for making and using same |
IT1303735B1 (it) * | 1998-11-11 | 2001-02-23 | Falorni Italia Farmaceutici S | Acidi ialuronici reticolati e loro usi medici. |
IT1303738B1 (it) | 1998-11-11 | 2001-02-23 | Aquisitio S P A | Processo di reticolazione di polisaccaridi carbossilati. |
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1998
- 1998-11-11 IT IT1998MI002443A patent/IT1303738B1/it active
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105566511A (zh) * | 2016-01-27 | 2016-05-11 | 天津医科大学 | 电荷翻转普鲁兰多糖衍生物及其合成方法和用途 |
CN105566511B (zh) * | 2016-01-27 | 2017-11-03 | 天津医科大学 | 电荷翻转普鲁兰多糖衍生物及其合成方法和用途 |
CN110961057A (zh) * | 2020-01-16 | 2020-04-07 | 江苏罗格斯生物科技有限公司 | 一种绿色生物水凝胶输送系统及其制备方法 |
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