DE2625257A1 - Verfahren zur vernetzung von proteinen und nach dem verfahren hergestellte produkte - Google Patents
Verfahren zur vernetzung von proteinen und nach dem verfahren hergestellte produkteInfo
- Publication number
- DE2625257A1 DE2625257A1 DE19762625257 DE2625257A DE2625257A1 DE 2625257 A1 DE2625257 A1 DE 2625257A1 DE 19762625257 DE19762625257 DE 19762625257 DE 2625257 A DE2625257 A DE 2625257A DE 2625257 A1 DE2625257 A1 DE 2625257A1
- Authority
- DE
- Germany
- Prior art keywords
- poly
- radical
- ethylene oxide
- acid
- crosslinking agent
- 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.)
- Ceased
Links
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- 102000004169 proteins and genes Human genes 0.000 title claims description 33
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- -1 isocyanato, isothiocyanato Chemical group 0.000 claims description 45
- 102000004190 Enzymes Human genes 0.000 claims description 43
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- 239000003431 cross linking reagent Substances 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
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- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- OHCXVBBPKJAIBJ-UHFFFAOYSA-N hydroxysulfonothioyl hydrogen carbonate Chemical compound OC(=O)OS(O)(=O)=S OHCXVBBPKJAIBJ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
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- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 2
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
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- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 1
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- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 108700040099 Xylose isomerases Proteins 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012982 microporous membrane Substances 0.000 description 1
- GFFRQCYOONZQMW-UCGGBYDDSA-N n-[(2s)-1-[[(5s)-5-[(3-amino-4-fluorophenyl)sulfonyl-(2-methylpropyl)amino]-6-hydroxyhexyl]amino]-3-naphthalen-1-yl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound N([C@@H](CC=1C2=CC=CC=C2C=CC=1)C(=O)NCCCC[C@@H](CO)N(CC(C)C)S(=O)(=O)C=1C=C(N)C(F)=CC=1)C(=O)N1CCOCC1 GFFRQCYOONZQMW-UCGGBYDDSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H1/00—Macromolecular products derived from proteins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/81—Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
- Y10S530/812—Peptides or proteins is immobilized on, or in, an organic carrier
- Y10S530/815—Carrier is a synthetic polymer
- Y10S530/816—Attached to the carrier via a bridging agent
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL47468A IL47468A (en) | 1975-06-12 | 1975-06-12 | Process for the cross-linking of proteins using water soluble cross-linking agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2625257A1 true DE2625257A1 (de) | 1976-12-30 |
Family
ID=11048277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762625257 Ceased DE2625257A1 (de) | 1975-06-12 | 1976-06-04 | Verfahren zur vernetzung von proteinen und nach dem verfahren hergestellte produkte |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4101380A (https=) |
| CH (1) | CH601388A5 (https=) |
| DE (1) | DE2625257A1 (https=) |
| IL (1) | IL47468A (https=) |
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| DE2862449D1 (en) * | 1977-08-22 | 1984-11-22 | Nat Res Dev | Macromolecular covalent conjugates, methods for preparing and pharmaceutical compositions containing them |
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| US4839345A (en) * | 1985-03-09 | 1989-06-13 | Nippon Oil And Fats Co., Ltd. | Hydrated adhesive gel and method for preparing the same |
| US5306615A (en) * | 1986-05-15 | 1994-04-26 | E. I. Du Pont De Nemours And Company | Immunoassays and nucleic acid assays with liquid exchange supports |
| US5268307A (en) * | 1986-05-15 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Preparation of liquid affinity supports for bioaffinity an ion exchange separations |
| US5268456A (en) * | 1986-05-15 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Bioaffinity and ion exchange separations with liquid exchange supports |
| US4810638A (en) * | 1986-07-24 | 1989-03-07 | Miles Inc. | Enzyme-labeled antibody reagent with polyalkyleneglycol linking group |
| US6007817A (en) | 1988-10-11 | 1999-12-28 | University Of Southern California | Vasopermeability enhancing immunoconjugates |
| US5238831A (en) * | 1989-04-28 | 1993-08-24 | Gist-Brocades | Stabilization of carboxyl esterase |
| KR100204837B1 (ko) * | 1989-04-28 | 1999-06-15 | 기스트 브로카데스 나암로제 베노오트하프 | 카르복실 에스테라제의 안정화 |
| US5240747A (en) * | 1989-05-11 | 1993-08-31 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Process for modifying surfaces of materials |
| US5252714A (en) * | 1990-11-28 | 1993-10-12 | The University Of Alabama In Huntsville | Preparation and use of polyethylene glycol propionaldehyde |
| US5416191A (en) * | 1991-04-01 | 1995-05-16 | Cortech, Inc. | Bradykinin antagonists |
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| DK0746582T3 (da) * | 1993-04-27 | 2000-08-21 | Cytotherapeutics Inc | Membran dannet af en acrylonitril-baseret polymer |
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| US20090227689A1 (en) * | 2007-03-05 | 2009-09-10 | Bennett Steven L | Low-Swelling Biocompatible Hydrogels |
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| US8067028B2 (en) * | 2007-08-13 | 2011-11-29 | Confluent Surgical Inc. | Drug delivery device |
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| JP5890182B2 (ja) * | 2009-02-12 | 2016-03-22 | インセプト エルエルシー | ヒドロゲルプラグによる薬物送達 |
| US20100256671A1 (en) * | 2009-04-07 | 2010-10-07 | Biomedica Management Corporation | Tissue sealant for use in noncompressible hemorrhage |
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| US10226417B2 (en) | 2011-09-16 | 2019-03-12 | Peter Jarrett | Drug delivery systems and applications |
| MX2014010209A (es) | 2012-02-29 | 2014-11-21 | Toray Industries | Agente inhibidor para acumulacion de fluido de la cavidad corporal. |
| CN114025706A (zh) | 2019-06-26 | 2022-02-08 | 达沃有限公司 | 包含亲核物质和多官能改性的基于聚乙二醇的交联剂的反应性干粉状止血材料 |
| CA3175344A1 (en) | 2020-03-20 | 2021-09-23 | Bard Peripheral Vascular, Inc. | Reactive hydrogel forming formulations and related methods |
| US12161777B2 (en) | 2020-07-02 | 2024-12-10 | Davol Inc. | Flowable hemostatic suspension |
| US11739166B2 (en) | 2020-07-02 | 2023-08-29 | Davol Inc. | Reactive polysaccharide-based hemostatic agent |
| JP2024500994A (ja) | 2020-12-28 | 2024-01-10 | デボル，インコーポレイテッド | タンパク質及び多官能化変性ポリエチレングリコール系架橋剤を含む反応性乾燥粉末状止血用材料 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3796634A (en) * | 1970-03-19 | 1974-03-12 | Us Health Education & Welfare | Insolubilized biologically active enzymes |
| US4009267A (en) * | 1975-09-09 | 1977-02-22 | Diagnostic Data, Inc. | Cross-linked orgotein |
-
1975
- 1975-06-12 IL IL47468A patent/IL47468A/xx unknown
-
1976
- 1976-06-04 DE DE19762625257 patent/DE2625257A1/de not_active Ceased
- 1976-06-11 CH CH742976A patent/CH601388A5/xx not_active IP Right Cessation
- 1976-06-11 US US05/695,030 patent/US4101380A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IL47468A0 (en) | 1975-08-31 |
| US4101380A (en) | 1978-07-18 |
| IL47468A (en) | 1979-05-31 |
| CH601388A5 (https=) | 1978-07-14 |
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