SE450834B - Sett att binda ett protein till en berare innehallande hydroxylgrupper - Google Patents

Sett att binda ett protein till en berare innehallande hydroxylgrupper

Info

Publication number: SE450834B
Authority: SE; Sweden
Prior art keywords: diisocyanate; bound; isocyanate compound; support; protein
Prior art date: 1980-11-19

Application number

SE8008096A

Other languages

English (en)

Swedish (sv)

Other versions

SE8008096L (sv

Inventor

H-D Lehmann

G G Krisam

R S Golla

Original Assignee

Biocompat Inc

Priority date (The priority date 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 date listed.)

1980-11-19

Filing date

1980-11-19

Publication date

1987-08-03

1980-11-19 Application filed by Biocompat Inc filed Critical Biocompat Inc

1980-11-19 Priority to SE8008096A priority Critical patent/SE450834B/sv

1981-11-12 Priority to US06/320,215 priority patent/US4412000A/en

1981-11-16 Priority to EP81109709A priority patent/EP0052365B1/de

1981-11-16 Priority to AT81109709T priority patent/ATE4223T1/de

1981-11-16 Priority to DE8181109709T priority patent/DE3160656D1/de

1981-11-19 Priority to JP56186076A priority patent/JPS57117868A/ja

1982-05-20 Publication of SE8008096L publication Critical patent/SE8008096L/

1987-08-03 Publication of SE450834B publication Critical patent/SE450834B/sv

Links

-1 HYDROXYL GROUPS Chemical group 0.000 title claims abstract description 24
108090000623 proteins and genes Proteins 0.000 title claims abstract description 10
102000004169 proteins and genes Human genes 0.000 title claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 24
239000012948 isocyanate Substances 0.000 claims abstract description 22
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims abstract description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
238000009739 binding Methods 0.000 claims abstract description 11
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 7
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 3
150000002148 esters Chemical class 0.000 claims abstract description 3
239000010936 titanium Substances 0.000 claims abstract description 3
229910052719 titanium Inorganic materials 0.000 claims abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 26
108010046334 Urease Proteins 0.000 claims description 22
125000005442 diisocyanate group Chemical group 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 9
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 9
229920002678 cellulose Polymers 0.000 claims description 8
239000001913 cellulose Substances 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
239000003440 toxic substance Substances 0.000 claims description 4
VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000005056 polyisocyanate Substances 0.000 claims description 2
229920001228 polyisocyanate Polymers 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract 2
239000002253 acid Substances 0.000 abstract 1
239000011149 active material Substances 0.000 abstract 1
231100000404 nontoxic agent Toxicity 0.000 abstract 1
239000000243 solution Substances 0.000 description 20
238000002474 experimental method Methods 0.000 description 17
230000000694 effects Effects 0.000 description 12
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
239000004202 carbamide Substances 0.000 description 6
239000000835 fiber Substances 0.000 description 6
239000012510 hollow fiber Substances 0.000 description 6
230000004913 activation Effects 0.000 description 5
239000000969 carrier Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
239000008363 phosphate buffer Substances 0.000 description 4
125000006850 spacer group Chemical group 0.000 description 4
231100000331 toxic Toxicity 0.000 description 4
230000002588 toxic effect Effects 0.000 description 4
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000004064 recycling Methods 0.000 description 3
239000012487 rinsing solution Substances 0.000 description 3
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
RONNRWUMUHMWOH-UHFFFAOYSA-N bromo cyanate Chemical compound BrOC#N RONNRWUMUHMWOH-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
150000004676 glycans Chemical class 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000008055 phosphate buffer solution Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920001282 polysaccharide Polymers 0.000 description 2
239000005017 polysaccharide Substances 0.000 description 2
LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical class O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
102000014914 Carrier Proteins Human genes 0.000 description 1
102000008186 Collagen Human genes 0.000 description 1
108010035532 Collagen Proteins 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
108091008324 binding proteins Proteins 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229920001436 collagen Polymers 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005517 mercerization Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
- C08G18/6446—Proteins and derivatives thereof
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Genetics & Genomics (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biotechnology (AREA)
Biomedical Technology (AREA)
Polymers & Plastics (AREA)
Microbiology (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
External Artificial Organs (AREA)
Peptides Or Proteins (AREA)
Materials For Medical Uses (AREA)

SE8008096A 1980-11-19 1980-11-19 Sett att binda ett protein till en berare innehallande hydroxylgrupper SE450834B (sv)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
SE8008096A SE450834B (sv)	1980-11-19	1980-11-19	Sett att binda ett protein till en berare innehallande hydroxylgrupper
US06/320,215 US4412000A (en)	1980-11-19	1981-11-12	Method of binding a biologically active material to a carrier containing hydroxyl groups
EP81109709A EP0052365B1 (de)	1980-11-19	1981-11-16	Verfahren zum Binden eines biologisch aktiven Materials, zum Beispiel eines Proteins, an einen Hydroxylgruppen enthaltenden Träger
AT81109709T ATE4223T1 (de)	1980-11-19	1981-11-16	Verfahren zum binden eines biologisch aktiven materials, zum beispiel eines proteins, an einen hydroxylgruppen enthaltenden traeger.
DE8181109709T DE3160656D1 (en)	1980-11-19	1981-11-16	Method of binding a biologically active material, e.g. a protein to a carrier containing hydroxyl groups
JP56186076A JPS57117868A (en)	1980-11-19	1981-11-19	Method of combining biological active substance to carrier containing hydroxyl group

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8008096A SE450834B (sv)	1980-11-19	1980-11-19	Sett att binda ett protein till en berare innehallande hydroxylgrupper

Publications (2)

Publication Number	Publication Date
SE8008096L SE8008096L (sv)	1982-05-20
SE450834B true SE450834B (sv)	1987-08-03

Family

ID=20342273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8008096A SE450834B (sv)	1980-11-19	1980-11-19	Sett att binda ett protein till en berare innehallande hydroxylgrupper

Country Status (6)

Country	Link
US (1)	US4412000A (de)
EP (1)	EP0052365B1 (de)
JP (1)	JPS57117868A (de)
AT (1)	ATE4223T1 (de)
DE (1)	DE3160656D1 (de)
SE (1)	SE450834B (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3106498A1 (de) *	1981-02-21	1982-09-09	Akzo Gmbh, 5600 Wuppertal	Einbettmasse aus polyurethanen
AU580548B2 (en) *	1983-02-14	1989-01-19	Cuno Incorporated	Polymer modified polysaccharide
US4663163A (en) *	1983-02-14	1987-05-05	Hou Kenneth C	Modified polysaccharide supports
DE3334846A1 (de) *	1983-09-27	1985-04-04	Hoechst Ag, 6230 Frankfurt	Immobilisierte acylase, verfahren zu ihrer herstellung und ihre verwendung
DE3334847A1 (de) *	1983-09-27	1985-04-04	Hoechst Ag, 6230 Frankfurt	Immobilisierte 5'-phosphodiesterase, verfahren zu ihrer herstellung und ihre verwendung
GB8334499D0 (en) *	1983-12-24	1984-02-01	Beecham Group Plc	Derivatives
US4632904A (en) *	1983-12-27	1986-12-30	Ciba Corning Diagnostics Corp.	Immobilized enzyme composites having carriers derivatized with an organotitanate
US4530905A (en) *	1984-10-25	1985-07-23	The Dow Chemical Company	Crosslinked gelatin foams
US4687820A (en) *	1984-08-22	1987-08-18	Cuno Incorporated	Modified polypeptide supports
JPS63186660A (ja) *	1986-09-24	1988-08-02	宇部興産株式会社	体液浄化剤
US4954444A (en) *	1987-03-02	1990-09-04	E. I. Du Pont De Nemours And Company	Enzyme immobilization and bioaffinity separations with perfluorocarbon polymer-based supports
US5079155A (en) *	1987-03-02	1992-01-07	E. I. Du Pont De Nemours And Company	Fluorocarbon polymer support for chromatographic separations, diagnostic assays and enzyme immobilization
US5403750A (en) *	1991-03-06	1995-04-04	W. R. Grace & Co.-Conn.	Biocompatible, low protein adsorption affinity matrix
DE59709797D1 (de) *	1996-09-18	2003-05-15	Biotechnolog Forschung Gmbh	Formgegenstand mit reaktiven funktionen
US7335400B2 (en) *	2001-07-24	2008-02-26	University Of Pittsburgh	Irreversible immobilization of enzymes into polyurethane coatings

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB857158A (en) *	1956-12-21	1960-12-29	Bayer Ag	Process for the production of elastomeric plastics with a polyisocyanate base
GB1346631A (en) *	1971-02-10	1974-02-13	Ranks Hovis Mcdougall Ltd	Enzymes
DE2621974A1 (de) *	1976-05-18	1977-11-24	Max Planck Gesellschaft	Verfahren zur herstellung eines zur kovalenten bindung mit biologisch aktivem material befaehigten traegermaterials

1980
- 1980-11-19 SE SE8008096A patent/SE450834B/sv not_active IP Right Cessation
1981
- 1981-11-12 US US06/320,215 patent/US4412000A/en not_active Expired - Fee Related
- 1981-11-16 AT AT81109709T patent/ATE4223T1/de not_active IP Right Cessation
- 1981-11-16 DE DE8181109709T patent/DE3160656D1/de not_active Expired
- 1981-11-16 EP EP81109709A patent/EP0052365B1/de not_active Expired
- 1981-11-19 JP JP56186076A patent/JPS57117868A/ja active Pending

Also Published As

Publication number	Publication date
JPS57117868A (en)	1982-07-22
US4412000A (en)	1983-10-25
EP0052365A1 (de)	1982-05-26
ATE4223T1 (de)	1983-08-15
EP0052365B1 (de)	1983-07-20
SE8008096L (sv)	1982-05-20
DE3160656D1 (en)	1983-08-25

Legal Events

Date

Code

Title

Description

1995-01-31

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Patent has lapsed

Ref document number: 8008096-3

Effective date: 19880322

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