DK2598884T3 - Kovalent immobilisering af molekyler omfattende en aminogruppe - Google Patents
Kovalent immobilisering af molekyler omfattende en aminogruppe Download PDFInfo
- Publication number
- DK2598884T3 DK2598884T3 DK11745945.3T DK11745945T DK2598884T3 DK 2598884 T3 DK2598884 T3 DK 2598884T3 DK 11745945 T DK11745945 T DK 11745945T DK 2598884 T3 DK2598884 T3 DK 2598884T3
- Authority
- DK
- Denmark
- Prior art keywords
- molecule
- groups
- oxidation
- amino group
- electro
- Prior art date
Links
- 125000003277 amino group Chemical group 0.000 title claims description 35
- 238000000034 method Methods 0.000 claims description 49
- 238000006056 electrooxidation reaction Methods 0.000 claims description 36
- 229910052737 gold Inorganic materials 0.000 claims description 13
- 229910000510 noble metal Inorganic materials 0.000 claims description 11
- 238000006479 redox reaction Methods 0.000 claims description 11
- 108090000623 proteins and genes Proteins 0.000 claims description 9
- 102000004169 proteins and genes Human genes 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 238000001212 derivatisation Methods 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000012620 biological material Substances 0.000 claims description 2
- 238000013375 chromatographic separation Methods 0.000 claims description 2
- 230000003100 immobilizing effect Effects 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- 239000010970 precious metal Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 238000010301 surface-oxidation reaction Methods 0.000 claims 1
- 239000002245 particle Substances 0.000 description 60
- 229920000936 Agarose Polymers 0.000 description 28
- 239000002953 phosphate buffered saline Substances 0.000 description 24
- 239000010931 gold Substances 0.000 description 16
- 230000003647 oxidation Effects 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 14
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 235000001014 amino acid Nutrition 0.000 description 10
- 150000001413 amino acids Chemical class 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 9
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 9
- 239000008351 acetate buffer Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000011324 bead Substances 0.000 description 8
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 7
- 239000006249 magnetic particle Substances 0.000 description 7
- 235000018102 proteins Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 150000003573 thiols Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- AXISYYRBXTVTFY-UHFFFAOYSA-N Isopropyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)C AXISYYRBXTVTFY-UHFFFAOYSA-N 0.000 description 4
- 102000004407 Lactalbumin Human genes 0.000 description 4
- 108090000942 Lactalbumin Proteins 0.000 description 4
- 229920002684 Sepharose Polymers 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 229940000635 beta-alanine Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 108010093096 Immobilized Enzymes Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 3
- JWDFQMWEFLOOED-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(pyridin-2-yldisulfanyl)propanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCSSC1=CC=CC=N1 JWDFQMWEFLOOED-UHFFFAOYSA-N 0.000 description 2
- 102100034668 Alpha-lactalbumin Human genes 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 101000946384 Homo sapiens Alpha-lactalbumin Proteins 0.000 description 2
- 108010058683 Immobilized Proteins Proteins 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 238000000813 microcontact printing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000013074 reference sample Substances 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 108091023037 Aptamer Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000002508 contact lithography Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- -1 platinum ions Chemical class 0.000 description 1
- 229920002502 poly(methyl methacrylate-co-methacrylic acid) Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000003498 protein array Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K17/00—Carrier-bound or immobilised peptides; Preparation thereof
- C07K17/02—Peptides being immobilised on, or in, an organic carrier
- C07K17/10—Peptides being immobilised on, or in, an organic carrier the carrier being a carbohydrate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K17/00—Carrier-bound or immobilised peptides; Preparation thereof
- C07K17/14—Peptides being immobilised on, or in, an inorganic carrier
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54353—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals with ligand attached to the carrier via a chemical coupling agent
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Hematology (AREA)
- Microbiology (AREA)
- Urology & Nephrology (AREA)
- Wood Science & Technology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Cell Biology (AREA)
- Analytical Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Physics & Mathematics (AREA)
- Food Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Peptides Or Proteins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Claims (13)
1. Fremgangsmåde til kovalent immobilisering af mindst et molekyle omfattende mindst en aminogruppe, fremgangsmåden omfattende de sekventielle trin: a. at tilvejebringe en overflade omfattende -SH-grupper, b. at oxidere overfladen omfattende -SH-grupper med redoxreaktioner under tilstedeværelsen af mindst en ædelmetal-ion, for at opnå reaktive svovl-ædelmetal-ion-clustere, c. at bringe overfladen i kontakt med mindst et molekyle omfattende mindst en aminogruppe for at opnå en kovalent binding af det mindst ene molekyle til overfladen, hvor den mindst ene aminogruppe er involveret i opnåelsen af den kovalente binding til svovl-ædelmetal-ion-clusteret.
2. Fremgangsmåden ifølge krav 1, hvor den mindst ene ædelmetal-ion vælges fra gruppen bestående af Au og Pt.
3. Fremgangsmåden ifølge krav 2, hvor mindst en fraktion af -SH-grupperne reageres med hinanden før trinnet med oxidering af overfladen under anvendelse af redoxreaktioner.
4. Fremgangsmåden ifølge et hvilket som helst af kravene 1-3, hvor det mindst ene molekyle omfattende mindst en aminogruppe er mindst et molekyle valgt fra gruppen bestående af et protein, og et antistof.
5. Fremgangsmåden ifølge et hvilket som helst af kravene 1-4, hvor redoxreaktionen omfatter elektro-oxidering, og hvor elektro-oxideringen udføres under anvendelse af en spænding fra 0,5 til 3 V.
6. Fremgangsmåden ifølge et hvilket som helst af kravene 1-5, hvor redoxreaktionen omfatter elektro-oxidering, og hvor elektro-oxideringen udføres over en tidsperiode fra 1 sekund til 10 minutter.
7. Fremgangsmåden ifølge et hvilket som helst af kravene 1-6, hvor overfladen udsættes for derivatisering for at opnå funktionelle grupper på overfladen, hvor de funktionelle grupper vælges fra gruppen bestående af -SH-grupper og -SS-grupper.
8. Genstand omfattende mindst en overflade, hvor mindst et molekyle omfattende mindst en aminogruppe er kovalent bundet til overfladen, hvor det mindst ene molekyle immobiliseres på overfladen med fremgangsmåden ifølge et hvilket som helst af kravene 1-7.
9. Genstanden ifølge krav 8, hvor genstanden er en sensor.
10. Genstanden ifølge et hvilket som helst af kravene 8-9, hvor genstanden er et kromatografisk separationsmedium.
11. Genstanden ifølge et hvilket som helst af kravene 8-10, hvor genstanden er et biomateriale.
12. Genstanden ifølge et hvilket som helst af kravene 8-11, hvor mindst en overflade omfattende oxiderede thiol-grupper forbindes med mindst en overflade omfattende aminogrupper.
13. Genstanden ifølge et hvilket som helst af kravene 8-12, hvor det mindst ene molekyle omfattende mindst en aminogruppe er mindst et molekyle valgt fra gruppen bestående af et protein, og et antistof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36807610P | 2010-07-27 | 2010-07-27 | |
| SE1050833 | 2010-07-27 | ||
| PCT/EP2011/062865 WO2012013693A1 (en) | 2010-07-27 | 2011-07-27 | Covalent immobilization of molecules comprising an amino group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2598884T3 true DK2598884T3 (da) | 2016-06-20 |
Family
ID=44543201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK11745945.3T DK2598884T3 (da) | 2010-07-27 | 2011-07-27 | Kovalent immobilisering af molekyler omfattende en aminogruppe |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8679807B2 (da) |
| EP (1) | EP2598884B1 (da) |
| JP (1) | JP5845257B2 (da) |
| CN (1) | CN103168238B (da) |
| BR (1) | BR112013002038A2 (da) |
| DK (1) | DK2598884T3 (da) |
| ES (1) | ES2575224T3 (da) |
| WO (1) | WO2012013693A1 (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2923817C (en) | 2013-09-09 | 2021-12-28 | Lab-On-A-Bead Ab | Manufacture of magnetic particles |
| EP3043903B1 (en) * | 2013-09-09 | 2022-04-06 | Lab-on-a-Bead AB | Process and system for magnetic separation |
| WO2018234115A1 (en) | 2017-06-19 | 2018-12-27 | Lab-On-A-Bead Ab | COMBINATORY SEPARATION |
| CN112763703B (zh) * | 2020-12-31 | 2023-04-28 | 深圳天深医疗器械有限公司 | 一种免疫磁珠及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4061575B2 (ja) * | 2001-06-01 | 2008-03-19 | ソニー株式会社 | 導電性触媒粒子及びその製造方法、ガス拡散性触媒電極及び電気化学デバイス |
| ATE546221T1 (de) * | 2007-12-13 | 2012-03-15 | Sven Oscarsson | Partielle derivatisierung von partikeln |
-
2011
- 2011-07-27 US US13/812,101 patent/US8679807B2/en active Active
- 2011-07-27 EP EP11745945.3A patent/EP2598884B1/en active Active
- 2011-07-27 BR BR112013002038A patent/BR112013002038A2/pt not_active Application Discontinuation
- 2011-07-27 ES ES11745945.3T patent/ES2575224T3/es active Active
- 2011-07-27 JP JP2013521119A patent/JP5845257B2/ja active Active
- 2011-07-27 WO PCT/EP2011/062865 patent/WO2012013693A1/en active Application Filing
- 2011-07-27 CN CN201180037062.4A patent/CN103168238B/zh active Active
- 2011-07-27 DK DK11745945.3T patent/DK2598884T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| CN103168238B (zh) | 2016-08-03 |
| EP2598884B1 (en) | 2016-03-30 |
| US20130197195A1 (en) | 2013-08-01 |
| ES2575224T3 (es) | 2016-06-27 |
| CN103168238A (zh) | 2013-06-19 |
| JP2013532825A (ja) | 2013-08-19 |
| EP2598884A1 (en) | 2013-06-05 |
| WO2012013693A1 (en) | 2012-02-02 |
| BR112013002038A2 (pt) | 2016-05-31 |
| US8679807B2 (en) | 2014-03-25 |
| JP5845257B2 (ja) | 2016-01-20 |
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