CA2496141A1 - Procedes et reactifs destines a fonctionnaliser une surface - Google Patents
Procedes et reactifs destines a fonctionnaliser une surface Download PDFInfo
- Publication number
- CA2496141A1 CA2496141A1 CA002496141A CA2496141A CA2496141A1 CA 2496141 A1 CA2496141 A1 CA 2496141A1 CA 002496141 A CA002496141 A CA 002496141A CA 2496141 A CA2496141 A CA 2496141A CA 2496141 A1 CA2496141 A1 CA 2496141A1
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- CA
- Canada
- Prior art keywords
- reagent
- substrate
- group
- monolayer
- array
- 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.)
- Abandoned
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- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 116
- 238000000034 method Methods 0.000 title claims abstract description 73
- 238000006557 surface reaction Methods 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 100
- 239000000758 substrate Substances 0.000 claims description 112
- 239000002356 single layer Substances 0.000 claims description 83
- 125000000524 functional group Chemical group 0.000 claims description 80
- 108090000623 proteins and genes Proteins 0.000 claims description 75
- 102000004169 proteins and genes Human genes 0.000 claims description 73
- -1 silyl halide Chemical class 0.000 claims description 54
- 239000010409 thin film Substances 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 31
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical group N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 24
- 150000001299 aldehydes Chemical class 0.000 claims description 23
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 108010090804 Streptavidin Proteins 0.000 claims description 17
- 230000003993 interaction Effects 0.000 claims description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 15
- 229960002685 biotin Drugs 0.000 claims description 14
- 239000011616 biotin Substances 0.000 claims description 14
- 239000011521 glass Substances 0.000 claims description 14
- 238000006352 cycloaddition reaction Methods 0.000 claims description 13
- 239000010931 gold Substances 0.000 claims description 13
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 12
- 150000001540 azides Chemical class 0.000 claims description 12
- 235000020958 biotin Nutrition 0.000 claims description 12
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052737 gold Inorganic materials 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 229920001223 polyethylene glycol Polymers 0.000 claims description 11
- 239000010703 silicon Substances 0.000 claims description 11
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 238000010653 organometallic reaction Methods 0.000 claims description 8
- 238000010791 quenching Methods 0.000 claims description 8
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 238000005917 acylation reaction Methods 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 230000000171 quenching effect Effects 0.000 claims description 6
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000000395 magnesium oxide Substances 0.000 claims description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 5
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 5
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 claims description 5
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 5
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- 229910001936 tantalum oxide Inorganic materials 0.000 claims description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 4
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- 239000010453 quartz Substances 0.000 claims description 4
- 150000001408 amides Chemical group 0.000 claims description 3
- 125000003827 glycol group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical group 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims 4
- 238000005804 alkylation reaction Methods 0.000 claims 4
- 238000006845 Michael addition reaction Methods 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical group [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 claims 1
- 125000002228 disulfide group Chemical group 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- 150000003949 imides Chemical group 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 125000002525 phosphocholine group Chemical group OP(=O)(OCC[N+](C)(C)C)O* 0.000 claims 1
- 229920002492 poly(sulfone) Polymers 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 238000003491 array Methods 0.000 abstract description 29
- 238000007877 drug screening Methods 0.000 abstract description 2
- 235000018102 proteins Nutrition 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 21
- 239000012634 fragment Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 239000011248 coating agent Substances 0.000 description 17
- 238000000576 coating method Methods 0.000 description 17
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 16
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 16
- 125000005647 linker group Chemical group 0.000 description 14
- 229910052720 vanadium Inorganic materials 0.000 description 14
- 239000012491 analyte Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 239000000872 buffer Substances 0.000 description 12
- 239000002953 phosphate buffered saline Substances 0.000 description 12
- 108090000765 processed proteins & peptides Proteins 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000027455 binding Effects 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
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- 229920000642 polymer Polymers 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 229920001213 Polysorbate 20 Polymers 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 9
- 150000001413 amino acids Chemical class 0.000 description 9
- 238000001514 detection method Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 230000006287 biotinylation Effects 0.000 description 8
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- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 8
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical group ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 150000003573 thiols Chemical class 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 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 6
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
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- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 4
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical class ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 description 4
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- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
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- 229910052990 silicon hydride Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
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- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 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
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
Landscapes
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Biomedical Technology (AREA)
- Nanotechnology (AREA)
- Hematology (AREA)
- General Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Cell Biology (AREA)
- Pathology (AREA)
- Food Science & Technology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Composite Materials (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biotechnology (AREA)
- Peptides Or Proteins (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
L'invention concerne des réactifs et un procédé permettant de constituer des réseaux d'agents d'affinité. L'invention concerne également des procédés utilisant lesdits réseaux d'agents d'affinité. Ces réseaux sont particulièrement utiles pour cribler des médicaments à débit élevé et dans des applications de diagnostics cliniques.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40397102P | 2002-08-16 | 2002-08-16 | |
| US60/403,971 | 2002-08-16 | ||
| PCT/US2003/025927 WO2004017042A2 (fr) | 2002-08-16 | 2003-08-18 | Procedes et reactifs destines a fonctionnaliser une surface |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2496141A1 true CA2496141A1 (fr) | 2004-02-26 |
Family
ID=31888306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002496141A Abandoned CA2496141A1 (fr) | 2002-08-16 | 2003-08-18 | Procedes et reactifs destines a fonctionnaliser une surface |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1537202A4 (fr) |
| JP (1) | JP2005535898A (fr) |
| AU (1) | AU2003263922A1 (fr) |
| CA (1) | CA2496141A1 (fr) |
| WO (1) | WO2004017042A2 (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2005123273A1 (fr) * | 2004-06-21 | 2005-12-29 | Wageningen University | Surfaces en silicium et/ou germanium fonctionnalisees sur mesure |
| JP4538395B2 (ja) * | 2005-09-26 | 2010-09-08 | 富士フイルム株式会社 | バイオセンサー |
| US7763423B2 (en) | 2005-09-30 | 2010-07-27 | Pacific Biosciences Of California, Inc. | Substrates having low density reactive groups for monitoring enzyme activity |
| US8975216B2 (en) | 2006-03-30 | 2015-03-10 | Pacific Biosciences Of California | Articles having localized molecules disposed thereon and methods of producing same |
| DE102007002420A1 (de) | 2007-01-17 | 2008-07-24 | Universität Regensburg | Polymere Anionen/Kationen |
| EP2140264A1 (fr) | 2007-04-19 | 2010-01-06 | 3M Innovative Properties Company | Procédés d'utilisation d'un matériau de support solide destiné à lier des biomolécules |
| JP5361221B2 (ja) * | 2008-03-10 | 2013-12-04 | 国立大学法人九州大学 | 混合samの作製方法 |
| JP2010096677A (ja) * | 2008-10-17 | 2010-04-30 | Toray Ind Inc | 抗体/抗原結合能を有する高感度免疫学測定用ナノ粒子 |
| US8501406B1 (en) | 2009-07-14 | 2013-08-06 | Pacific Biosciences Of California, Inc. | Selectively functionalized arrays |
| US11079377B2 (en) | 2018-08-24 | 2021-08-03 | International Business Machines Corporation | Nanopore coating for sensing chemical bond formation |
| AU2019343994A1 (en) * | 2018-09-21 | 2021-05-13 | Berkeley Lights, Inc. | Functionalized well plate, methods of preparation and use thereof |
| CN111621076A (zh) * | 2020-06-11 | 2020-09-04 | 哈尔滨理工大学 | 一种用于紫外光交联的新型纳米杂化光交联剂的制备方法 |
| JP7694896B2 (ja) * | 2021-02-19 | 2025-06-18 | 横浜ゴム株式会社 | シランカップリング剤の製造方法 |
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| US5736257A (en) * | 1995-04-25 | 1998-04-07 | Us Navy | Photoactivatable polymers for producing patterned biomolecular assemblies |
| US6552060B1 (en) * | 1997-08-11 | 2003-04-22 | Prolx Pharmaceuticals, Inc. | Asymmetric disulfides and methods of using same |
| US6406921B1 (en) * | 1998-07-14 | 2002-06-18 | Zyomyx, Incorporated | Protein arrays for high-throughput screening |
| US6579673B2 (en) * | 1998-12-17 | 2003-06-17 | Kimberly-Clark Worldwide, Inc. | Patterned deposition of antibody binding protein for optical diffraction-based biosensors |
| US6489102B2 (en) * | 1999-08-05 | 2002-12-03 | Wisconsin Alumni Research Foundation | Biomolecule and/or cellular arrays on metal surfaces and product produced thereby |
| US6518194B2 (en) * | 2000-12-28 | 2003-02-11 | Thomas Andrew Winningham | Intermediate transfer layers for nanoscale pattern transfer and nanostructure formation |
-
2003
- 2003-08-18 JP JP2004529123A patent/JP2005535898A/ja active Pending
- 2003-08-18 EP EP03788638A patent/EP1537202A4/fr not_active Withdrawn
- 2003-08-18 WO PCT/US2003/025927 patent/WO2004017042A2/fr not_active Ceased
- 2003-08-18 AU AU2003263922A patent/AU2003263922A1/en not_active Abandoned
- 2003-08-18 CA CA002496141A patent/CA2496141A1/fr not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003263922A1 (en) | 2004-03-03 |
| WO2004017042A2 (fr) | 2004-02-26 |
| JP2005535898A (ja) | 2005-11-24 |
| WO2004017042A3 (fr) | 2004-12-09 |
| EP1537202A2 (fr) | 2005-06-08 |
| EP1537202A4 (fr) | 2007-09-19 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |