CA3043329A1 - Coatings with tunable amine density - Google Patents
Coatings with tunable amine densityInfo
- Publication number
- CA3043329A1 CA3043329A1 CA3043329A CA3043329A CA3043329A1 CA 3043329 A1 CA3043329 A1 CA 3043329A1 CA 3043329 A CA3043329 A CA 3043329A CA 3043329 A CA3043329 A CA 3043329A CA 3043329 A1 CA3043329 A1 CA 3043329A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- alkyl
- substituted
- molecule
- salt
- 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
Links
- 238000000576 coating method Methods 0.000 title claims description 80
- 150000001412 amines Chemical class 0.000 title description 18
- 238000000034 method Methods 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Chemical group 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 239000011593 sulfur Chemical group 0.000 claims abstract description 6
- -1 heteroalkylamine Chemical class 0.000 claims description 80
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000003277 amino group Chemical group 0.000 claims description 65
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 48
- 230000027455 binding Effects 0.000 claims description 44
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 239000007790 solid phase Substances 0.000 claims description 24
- 239000011248 coating agent Substances 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 239000012634 fragment Substances 0.000 claims description 20
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 230000008878 coupling Effects 0.000 claims description 17
- 238000010168 coupling process Methods 0.000 claims description 17
- 108091023037 Aptamer Proteins 0.000 claims description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 15
- 108091033319 polynucleotide Proteins 0.000 claims description 15
- 239000002157 polynucleotide Substances 0.000 claims description 15
- 102000040430 polynucleotide Human genes 0.000 claims description 15
- 229910052710 silicon Inorganic materials 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 108010043958 Peptoids Proteins 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 13
- 229920000083 poly(allylamine) Polymers 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 12
- 150000001720 carbohydrates Chemical class 0.000 claims description 12
- 239000002777 nucleoside Substances 0.000 claims description 12
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 12
- 239000002773 nucleotide Substances 0.000 claims description 12
- 125000003729 nucleotide group Chemical group 0.000 claims description 12
- 238000005229 chemical vapour deposition Methods 0.000 claims description 11
- 238000000151 deposition Methods 0.000 claims description 11
- 239000012071 phase Substances 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 230000008021 deposition Effects 0.000 claims description 10
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical group CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 10
- 150000002118 epoxides Chemical class 0.000 claims description 9
- 239000010703 silicon Substances 0.000 claims description 9
- 150000003573 thiols Chemical group 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 150000005215 alkyl ethers Chemical class 0.000 claims description 8
- 125000005012 alkyl thioether group Chemical group 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000004676 glycans Chemical class 0.000 claims description 6
- 229920001282 polysaccharide Polymers 0.000 claims description 6
- 239000005017 polysaccharide Substances 0.000 claims description 6
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 6
- 125000005864 sulfonamidyl group Chemical group 0.000 claims description 6
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 229910052711 selenium Chemical group 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- 101150020251 NR13 gene Proteins 0.000 claims description 2
- OBNDGIHQAIXEAO-UHFFFAOYSA-N [O].[Si] Chemical compound [O].[Si] OBNDGIHQAIXEAO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000412 dendrimer Substances 0.000 claims description 2
- 229920000736 dendritic polymer Polymers 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- BTWRPQHFJAFXJR-UHFFFAOYSA-N n-[2-(ethylaminooxy)ethoxy]ethanamine Chemical compound CCNOCCONCC BTWRPQHFJAFXJR-UHFFFAOYSA-N 0.000 claims description 2
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 claims description 2
- 239000011669 selenium Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 3
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000002405 diagnostic procedure Methods 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 34
- 201000010099 disease Diseases 0.000 description 32
- 238000004458 analytical method Methods 0.000 description 24
- 102000004196 processed proteins & peptides Human genes 0.000 description 16
- 238000003491 array Methods 0.000 description 15
- 239000012491 analyte Substances 0.000 description 11
- 238000003556 assay Methods 0.000 description 11
- 230000003993 interaction Effects 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- 239000011247 coating layer Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 238000011065 in-situ storage Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 208000023275 Autoimmune disease Diseases 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 238000003745 diagnosis Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920001184 polypeptide Polymers 0.000 description 6
- 238000000159 protein binding assay Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 5
- 238000004630 atomic force microscopy Methods 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- 239000000020 Nitrocellulose Substances 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 4
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 4
- 125000005236 alkanoylamino group Chemical group 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 230000009266 disease activity Effects 0.000 description 4
- 238000000572 ellipsometry Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000000696 magnetic material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 201000006417 multiple sclerosis Diseases 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 229920001220 nitrocellulos Polymers 0.000 description 4
- 238000010647 peptide synthesis reaction Methods 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- FSMHYZUFHYGNHS-UHFFFAOYSA-N 3-[ethoxy-di(propan-2-yl)silyl]propan-1-amine Chemical compound CCO[Si](C(C)C)(C(C)C)CCCN FSMHYZUFHYGNHS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 208000003950 B-cell lymphoma Diseases 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
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- 108020004414 DNA Proteins 0.000 description 3
- 238000002965 ELISA Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 208000024777 Prion disease Diseases 0.000 description 3
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
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- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
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- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
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- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
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- 125000006041 3-hexenyl group Chemical group 0.000 description 1
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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- B05D1/60—Deposition of organic layers from vapour phase
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F7/087—Compounds of unknown structure containing a Si-O-Si sequence
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
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- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
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- 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
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- G—PHYSICS
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- 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
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
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- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00603—Making arrays on substantially continuous surfaces
- B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
Landscapes
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- Peptides Or Proteins (AREA)
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- Chemical Vapour Deposition (AREA)
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| EP3538536A4 (en) | 2016-11-09 | 2020-05-13 | Healthtell Inc. | PRE-ASSEMBLED, PROTECTED, CHEMICALLY STABLE, CHEMOSELECTIVE LEFT |
| CN110168370A (zh) | 2016-11-11 | 2019-08-23 | 健康之语公司 | 用于鉴定候选生物标志物的方法 |
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| CN108957005A (zh) | 2012-08-29 | 2018-12-07 | 亚利桑那州评议委员会,亚利桑那州法人团体,代理和代表亚利桑那州立大学 | 免疫特征分析：通向早期诊断和健康监测的途径 |
| EP2893061B1 (en) | 2012-09-05 | 2019-05-22 | Arizona Board of Regents, a Body Corporate of the State of Arizona acting for and on behalf of Arizona State University | Methods for discovering therapeutic targets |
| US10046293B2 (en) | 2012-10-17 | 2018-08-14 | Arizona Board Of Regents, A Body Corporate Of The State Of Arizona | In situ chemical patterning |
| US9970932B2 (en) | 2013-03-15 | 2018-05-15 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-covalent patterned chemical features and use thereof in MALDI-based quality control |
| US9409139B2 (en) | 2013-08-05 | 2016-08-09 | Twist Bioscience Corporation | De novo synthesized gene libraries |
| WO2016011364A1 (en) | 2014-07-18 | 2016-01-21 | Cdi Laboratories, Inc. | Methods and compositions to identify, quantify, and characterize target analytes and binding moieties |
| EP3177640B1 (en) | 2014-08-08 | 2020-05-06 | The Board of Trustees of the Leland Stanford Junior University | High affinity pd-1 agents and methods of use |
| US20160367961A1 (en) | 2015-04-23 | 2016-12-22 | Roche Sequencing Solutions, Inc. | Method and composition for peptide cyclization and protease treatment |
| US10094825B2 (en) | 2015-07-30 | 2018-10-09 | The Florida International University Board Of Trustees | Predictive biomarkers for detection of organ damage in autoimmune illnesses and other diseases |
| AU2017240164A1 (en) | 2016-04-01 | 2018-11-15 | HealthTell, Inc. | Array-based peptide libraries for therapeutic antibody characterization |
| CA3043329A1 (en) | 2016-11-09 | 2018-05-17 | Healthtell Inc. | Coatings with tunable amine density |
| EP3538536A4 (en) | 2016-11-09 | 2020-05-13 | Healthtell Inc. | PRE-ASSEMBLED, PROTECTED, CHEMICALLY STABLE, CHEMOSELECTIVE LEFT |
| JP2020524275A (ja) | 2017-06-19 | 2020-08-13 | ヘルステル・インコーポレイテッドＨｅａｌｔｈｔｅｌｌ Ｉｎｃ． | 鑑別診断のための免疫シグネチャー |
| EP3749676A4 (en) | 2018-02-09 | 2021-12-22 | Healthtell Inc. | NETWORK BASED CYCLIC PEPTIDE BANKS |
| US20220010301A1 (en) | 2018-11-14 | 2022-01-13 | Cowper Sciences Inc. | Methods of selecting functional interface mimics, and compositions thereof |
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2017
- 2017-11-08 CA CA3043329A patent/CA3043329A1/en not_active Abandoned
- 2017-11-08 EP EP17870436.7A patent/EP3538591A4/en not_active Withdrawn
- 2017-11-08 AU AU2017359450A patent/AU2017359450A1/en not_active Abandoned
- 2017-11-08 CN CN201780073240.6A patent/CN110036058A/zh active Pending
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- 2017-11-08 KR KR1020197016059A patent/KR20190082275A/ko not_active Withdrawn
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2022
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| EP3538591A4 (en) | 2020-07-29 |
| EP3538591A1 (en) | 2019-09-18 |
| US11359112B2 (en) | 2022-06-14 |
| CN110036058A (zh) | 2019-07-19 |
| US20190359854A1 (en) | 2019-11-28 |
| US20220290005A1 (en) | 2022-09-15 |
| WO2018089556A1 (en) | 2018-05-17 |
| JP2019536860A (ja) | 2019-12-19 |
| KR20190082275A (ko) | 2019-07-09 |
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