JP5557229B2 - 光分解性ヘテロ二価性架橋剤 - Google Patents
光分解性ヘテロ二価性架橋剤 Download PDFInfo
- Publication number
- JP5557229B2 JP5557229B2 JP2009114028A JP2009114028A JP5557229B2 JP 5557229 B2 JP5557229 B2 JP 5557229B2 JP 2009114028 A JP2009114028 A JP 2009114028A JP 2009114028 A JP2009114028 A JP 2009114028A JP 5557229 B2 JP5557229 B2 JP 5557229B2
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- photodegradable
- group
- reactive group
- alkyne
- 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.)
- Expired - Fee Related
Links
- 239000003431 cross linking reagent Substances 0.000 title claims description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 88
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- 239000000758 substrate Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 150000001875 compounds Chemical class 0.000 description 34
- 150000001345 alkine derivatives Chemical class 0.000 description 33
- -1 2-nitrobenzyl Chemical class 0.000 description 32
- 150000001540 azides Chemical class 0.000 description 29
- 150000003573 thiols Chemical class 0.000 description 28
- 239000004793 Polystyrene Substances 0.000 description 26
- 229920001223 polyethylene glycol Polymers 0.000 description 26
- 239000002202 Polyethylene glycol Substances 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- 229920002223 polystyrene Polymers 0.000 description 25
- 150000001412 amines Chemical class 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 235000002597 Solanum melongena Nutrition 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 229920000575 polymersome Polymers 0.000 description 19
- 239000000126 substance Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- DEGAKNSWVGKMLS-UHFFFAOYSA-N calcein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(O)=O)CC(O)=O)=C(O)C=C1OC1=C2C=C(CN(CC(O)=O)CC(=O)O)C(O)=C1 DEGAKNSWVGKMLS-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 229960002378 oftasceine Drugs 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000013545 self-assembled monolayer Substances 0.000 description 14
- 229920001400 block copolymer Polymers 0.000 description 13
- 229920000469 amphiphilic block copolymer Polymers 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 11
- 229920001427 mPEG Polymers 0.000 description 11
- 238000006303 photolysis reaction Methods 0.000 description 11
- 239000002094 self assembled monolayer Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000010453 quartz Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 238000002211 ultraviolet spectrum Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000021164 cell adhesion Effects 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 230000015843 photosynthesis, light reaction Effects 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- IHPYMWDTONKSCO-UHFFFAOYSA-N 2,2'-piperazine-1,4-diylbisethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCN(CCS(O)(=O)=O)CC1 IHPYMWDTONKSCO-UHFFFAOYSA-N 0.000 description 7
- 239000007990 PIPES buffer Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 125000006850 spacer group Chemical group 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000108 ultra-filtration Methods 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- ZPZDIFSPRVHGIF-UHFFFAOYSA-N 3-aminopropylsilicon Chemical group NCCC[Si] ZPZDIFSPRVHGIF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- DWUCCPNOMFYDOL-UHFFFAOYSA-N propyl(sulfanyl)silicon Chemical group CCC[Si]S DWUCCPNOMFYDOL-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000000682 scanning probe acoustic microscopy Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- HRUAWSQBQLYDKH-UHFFFAOYSA-N 1-(3-methoxy-4-phenylmethoxyphenyl)ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCC1=CC=CC=C1 HRUAWSQBQLYDKH-UHFFFAOYSA-N 0.000 description 2
- DDNCKEFSRTWLFW-UHFFFAOYSA-N 1-(5-methoxy-2-nitro-4-phenylmethoxyphenyl)ethanol Chemical compound COC1=CC(C(C)O)=C([N+]([O-])=O)C=C1OCC1=CC=CC=C1 DDNCKEFSRTWLFW-UHFFFAOYSA-N 0.000 description 2
- DACNMURXMLMAPR-UHFFFAOYSA-N 1-(5-methoxy-2-nitro-4-prop-2-ynoxyphenyl)ethanol Chemical compound COC=1C(=CC(=C(C1)C(C)O)[N+](=O)[O-])OCC#C DACNMURXMLMAPR-UHFFFAOYSA-N 0.000 description 2
- HEFMYOVSBNZWLX-UHFFFAOYSA-N 3-azidopropylsilane Chemical group [SiH3]CCCN=[N+]=[N-] HEFMYOVSBNZWLX-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 2
- 239000006059 cover glass Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000007783 nanoporous material Substances 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 238000001782 photodegradation Methods 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- ZJIFDEVVTPEXDL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) hydrogen carbonate Chemical compound OC(=O)ON1C(=O)CCC1=O ZJIFDEVVTPEXDL-UHFFFAOYSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- IYFZIPQRWIOYTR-UHFFFAOYSA-N 1-(1-bromoethyl)-5-methoxy-2-nitro-4-phenylmethoxybenzene Chemical compound C(C1=CC=CC=C1)OC1=CC(=C(C=C1OC)C(C)Br)[N+](=O)[O-] IYFZIPQRWIOYTR-UHFFFAOYSA-N 0.000 description 1
- CWXZAJNUTOBAOI-UHFFFAOYSA-N 1-(2,3-dimethoxyphenyl)-2-hydroxy-2-phenylethanone Chemical group COC1=CC=CC(C(=O)C(O)C=2C=CC=CC=2)=C1OC CWXZAJNUTOBAOI-UHFFFAOYSA-N 0.000 description 1
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- JTWHVBNYYWFXSI-UHFFFAOYSA-N 2-nitro-1-phenylethanone Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1 JTWHVBNYYWFXSI-UHFFFAOYSA-N 0.000 description 1
- PFEFOHMLVFUELJ-UHFFFAOYSA-N 3-sulfanylideneisoindol-1-one Chemical compound C1=CC=C2C(=O)NC(=S)C2=C1 PFEFOHMLVFUELJ-UHFFFAOYSA-N 0.000 description 1
- 101710141544 Allatotropin-related peptide Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000252506 Characiformes Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 238000000018 DNA microarray Methods 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000012650 click reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000012744 immunostaining Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical group OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 235000019187 sodium-L-ascorbate Nutrition 0.000 description 1
- 239000011755 sodium-L-ascorbate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009114028A JP5557229B2 (ja) | 2009-05-08 | 2009-05-08 | 光分解性ヘテロ二価性架橋剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009114028A JP5557229B2 (ja) | 2009-05-08 | 2009-05-08 | 光分解性ヘテロ二価性架橋剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010260831A JP2010260831A (ja) | 2010-11-18 |
| JP2010260831A5 JP2010260831A5 (enExample) | 2012-07-05 |
| JP5557229B2 true JP5557229B2 (ja) | 2014-07-23 |
Family
ID=43359234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009114028A Expired - Fee Related JP5557229B2 (ja) | 2009-05-08 | 2009-05-08 | 光分解性ヘテロ二価性架橋剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5557229B2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014001196A (ja) * | 2011-09-12 | 2014-01-09 | Univ Kanagawa | 光分解性カップリング剤 |
| JP6657721B2 (ja) | 2015-09-30 | 2020-03-04 | ソニー株式会社 | 細胞の分析方法、細胞分析用チップ、細胞分析用試薬、細胞分析用キット及び細胞分析用装置 |
| EP3438236B1 (en) | 2016-03-28 | 2022-08-24 | Sony Group Corporation | Cell culture container, cell culture system, cell culture kit and cell culture method |
| JP6953679B2 (ja) | 2016-03-30 | 2021-10-27 | ソニーグループ株式会社 | 試料分取キット、試料分取装置 |
| CN108976758B (zh) * | 2018-07-26 | 2020-09-01 | 浙江大学 | 一种光敏性聚乙二醇基抗菌水凝胶敷料及其制备方法 |
| EP4299712A1 (en) | 2021-02-24 | 2024-01-03 | Sony Group Corporation | Cell processing system, cell processing method, and learning data creation method |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0746098B2 (ja) * | 1986-10-24 | 1995-05-17 | 旭化成工業株式会社 | 液体クロマトグラフィー用充填剤 |
| JPH05216219A (ja) * | 1992-02-03 | 1993-08-27 | Hitachi Ltd | 感光性組成物及びそれを用いたパターン形成方法 |
| JP4014142B2 (ja) * | 2002-05-02 | 2007-11-28 | 独立行政法人科学技術振興機構 | 光分解性シランカップリング剤 |
| JP2008504531A (ja) * | 2004-06-24 | 2008-02-14 | ザ スクリップス リサーチ インスティテュート | 切断可能なリンカーを有するアレイ |
| JP5196287B2 (ja) * | 2006-01-16 | 2013-05-15 | 学校法人神奈川大学 | 光分解性カップリング剤 |
| JP5093641B2 (ja) * | 2006-04-25 | 2012-12-12 | 学校法人神奈川大学 | 光分解性カップリング剤 |
| JP2008050321A (ja) * | 2006-08-28 | 2008-03-06 | Univ Kanagawa | 光分解性カップリング剤 |
-
2009
- 2009-05-08 JP JP2009114028A patent/JP5557229B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010260831A (ja) | 2010-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5557229B2 (ja) | 光分解性ヘテロ二価性架橋剤 | |
| FR2640801A1 (fr) | Polyelectrolyte solide et procede pour sa preparation | |
| JP2003321479A (ja) | 光分解性シランカップリング剤 | |
| CN114516871B (zh) | 一种苝酰亚胺衍生物纳米材料及其制备方法和应用 | |
| TWI613206B (zh) | 光分解性材料、基板及其圖型形成方法 | |
| CN1747986A (zh) | 键合有葫芦脲的硅胶 | |
| JP5612467B2 (ja) | Fmocをベースとした加水分解性リンカーの調製方法 | |
| US20110278175A1 (en) | Aniline Derivatives, Polymers, and Uses Thereof | |
| JP5196287B2 (ja) | 光分解性カップリング剤 | |
| JP6308540B2 (ja) | 光分解性カップリング剤 | |
| JP4376540B2 (ja) | 金属表面修飾剤および新規含硫黄化合物 | |
| US8507572B2 (en) | Functionalization of organic surfaces | |
| Chen et al. | A photo-selective chain-end modification of polyacrylate-iodide and its application in patterned polymer brush synthesis | |
| CN110372836B (zh) | 一种乙烯基砜表面引发水相阴离子聚合方法 | |
| JP5093641B2 (ja) | 光分解性カップリング剤 | |
| JP4200212B2 (ja) | アゾアリールメルカプトアルキルポリエチレングリコール | |
| JP6854839B2 (ja) | カリケアマイシン誘導体を合成するための中間体および方法 | |
| CN110475801A (zh) | 在末端具有多个羟基的聚氧乙烯衍生物的制造方法 | |
| JP4841551B2 (ja) | 感光性保護基を含むカップリング剤及び、固体支持体の官能化のためのような、その使用 | |
| JP5721228B2 (ja) | 光分解性ヘテロ二価性架橋剤 | |
| JP2002363154A (ja) | 保護チオール化合物及び保護ジスルフィド化合物 | |
| WO2024261308A1 (en) | Low temperature reactive aryl azides | |
| JP3538633B2 (ja) | アゾベンゼン誘導体化合物及びそれからなる自己組織化膜 | |
| JP6202431B2 (ja) | かご型シルセスキオキサン誘導体 | |
| JP5267096B2 (ja) | N,S−ジ−tert−ブトキシカルボニルグルタチオン蛍光誘導体及びそれを中間体として用いるグルタチオン蛍光誘導体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120418 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20120419 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120518 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131209 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140206 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140226 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140425 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140528 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140528 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5557229 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |