JP7398566B2 - 遷移金属錯体、電子伝達媒介体として使用される化合物、遷移金属錯体の製造方法、遷移金属錯体を電子伝達媒介体として含む装置、電気化学的バイオセンサ用センシング膜 - Google Patents
遷移金属錯体、電子伝達媒介体として使用される化合物、遷移金属錯体の製造方法、遷移金属錯体を電子伝達媒介体として含む装置、電気化学的バイオセンサ用センシング膜 Download PDFInfo
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- JP7398566B2 JP7398566B2 JP2022537823A JP2022537823A JP7398566B2 JP 7398566 B2 JP7398566 B2 JP 7398566B2 JP 2022537823 A JP2022537823 A JP 2022537823A JP 2022537823 A JP2022537823 A JP 2022537823A JP 7398566 B2 JP7398566 B2 JP 7398566B2
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- 229910052723 transition metal Inorganic materials 0.000 title claims description 38
- 150000003624 transition metals Chemical class 0.000 title claims description 38
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- 238000000034 method Methods 0.000 title claims description 7
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- 238000006243 chemical reaction Methods 0.000 claims description 28
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- 102000004190 Enzymes Human genes 0.000 claims description 22
- 108090000790 Enzymes Proteins 0.000 claims description 22
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- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 10
- MMXZSJMASHPLLR-UHFFFAOYSA-N pyrroloquinoline quinone Chemical compound C12=C(C(O)=O)C=C(C(O)=O)N=C2C(=O)C(=O)C2=C1NC(C(=O)O)=C2 MMXZSJMASHPLLR-UHFFFAOYSA-N 0.000 claims description 10
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- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-M 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- QUMXRZNAUFKBAS-UHFFFAOYSA-N 2-(4-methoxyphenyl)pyridine Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=N1 QUMXRZNAUFKBAS-UHFFFAOYSA-N 0.000 description 1
- KJNZQKYSNAQLEO-UHFFFAOYSA-N 2-(4-methylphenyl)pyridine Chemical compound C1=CC(C)=CC=C1C1=CC=CC=N1 KJNZQKYSNAQLEO-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- WYKHSBAVLOPISI-UHFFFAOYSA-N 2-phenyl-1,3-thiazole Chemical compound C1=CSC(C=2C=CC=CC=2)=N1 WYKHSBAVLOPISI-UHFFFAOYSA-N 0.000 description 1
- RVRASVNRDWXDFX-UHFFFAOYSA-N 2-pyridin-2-yl-3H-cyclopenta[e]thiazine Chemical compound C1C=C2C=CC=C2SN1C3=CC=CC=N3 RVRASVNRDWXDFX-UHFFFAOYSA-N 0.000 description 1
- NMLYGLCBSFKJFI-UHFFFAOYSA-N 4-pyridin-2-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=N1 NMLYGLCBSFKJFI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 108010024957 Ascorbate Oxidase Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 108700023156 Glutamate dehydrogenases Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 101710138959 NAD-specific glutamate dehydrogenase Proteins 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229960005219 gentisic acid Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000005638 hydrazono group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- PFCMCBTZGOMQIN-UHFFFAOYSA-N indeno[1,2-d]pyridazin-1-one Chemical compound C1=CC=C2C3=CN=NC(=O)C3=CC2=C1 PFCMCBTZGOMQIN-UHFFFAOYSA-N 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229950006238 nadide Drugs 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- IHUHXSNGMLUYES-UHFFFAOYSA-J osmium(iv) chloride Chemical compound Cl[Os](Cl)(Cl)Cl IHUHXSNGMLUYES-UHFFFAOYSA-J 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 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
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
- G01N27/3275—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction
- G01N27/3277—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction being a redox reaction, e.g. detection by cyclic voltammetry
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
- A61B5/14532—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue for measuring glucose, e.g. by tissue impedance measurement
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
- G01N27/3271—Amperometric enzyme electrodes for analytes in body fluids, e.g. glucose in blood
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
- A61B5/1468—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using chemical or electrochemical methods, e.g. by polarographic means
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
- A61B5/1486—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using enzyme electrodes, e.g. with immobilised oxidase
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
- A61B5/1486—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using enzyme electrodes, e.g. with immobilised oxidase
- A61B5/14865—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using enzyme electrodes, e.g. with immobilised oxidase invasive, e.g. introduced into the body by a catheter or needle or using implanted sensors
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/001—Enzyme electrodes
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Pathology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Optics & Photonics (AREA)
- Medical Informatics (AREA)
- Biomedical Technology (AREA)
- Surgery (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Electrochemistry (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Hematology (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
αは1~3の整数であり;
C-Nはフェニル環および一つ以上の窒素原子を有するヘテロ環を含むバイデンテート(bidentate、以下、“二座配位子”とも言う)リガンドであり;
具体的な様態で、前記一つ以上の窒素原子を有するヘテロ環は一つ以上の窒素原子、好ましくは1~3の窒素原子を含むヘテロ環であるか、または一つ以上の窒素原子と共に、OおよびSからなる群より選択される1または2のヘテロ原子を共に含むヘテロ環であってもよい。また、前記ヘテロ環はモノ、ジ、トリまたはマルチヘテロ環であってもよく、4員(membered)~16員、5員~15員または5員~14員のヘテロ環であってもよいが、これに制限されるわけではない。
N-Nは窒素原子を含むヘテロ環であるバイデンテートリガンドであり;
mは-1~-5または1~5を示す負電荷あるいは正電荷であり;
dは0~2の整数であり;
Xは対イオン(counter ion)であり、好ましくは、F、Cl、Br、IおよびPF6からなる群より選択される対イオンである。
mは-1~-5または1~5を示す負電荷あるいは正電荷であり;
dは0~2の整数であり;
Xは対イオン(counter ion)であり、好ましくF、Cl、Br、IおよびPF6からなる群より選択される対イオンである。
RLはヘテロ環式化合物Lcの全ての官能基であり;
RL、R2、R3、R4、R5はそれぞれ独立して、-H、-F、-Cl、-Br、-I、-NO2、-CN、-C(=O)H、-CO2H、-SO3H、-NHNH2、-SH、-OH、-NH2、置換もしくは非置換のアルコキシカルボニル、置換もしくは非置換のアルキルアミノカルボニル、置換もしくは非置換のジアルキルアミノカルボニル、置換もしくは非置換のアルコキシ、置換もしくは非置換のアルキルアミノ、置換もしくは非置換のジアルキルアミノ、置換もしくは非置換のアルカニルアミノ、置換もしくは非置換のアリールカルボキシアミド、置換もしくは非置換のヒドラジノ、置換もしくは非置換のアルキルヒドラジノ、置換もしくは非置換のヒドロキシアミノ、置換もしくは非置換のアルコキシアミノ、置換もしくは非置換のアルキルチオ、置換もしくは非置換のアルケニル、置換もしくは非置換のアリールおよび置換もしくは非置換のアルキルからなる群より選択されるものであってもよく;
R1は遷移金属と配位する部分である。
前記、RLはヘテロ環であるLN1およびLN2の官能基であり、それぞれ-H、-F、-Cl、-Br、-I、-NO2、-CN、-C(=O)H、-CO2H、-SO3H、-NHNH2、-SH、-OH、-NH2または置換もしくは非置換のアルコキシカルボニル、置換もしくは非置換のアルキルアミノカルボニル、置換もしくは非置換のジアルキルアミノカルボニル、置換もしくは非置換のアルコキシ、置換もしくは非置換のアルキルアミノ、置換もしくは非置換のジアルキルアミノ、置換もしくは非置換のアルカニルアミノ、置換もしくは非置換のアリールカルボキシアミド、置換もしくは非置換のヒドラジノ、置換もしくは非置換のアルキルヒドラジノ、置換もしくは非置換のヒドロキシアミノ、置換もしくは非置換のアルコキシアミノ、置換もしくは非置換のアルキルチオ、置換もしくは非置換のアルケニル、置換もしくは非置換のアリール、置換もしくは非置換のアルキルであってもよいか、または
前記LN1およびLN2にそれぞれ連結されている2種のRLが互いに連結されてLN1およびLN2と共に置換もしくは非置換の3環のヘテロ環を形成することができる。この時、前記LN1およびLN2にそれぞれ連結されている2種のRLが互いに連結されて形成される環(即ち、前記3環のうちの中間に位置した環)は5員~7員の環(例えば、シクロアルキル、ヘテロシクロアルキル)であってもよく、この時、前記5員~7員の環はoxo(=O)、-CO2H、-SO3H、-NHNH2、-SH、-OH、-NH2または置換もしくは非置換のアルコキシカルボニル、置換もしくは非置換のアルキルアミノカルボニル、置換もしくは非置換のジアルキルアミノカルボニル、置換もしくは非置換のアルコキシ、置換もしくは非置換のアルキルアミノ、置換もしくは非置換のジアルキルアミノ、置換もしくは非置換のアルカニルアミノ、置換もしくは非置換のアリールカルボキシアミド、置換もしくは非置換のヒドラジノ、置換もしくは非置換のアルキルヒドラジノ、置換もしくは非置換のヒドロキシアミノ、置換もしくは非置換のアルコキシアミノ、置換もしくは非置換のアルキルチオ、置換もしくは非置換のアルケニル、置換もしくは非置換のアリール、置換もしくは非置換のアルキルが置換されるかまたは非置換であってもよい。
i)ヘキサクロロオスミウムアンモニウム塩を1,3-シクロヘキサジエンと反応させてオスミウム二量体である化学式7のビス[(η6-ベンゼン)ジクロロジオスミウム[(η6-bz)OsCl2]2を製造する段階;
ii)前記段階i)で製造されたビス[(η6-ベンゼン)ジクロロジオスミウム[(η6-bz)OsCl2]2にC-Nリガンドを導入してC-N複合体を製造する段階;および
iii)前記段階ii)で製造されたC-N複合体にN-Nリガンドを導入して前記化学式1の遷移金属複合体を製造する段階。
実験材料
商業的に購入した溶媒と試薬はそれ以上の精製過程を経ずに使用した。金属錯体精製のためのアルミナの場合にはAldrich社の中性アルミナを10mLピペットを用いてろ過した。錯体のクロリド対イオン交換のためのレジンの場合、Aldrich社のDowex 1×4 chloride form、50-100meshを使用した。
化学式1で表されるオスミウム錯体の場合には商業的に販売されるハロゲン化オスミウム塩[(NH--4)2OsCl6]から三段階を経て合成することができる。第1段階は、4価イオン状態のオスミウム塩を2価イオン状態のオスミウム二量体の形態に合成する段階である。第2段階は、合成されたオスミウム二量体を一番目のリガンドであるC-Nリガンドが結合された形態のオスミウム錯体を合成する段階である。第3段階は、残り同一なN-Nリガンドが結合されて化学式1で表されるオスミウム錯体を合成する段階である。
化学式7のようなベンゼンが上下に付いたオスミウム二量体の合成時、商業的に購買できるオスミウム開始物質としては水和物形態のオスミウム塩(OsCl3・xH2O、H2OsCl6・xH2O)や対イオンがソジウムであるハロゲン化オスミウム塩(Na2OsCl6)を用いて合成した。
-化合物A;質量回収:2.9g;1H-NMR(400MHz、DMSO):δ=7.20(s、6H)、6.17(s、6H);13C-NMR(100MHz、CDCl3):δ=88.32、79.51.
このように得られた化合物Aは追加精製なく第2合成段階に使用してオスミウム錯体を合成した後、精製および分析を実施した。
前記段階で合成した化合物Aを用いて一番目のリガンドであるC-Nリガンドを導入する段階である。提案された合成方法で図2に示されたC-Nリガンドを有する様々なオスミウム錯体を合成した。
1)(η6-ベンゼン)[2-(1-メチル-イミダゾール-κN)フェニル-κC][1-メチル-2-フェニル-イミダゾール-κN]オスミウムクロライド{(η6-Benzene)[2-(1-Methyl-imidazole-κN)phenyl-κC][1-Methyl-2-phenyl-imidazole-κN]osmiumchloride}の合成(C-N complex 1)
第3段階は、第2段階でC-Nリガンドを導入したオスミウム錯体に同一なN-Nリガンド二つを導入する過程である。提案された合成方法を通じて図3a-cのような化学式1に該当する様々なオスミウム有機金属錯体を合成した。生成された有機金属錯体は、ESI-MSを通じて合成された結果と物質の酸化状態を決定した。収率は高い酸化状態による基準で計算した。
[Os(2-(1-メチル-イミダゾール-κN)フェニル-κC)(ビチアゾール)2]2PF6 ([Os(2-(1-Methyl-imidazole-κN)phenyl-κC)(bithiazole)2]2PF6)
[Os(2-(1-メチル-イミダゾール-κN)フェニル-κC)(ビピリジン)2]2PF6 ([Os(2-(1-Methyl-imidazole-κN)phenyl-κC)(bipyridine)2]2PF6)
[Os(2-(2-ピリジン-κN)フェニル-κC)(1,1’-ジメチル-2,2’-ビピリジン)2]2PF6 ([Os(2-(2-pyridine-κN)phenyl-κC)(1,1’-dimethyl-2,2’-bipyridine)2]2PF6)
[Os(2-(2-ピリジン-κN)フェニル-κC)(2-チアゾール-2-イル-4,5-ジヒドロ-オキサゾール)2]2PF6 ([Os(2-(2-pyridine-κN)phenyl-κC)(2-Thiazol-2-yl-4,5-dihydro-oxazole)2]2PF6)
[Os(2-(2-ピリジン-κN)フェニル-κC)(2-ピリジン-2-イル-ベンゾチアゾール)2]PF6 ([Os(2-(2-pyridine-κN)phenyl-κC)(2-Pyridin-2-yl-benzothiazole)2]PF6)
[Os(2-(2-ピリジン-κN)フェニル-κC)(2-ピリジン-2-イル-ベンゾオキサゾール)2]PF6 ([Os(2-(2-pyridine-κN)phenyl-κC)(2-Pyridin-2-yl-benzooxazole)2]PF6)
[Os(2-(2-チアゾール-κN)フェニル-κC)(1、1’-ジメチル-2,2’-ビピリジン)2]2PF6 ([Os(2-(2-thiazole-κN)phenyl-κC)(1、1’-dimethyl-2,2’-bipyridine)2]2PF6)
[Os(2-(2-チアゾール-κN)フェニル-κC)(4,5-ジアザフルオレンオン)2]PF6 ([Os(2-(2-thiazole-κN)phenyl-κC)(4,5-Diazafluorenone)2]PF6)
[Os(2-(1-メチル-ベンゾイミダゾール-κN)フェニル-κC)(ビピリジン)2]2PF6 ([Os(2-(1-Methyl-benzoimidazole-κN)phenyl-κC)(bipyridine)2]2PF6)
[Os(2-(2-[1-アリル-ベンズイミダゾール]-κN)フェニル-κC)(4,4’-ジメチル-2,2’-ビピリジン)2]2PF6 ([Os(2-(2-[1-allyl-benzimidazole]-κN)phenyl-κC)(4,4’-dimethyl-2,2’-bipyridine)2]2PF6)
[Os(2-(2-ピリジニル-κN)-4-アリル-フェニル-κC)(4,4’-ジメチル-2,2’-ビピリジン)2]2PF6 ([Os(2-(2-pyridinyl-κN)-4-allyl-phenyl-κC)(4,4’-dimethyl-2,2’-bipyridine)2]2PF6)
[Os(2-(2-ピリジニル-κN)-4-アリル-フェニル-κC)(ビピリジン)2]2PF6 ([Os(2-(2-pyridinyl-κN)-4-allyl-phenyl-κC)(bipyridine)2]2PF6)
[Os(2-(2-ピリジニル-κN)-5-メタンアミン-フェニル-κC)(ビピリジン)2]2PF6 ([Os(2-(2-pyridinyl-κN)-5-methaneamine-phenyl-κC)(bipyridine)2]2PF6)
[Os(2-(2-ピリジニル-κN)-5-メタンアミン-フェニル-κC)(4,4’-ジメチル-2,2’-ビピリジン)2]2PF6 ([Os(2-(2-pyridinyl-κN)-5-methaneamine-phenyl-κC)(4,4’-dimethyl-2,2’-bipyridine)2]2PF6)
[Os(2-(2-ピリジニル-κN)-5-メタンアミン-フェニル-κC)(4,4’-ジメトキシ-2,2’-ビピリジン)2]2PF6 ([Os(2-(2-pyridinyl-κN)-5-methaneamine-phenyl-κC)(4,4’-dimethoxy-2,2’-bipyridine)2]2PF6)
[Os(2-(2-ピリジニル-κN)-5-メタンアミン-フェニル-κC)(ビチアゾール)2]2PF6 ([Os(2-(2-pyridinyl-κN)-5-methaneamine-phenyl-κC)(bithiazole)2]2PF6)
[Os(2-(2-ピリジニル-κN)-5-ホルミル-フェニル-κC)(ビピリジン)2]PF6 ([Os(2-(2-pyridinyl-κN)-5-formyl-phenyl-κC)(bipyidine)2]PF6)
[Os(2-(2-ピリジニル-κN)-5-ホルミル-フェニル-κC)(4,4’-ジメチル-2,2’-ビピリジン)2]Cl ([Os(2-(2-pyridinyl-κN)-5-formyl-phenyl-κC)(4,4’-dimethyl-2,2’-bipyridine)2]Cl)
[Os(2-(2-ピリジン-κN)-5-メチル-フェニル-κC)(4-メチル-4’-カルバルデヒド-2,2’-ビピリジン)2]2Cl ([Os(2-(2-pyridine-κN)-5-methyl-phenyl-κC)(4-methyl-4’-carbaldehyde-2,2’-bipyridine)2]2Cl)
[Os(2-(2-ピリジン-κN)フェニル-κC)(4-メチル-4’-カルバルデヒド-2,2’-ビピリジン)2]2Cl ([Os(2-(2-pyridine-κN)phenyl-κC)(4-methyl-4’-carbaldehyde-2,2’-bipyridine)2]2Cl)(Os-complex 20)
[Os(2-(2-ピリジン-κN)フェニル-κC)(4-メトキシ-4’-カルバルデヒド-2,2’-ビピリジン)2]2Cl ([Os(2-(2-pyridine-κN)phenyl-κC)(4-metoxy-4’-carbaldehyde-2,2’-bipyridine)2]2Cl)(Os-complex 21)
Claims (13)
- 下記の化学構造式を有する電子伝達媒介体として有用な遷移金属錯体:
[化学式1]
[M(C-N)α(N-N)3-α]mdX
上記式中、MはOsであり、
αは1であり;
mは-1~-5または1~5を示す負電荷あるいは正電荷であり;
dは0~2の整数であり;
Xは対イオン(counter ion)であり、
前記C-Nは、
前記N-Nは、
- 前記対イオンはF、Cl、Br、IおよびPF6からなる群より選択されるものである、請求項1に記載の遷移金属錯体。
- 次の化合物からなる群より選択される、電子伝達媒介体として使用される化合物:(ただし、下記化学式においてMeはメチルである。)
- 対イオンがアンモニウムである遷移金属のハロゲン化塩を用いて遷移金属の二量体を合成する段階;前記遷移金属の二量体にC-Nリガンドを導入してC-N複合体を製造する段階;前記C-N複合体にN-Nリガンドを導入して化学式1の遷移金属錯体を製造する段階を含む請求項1による遷移金属錯体の製造方法であって、
前記C-Nは、
前記N-Nは、
- i)対イオンがアンモニウムである遷移金属のハロゲン化塩としてヘキサクロロオスミウムアンモニウム塩を1,3-シクロヘキサジエンと反応させてオスミウム二量体である化学式7のビス[(η6-ベンゼン)ジクロロジオスミウム[(η6-bz)OsCl2]2を製造する段階;
ii)前記段階i)で製造されたビス[(η6-ベンゼン)ジクロロジオスミウム[(η6-bz)OsCl2]2にC-Nリガンドを導入してC-N複合体を製造する段階;および
iii)前記段階ii)で製造されたC-N複合体にN-Nリガンドを導入して前記化学式1の遷移金属錯体を製造する段階、
を含む請求項1による化学式1の遷移金属錯体の製造方法:
前記N-Nは、
- 段階i)のヘキサクロロオスミウムアンモニウム塩に対して1,3-シクロヘキサジエンを7~10当量使用し、反応温度は90~100℃であり、反応時間は48~72時間である、請求項5に記載の遷移金属錯体の製造方法。
- 前記C-Nリガンドは化学式7のオスミウム二量体に対して2当量~4当量使用し、反応温度は80~160℃であり、反応時間は6~48時間である、請求項5に記載の遷移金属錯体の製造方法。
- 前記C-N複合体は次の化合物からなる群より選択される構造を有するものである、請求項5に記載の遷移金属錯体の製造方法:
- 前記N-Nリガンドは化学式7のオスミウム二量体に対して2当量~2.2当量使用し、反応温度は70~90℃であり、反応時間は3~36時間である、請求項5に記載の遷移金属錯体の製造方法。
- 請求項1~3のうちのいずれか一項による遷移金属錯体を電子伝達媒介体として含む装置。
- 前記装置は電気化学的バイオセンサである、請求項10に記載の装置。
- 液体性生体試料を酸化還元させることができる酵素;および
請求項1~3のうちのいずれか一項の遷移金属錯体を電子伝達媒介体として含む電気化学的バイオセンサ用センシング膜。 - 前記酵素は
脱水素酵素(dehydrogenase)、酸化酵素(oxidase)、およびエステル化酵素(esterase)からなる群より選択された1種以上の酸化還元酵素;または
脱水素酵素、酸化酵素、およびエステル化酵素からなる群より選択された1種以上の酸化還元酵素とフラビンアデニンジヌクレオチド(flavin adenine dinucleotide、FAD)、ニコチンアミドアデニンジヌクレオチド(nicotinamide adenine dinucleotide、NAD)、およびピロロキノリンキノン(Pyrroloquinoline quinone、PQQ)からなる群より選択された1種以上の補助因子を含むものである、請求項12に記載の電気化学的バイオセンサ用センシング膜。
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US20120215000A1 (en) | 2011-02-23 | 2012-08-23 | Jui-Yi Tsai | Methods of making bis-tridentate carbene complexes of ruthenium and osmium |
WO2013117870A1 (fr) | 2012-02-10 | 2013-08-15 | Almetis | Méthodes et compositions pour le traitement de cancer |
US20140138653A1 (en) | 2012-11-20 | 2014-05-22 | Universal Display Corporation | Osmium (iv) complexes for oled material |
US20170350850A1 (en) | 2014-12-31 | 2017-12-07 | I-Sens, Inc. | Electrochemical biosensor |
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US20110155238A1 (en) * | 2008-04-24 | 2011-06-30 | Xiuliang Shen | Pyridine type metal complex, photoelectrode comprising the metal complex, and dye-sensitized solar cell comprising the photoelectrode |
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JP2009131183A (ja) | 2007-11-29 | 2009-06-18 | Momoya Co Ltd | 米類の乳酸発酵食品およびその製造方法 |
US20120215000A1 (en) | 2011-02-23 | 2012-08-23 | Jui-Yi Tsai | Methods of making bis-tridentate carbene complexes of ruthenium and osmium |
WO2013117870A1 (fr) | 2012-02-10 | 2013-08-15 | Almetis | Méthodes et compositions pour le traitement de cancer |
US20140138653A1 (en) | 2012-11-20 | 2014-05-22 | Universal Display Corporation | Osmium (iv) complexes for oled material |
US20170350850A1 (en) | 2014-12-31 | 2017-12-07 | I-Sens, Inc. | Electrochemical biosensor |
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US20230125122A1 (en) | 2023-04-27 |
EP4079740A1 (en) | 2022-10-26 |
EP4079740A4 (en) | 2023-06-07 |
JP2023516242A (ja) | 2023-04-19 |
WO2021125791A1 (ko) | 2021-06-24 |
CN114867732A (zh) | 2022-08-05 |
AU2020409909B2 (en) | 2024-03-14 |
AU2020409909A1 (en) | 2022-07-21 |
KR20210076878A (ko) | 2021-06-24 |
KR102610156B1 (ko) | 2023-12-05 |
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