JP6522003B2 - フェナジニウムメディエーター - Google Patents
フェナジニウムメディエーター Download PDFInfo
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- JP6522003B2 JP6522003B2 JP2016559436A JP2016559436A JP6522003B2 JP 6522003 B2 JP6522003 B2 JP 6522003B2 JP 2016559436 A JP2016559436 A JP 2016559436A JP 2016559436 A JP2016559436 A JP 2016559436A JP 6522003 B2 JP6522003 B2 JP 6522003B2
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- SQHWUYVHKRVCMD-UHFFFAOYSA-N 2-n,2-n-dimethyl-10-phenylphenazin-10-ium-2,8-diamine;chloride Chemical compound [Cl-].C12=CC(N(C)C)=CC=C2N=C2C=CC(N)=CC2=[N+]1C1=CC=CC=C1 SQHWUYVHKRVCMD-UHFFFAOYSA-N 0.000 title description 4
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
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- 125000003118 aryl group Chemical group 0.000 claims description 24
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
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- QWUFXJHVFNRNCU-UHFFFAOYSA-N phenazin-1-amine Chemical class C1=CC=C2N=C3C(N)=CC=CC3=NC2=C1 QWUFXJHVFNRNCU-UHFFFAOYSA-N 0.000 description 9
- 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 description 9
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- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 7
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- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 7
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 6
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- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000003410 quininyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 102200122471 rs104894207 Human genes 0.000 description 1
- 102200053925 rs59115483 Human genes 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 210000001138 tear Anatomy 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
- QIQCZROILFZKAT-UHFFFAOYSA-N tetracarbon dioxide Chemical group O=C=C=C=C=O QIQCZROILFZKAT-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
-
- 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
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01D—MEASURING NOT SPECIALLY ADAPTED FOR A SPECIFIC VARIABLE; ARRANGEMENTS FOR MEASURING TWO OR MORE VARIABLES NOT COVERED IN A SINGLE OTHER SUBCLASS; TARIFF METERING APPARATUS; MEASURING OR TESTING NOT OTHERWISE PROVIDED FOR
- G01D21/00—Measuring or testing not otherwise provided for
- G01D21/02—Measuring two or more variables by means not covered by a single other subclass
-
- 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
-
- 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
- G01N33/544—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being organic
-
- 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
- G01N33/66—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood sugars, e.g. galactose
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2400/00—Assays, e.g. immunoassays or enzyme assays, involving carbohydrates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Pathology (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14164571 | 2014-04-14 | ||
| EP14164571.3 | 2014-04-14 | ||
| PCT/EP2015/057933 WO2015158645A1 (en) | 2014-04-14 | 2015-04-13 | Phenazinium mediators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017517480A JP2017517480A (ja) | 2017-06-29 |
| JP2017517480A5 JP2017517480A5 (enExample) | 2018-05-17 |
| JP6522003B2 true JP6522003B2 (ja) | 2019-05-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016559436A Active JP6522003B2 (ja) | 2014-04-14 | 2015-04-13 | フェナジニウムメディエーター |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9988358B2 (enExample) |
| EP (1) | EP3131882B1 (enExample) |
| JP (1) | JP6522003B2 (enExample) |
| KR (1) | KR101896820B1 (enExample) |
| CN (1) | CN106164054B (enExample) |
| CA (1) | CA2945612C (enExample) |
| WO (1) | WO2015158645A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3523639T3 (pl) | 2016-10-05 | 2025-03-17 | F. Hoffmann-La Roche Ag | Odczynniki wykrywające i układy elektrod do elementów diagnostycznych testów wieloanalitowych oraz sposoby ich zastosowania |
| CN111936050A (zh) | 2018-03-30 | 2020-11-13 | 普和希控股公司 | 使用吩嗪衍生物或含有吩嗪衍生物的高分子量氧化还原聚合物的传感器 |
| JP7285332B2 (ja) * | 2019-09-30 | 2023-06-01 | Ｐｈｃホールディングス株式会社 | 高分子量レドックスポリマー及びそれを用いたバイオセンサ |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3228542A1 (de) | 1982-07-30 | 1984-02-02 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur bestimmung der konzentration elektrochemisch umsetzbarer stoffe |
| JPS60114193A (ja) * | 1983-11-22 | 1985-06-20 | Toyo Jozo Co Ltd | 新規なマルトースデヒドロゲナーゼおよびその製法それを用いる分析法 |
| US5108564A (en) | 1988-03-15 | 1992-04-28 | Tall Oak Ventures | Method and apparatus for amperometric diagnostic analysis |
| US5054039A (en) | 1990-08-30 | 1991-10-01 | The United States Of America As Represented By The Secretary Of The Navy | Digital calibration circuit employing composite sine wave signals |
| DE19629656A1 (de) | 1996-07-23 | 1998-01-29 | Boehringer Mannheim Gmbh | Diagnostischer Testträger mit mehrschichtigem Testfeld und Verfahren zur Bestimmung von Analyt mit dessen Hilfe |
| US5801006A (en) | 1997-02-04 | 1998-09-01 | Specialty Assays, Inc. | Use of NADPH and NADH analogs in the measurement of enzyme activities and metabolites |
| JP4070050B2 (ja) | 1998-07-24 | 2008-04-02 | テルモ株式会社 | 血糖値測定方法及び装置 |
| US6380380B1 (en) | 1999-01-04 | 2002-04-30 | Specialty Assays, Inc. | Use of nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucliotide phosphate (NADP) analogs to measure enzyme activities metabolites and substrates |
| WO2002034919A1 (en) | 2000-10-27 | 2002-05-02 | Roche Diagnostics Gmbh | Variants of soluble pyrroloquinoline quinone-dependent glucose dehydrogenase |
| US7867369B2 (en) | 2003-06-20 | 2011-01-11 | Roche Diagnostics Operations, Inc. | Biosensor with multiple electrical functionalities |
| MXPA06001719A (es) | 2003-08-11 | 2006-05-19 | Codexis Inc | Polipeptidos de glucosa deshidrogenasa mejorados, y polinucleotidos relacionados. |
| DE102005035461A1 (de) | 2005-07-28 | 2007-02-15 | Roche Diagnostics Gmbh | Stabile NAD/NADH-Derivate |
| DE502006004037D1 (de) | 2005-12-19 | 2009-07-30 | Roche Diagnostics Gmbh | Sandwichsensor zur ermittlung einer analytkonzentration |
| EP2093284A1 (de) | 2008-02-19 | 2009-08-26 | F.Hoffmann-La Roche Ag | Stabilisierung von Dehydrogenasen mit stabilen Coenzymen |
| US8008037B2 (en) * | 2008-03-27 | 2011-08-30 | Roche Diagnostics Operations, Inc. | Matrix composition with alkylphenazine quaternary salt and a nitrosoaniline |
| EP3838147B1 (en) | 2012-06-29 | 2023-12-06 | Roche Diabetes Care GmbH | Sensor element for detecting an analyte in a body fluid |
| JP2014194411A (ja) * | 2013-02-28 | 2014-10-09 | Aisin Seiki Co Ltd | 修飾電極、当該修飾電極の製造方法、当該修飾電極を備えるバイオ電池並びにバイオセンサー |
| CN111848578B (zh) * | 2014-08-22 | 2023-10-31 | 豪夫迈·罗氏有限公司 | 氧化还原指示剂 |
-
2015
- 2015-04-13 CN CN201580019437.2A patent/CN106164054B/zh active Active
- 2015-04-13 KR KR1020167028460A patent/KR101896820B1/ko active Active
- 2015-04-13 EP EP15718466.4A patent/EP3131882B1/en active Active
- 2015-04-13 JP JP2016559436A patent/JP6522003B2/ja active Active
- 2015-04-13 CA CA2945612A patent/CA2945612C/en not_active Expired - Fee Related
- 2015-04-13 WO PCT/EP2015/057933 patent/WO2015158645A1/en not_active Ceased
-
2016
- 2016-10-11 US US15/290,440 patent/US9988358B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP3131882A1 (en) | 2017-02-22 |
| KR20160132970A (ko) | 2016-11-21 |
| US9988358B2 (en) | 2018-06-05 |
| JP2017517480A (ja) | 2017-06-29 |
| CA2945612C (en) | 2019-09-10 |
| EP3131882B1 (en) | 2020-07-15 |
| KR101896820B1 (ko) | 2018-09-07 |
| US20170226068A1 (en) | 2017-08-10 |
| CN106164054B (zh) | 2019-05-07 |
| CA2945612A1 (en) | 2015-10-22 |
| CN106164054A (zh) | 2016-11-23 |
| WO2015158645A1 (en) | 2015-10-22 |
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