JP3997436B2 - 電気化学発光技術による化合物のモニターリング - Google Patents

電気化学発光技術による化合物のモニターリング Download PDF

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Publication number: JP3997436B2
Authority: JP; Japan
Prior art keywords: reagent; label; ecl; ctfc; compound
Prior art date: 1995-06-07
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

Application number

JP50202097A

Other languages

English (en)

Japanese (ja)

Other versions

JPH11507533A5 (2

JPH11507533A (ja

Inventor

ティー．マーチン，マーク

リアング，パム

ドング，リウエン

Original Assignee

バイオヴェリスコーポレイション

Priority date (The priority date 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 date listed.)

1995-06-07

Filing date

1996-06-07

Publication date

2007-10-24

1996-06-07 Application filed by バイオヴェリスコーポレイション filed Critical バイオヴェリスコーポレイション

1999-07-06 Publication of JPH11507533A publication Critical patent/JPH11507533A/ja

2004-07-29 Publication of JPH11507533A5 publication Critical patent/JPH11507533A5/ja

2007-10-24 Application granted granted Critical

2007-10-24 Publication of JP3997436B2 publication Critical patent/JP3997436B2/ja

2016-06-07 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 115
238000012544 monitoring process Methods 0.000 title claims abstract description 19
238000005516 engineering process Methods 0.000 title description 5
238000000034 method Methods 0.000 claims abstract description 33
238000006243 chemical reaction Methods 0.000 claims description 59
238000004020 luminiscence type Methods 0.000 claims description 42
229950006238 nadide Drugs 0.000 claims description 33
102000004190 Enzymes Human genes 0.000 claims description 32
108090000790 Enzymes Proteins 0.000 claims description 32
239000000758 substrate Substances 0.000 claims description 29
150000003952 β-lactams Chemical class 0.000 claims description 27
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 25
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 25
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 24
229960000723 ampicillin Drugs 0.000 claims description 24
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 24
239000000126 substance Substances 0.000 claims description 19
BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims description 16
239000012488 sample solution Substances 0.000 claims description 14
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 claims description 13
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229910052751 metal Inorganic materials 0.000 claims description 10
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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 claims description 8
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HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 3
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JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 4
HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 claims 4
230000003197 catalytic effect Effects 0.000 claims 3
JWCSIUVGFCSJCK-CAVRMKNVSA-N Disodium Moxalactam Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C1=CC=C(O)C=C1 JWCSIUVGFCSJCK-CAVRMKNVSA-N 0.000 claims 2
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PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims 2
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QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 claims 2
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239000010452 phosphate Substances 0.000 claims 2
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WZOZEZRFJCJXNZ-ZBFHGGJFSA-N cefoxitin Chemical compound N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)CC1=CC=CS1 WZOZEZRFJCJXNZ-ZBFHGGJFSA-N 0.000 claims 1
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
230000007062 hydrolysis Effects 0.000 description 34
238000006460 hydrolysis reaction Methods 0.000 description 34
239000003638 chemical reducing agent Substances 0.000 description 27
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230000000694 effects Effects 0.000 description 15
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150000001768 cations Chemical class 0.000 description 7
238000011534 incubation Methods 0.000 description 7
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238000002360 preparation method Methods 0.000 description 7
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239000012327 Ruthenium complex Substances 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
125000003460 beta-lactamyl group Chemical group 0.000 description 6
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238000001514 detection method Methods 0.000 description 6
238000005424 photoluminescence Methods 0.000 description 6
238000012546 transfer Methods 0.000 description 6
0 C*1=CC=C[C@]2OC2C1C1NCCCCC1 Chemical compound C*1=CC=C[C@]2OC2C1C1NCCCCC1 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000003446 ligand Substances 0.000 description 5
NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 4
VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 4
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
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230000035945 sensitivity Effects 0.000 description 4
239000001488 sodium phosphate Substances 0.000 description 4
229910000162 sodium phosphate Inorganic materials 0.000 description 4
238000012360 testing method Methods 0.000 description 4
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 4
241000193755 Bacillus cereus Species 0.000 description 3
108020005199 Dehydrogenases Proteins 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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238000002835 absorbance Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
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DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
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108010087702 Penicillinase Proteins 0.000 description 2
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230000008033 biological extinction Effects 0.000 description 2
239000012472 biological sample Substances 0.000 description 2
230000021615 conjugation Effects 0.000 description 2
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229910052762 osmium Inorganic materials 0.000 description 2
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
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239000003643 water by type Substances 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
102000007698 Alcohol dehydrogenase Human genes 0.000 description 1
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JEGMWWXJUXDNJN-UHFFFAOYSA-O CC1C[NH2+]CCC1 Chemical compound CC1C[NH2+]CCC1 JEGMWWXJUXDNJN-UHFFFAOYSA-O 0.000 description 1
241001660259 Cereus <cactus> Species 0.000 description 1
DRSFVGQMPYTGJY-GNSLJVCWSA-N Deprodone propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)CC)[C@@]1(C)C[C@@H]2O DRSFVGQMPYTGJY-GNSLJVCWSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
108010050375 Glucose 1-Dehydrogenase Proteins 0.000 description 1
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102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
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229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000003321 amplification Effects 0.000 description 1
238000003149 assay kit Methods 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
238000011953 bioanalysis Methods 0.000 description 1
239000012620 biological material Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000005515 coenzyme Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000003487 electrochemical reaction Methods 0.000 description 1
230000005518 electrochemistry Effects 0.000 description 1
230000005670 electromagnetic radiation Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000001952 enzyme assay Methods 0.000 description 1
230000005281 excited state Effects 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
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238000011065 in-situ storage Methods 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229960003966 nicotinamide Drugs 0.000 description 1
235000005152 nicotinamide Nutrition 0.000 description 1
239000011570 nicotinamide Substances 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006479 redox reaction Methods 0.000 description 1
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238000011069 regeneration method Methods 0.000 description 1
230000027756 respiratory electron transport chain Effects 0.000 description 1
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238000001542 size-exclusion chromatography Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Images

Classifications

- 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
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/914—Hydrolases (3)
- G01N2333/978—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
- G01N2333/986—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in cyclic amides (3.5.2), e.g. beta-lactamase (penicillinase, 3.5.2.6), creatinine amidohydrolase (creatininase, EC 3.5.2.10), N-methylhydantoinase (3.5.2.6)
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2415/00—Assays, e.g. immunoassays or enzyme assays, involving penicillins or cephalosporins
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/30—Electrochemically active labels
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/40—Rare earth chelates

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
General Engineering & Computer Science (AREA)
Microbiology (AREA)
Molecular Biology (AREA)
Analytical Chemistry (AREA)
Biotechnology (AREA)
Physics & Mathematics (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Electroluminescent Light Sources (AREA)
Plural Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)

JP50202097A 1995-06-07 1996-06-07 電気化学発光技術による化合物のモニターリング Expired - Fee Related JP3997436B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/485,419 US5643713A (en)	1995-06-07	1995-06-07	Electrochemiluminescent monitoring of compounds
US08/485,419		1995-06-07
PCT/US1996/009805 WO1996040978A1 (en)	1995-06-07	1996-06-07	Electrochemiluminescent monitoring of compounds

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2006335216A Division JP2007176939A (ja)	1995-06-07	2006-12-13	電気化学発光技術による化合物のモニターリング

Publications (3)

Publication Number	Publication Date
JPH11507533A JPH11507533A (ja)	1999-07-06
JPH11507533A5 JPH11507533A5 (2)	2004-07-29
JP3997436B2 true JP3997436B2 (ja)	2007-10-24

Family

ID=23928088

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP50202097A Expired - Fee Related JP3997436B2 (ja)	1995-06-07	1996-06-07	電気化学発光技術による化合物のモニターリング
JP2006335216A Abandoned JP2007176939A (ja)	1995-06-07	2006-12-13	電気化学発光技術による化合物のモニターリング

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US (2)	US5643713A (2)
EP (1)	EP0836651B1 (2)
JP (2)	JP3997436B2 (2)
AT (1)	ATE317913T1 (2)
CA (1)	CA2222926C (2)
DE (1)	DE69635822T2 (2)
ES (1)	ES2258777T3 (2)
WO (1)	WO1996040978A1 (2)

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1996
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- 1996-06-07 ES ES96923255T patent/ES2258777T3/es not_active Expired - Lifetime
- 1996-06-07 EP EP96923255A patent/EP0836651B1/en not_active Expired - Lifetime
- 1996-06-07 JP JP50202097A patent/JP3997436B2/ja not_active Expired - Fee Related
- 1996-06-07 WO PCT/US1996/009805 patent/WO1996040978A1/en not_active Ceased
- 1996-06-07 CA CA002222926A patent/CA2222926C/en not_active Expired - Fee Related
- 1996-06-07 DE DE69635822T patent/DE69635822T2/de not_active Expired - Fee Related
1997
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2006
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Also Published As

Publication number	Publication date
EP0836651A1 (en)	1998-04-22
US6165708A (en)	2000-12-26
WO1996040978A1 (en)	1996-12-19
EP0836651A4 (en)	2004-07-14
JPH11507533A (ja)	1999-07-06
DE69635822T2 (de)	2006-10-19
EP0836651B1 (en)	2006-02-15
CA2222926C (en)	2008-09-16
US5643713A (en)	1997-07-01
CA2222926A1 (en)	1996-12-19
ES2258777T3 (es)	2006-09-01
JP2007176939A (ja)	2007-07-12
AU6381796A (en)	1996-12-30
DE69635822D1 (de)	2006-04-20
ATE317913T1 (de)	2006-03-15
AU708865B2 (en)	1999-08-12

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Publication	Publication Date	Title
JP3997436B2 (ja)	2007-10-24	電気化学発光技術による化合物のモニターリング
JP3784072B2 (ja)	2006-06-07	電気化学発光酵素イムノアッセイ
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ES2249065T3 (es)	2006-03-16	Medicion de hidruro mediante el uso de compuestos quimioluminiscentes de acridinio.
US6316180B1 (en)	2001-11-13	Electrochemiluminescent monitoring of compounds/electrochemiluminescence assays
JP2005118014A (ja)	2005-05-12	分析方法およびそれに用いる試薬
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JP4702341B2 (ja)	2011-06-15	フェニルアラニンセンサ及びフェニルアラニン測定方法
AU708865C (en)	2000-03-09	Electrochemiluminescent monitoring of compounds
JPH04507194A (ja)	1992-12-17	化学発光組成物、化学発光法、及び分析的検定におけるその使用
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Alpuche-Aviles	2024	Electrochemical Sensors with Inorganic Redox Mediators
Martin	1995	Chemiluminescence detection of NADH and enzyme substrates with immobilized tris (2, 2'-bipyridyl) ruthenium (II) and dehydrogenase enzymes