AU698465B2 - Electrochemiluminescent enzyme biosensors - Google Patents
Electrochemiluminescent enzyme biosensors Download PDFInfo
- Publication number
- AU698465B2 AU698465B2 AU63822/96A AU6382296A AU698465B2 AU 698465 B2 AU698465 B2 AU 698465B2 AU 63822/96 A AU63822/96 A AU 63822/96A AU 6382296 A AU6382296 A AU 6382296A AU 698465 B2 AU698465 B2 AU 698465B2
- Authority
- AU
- Australia
- Prior art keywords
- conjugate
- dehydrogenase
- enzyme
- nad
- oxidoreductase
- 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.)
- Ceased
Links
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 86
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 86
- 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 abstract description 31
- 238000003556 assay Methods 0.000 claims abstract description 29
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims abstract description 28
- 101710088194 Dehydrogenase Proteins 0.000 claims abstract description 21
- 108010050375 Glucose 1-Dehydrogenase Proteins 0.000 claims abstract description 17
- 239000007787 solid Substances 0.000 claims abstract description 4
- 239000000758 substrate Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 108090000854 Oxidoreductases Proteins 0.000 claims description 23
- 102000004316 Oxidoreductases Human genes 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000012491 analyte Substances 0.000 claims description 20
- 230000002255 enzymatic effect Effects 0.000 claims description 13
- 238000005259 measurement Methods 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 238000005516 engineering process Methods 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 8
- 108010021809 Alcohol dehydrogenase Proteins 0.000 claims description 7
- 239000000523 sample Substances 0.000 claims description 7
- 239000000872 buffer Substances 0.000 claims description 6
- 239000005515 coenzyme Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 102000007698 Alcohol dehydrogenase Human genes 0.000 claims description 4
- 230000003993 interaction Effects 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- 230000018109 developmental process Effects 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 2
- 235000018417 cysteine Nutrition 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims 1
- 238000001378 electrochemiluminescence detection Methods 0.000 claims 1
- 238000003018 immunoassay Methods 0.000 claims 1
- ZEGFMFQPWDMMEP-UHFFFAOYSA-N strontium;sulfide Chemical compound [S-2].[Sr+2] ZEGFMFQPWDMMEP-UHFFFAOYSA-N 0.000 claims 1
- 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 abstract description 49
- 229950006238 nadide Drugs 0.000 abstract description 46
- 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 abstract description 24
- 239000008103 glucose Substances 0.000 abstract description 24
- 238000002360 preparation method Methods 0.000 abstract description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052707 ruthenium Inorganic materials 0.000 abstract description 10
- 239000012327 Ruthenium complex Substances 0.000 abstract description 2
- 230000009467 reduction Effects 0.000 abstract description 2
- WZSDNEJJUSYNSG-UHFFFAOYSA-N azocan-1-yl-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2CCCCCCC2)=C1 WZSDNEJJUSYNSG-UHFFFAOYSA-N 0.000 abstract 1
- 150000002303 glucose derivatives Chemical class 0.000 abstract 1
- 229940088598 enzyme Drugs 0.000 description 79
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 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 22
- 239000000243 solution Substances 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- BAWFJGJZGIEFAR-NNYOXOHSSA-O NAD(+) Chemical class 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-O 0.000 description 9
- 235000018102 proteins Nutrition 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- -1 ruthenium (II) tris(bipyridyl) Chemical group 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 5
- 108020005199 Dehydrogenases Proteins 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 108010015776 Glucose oxidase Proteins 0.000 description 3
- 239000004366 Glucose oxidase Substances 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229940116332 glucose oxidase Drugs 0.000 description 3
- 235000019420 glucose oxidase Nutrition 0.000 description 3
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 3
- 229960003966 nicotinamide Drugs 0.000 description 3
- 235000005152 nicotinamide Nutrition 0.000 description 3
- 239000011570 nicotinamide Substances 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 102000008300 Mutant Proteins Human genes 0.000 description 2
- 108010021466 Mutant Proteins Proteins 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 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 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- JMIAPORGEDIDLT-UHFFFAOYSA-N ethyl ethanimidate Chemical compound CCOC(C)=N JMIAPORGEDIDLT-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 235000012209 glucono delta-lactone Nutrition 0.000 description 2
- 229960003681 gluconolactone Drugs 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000002703 mutagenesis Methods 0.000 description 2
- 231100000350 mutagenesis Toxicity 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010188 recombinant method Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 239000012064 sodium phosphate buffer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WQJXDCPENDFBMZ-UHFFFAOYSA-N 1-ethylphenazine Chemical group C1=CC=C2N=C3C(CC)=CC=CC3=NC2=C1 WQJXDCPENDFBMZ-UHFFFAOYSA-N 0.000 description 1
- VDJKJPMLWJWQIH-UHFFFAOYSA-M 5-ethylphenazin-5-ium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.C1=CC=C2[N+](CC)=C(C=CC=C3)C3=NC2=C1 VDJKJPMLWJWQIH-UHFFFAOYSA-M 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 1
- 108700033069 EC 1.97.-.- Proteins 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 108010044467 Isoenzymes Proteins 0.000 description 1
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 1
- 108090000417 Oxygenases Proteins 0.000 description 1
- 102000004020 Oxygenases Human genes 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- LNQVTSROQXJCDD-UHFFFAOYSA-N adenosine monophosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)C(OP(O)(O)=O)C1O LNQVTSROQXJCDD-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000002820 assay format Methods 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000007247 enzymatic mechanism Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000005480 nicotinamides Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000012857 radioactive material Substances 0.000 description 1
- 238000011897 real-time detection Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- 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
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/535—Production of labelled immunochemicals with enzyme label or co-enzymes, co-factors, enzyme inhibitors or enzyme substrates
-
- 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
- C12Q1/005—Enzyme electrodes involving specific analytes or enzymes
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/66—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light electrically excited, e.g. electroluminescence
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/76—Chemiluminescence; Bioluminescence
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Urology & Nephrology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Biotechnology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Plasma & Fusion (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cell Biology (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/467,712 US6852502B1 (en) | 1995-06-06 | 1995-06-06 | Electrochemiluminescent enzyme biosensors |
| US08/467712 | 1995-06-06 | ||
| PCT/US1996/009869 WO1996039534A1 (en) | 1995-06-06 | 1996-06-06 | Electrochemiluminescent enzyme biosensors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6382296A AU6382296A (en) | 1996-12-24 |
| AU698465B2 true AU698465B2 (en) | 1998-10-29 |
Family
ID=23856828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU63822/96A Ceased AU698465B2 (en) | 1995-06-06 | 1996-06-06 | Electrochemiluminescent enzyme biosensors |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6852502B1 (enExample) |
| EP (1) | EP0837949B1 (enExample) |
| JP (1) | JP3618759B2 (enExample) |
| AT (1) | ATE254186T1 (enExample) |
| AU (1) | AU698465B2 (enExample) |
| CA (1) | CA2223017A1 (enExample) |
| DE (1) | DE69630688T2 (enExample) |
| WO (1) | WO1996039534A1 (enExample) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010003647A1 (en) * | 1995-06-07 | 2001-06-14 | Ji Sun | Coreatant-including electrochemiluminescent compounds, methods, systems and kits utilizing same |
| US6673533B1 (en) | 1995-03-10 | 2004-01-06 | Meso Scale Technologies, Llc. | Multi-array multi-specific electrochemiluminescence testing |
| CN1192097C (zh) * | 1995-03-10 | 2005-03-09 | 梅索磅秤技术有限公司 | 多阵列、多特异性的电化学发光检验 |
| US6140045A (en) * | 1995-03-10 | 2000-10-31 | Meso Scale Technologies | Multi-array, multi-specific electrochemiluminescence testing |
| US6319670B1 (en) | 1995-05-09 | 2001-11-20 | Meso Scale Technology Llp | Methods and apparatus for improved luminescence assays using microparticles |
| US6724309B2 (en) | 2000-11-03 | 2004-04-20 | Excel Corporation | Method and apparatus for tracking carcasses |
| US7766730B2 (en) | 2000-11-03 | 2010-08-03 | Cargill, Incorporated | Carcass tracking |
| US7400256B2 (en) | 2000-11-03 | 2008-07-15 | Cargill, Incorporated | Chill cooler storage and selection system |
| EP1522592B1 (en) | 2002-06-17 | 2008-08-06 | ARKRAY, Inc. | Glucose sensor with the use of glucose dehydrogenase |
| CA2609379C (en) * | 2005-06-03 | 2016-11-29 | Allen J. Bard | Electrochemistry and electrogenerated chemiluminescence with a single faradaic electrode |
| DE602006020158D1 (de) | 2005-11-08 | 2011-03-31 | Surmodics Inc | Ultradünne photopolymer-beschichtungen und verwendungen davon |
| JP2010523084A (ja) | 2007-03-30 | 2010-07-15 | アンブルックス，インコーポレイテッド | 修飾ｆｇｆ−２１ポリペプチド |
| US8008037B2 (en) * | 2008-03-27 | 2011-08-30 | Roche Diagnostics Operations, Inc. | Matrix composition with alkylphenazine quaternary salt and a nitrosoaniline |
| KR101603354B1 (ko) | 2008-04-11 | 2016-03-14 | 보드 오브 리전츠 오브 더 유니버시티 오브 텍사스 시스템 | 나노입자 전기발생 화학발광 증폭 방법 및 시스템 |
| EP2294387B1 (en) | 2008-05-08 | 2017-08-23 | Board of Regents of the University of Texas System | Luminescent nanostructured materials for use in electrogenerated chemiluminescence |
| US9213043B2 (en) | 2012-05-15 | 2015-12-15 | Wellstat Diagnostics, Llc | Clinical diagnostic system including instrument and cartridge |
| US9075042B2 (en) | 2012-05-15 | 2015-07-07 | Wellstat Diagnostics, Llc | Diagnostic systems and cartridges |
| US9625465B2 (en) | 2012-05-15 | 2017-04-18 | Defined Diagnostics, Llc | Clinical diagnostic systems |
| CN107108710B (zh) | 2014-10-24 | 2022-02-15 | 百时美施贵宝公司 | 修饰的fgf-21多肽及其用途 |
| PL3338094T3 (pl) | 2015-08-20 | 2019-09-30 | F. Hoffmann-La Roche Ag | Test immunologiczny oparty na cząstkach z zastosowaniem pegylowanego swoistego względem analitu czynnika wiążącego |
| CN108780092A (zh) | 2016-03-07 | 2018-11-09 | 豪夫迈·罗氏有限公司 | 抗p53抗体的检测 |
| WO2018141768A1 (en) | 2017-02-02 | 2018-08-09 | Roche Diagnostics Gmbh | Immunoassay using at least two pegylated analyte-specific binding agents |
| WO2019201901A1 (en) | 2018-04-18 | 2019-10-24 | F. Hoffmann-La Roche Ag | Novel anti-thymidine kinase antibodies |
| EP3844503B1 (en) | 2018-08-31 | 2024-05-29 | F. Hoffmann-La Roche AG | Thymidine kinase (tk-1) in prognostic indices for dlbcl |
| CN110938667A (zh) * | 2018-09-21 | 2020-03-31 | 中国科学院天津工业生物技术研究所 | 一种酶电极、生物传感器及其制备方法和用途 |
| WO2021013781A1 (en) | 2019-07-22 | 2021-01-28 | F. Hoffmann-La Roche Ag | Substance p as blood biomarker for the non-invasive diagnosis of endometriosis |
| WO2021013783A1 (en) | 2019-07-22 | 2021-01-28 | F. Hoffmann-La Roche Ag | S100a12 as blood biomarker for the non-invasive diagnosis of endometriosis |
| WO2021013786A1 (en) | 2019-07-22 | 2021-01-28 | F. Hoffmann-La Roche Ag | S100a6 as blood biomarker for the non-invasive diagnosis of endometriosis |
| BR112022000172A2 (pt) | 2019-07-22 | 2022-02-22 | Hoffmann La Roche | Métodos para avaliar se uma paciente tem endometriose, para selecionar uma paciente para terapia e para monitorar uma paciente |
| KR20220024782A (ko) | 2019-07-22 | 2022-03-03 | 에프. 호프만-라 로슈 아게 | 자궁내막증의 비침습적 진단을 위한 혈액 바이오마커로서의 s100a8 |
| BR112022009371A2 (pt) | 2019-11-15 | 2022-08-09 | Hoffmann La Roche | Métodos para determinar a quantidade ou concentração de um ou mais analitos antibióticos, tubos de amostragem, usos de um reagente de derivatização nucleofílica e analito antibiótico |
| EP4237441A1 (en) | 2020-11-02 | 2023-09-06 | F. Hoffmann-La Roche AG | Sars-cov-2 nucleocapsid antibodies |
| WO2022207628A1 (en) | 2021-03-30 | 2022-10-06 | F. Hoffmann-La Roche Ag | Scf as blood biomarker for the non-invasive diagnosis of endometriosis |
| WO2022207685A1 (en) | 2021-04-01 | 2022-10-06 | F. Hoffmann-La Roche Ag | Psp94 as blood biomarker for the non-invasive diagnosis of endometriosis |
| US20240272177A1 (en) | 2021-05-17 | 2024-08-15 | Roche Diagnostics Operations, Inc. | sFRP4 AS BLOOD BIOMARKER FOR THE NON-INVASIVE DIAGNOSIS OF ADENOMYOSIS |
| JP2024541945A (ja) | 2021-10-26 | 2024-11-13 | エフ． ホフマン－ラ ロシュ アーゲー | ＳＡＲＳ－ＣｏＶ－２受容体結合ドメイン抗体 |
| KR20230060229A (ko) * | 2021-10-27 | 2023-05-04 | 한국전기연구원 | 광열 모듈레이션 레이저 스펙클 영상을 이용한 포도당 농도 측정 시스템, 방법, 및 상기 방법을 실행시키기 위한 컴퓨터 판독 가능한 프로그램을 기록한 기록 매체 |
| WO2023131594A1 (en) | 2022-01-05 | 2023-07-13 | F. Hoffmann-La Roche Ag | Derivatization of compounds in patient samples for therapeutic drug monitoring (tdm) |
| WO2023247752A1 (en) | 2022-06-23 | 2023-12-28 | F. Hoffmann-La Roche Ag | Method for diagnosing endometriosis and for classifying the stage of endometriosis |
| CN119585618A (zh) | 2022-07-22 | 2025-03-07 | 豪夫迈·罗氏有限公司 | 成纤维细胞生长因子结合蛋白1(fgfbp1)作为（血液）生物标志物用于诊断多囊卵巢综合征 |
| CN119604768A (zh) | 2022-07-22 | 2025-03-11 | 豪夫迈·罗氏有限公司 | 白三烯a4水解酶(lta4h)作为（血液）生物标志物用于诊断多囊卵巢综合征 |
| CN119585617A (zh) | 2022-07-22 | 2025-03-07 | 豪夫迈·罗氏有限公司 | 镍纹蛋白样蛋白(metrnl)作为（血液）生物标志物用于诊断多囊卵巢综合征 |
| CN120693408A (zh) | 2022-12-05 | 2025-09-23 | 直接传感有限公司 | 非乳酸羟基酸的酶促检测 |
| WO2025017135A1 (en) | 2023-07-20 | 2025-01-23 | F. Hoffmann-La Roche Ag | Screening methods for antibody compositions |
| WO2025026908A1 (en) | 2023-07-28 | 2025-02-06 | Roche Diagnostics Gmbh | Serum epha1 as biomarker for endometriosis |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5310687A (en) | 1984-10-31 | 1994-05-10 | Igen, Inc. | Luminescent metal chelate labels and means for detection |
| US5221605A (en) | 1984-10-31 | 1993-06-22 | Igen, Inc. | Luminescent metal chelate labels and means for detection |
| US5147806A (en) | 1988-04-29 | 1992-09-15 | Igen, Inc. | Method and apparatus for conducting electrochemiluminescence measurements |
| US5250415A (en) | 1987-04-08 | 1993-10-05 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Process for the preparation of glucose dehydrogenase from Bacillus megaterium |
| US5061455A (en) | 1987-04-30 | 1991-10-29 | United Technologies Corporation | Apparatus for removing carbon dioxide from air |
| US5093268A (en) | 1988-04-28 | 1992-03-03 | Igen, Inc. | Apparatus for conducting a plurality of simultaneous measurements of electrochemiluminescent phenomena |
| US5340722A (en) | 1988-08-24 | 1994-08-23 | Avl Medical Instruments Ag | Method for the determination of the concentration of an enzyme substrate and a sensor for carrying out the method |
| US5068088A (en) | 1988-11-03 | 1991-11-26 | Igen, Inc. | Method and apparatus for conducting electrochemiluminescent measurements |
| US5235808A (en) | 1990-02-12 | 1993-08-17 | General Electric Company | Exhaust nozzle including idle thrust spoiling |
| US5324835A (en) | 1990-03-30 | 1994-06-28 | Biosensor Laboratories Co., Ltd. | Pyridazinoquinoxalinones for use as chemiluminescent agents |
| US5229202A (en) | 1990-05-22 | 1993-07-20 | Mitsubishi Kasei Corporation | Carbon fiber and carbon fiber-reinforced resin composition using it |
| US5264092A (en) | 1991-10-02 | 1993-11-23 | Moltech Corporation | Redox polymer modified electrode for the electrochemical regeneration of coenzyme |
| JP2541081B2 (ja) | 1992-08-28 | 1996-10-09 | 日本電気株式会社 | バイオセンサ及びバイオセンサの製造・使用方法 |
| US5527710A (en) * | 1994-12-02 | 1996-06-18 | Igen, Inc. | Rate measurements of biomolecular reactions using electrochemiluminescence |
| CN1192097C (zh) * | 1995-03-10 | 2005-03-09 | 梅索磅秤技术有限公司 | 多阵列、多特异性的电化学发光检验 |
-
1995
- 1995-06-06 US US08/467,712 patent/US6852502B1/en not_active Expired - Fee Related
-
1996
- 1996-06-06 DE DE69630688T patent/DE69630688T2/de not_active Expired - Fee Related
- 1996-06-06 AT AT96923261T patent/ATE254186T1/de not_active IP Right Cessation
- 1996-06-06 EP EP96923261A patent/EP0837949B1/en not_active Expired - Lifetime
- 1996-06-06 CA CA002223017A patent/CA2223017A1/en not_active Abandoned
- 1996-06-06 AU AU63822/96A patent/AU698465B2/en not_active Ceased
- 1996-06-06 JP JP50205997A patent/JP3618759B2/ja not_active Expired - Fee Related
- 1996-06-06 WO PCT/US1996/009869 patent/WO1996039534A1/en not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| CLIN CHEM 37(9) 1991 G.F. BLACKBURNE ET AL PP1534-39 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1996039534A1 (en) | 1996-12-12 |
| EP0837949A4 (en) | 2000-05-17 |
| ATE254186T1 (de) | 2003-11-15 |
| JPH11507536A (ja) | 1999-07-06 |
| EP0837949A1 (en) | 1998-04-29 |
| AU6382296A (en) | 1996-12-24 |
| EP0837949B1 (en) | 2003-11-12 |
| CA2223017A1 (en) | 1996-12-12 |
| DE69630688D1 (de) | 2003-12-18 |
| DE69630688T2 (de) | 2004-09-23 |
| JP3618759B2 (ja) | 2005-02-09 |
| US6852502B1 (en) | 2005-02-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU698465B2 (en) | Electrochemiluminescent enzyme biosensors | |
| Byfield et al. | Biochemical aspects of biosensors | |
| AU718767B2 (en) | Electrochemiluminescent enzyme immunoassay | |
| Blum | Bio-and chemi-luminescent sensors | |
| Rubinstein et al. | Electrogenerated chemiluminescent determination of oxalate | |
| Sharma et al. | Biomolecules for development of biosensors and their applications | |
| Marquette et al. | Electro-chemiluminescent biosensing | |
| EP0871891B1 (en) | Rate measurements of biomolecular reactions using electrochemiluminescence | |
| US4234681A (en) | Immobolized light emitting systems | |
| Gautier et al. | Multi-function fibre-optic sensor for the bioluminescent flow determination of ATP or NADH | |
| JPS60156400A (ja) | アデノシン三燐酸及びフラビンモノヌクレオチドの酵素的試験法 | |
| CA1094477A (en) | Assays utilizing localized electromagnetic radiation sources | |
| Li et al. | Determination of various alcohols based on a new immobilized enzyme fluorescence capillary analysis | |
| Zheng et al. | Sensitive chemically amplified electrochemical detection of ruthenium tris-(2, 2′-bipyridine) on tin-doped indium oxide electrode | |
| JP4702341B2 (ja) | 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 | |
| Monroe | Amperometric immunoassay | |
| Salomi et al. | Electrochemical and spectrophotometric studies on dyes and proteins labelled with dyes | |
| Tabata et al. | A chemiluminometric method for NADPH and NADH using a two‐enzyme bioreactor and its application to the determination of magnesium in serum | |
| Olsson et al. | Chemiluminescence and its use in immunoassay | |
| JPH05196601A (ja) | 新規な電気化学的測定法 | |
| Alpuche-Aviles | Electrochemical Sensors with Inorganic Redox Mediators | |
| Ngo | Prosthetic group labeled enzyme immunoassay | |
| Blum et al. | Biosensors. From the glucose electrode to the biochip | |
| Brodelius | Enzyme assays | |
| Worsfold et al. | Immobilized bioluminescent reagents in continuous flow systems |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Assignment registered |
Owner name: BIOVERIS CORPORATION Free format text: FORMER OWNER WAS: IGEN INTERNATIONAL, INC. |