ES2663397T3 - Compuestos de etiquetado y su uso en los ensayos - Google Patents
Compuestos de etiquetado y su uso en los ensayos Download PDFInfo
- Publication number
- ES2663397T3 ES2663397T3 ES14784356.9T ES14784356T ES2663397T3 ES 2663397 T3 ES2663397 T3 ES 2663397T3 ES 14784356 T ES14784356 T ES 14784356T ES 2663397 T3 ES2663397 T3 ES 2663397T3
- Authority
- ES
- Spain
- Prior art keywords
- propan
- ferrocenylmethoxy
- compound
- substrate
- nucleic acid
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 129
- 238000012360 testing method Methods 0.000 title claims description 19
- 238000002372 labelling Methods 0.000 title description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 27
- 125000001424 substituent group Chemical group 0.000 claims abstract description 26
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 20
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011630 iodine Substances 0.000 claims abstract description 10
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 101100149678 Caenorhabditis elegans snr-3 gene Proteins 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 239000011737 fluorine Substances 0.000 claims abstract description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 9
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- 239000000758 substrate Substances 0.000 claims description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 81
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 66
- 150000007523 nucleic acids Chemical class 0.000 claims description 57
- 108020004707 nucleic acids Proteins 0.000 claims description 52
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- -1 (2-tert-Butylsulfonyl) -ferrocenylmethoxy Chemical group 0.000 claims description 45
- 239000000523 sample Substances 0.000 claims description 35
- 239000002773 nucleotide Substances 0.000 claims description 28
- 125000003729 nucleotide group Chemical group 0.000 claims description 28
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- 238000003556 assay Methods 0.000 claims description 21
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- HBLIKBBMOJVJIF-UHFFFAOYSA-N cyclopenta-1,3-diene iron(2+) 3-[(2-tributylsilylcyclopenta-1,4-dien-1-yl)methoxy]propan-1-ol Chemical compound [Fe++].c1cc[cH-]c1.CCCC[Si](CCCC)(CCCC)c1ccc[c-]1COCCCO HBLIKBBMOJVJIF-UHFFFAOYSA-N 0.000 claims description 16
- SXADIBFZNXBEGI-UHFFFAOYSA-N phosphoramidous acid Chemical group NP(O)O SXADIBFZNXBEGI-UHFFFAOYSA-N 0.000 claims description 15
- 150000001413 amino acids Chemical class 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 14
- LQXDTRWMWSJQEJ-UHFFFAOYSA-N iron(2+) 1,2,3,4,5-pentamethylcyclopenta-1,3-diene 3-[(2,3,4,5-tetramethylcyclopenta-1,4-dien-1-yl)methoxy]propan-1-ol Chemical compound [Fe++].Cc1c(C)c(C)[c-](C)c1C.Cc1c(C)c(COCCCO)[c-](C)c1C LQXDTRWMWSJQEJ-UHFFFAOYSA-N 0.000 claims description 13
- VFCYHMLFGKMDMC-UHFFFAOYSA-N 2-chlorocyclopenta-1,3-diene 3-(cyclopenta-1,4-dien-1-ylmethoxy)propan-1-ol iron(2+) Chemical compound [Fe++].Cl[c-]1cccc1.OCCCOC[c-]1cccc1 VFCYHMLFGKMDMC-UHFFFAOYSA-N 0.000 claims description 12
- NPWXCKQPJLKMGM-UHFFFAOYSA-N [C-]1(C=CC=C1)CCCOCCO.[CH-]1C=CC=C1.[Fe+2] Chemical compound [C-]1(C=CC=C1)CCCOCCO.[CH-]1C=CC=C1.[Fe+2] NPWXCKQPJLKMGM-UHFFFAOYSA-N 0.000 claims description 12
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 10
- 230000000295 complement effect Effects 0.000 claims description 10
- AIOVUSYPXMFPBI-UHFFFAOYSA-N cyclopenta-1,3-diene 3-(cyclopenta-1,4-dien-1-ylmethoxy)propan-1-ol iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.OCCCOC[c-]1cccc1 AIOVUSYPXMFPBI-UHFFFAOYSA-N 0.000 claims description 9
- PWQLUURAEVTFMH-UHFFFAOYSA-N cyclopenta-1,3-diene 3-[(2-iodocyclopenta-1,4-dien-1-yl)methoxy]propan-1-ol iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.OCCCOC[c-]1cccc1I PWQLUURAEVTFMH-UHFFFAOYSA-N 0.000 claims description 9
- QTMWDVDGWKIUDQ-UHFFFAOYSA-N C[Sn](C=1[C-](C=CC1)COCCCO)(C)C.[CH-]1C=CC=C1.[Fe+2] Chemical compound C[Sn](C=1[C-](C=CC1)COCCCO)(C)C.[CH-]1C=CC=C1.[Fe+2] QTMWDVDGWKIUDQ-UHFFFAOYSA-N 0.000 claims description 7
- 235000014633 carbohydrates Nutrition 0.000 claims description 7
- FCGHWZDXRNRMBM-UHFFFAOYSA-N C(=C)C=1[C-](C=CC1)COCCCO.[CH-]1C=CC=C1.[Fe+2] Chemical compound C(=C)C=1[C-](C=CC1)COCCCO.[CH-]1C=CC=C1.[Fe+2] FCGHWZDXRNRMBM-UHFFFAOYSA-N 0.000 claims description 6
- 108020004711 Nucleic Acid Probes Proteins 0.000 claims description 6
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- IIKCYIWPTQAOLY-UHFFFAOYSA-N C[Si](C=1[C-](C=CC1)COCCCO)(C)C.[CH-]1C=CC=C1.[Fe+2] Chemical compound C[Si](C=1[C-](C=CC1)COCCCO)(C)C.[CH-]1C=CC=C1.[Fe+2] IIKCYIWPTQAOLY-UHFFFAOYSA-N 0.000 claims description 5
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- 235000020958 biotin Nutrition 0.000 claims description 5
- 239000011616 biotin Substances 0.000 claims description 5
- 230000015556 catabolic process Effects 0.000 claims description 5
- 238000006731 degradation reaction Methods 0.000 claims description 5
- 238000007812 electrochemical assay Methods 0.000 claims description 5
- 244000052769 pathogen Species 0.000 claims description 5
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- 241000588652 Neisseria gonorrhoeae Species 0.000 claims description 4
- 241000224527 Trichomonas vaginalis Species 0.000 claims description 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 4
- BIVIXXXEPPIGSS-UHFFFAOYSA-N 2-[amino(propan-2-yloxy)phosphanyl]oxypropane Chemical compound CC(C)OP(N)OC(C)C BIVIXXXEPPIGSS-UHFFFAOYSA-N 0.000 claims description 3
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 3
- 241000204051 Mycoplasma genitalium Species 0.000 claims description 3
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- 230000000593 degrading effect Effects 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229960003085 meticillin Drugs 0.000 claims description 3
- 108060002716 Exonuclease Proteins 0.000 claims description 2
- 102000013165 exonuclease Human genes 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000000837 carbohydrate group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 148
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 96
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
- 235000019439 ethyl acetate Nutrition 0.000 description 74
- 239000000243 solution Substances 0.000 description 69
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 46
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 235000019502 Orange oil Nutrition 0.000 description 38
- 239000010502 orange oil Substances 0.000 description 38
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 37
- 235000019341 magnesium sulphate Nutrition 0.000 description 37
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- 239000012267 brine Substances 0.000 description 25
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
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- 239000003550 marker Substances 0.000 description 15
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- 238000001514 detection method Methods 0.000 description 12
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- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- SEYZDJPFVVXSRB-UHFFFAOYSA-N iron(2+);1,2,3,4,5-pentamethylcyclopenta-1,3-diene Chemical compound [Fe+2].CC=1C(C)=C(C)[C-](C)C=1C.CC=1C(C)=C(C)[C-](C)C=1C SEYZDJPFVVXSRB-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000006249 magnetic particle Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000001823 molecular biology technique Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- RLACULXPDZPTLO-UHFFFAOYSA-N propoxyphosphonamidous acid Chemical compound CCCOP(N)O RLACULXPDZPTLO-UHFFFAOYSA-N 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction 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
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 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
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
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
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6876—Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes
- C12Q1/6888—Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes for detection or identification of organisms
- C12Q1/689—Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes for detection or identification of organisms for bacteria
-
- 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
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- 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
- C07F15/02—Iron compounds
-
- 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
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
- C12Q1/6816—Hybridisation assays characterised by the detection means
-
- 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
- G01N27/3276—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction being a hybridisation with immobilised receptors
-
- 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
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
-
- 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
- C12Q2563/00—Nucleic acid detection characterized by the use of physical, structural and functional properties
- C12Q2563/113—Nucleic acid detection characterized by the use of physical, structural and functional properties the label being electroactive, e.g. redox labels
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- General Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- General Physics & Mathematics (AREA)
- Urology & Nephrology (AREA)
- Pathology (AREA)
- Hematology (AREA)
- Cell Biology (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Electrochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201317787 | 2013-10-08 | ||
| GBGB1317787.8A GB201317787D0 (en) | 2013-10-08 | 2013-10-08 | Labelling compounds and their use in assays |
| GB201413931 | 2014-08-06 | ||
| GB201413931A GB201413931D0 (en) | 2014-08-06 | 2014-08-06 | Labelling compounds and their use in assays |
| PCT/GB2014/053031 WO2015052516A1 (en) | 2013-10-08 | 2014-10-08 | Labelling compounds and their use in assays |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2663397T3 true ES2663397T3 (es) | 2018-04-12 |
Family
ID=51726852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14784356.9T Active ES2663397T3 (es) | 2013-10-08 | 2014-10-08 | Compuestos de etiquetado y su uso en los ensayos |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US9822398B2 (enExample) |
| EP (1) | EP3055317B1 (enExample) |
| JP (1) | JP2016540724A (enExample) |
| CN (1) | CN105722847A (enExample) |
| AU (1) | AU2014333542B2 (enExample) |
| BR (1) | BR112016006955A2 (enExample) |
| CA (1) | CA2924750A1 (enExample) |
| EA (1) | EA201690434A1 (enExample) |
| ES (1) | ES2663397T3 (enExample) |
| WO (1) | WO2015052516A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201021896D0 (en) | 2010-12-22 | 2011-02-02 | Atlas Genetics Ltd | Novel compounds and their use in analytical methods |
| AU2016367306B2 (en) * | 2015-12-09 | 2021-04-22 | Medizinische Universität Wien | Monomaleimide-functionalized platinum compounds for cancer therapy |
| CN106866748B (zh) * | 2017-03-29 | 2018-05-15 | 厦门云凡医药科技有限公司 | 化合物的制备方法 |
| CN112630283B (zh) * | 2020-12-18 | 2023-01-17 | 河南城建学院 | (e, e)-1,1′-双(2-吡啶乙烯基)二茂铁作为电化学传感器的应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3855770T2 (de) * | 1987-03-31 | 1997-05-07 | Idemitsu Kosan Co | Ferrocenderivate, diese enthaltende oberflächenaktive stoffe und verfahren zur herstellung dünner organischer filme |
| JPH0283386A (ja) * | 1988-09-20 | 1990-03-23 | Idemitsu Kosan Co Ltd | 新規フェロセン誘導体，それを含有する界面活性剤及び有機薄膜の製造方法 |
| US6753143B2 (en) | 2000-05-01 | 2004-06-22 | Clinical Micro Sensors, Inc. | Target analyte detection using asymmetrical self-assembled monolayers |
| US20030143556A1 (en) | 2001-04-03 | 2003-07-31 | Gary Blackburn | Nucleic acid reactions using labels with different redox potentials |
| GB0205455D0 (en) | 2002-03-07 | 2002-04-24 | Molecular Sensing Plc | Nucleic acid probes, their synthesis and use |
| GB0316075D0 (en) | 2003-07-09 | 2003-08-13 | Molecular Sensing Plc | Protease detection assay |
| FR2888240B1 (fr) * | 2005-07-11 | 2007-09-07 | Biomerieux Sa | Monomeres electropolymerisables solubles en solution aqueuse et sondes electroactives susceptibles d'etre obtenues avec de tels monomeres |
| EP2220102B1 (en) * | 2007-11-06 | 2014-04-16 | Clinical Micro Sensors, Inc. | Baseless nucleotide analogues and uses thereof |
| GB0922097D0 (en) | 2009-12-17 | 2010-02-03 | Atlas Genetics Ltd | Microbial assay |
| GB201021896D0 (en) * | 2010-12-22 | 2011-02-02 | Atlas Genetics Ltd | Novel compounds and their use in analytical methods |
| GB201211157D0 (en) | 2012-06-22 | 2012-08-08 | Atlas Genetics Ltd | Novel compounds and their use in analytical methods |
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2014
- 2014-10-08 CA CA2924750A patent/CA2924750A1/en not_active Abandoned
- 2014-10-08 US US15/026,454 patent/US9822398B2/en active Active
- 2014-10-08 WO PCT/GB2014/053031 patent/WO2015052516A1/en not_active Ceased
- 2014-10-08 ES ES14784356.9T patent/ES2663397T3/es active Active
- 2014-10-08 JP JP2016516600A patent/JP2016540724A/ja active Pending
- 2014-10-08 BR BR112016006955A patent/BR112016006955A2/pt not_active IP Right Cessation
- 2014-10-08 EP EP14784356.9A patent/EP3055317B1/en active Active
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- 2014-10-08 EA EA201690434A patent/EA201690434A1/ru unknown
- 2014-10-08 CN CN201480055580.2A patent/CN105722847A/zh active Pending
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2017
- 2017-10-13 US US15/783,130 patent/US10968490B2/en active Active
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2021
- 2021-04-05 US US17/222,484 patent/US11572592B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015052516A1 (en) | 2015-04-16 |
| AU2014333542A1 (en) | 2016-04-14 |
| US11572592B2 (en) | 2023-02-07 |
| US20180037937A1 (en) | 2018-02-08 |
| JP2016540724A (ja) | 2016-12-28 |
| EA201690434A1 (ru) | 2016-08-31 |
| CA2924750A1 (en) | 2015-04-16 |
| CN105722847A (zh) | 2016-06-29 |
| US20220025440A1 (en) | 2022-01-27 |
| EP3055317A1 (en) | 2016-08-17 |
| US20160244815A1 (en) | 2016-08-25 |
| EP3055317B1 (en) | 2018-01-31 |
| AU2014333542B2 (en) | 2019-08-01 |
| US10968490B2 (en) | 2021-04-06 |
| BR112016006955A2 (pt) | 2017-08-01 |
| US9822398B2 (en) | 2017-11-21 |
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