JP2016540724A5 - - Google Patents
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- Publication number
- JP2016540724A5 JP2016540724A5 JP2016516600A JP2016516600A JP2016540724A5 JP 2016540724 A5 JP2016540724 A5 JP 2016540724A5 JP 2016516600 A JP2016516600 A JP 2016516600A JP 2016516600 A JP2016516600 A JP 2016516600A JP 2016540724 A5 JP2016540724 A5 JP 2016540724A5
- Authority
- JP
- Japan
- Prior art keywords
- propan
- ferrocenylmethoxy
- substrate
- cyanoethyl
- compound
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000000758 substrate Substances 0.000 claims description 34
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 32
- 150000007523 nucleic acids Chemical class 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 108020004707 nucleic acids Proteins 0.000 claims description 25
- 102000039446 nucleic acids Human genes 0.000 claims description 25
- -1 3- (ferrocenyl methoxy) propane - 1-O Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- 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 15
- 239000000523 sample Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 238000003556 assay Methods 0.000 claims description 7
- 108020004711 Nucleic Acid Probes Proteins 0.000 claims description 6
- 230000000295 complement effect Effects 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000003149 assay kit Methods 0.000 claims description 5
- 239000002853 nucleic acid probe Substances 0.000 claims description 5
- SXADIBFZNXBEGI-UHFFFAOYSA-N phosphoramidous acid Chemical group NP(O)O SXADIBFZNXBEGI-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- 230000015556 catabolic process Effects 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 4
- 230000000593 degrading effect Effects 0.000 claims description 4
- 238000007812 electrochemical assay Methods 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 238000009396 hybridization Methods 0.000 claims description 4
- 244000052769 pathogen Species 0.000 claims description 4
- 230000001717 pathogenic effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 108091093088 Amplicon Proteins 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 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 2
- 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 2
- 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 2
- 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 2
- 241000606161 Chlamydia Species 0.000 claims description 2
- 108060002716 Exonuclease Proteins 0.000 claims description 2
- 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 2
- 241000204051 Mycoplasma genitalium Species 0.000 claims description 2
- 241000588652 Neisseria gonorrhoeae Species 0.000 claims description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 2
- 241000191967 Staphylococcus aureus Species 0.000 claims description 2
- 241000224526 Trichomonas Species 0.000 claims description 2
- 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 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 229960002685 biotin Drugs 0.000 claims description 2
- 235000020958 biotin Nutrition 0.000 claims description 2
- 239000011616 biotin Substances 0.000 claims description 2
- 235000014633 carbohydrates Nutrition 0.000 claims description 2
- 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 2
- 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 2
- YDNDQLBFIPQSAO-UHFFFAOYSA-N cyclopenta-1,3-diene iron(2+) 3-[(2-tributylstannylcyclopenta-1,4-dien-1-yl)methoxy]propan-1-ol Chemical compound [Fe++].c1cc[cH-]c1.CCCC[Sn](CCCC)(CCCC)c1ccc[c-]1COCCCO YDNDQLBFIPQSAO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 102000013165 exonuclease Human genes 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 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 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229960003085 meticillin Drugs 0.000 claims description 2
- 229920001184 polypeptide Polymers 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 239000002773 nucleotide Substances 0.000 claims 6
- 125000003729 nucleotide group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000000837 carbohydrate group Chemical group 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 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 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1317787.8 | 2013-10-08 | ||
| GBGB1317787.8A GB201317787D0 (en) | 2013-10-08 | 2013-10-08 | Labelling compounds and their use in assays |
| GB1413931.5 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2016540724A JP2016540724A (ja) | 2016-12-28 |
| JP2016540724A5 true JP2016540724A5 (enExample) | 2017-11-16 |
Family
ID=51726852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016516600A Pending JP2016540724A (ja) | 2013-10-08 | 2014-10-08 | 標識用化合物およびアッセイにおけるそれらの使用 |
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 |
-
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
- 2014-10-08 AU AU2014333542A patent/AU2014333542B2/en not_active Expired - Fee Related
- 2014-10-08 EA EA201690434A patent/EA201690434A1/ru unknown
- 2014-10-08 CN CN201480055580.2A patent/CN105722847A/zh active Pending
-
2017
- 2017-10-13 US US15/783,130 patent/US10968490B2/en active Active
-
2021
- 2021-04-05 US US17/222,484 patent/US11572592B2/en active Active
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