JP2020529442A5 - - Google Patents
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- Publication number
- JP2020529442A5 JP2020529442A5 JP2020506187A JP2020506187A JP2020529442A5 JP 2020529442 A5 JP2020529442 A5 JP 2020529442A5 JP 2020506187 A JP2020506187 A JP 2020506187A JP 2020506187 A JP2020506187 A JP 2020506187A JP 2020529442 A5 JP2020529442 A5 JP 2020529442A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- optionally substituted
- formula
- groups
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 239000000203 mixture Substances 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 48
- -1 Benzothiazole luciferin analog Chemical class 0.000 claims description 41
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical class [H]O* 0.000 claims description 25
- 125000004043 oxo group Chemical class O=* 0.000 claims description 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 230000002255 enzymatic effect Effects 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 238000000354 decomposition reaction Methods 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000002466 imines Chemical class 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000001727 in vivo Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 230000015556 catabolic process Effects 0.000 claims description 6
- 238000006731 degradation reaction Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
- JEOQACOXAOEPLX-WCCKRBBISA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;1,3-thiazolidine-4-carboxylic acid Chemical compound OC(=O)C1CSCN1.OC(=O)[C@@H](N)CCCN=C(N)N JEOQACOXAOEPLX-WCCKRBBISA-N 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- UMWWHOXOVPIGFD-UHFFFAOYSA-N 2-methyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CN1NC(=O)C(=O)N=C1S UMWWHOXOVPIGFD-UHFFFAOYSA-N 0.000 claims description 4
- YWUNWMADAOHUTF-UHFFFAOYSA-N 3-(5-oxo-3-sulfanylidene-2h-1,2,4-triazin-6-yl)propanoic acid Chemical compound OC(=O)CCC1=NNC(=S)NC1=O YWUNWMADAOHUTF-UHFFFAOYSA-N 0.000 claims description 4
- BMFVHRIQGZKRSH-UHFFFAOYSA-N 3-sulfanylidene-6-(trifluoromethyl)-2H-1,2,4-triazin-5-one Chemical compound S=C1NN=C(C(N1)=O)C(F)(F)F BMFVHRIQGZKRSH-UHFFFAOYSA-N 0.000 claims description 4
- JCIODXDOCJZABZ-UHFFFAOYSA-N 4-(furan-2-ylmethylideneamino)-6-methyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound O=C1C(C)=NNC(=S)N1N=CC1=CC=CO1 JCIODXDOCJZABZ-UHFFFAOYSA-N 0.000 claims description 4
- BRTAAZXLXLRRFH-UHFFFAOYSA-N 4-amino-6-methyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound CC1=NNC(=S)N(N)C1=O BRTAAZXLXLRRFH-UHFFFAOYSA-N 0.000 claims description 4
- FVLMRSJALFJPOF-UHFFFAOYSA-N 6-benzyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound O=C1NC(=S)NN=C1CC1=CC=CC=C1 FVLMRSJALFJPOF-UHFFFAOYSA-N 0.000 claims description 4
- ODLMWHHWCVYVOX-UHFFFAOYSA-N 6-cyclopropyl-3-sulfanylidene-2H-1,2,4-triazin-5-one Chemical compound C1(CC1)C=1C(NC(NN1)=S)=O ODLMWHHWCVYVOX-UHFFFAOYSA-N 0.000 claims description 4
- AEIJIVSLBHKEDO-BJMVGYQFSA-N 6-methyl-3-sulfanylidene-4-[(e)-thiophen-2-ylmethylideneamino]-2h-1,2,4-triazin-5-one Chemical compound O=C1C(C)=NNC(=S)N1\N=C\C1=CC=CS1 AEIJIVSLBHKEDO-BJMVGYQFSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 239000008247 solid mixture Substances 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 229920001774 Perfluoroether Polymers 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- NKOPQOSBROLOFP-UHFFFAOYSA-N 6-methyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound CC1=NNC(=S)NC1=O NKOPQOSBROLOFP-UHFFFAOYSA-N 0.000 claims description 2
- 108060001084 Luciferase Proteins 0.000 claims description 2
- 239000005089 Luciferase Substances 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- DIAVYQVEXCPHAD-WUXMJOGZSA-N 6-methyl-4-[(e)-(3-nitrophenyl)methylideneamino]-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound O=C1C(C)=NNC(=S)N1\N=C\C1=CC=CC([N+]([O-])=O)=C1 DIAVYQVEXCPHAD-WUXMJOGZSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical class OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762541350P | 2017-08-04 | 2017-08-04 | |
| US62/541,350 | 2017-08-04 | ||
| PCT/US2018/045040 WO2019028272A1 (en) | 2017-08-04 | 2018-08-02 | COMPOSITIONS AND METHODS FOR STABILIZING LUCIFERIN BENZOTHIAZOLE ANALOGS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020529442A JP2020529442A (ja) | 2020-10-08 |
| JP2020529442A5 true JP2020529442A5 (enExample) | 2021-09-09 |
| JP7350713B2 JP7350713B2 (ja) | 2023-09-26 |
Family
ID=63209736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020506187A Active JP7350713B2 (ja) | 2017-08-04 | 2018-08-02 | ベンゾチアゾールルシフェリンアナログを安定化させるための組成物及び方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US11136615B2 (enExample) |
| EP (1) | EP3661932B1 (enExample) |
| JP (1) | JP7350713B2 (enExample) |
| WO (1) | WO2019028272A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3548470B1 (en) | 2016-12-01 | 2023-11-01 | Promega Corporation | 5,5-disubstituted luciferins and their use in luciferase-based assays |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3537877A1 (de) | 1985-10-24 | 1987-04-30 | Geiger Reinhard | Luciferin-derivate und immunoassays unter einsatz derartiger luciferin-derivate |
| US6602677B1 (en) | 1997-09-19 | 2003-08-05 | Promega Corporation | Thermostable luciferases and methods of production |
| JP4478231B2 (ja) | 1998-12-09 | 2010-06-09 | 栄研化学株式会社 | 生物発光試薬の安定化方法 |
| JP4379644B2 (ja) | 1999-03-08 | 2009-12-09 | 栄研化学株式会社 | ホタルルシフェリンの安定化方法 |
| JP4503724B2 (ja) | 1999-05-10 | 2010-07-14 | 栄研化学株式会社 | ホタルルシフェリンの安定化方法 |
| US7118878B1 (en) | 2000-06-09 | 2006-10-10 | Promega Corporation | Method for increasing luminescence assay sensitivity |
| EP1546162B1 (en) | 2002-09-20 | 2011-06-22 | Promega Corporation | Luminescence-based methods and probes for measuring cytochrome p450 activity |
| JPWO2006013837A1 (ja) | 2004-08-05 | 2008-05-29 | 東洋ビーネット株式会社 | ルシフェラーゼ発光方法および発光試薬 |
| EP2778234B1 (en) | 2005-05-31 | 2017-09-27 | Promega Corporation | Luminogenic and fluorogenic compounds and methods to detect molecules or conditions |
| WO2008109459A1 (en) | 2007-03-02 | 2008-09-12 | University Of Massachusetts | Luciferins |
| JP6075723B2 (ja) | 2012-08-21 | 2017-02-08 | 栄研化学株式会社 | Ｎ−（２−アセトアミド）イミノ二酢酸を用いる発光増強方法 |
| EP2959010B1 (en) | 2013-02-22 | 2020-07-29 | Promega Corporation | Stabilized formulation for luminescent detection of luciferase and nucleoside phosphates |
| WO2014159044A1 (en) | 2013-03-12 | 2014-10-02 | Promega Corporation | Red-shifted luciferins and methods of using same |
| EP3146066B1 (en) * | 2014-05-23 | 2018-03-14 | Promega Corporation | Compositions and methods for stabilizing luminogenic substrates |
| US9732373B2 (en) * | 2014-09-11 | 2017-08-15 | Promega Corporation | Luciferase sequences utilizing infrared-emitting substrates to produce enhanced luminescence |
| WO2017057672A1 (ja) | 2015-09-30 | 2017-04-06 | 栄研化学株式会社 | ルシフェリンの安定化方法及び生物発光の測定方法 |
| EP3548470B1 (en) | 2016-12-01 | 2023-11-01 | Promega Corporation | 5,5-disubstituted luciferins and their use in luciferase-based assays |
-
2018
- 2018-08-02 EP EP18755670.9A patent/EP3661932B1/en active Active
- 2018-08-02 US US16/053,413 patent/US11136615B2/en active Active
- 2018-08-02 JP JP2020506187A patent/JP7350713B2/ja active Active
- 2018-08-02 WO PCT/US2018/045040 patent/WO2019028272A1/en not_active Ceased
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