JP2017519977A5 - - Google Patents
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- Publication number
- JP2017519977A5 JP2017519977A5 JP2016569444A JP2016569444A JP2017519977A5 JP 2017519977 A5 JP2017519977 A5 JP 2017519977A5 JP 2016569444 A JP2016569444 A JP 2016569444A JP 2016569444 A JP2016569444 A JP 2016569444A JP 2017519977 A5 JP2017519977 A5 JP 2017519977A5
- Authority
- JP
- Japan
- Prior art keywords
- tak
- triazin
- thioxo
- composition
- source substrate
- 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
Links
- 239000000203 mixture Substances 0.000 claims description 51
- 239000000758 substrate Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 33
- YHIPILPTUVMWQT-UHFFFAOYSA-N Oplophorus luciferin Chemical group C1=CC(O)=CC=C1CC(C(N1C=C(N2)C=3C=CC(O)=CC=3)=O)=NC1=C2CC1=CC=CC=C1 YHIPILPTUVMWQT-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 30
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- 230000015556 catabolic process Effects 0.000 claims description 13
- 238000006731 degradation reaction Methods 0.000 claims description 13
- -1 NR a R b Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 150000002466 imines Chemical class 0.000 claims description 8
- 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 5
- JKNCBDOZPMOPLE-MHWRWJLKSA-N 4-[(e)-[4-(diethylamino)phenyl]methylideneamino]-6-methyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound C1=CC(N(CC)CC)=CC=C1\C=N\N1C(=O)C(C)=NNC1=S JKNCBDOZPMOPLE-MHWRWJLKSA-N 0.000 claims description 5
- 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 5
- BZUZUVWERCAEPE-UHFFFAOYSA-N 6-(hydroxymethyl)-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound OCC1=NNC(S)=NC1=O BZUZUVWERCAEPE-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 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 description 5
- UDRLQUBSFWAFSO-UHFFFAOYSA-N 3-(4-amino-5-oxo-3-sulfanylidene-2h-1,2,4-triazin-6-yl)propanoic acid Chemical compound NN1C(=S)NN=C(CCC(O)=O)C1=O UDRLQUBSFWAFSO-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
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 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 3
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 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 2
- 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 1
- 238000000354 decomposition reaction Methods 0.000 description 18
- JCIODXDOCJZABZ-BJMVGYQFSA-N 4-[(e)-furan-2-ylmethylideneamino]-6-methyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound O=C1C(C)=NNC(=S)N1\N=C\C1=CC=CO1 JCIODXDOCJZABZ-BJMVGYQFSA-N 0.000 description 3
- 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 description 2
- 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 description 2
- HTBLMRUZSCCOLL-UHFFFAOYSA-N 8-benzyl-2-(furan-2-ylmethyl)-6-phenylimidazo[1,2-a]pyrazin-3-ol Chemical group OC1=C(CC2=CC=CO2)N=C2N1C=C(N=C2CC1=CC=CC=C1)C1=CC=CC=C1 HTBLMRUZSCCOLL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462002363P | 2014-05-23 | 2014-05-23 | |
| US62/002,363 | 2014-05-23 | ||
| PCT/US2015/032439 WO2015179864A1 (en) | 2014-05-23 | 2015-05-26 | Compositions and methods for stabilizing luminogenic substrates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017519977A JP2017519977A (ja) | 2017-07-20 |
| JP2017519977A5 true JP2017519977A5 (enExample) | 2018-06-21 |
| JP6641297B2 JP6641297B2 (ja) | 2020-02-05 |
Family
ID=53434457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016569444A Active JP6641297B2 (ja) | 2014-05-23 | 2015-05-26 | 発光源基質を安定させる組成物及び方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9676997B2 (enExample) |
| EP (1) | EP3146066B1 (enExample) |
| JP (1) | JP6641297B2 (enExample) |
| KR (1) | KR102456212B1 (enExample) |
| CN (1) | CN106661028B (enExample) |
| AU (1) | AU2015263901B2 (enExample) |
| BR (1) | BR112016027504B1 (enExample) |
| CA (1) | CA2949447C (enExample) |
| SG (1) | SG11201609382WA (enExample) |
| WO (1) | WO2015179864A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019028272A1 (en) * | 2017-08-04 | 2019-02-07 | Promega Corporation | COMPOSITIONS AND METHODS FOR STABILIZING LUCIFERIN BENZOTHIAZOLE ANALOGS |
| CA3114424A1 (en) | 2018-10-03 | 2020-04-09 | Promega Corporation | Compositions and methods for stabilizing coelenterazine and analogs and derivatives thereof |
| CN111116594B (zh) * | 2019-12-03 | 2021-05-28 | 山东大学 | 一种C-6位改造NanoLuc类型类似物及其制备方法与应用 |
| WO2025242077A1 (zh) * | 2024-05-21 | 2025-11-27 | 深圳琅技生命科技有限公司 | 用于稳定腔肠素及其类似物的组合物及方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2000622A1 (de) * | 1970-01-08 | 1971-07-22 | Agfa Gevaert Ag | Verfahren zur Stabilisierung von Silberbildern |
| JP4639904B2 (ja) * | 2005-03-30 | 2011-02-23 | チッソ株式会社 | 蛍光活性を有するルシフェラーゼの活性増強方法 |
| JP4761150B2 (ja) * | 2006-07-24 | 2011-08-31 | 独立行政法人産業技術総合研究所 | ハイスループット発光活性測定のためのセレンテラジン（ウミシイタケルシフェリン）溶液の安定化組成物および安定化法 |
| US7718389B2 (en) * | 2006-07-24 | 2010-05-18 | National Institute Of Advanced Industrial Science And Technology | Stabilizing composition and stabilizing method of coelenterazine solution for high-throughput measurement of luciferase activity |
| EP3141905B1 (en) * | 2008-03-27 | 2019-03-06 | Promega Corporation | Protein labeling with cyanobenzothiazole conjugates |
| EP3498709B1 (en) | 2010-11-02 | 2025-12-31 | Promega Corporation | Luciferases from Oplophorus: Novel Coelenterazine Substrates and Their Methods of Use |
-
2015
- 2015-05-26 JP JP2016569444A patent/JP6641297B2/ja active Active
- 2015-05-26 KR KR1020167033229A patent/KR102456212B1/ko active Active
- 2015-05-26 SG SG11201609382WA patent/SG11201609382WA/en unknown
- 2015-05-26 WO PCT/US2015/032439 patent/WO2015179864A1/en not_active Ceased
- 2015-05-26 AU AU2015263901A patent/AU2015263901B2/en active Active
- 2015-05-26 US US14/721,727 patent/US9676997B2/en active Active
- 2015-05-26 CN CN201580026864.3A patent/CN106661028B/zh active Active
- 2015-05-26 BR BR112016027504-7A patent/BR112016027504B1/pt active IP Right Grant
- 2015-05-26 CA CA2949447A patent/CA2949447C/en active Active
- 2015-05-26 EP EP15730321.5A patent/EP3146066B1/en active Active
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