JP5550035B2 - 波長が制御されたルシフェラーゼの発光基質および製造方法 - Google Patents
波長が制御されたルシフェラーゼの発光基質および製造方法 Download PDFInfo
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- JP5550035B2 JP5550035B2 JP2009064595A JP2009064595A JP5550035B2 JP 5550035 B2 JP5550035 B2 JP 5550035B2 JP 2009064595 A JP2009064595 A JP 2009064595A JP 2009064595 A JP2009064595 A JP 2009064595A JP 5550035 B2 JP5550035 B2 JP 5550035B2
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- Prior art keywords
- luciferin
- mmol
- compound
- luminescent
- nmr
- 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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- 239000000758 substrate Substances 0.000 title claims description 49
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- 238000004519 manufacturing process Methods 0.000 title description 18
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- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000000504 luminescence detection Methods 0.000 claims description 2
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- BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 description 29
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- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 6
- QIJRTFXNRTXDIP-YBBRRFGFSA-N (2s)-2-amino-3-sulfanylpropanoic acid;hydrate;hydrochloride Chemical compound O.Cl.SC[C@@H](N)C(O)=O QIJRTFXNRTXDIP-YBBRRFGFSA-N 0.000 description 5
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- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
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| JP2009064595A JP5550035B2 (ja) | 2009-03-17 | 2009-03-17 | 波長が制御されたルシフェラーゼの発光基質および製造方法 |
| PCT/JP2010/053177 WO2010106896A1 (ja) | 2009-03-17 | 2010-02-28 | 波長が制御されたルシフェラーゼの発光基質および製造方法 |
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| JP2010215795A5 JP2010215795A5 (enExample) | 2012-05-10 |
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| EP2754657B1 (en) | 2011-08-24 | 2016-03-23 | The University of Electro-Communications | Luminescent substrate for luciferase |
| CN102532053B (zh) * | 2011-12-30 | 2014-08-06 | 广东省微生物研究所 | 一种高纯度d-荧光素的制备和纯化方法 |
| JP6011974B2 (ja) * | 2013-05-07 | 2016-10-25 | 国立大学法人電気通信大学 | 新規ハロゲン化水素塩 |
| JP6353751B2 (ja) * | 2013-09-25 | 2018-07-04 | 国立大学法人電気通信大学 | 新規複素環式化合物及びその塩、並びに、発光基質組成物 |
| JP6402969B2 (ja) * | 2014-04-15 | 2018-10-10 | Dic株式会社 | シラン化合物およびその重合体、ならびにその重合体からなる液晶配向層 |
| CN104262287B (zh) * | 2014-09-02 | 2016-06-08 | 苏州罗兰生物科技有限公司 | 一种亚硫酸根比率荧光探针的制备及应用 |
| WO2021193069A1 (ja) * | 2020-03-23 | 2021-09-30 | 黒金化成株式会社 | 新規複素環式化合物及びその塩、並びに発光基質組成物 |
| CN117720477A (zh) * | 2023-12-13 | 2024-03-19 | 广州博鹭腾生物科技有限公司 | 一种Akalumine盐酸盐的制备方法及其应用 |
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| US3164597A (en) * | 1962-12-17 | 1965-01-05 | Geigy Chem Corp | 5-carboxylic acid-2-phenyl-pyrrolines, corresponding pyrrolidines and functional derivatives thereof |
| JPS4730183B1 (enExample) * | 1970-09-16 | 1972-08-07 | ||
| WO2006130551A2 (en) * | 2005-05-31 | 2006-12-07 | Promega Corporation | Luminogenic and fluorogenic compounds and methods to detect molecules or conditions |
| JP4899046B2 (ja) * | 2005-09-30 | 2012-03-21 | 国立大学法人 東京大学 | 新規ルシフェリン誘導体 |
| WO2007116687A1 (ja) * | 2006-03-27 | 2007-10-18 | The University Of Electro-Communications | 複素環化合物及び発光方法 |
| JP5464311B2 (ja) * | 2008-02-02 | 2014-04-09 | 国立大学法人電気通信大学 | ルシフェラーゼの発光基質 |
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