JP7104702B2 - ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 - Google Patents

５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 Download PDF

Info

Publication number
JP7104702B2
JP7104702B2 JP2019529472A JP2019529472A JP7104702B2 JP 7104702 B2 JP7104702 B2 JP 7104702B2 JP 2019529472 A JP2019529472 A JP 2019529472A JP 2019529472 A JP2019529472 A JP 2019529472A JP 7104702 B2 JP7104702 B2 JP 7104702B2
Authority
JP
Japan
Prior art keywords
luciferase
alkyl
luciferin
cycloalkyl
heteroaryl
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.)
Active
Application number
JP2019529472A
Other languages
English (en)
Japanese (ja)
Other versions
JP2020503274A (ja
JP2020503274A5 (enExample
Inventor
マイケル キロラン
ランス ピー エンセル
メアリー ピー ホール
トーマス エイ カークランド
ポンチョ マイセンハイマー
ツェー シー
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Promega Corp
Original Assignee
Promega Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Promega Corp filed Critical Promega Corp
Publication of JP2020503274A publication Critical patent/JP2020503274A/ja
Publication of JP2020503274A5 publication Critical patent/JP2020503274A5/ja
Priority to JP2022110372A priority Critical patent/JP7696867B2/ja
Application granted granted Critical
Publication of JP7104702B2 publication Critical patent/JP7104702B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

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
    • C12Q1/66—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
    • A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
    • A61K49/003—Thiazine dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/10—Spiro-condensed systems
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/76—Chemiluminescence; Bioluminescence
    • G01N21/763—Bioluminescence

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Analytical Chemistry (AREA)
  • Immunology (AREA)
  • Biochemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • General Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pathology (AREA)
  • General Physics & Mathematics (AREA)
  • Plasma & Fusion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
JP2019529472A 2016-12-01 2017-12-01 ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用 Active JP7104702B2 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2022110372A JP7696867B2 (ja) 2016-12-01 2022-07-08 ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201662428707P 2016-12-01 2016-12-01
US62/428,707 2016-12-01
PCT/US2017/064284 WO2018102726A1 (en) 2016-12-01 2017-12-01 5,5-disubstituted luciferins and their use in luciferase-based assays

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2022110372A Division JP7696867B2 (ja) 2016-12-01 2022-07-08 ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用

Publications (3)

Publication Number Publication Date
JP2020503274A JP2020503274A (ja) 2020-01-30
JP2020503274A5 JP2020503274A5 (enExample) 2021-01-14
JP7104702B2 true JP7104702B2 (ja) 2022-07-21

Family

ID=60703215

Family Applications (2)

Application Number Title Priority Date Filing Date
JP2019529472A Active JP7104702B2 (ja) 2016-12-01 2017-12-01 ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用
JP2022110372A Active JP7696867B2 (ja) 2016-12-01 2022-07-08 ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP2022110372A Active JP7696867B2 (ja) 2016-12-01 2022-07-08 ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用

Country Status (4)

Country Link
US (2) US10400264B2 (enExample)
EP (1) EP3548470B1 (enExample)
JP (2) JP7104702B2 (enExample)
WO (1) WO2018102726A1 (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
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
EP3661932B1 (en) 2017-08-04 2021-10-06 Promega Corporation Compositions and methods for stabilizing benzothiazole luciferin analogs
KR20210015892A (ko) 2018-05-29 2021-02-10 세르시 테라퓨틱스 인코포레이티드 통증 치료를 위한 화합물, 이를 포함하는 조성물 및 이를 사용하는 방법
US11767517B2 (en) 2018-06-05 2023-09-26 Promega Corporation Luciferase enzymes for use with thermostable luciferins in bioluminescent assays
WO2020096775A1 (en) * 2018-11-09 2020-05-14 R.P. Scherer Technologies, Llc Sulfatase-cleavable linkers for antibody-drug conjugates
US20200246317A1 (en) * 2019-02-01 2020-08-06 Cersci Therapeutics, Inc. Methods of treating diabetic neuropathy with a thiazoline anti-hyperalgesic agent
WO2020159565A1 (en) * 2019-02-01 2020-08-06 Cersci Therapeutics, Inc. Methods of treating post-surgical pain with a thiazoline anti-hyperalgesic agent
CA3136102A1 (en) 2019-05-10 2020-11-19 Cersci Therapeutics, Inc. Manufacturing methods and polymorphs of a thiazoline anti-hyperalgesic agent
CN110590700B (zh) * 2019-09-12 2021-09-21 山东大学 多元杂环化合物与制备方法及其在检测半胱氨酸中的应用
WO2021061057A2 (en) * 2019-09-26 2021-04-01 Vidyasirimedhi Institute Of Science And Technology Luciferin derivatives and a method for synthesis thereof
CN114478578B (zh) * 2021-12-24 2024-03-29 上海中医药大学 测定羧酸酯酶1的特异性生物发光探针底物及其制备方法和应用
CN115745987B (zh) * 2022-08-05 2026-03-27 华东理工大学 一种荧光素酶底物及其制备方法和用途

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000169459A (ja) 1998-12-09 2000-06-20 Lumigen Inc 赤色の化学発光を生じさせる化合物及びその方法
JP2005500281A (ja) 2001-06-01 2005-01-06 エフ．ホフマン−ラ　ロシュ　アーゲー ルシフェリンヒドラジド
JP2008545746A (ja) 2005-05-31 2008-12-18 プロメガ コーポレイション 分子または状態を検出するための発光性化合物および蛍光性化合物、ならびに方法
JP2012533654A (ja) 2009-07-16 2012-12-27 ベックマン コールター， インコーポレイテッド 新規な蛍光色素およびその使用
US20140193340A1 (en) 2013-01-04 2014-07-10 University Of Massachusetts Luciferin Amides

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7074891B2 (en) 2003-02-07 2006-07-11 Posco Leukocyte stimulating peptides
CN103443121B (zh) * 2010-11-02 2016-04-20 普罗梅加公司 新型腔肠素底物及其使用方法
WO2014159044A1 (en) 2013-03-12 2014-10-02 Promega Corporation Red-shifted luciferins and methods of using same
EP3548470B1 (en) * 2016-12-01 2023-11-01 Promega Corporation 5,5-disubstituted luciferins and their use in luciferase-based assays
EP3661932B1 (en) 2017-08-04 2021-10-06 Promega Corporation Compositions and methods for stabilizing benzothiazole luciferin analogs

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000169459A (ja) 1998-12-09 2000-06-20 Lumigen Inc 赤色の化学発光を生じさせる化合物及びその方法
JP2005500281A (ja) 2001-06-01 2005-01-06 エフ．ホフマン−ラ　ロシュ　アーゲー ルシフェリンヒドラジド
JP2008545746A (ja) 2005-05-31 2008-12-18 プロメガ コーポレイション 分子または状態を検出するための発光性化合物および蛍光性化合物、ならびに方法
JP2012533654A (ja) 2009-07-16 2012-12-27 ベックマン コールター， インコーポレイテッド 新規な蛍光色素およびその使用
US20140193340A1 (en) 2013-01-04 2014-07-10 University Of Massachusetts Luciferin Amides

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
Biochemistry ，2004年，43，7255-7262
Biochemistry ，2014年，53，5208-5220
Eur. J. Med. Chem.，2015年，94，140-148
J. Am. Chem. Soc.，2010年，132，11566-11579
J. Am. Chem. Soc.，2014年，136，13277-13282
J. Org. Chem. ，1965年，30，2344-2348
J. Phys. Chem. A ，2013年，117，94-100
Photochem. Photoviol. Sci.，2012年，11，1281-1284
REGISTRY（STN）［online］，1984年，CAS 登録番号：18330-81-9

Also Published As

Publication number Publication date
EP3548470A1 (en) 2019-10-09
US10400264B2 (en) 2019-09-03
JP2022172059A (ja) 2022-11-15
JP2020503274A (ja) 2020-01-30
EP3548470B1 (en) 2023-11-01
WO2018102726A1 (en) 2018-06-07
US20190338340A1 (en) 2019-11-07
US10913972B2 (en) 2021-02-09
JP7696867B2 (ja) 2025-06-23
US20180155762A1 (en) 2018-06-07

Similar Documents

Publication Publication Date Title
JP7696867B2 (ja) ５，５－二置換ルシフェリン及びルシフェラーゼ系アッセイにおけるそれらの使用
Alaimo et al. Targeting the gatekeeper residue in phosphoinositide 3-kinases
JP6040157B2 (ja) セレンテラジン誘導体およびその使用方法
Bilyard et al. Natural, modified DNA bases
US11192894B2 (en) Cell impermeable coelenterazine analogues
EP2323996B1 (en) Luminogenic compounds and methods to detect cytochrome p450 3a enzymes
US10836767B2 (en) Serum stable pro-coelenterazine analogues
US8592172B2 (en) Bioluminescent assays using cyanobenzothiazole compounds
JP6978492B2 (ja) 二重保護されたプロセレンテラジン基質
JP7200102B2 (ja) エネルギー受容体に係留されたセレンテラジン類縁体
JP2021523111A (ja) ＮａｎｏＬｕｃ自殺基質としてのセレンテラジン化合物
He et al. Deciphering the metabolic fates of a green fluorescent protein (GFP)-like fluorophore: metabolite identification, isoenzyme contribution and species differences
Bishop et al. A gatekeeper residue for inhibitor sensitization of protein tyrosine phosphatases
JP2024540826A (ja) 一酸化窒素を検出するための化合物及び方法
Ahmed Mapping domains for ZIC3 molecular function

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20201130

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20201130

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20211021

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20211110

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20220209

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20220608

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20220708

R150 Certificate of patent or registration of utility model

Ref document number: 7104702

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250