CA2949447C - Compositions and methods for stabilizing luminogenic substrates - Google Patents

Compositions and methods for stabilizing luminogenic substrates Download PDF

Info

Publication number
CA2949447C
CA2949447C CA2949447A CA2949447A CA2949447C CA 2949447 C CA2949447 C CA 2949447C CA 2949447 A CA2949447 A CA 2949447A CA 2949447 A CA2949447 A CA 2949447A CA 2949447 C CA2949447 C CA 2949447C
Authority
CA
Canada
Prior art keywords
triazin
att
tak
composition
thioxo
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
CA2949447A
Other languages
English (en)
French (fr)
Other versions
CA2949447A1 (en
Inventor
Thomas Kirkland
Keith V. Wood
Mary Hall
Marie SCHWINN
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 CA2949447A1 publication Critical patent/CA2949447A1/en
Application granted granted Critical
Publication of CA2949447C publication Critical patent/CA2949447C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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 materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
    • C07D253/075—Two hetero atoms, in positions 3 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Wood Science & Technology (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Physics & Mathematics (AREA)
  • Biotechnology (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Materials Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Cell Biology (AREA)
  • Food Science & Technology (AREA)
  • Pathology (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2949447A 2014-05-23 2015-05-26 Compositions and methods for stabilizing luminogenic substrates Active CA2949447C (en)

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 (2)

Publication Number Publication Date
CA2949447A1 CA2949447A1 (en) 2015-11-26
CA2949447C true CA2949447C (en) 2022-10-04

Family

ID=53434457

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2949447A Active CA2949447C (en) 2014-05-23 2015-05-26 Compositions and methods for stabilizing luminogenic substrates

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3661932B1 (en) 2017-08-04 2021-10-06 Promega Corporation Compositions and methods for stabilizing benzothiazole luciferin analogs
IL318819A (en) 2018-10-03 2025-04-01 Promega Corp Compounds and methods for stabilizing cholinetyrazine and its derivatives
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
CN121399275A (zh) * 2024-05-21 2026-01-23 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)

* Cited by examiner, † Cited by third party
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
EP2626703B1 (en) * 2008-03-27 2017-05-03 Promega Corporation Protein labeling with cyanobenzothiazole conjugates
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

Also Published As

Publication number Publication date
EP3146066B1 (en) 2018-03-14
WO2015179864A1 (en) 2015-11-26
BR112016027504A2 (enExample) 2017-08-15
SG11201609382WA (en) 2016-12-29
AU2015263901A1 (en) 2016-11-24
JP2017519977A (ja) 2017-07-20
KR102456212B1 (ko) 2022-10-20
US20150337198A1 (en) 2015-11-26
BR112016027504B1 (pt) 2023-04-18
CN106661028B (zh) 2021-08-06
US9676997B2 (en) 2017-06-13
CA2949447A1 (en) 2015-11-26
EP3146066A1 (en) 2017-03-29
AU2015263901B2 (en) 2021-03-11
JP6641297B2 (ja) 2020-02-05
CN106661028A (zh) 2017-05-10
KR20170012271A (ko) 2017-02-02

Similar Documents

Publication Publication Date Title
AU2015263901B2 (en) Compositions and methods for stabilizing luminogenic substrates
Kalkanidis et al. Novel phenothiazine antimalarials: synthesis, antimalarial activity, and inhibition of the formation of β-haematin
Yoon et al. Benzimidazoles as new scaffold of sirtuin inhibitors: Green synthesis, in vitro studies, molecular docking analysis and evaluation of their anti-cancer properties
Khan et al. Oxindole derivatives: Synthesis and antiglycation activity
MX2013000333A (es) N-etil-n-fenil-1,2-dihidro-4-hidroxi-5-cloro-1-metil-2-oxoquinoli na-3-carboxamida deuterada, sales y usos de la misma.
Panda et al. Synthesis, antiinflammatory and antibacterial activity of novel indolyl-isoxazoles
Al-Abboodi et al. Anti-corrosion and antioxidant activities of new synthesised oxazepine and thaizolidinone derivatives linking to imidazo/pyridine
Pinson et al. Synthesis and pharmacological evaluation of 4-iminothiazolidinones for inhibition of PI3 kinase
EP3661932B1 (en) Compositions and methods for stabilizing benzothiazole luciferin analogs
Saeed et al. Design, Synthesis, and Antibacterial, Antifungal, and Antioxidant Activities of New Four Membered Rings from Derivatives Containing a 4 (3 H)-Quinazolinone Moiety, Activities
Liu et al. Synthesis and antimalarial activity of 2-guanidino-4-oxoimidazoline derivatives
Lozanovski et al. Development of a spectrophotometric method for assessment of the relative reactivity of monocarbonyl analogs of curcumin with 2-(dimethylamino) ethanethiol
Sicak et al. Synthesis, characterization, and antioxidant and anticholinesterase activities of pyrazolo derivatives
Al-Majidi et al. Synthesis and Evaluation Antibacterial Activity of Some New Substituted 5-Bromoisatin Containing Five, Six Heterocyclic Ring
Bhole et al. Design, synthesis and pharmacological evaluation of some 2-methylsulfanyl-1, 4-dihydropyrimidines derivatives as an analgesic agent
Alshubramy et al. Efficient Synthesis of New Fused Thiadiazines and Their Spectroscopic, In Silico Drug Likeness, and ADME Properties
Miliutina et al. Synthesis of chromeno [2, 3-c] pyrrol-9 (2 H)-ones by domino reactions of amino acids with ynones
Biradar et al. A mini library of novel triazolothiadiazepinylindole analogues: Synthesis, antioxidant and antimicrobial evaluations
Shindy et al. Effects of chemical structure, solvent and solution pH on the visible spectra of some new methine cyanine dyes
Bawa et al. Synthesis and antimicrobial activity of 2-chloroquinoline incorporated pyrazoline derivatives
Liu et al. Design, Synthesis and Biological Evaluation of Potent Piperazine-Based BioA Inhibitors Targeting Biotin Biosynthesis in Mycobacterium tuberculosis
Abed et al. Synthesis, Identification, and Antioxidant Activity Evaluation of New Diazine 2-Sulfanylbenzoxadiazole Derivatives
PL444571A1 (pl) 2-[(E)-2-(2-metoksyfenylo)etenylo]pirydo[2,3-d]pirymidino-4-ylo-4-metylobenzeno-1-sulfonian i jego zastosowanie
Porter et al. Pharmaceutical development of IPI‐504, an Hsp90 inhibitor and clinical candidate for the treatment of cancer
Naqvi et al. Synthesis and Antibacterial Evaluation of Substituted 3-methyl-2-pyrazolin-5-ones

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20200421

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 10TH ANNIV.) - STANDARD

Year of fee payment: 10

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250516

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250516