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Key Documents

233900

Sigma-Aldrich

Coelenterazine

≥90% (TLC), solid, chemiluminescence probe of the superoxide anion, Calbiochem®

Sinonimo/i:

Coelenterazine, 2-( p-Hydroxybenzyl)-6-( p-hydroxyphenyl)-8-benzylimidazo[1,2-a]pyrazin-3-(7H)-one, 2-(p-Hydroxybenzyl)-6-(p-hydroxyphenyl)-8-benzylimidazo[1,2-a]pyrazin-3-(7H)-one

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About This Item

Formula empirica (notazione di Hill):
C26H21N3O3
Numero CAS:
55779-48-1
Peso molecolare:
423.46
Numero MDL:
MFCD00467176
Codice UNSPSC:
12352200
NACRES:
NA.77

product name

Coelenterazine, A cell-permeable aequorin luminophore that acts as a very sensitive and specific chemiluminescence probe of the superoxide anion.

Livello qualitativo

100

Saggio

≥90% (TLC)

Forma fisica

solid

Produttore/marchio commerciale

Calbiochem®

Condizioni di stoccaggio

OK to freeze
protect from light

Colore

brown

Solubilità

methanol: 1 mg/mL
ethanol: soluble

Condizioni di spedizione

ambient

Temperatura di conservazione

−20°C

InChI

1S/C26H21N3O3/c30-20-10-6-18(7-11-20)15-23-26(32)29-16-24(19-8-12-21(31)13-9-19)27-22(25(29)28-23)14-17-4-2-1-3-5-17/h1-13,16,27,30-31H,14-15H2
YHIPILPTUVMWQT-UHFFFAOYSA-N

Descrizione generale

Coelenterazine (CTZ), a small prosthetic group, is a luciferin or light-producing compound present in luminous marine organisms. The imidazopyrazinone ring in CTZ is responsible for its luminous properties. This chemiluminescent dye is soluble in methanol and poorly soluble in water. CTZ can be oxidized with the help of bovine serum albumin (BSA) and several other luciferases.

Applicazioni

Coelenterazine - CAS 55779-48-1 – Calbiochem may be used:


  • to determine superoxide production
  • to determine free radical production
  • in cell suspension buffer for in vivo reconstitution of aequorin

Azioni biochim/fisiol

Coelenterazine (CTZ) is a cell-permeable aequorin luminophore that acts as a very sensitive and specific chemiluminescence probe of the superoxide anion. It can also be used for detecting changes in intracellular Ca2+ in cells that have been transfected with apoaequorin cDNA. CTZ functions as a powerful antioxidant. It serves as a substrate for multidrug resistance protein 1 (MDR1) P-glycoprotein (ATP-binding cassette sub-family B member 1 (ABCB1)/Pgp) and can bind with apoaequorin to form the active aequorin complex. It can be mainly used to quantify the formation of superoxide in neutrophils.

Confezionamento

Packaged under inert gas

Attenzione

Toxicity: Standard Handling (A)

Note legali

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

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Ryo Nishihara et al.
Bioconjugate chemistry, 31(12), 2679-2684 (2020-11-26)
A synthetic luciferin comprising an imidazopyrazinone core, named HuLumino1, was designed to generate specific bioluminescence with human serum albumin (HSA) in real serum samples. HuLumino1 was developed by attaching a methoxy-terminated alkyl chain to C-6 of coelenterazine and by eliminating
Tianyu Jiang et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 15(4), 466-480 (2016-03-25)
Bioluminescence-based techniques, such as bioluminescence imaging, BRET and dual-luciferase reporter assay systems, have been widely used to examine a myriad of biological processes. Coelenterazine (CTZ), a luciferin or light-producing compound found in bioluminescent organisms, has sparked great curiosity and interest
Sandeep Raha et al.
Free radical biology & medicine, 32(5), 421-430 (2002-02-28)
Human NADH CoQ oxidoreductase is composed of a total of 43 subunits and has been demonstrated to be a major site for the production of superoxide by mitochondria. Incubation of rat heart mitochondria with ATP resulted in the phosphorylation of
S Raha et al.
Free radical biology & medicine, 29(2), 170-180 (2000-09-12)
In this report we show that ubiquinone cytochrome c reductase (complex III) from isolated rat heart mitochondria when inhibited with antimycin A, produces a large amount of superoxide as measured by the chemiluminescent probe coelenterazine. When mitochondria are inhibited with
Olivier Lamotte et al.
Free radical biology & medicine, 40(8), 1369-1376 (2006-04-25)
In this study, we investigated a role for nitric oxide (NO) in mediating the elevation of the free cytosolic Ca(2+) concentration ([Ca(2+)](cyt)) in plants using Nicotiana plumbaginifolia cells expressing the Ca(2+) reporter apoaequorin. Hyperosmotic stress induced a fast increase of

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