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233900

Coelenterazine

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

Synonym(s):

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

Empirical Formula (Hill Notation):
C26H21N3O3
CAS Number:
55779-48-1
Molecular Weight:
423.46
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00467176
Assay:
≥90% (TLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, protect from light
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Product Name

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

Quality Level

100

assay

≥90% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

brown

solubility

methanol: 1 mg/mL, ethanol: soluble

shipped in

ambient

storage temp.

−20°C

SMILES string

[n]21c(nc([c]2=O)Cc5ccc(cc5)O)c([nH]c(c1)c4ccc(cc4)O)Cc3ccccc3

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

InChI key

YHIPILPTUVMWQT-UHFFFAOYSA-N

General description

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.

Application

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

Biochem/physiol Actions

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.

Packaging

Packaged under inert gas

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
View All Related Papers

Global Trade Item Number

SKUGTIN
233900-250UG04055977217933