Merck
CN
All Photos(1)

Documents

233900

Sigma-Aldrich

Coelenterazine

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

Sign Into View Organizational & Contract Pricing
All Photos(1)
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
Empirical Formula (Hill Notation):
C26H21N3O3
CAS Number:
55779-48-1
Molecular Weight:
423.46
MDL number:
MFCD00467176

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

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

Warning

Toxicity: Standard Handling (A)

Legal Information

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

Storage Class Code

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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

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
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
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
Bioluminescence Imaging
Keyaerts, M, et al.
"Handbook of Poylmer-Liquid Interaction Parameters and Solubility Parameters ", 4, 245-256 (2014)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service