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C2230

Sigma-Aldrich

Coelenterazine, native

solid

Synonym(s):

3,2-Dihydro-2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-8-benzylimidazolo[1,2-a]pyrazin-3-one, CLZN

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About This Item

Empirical Formula (Hill Notation):
C26H21N3O3
CAS Number:
55779-48-1
Molecular Weight:
423.46
MDL number:
MFCD00467176
UNSPSC Code:
12352200
PubChem Substance ID:
24892477
NACRES:
NA.32

Assay

≥95% (TLC)

form

solid

solubility

methanol and ethanol: soluble

storage temp.

−20°C

SMILES string

Oc1ccc(CC2=NC3=C(Cc4ccccc4)NC(=CN3C2=O)c5ccc(O)cc5)cc1

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 is a luciferin molecule, which is utilized by several luciferases, such as Renilla, Oplophorus and Periphylla.

Application

Coelenterazine, native was used:-
  • For Aequorin assays
  • For measuring the intracellular calcium concentration in response to ionomycin or PMA using aequorin in COS-7 cells
  • In Bioluminescence imaging for analysing the presence of virus-dependent luciferase activity

Biochem/physiol Actions

Luminophore of the aequorin complex which is oxidized by oxygen to illuminate at 465 nm when Ca2+ binds to the complex; used to measure Ca2+ concentration in cells with high sensitivity and large dynamic range.

Caution

Protect from exposure to light

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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New bioluminescent coelenterazine derivatives with various C-6 substitutions
Jiang T, et al.
Organic & Biomolecular Chemistry, 15(33), 7008-7018 (2017)
Darren R Ritsick et al.
Free radical biology & medicine, 43(1), 31-38 (2007-06-15)
The catalytic subunit gp91phox (Nox2) of the NADPH oxidase of mammalian phagocytes is activated by microbes and immune mediators to produce large amounts of reactive oxygen species (ROS) which participate in microbial killing. Homologs of gp91phox, the Nox and Duox
I Gentschev et al.
Cancer gene therapy, 16(4), 320-328 (2008-10-25)
Mammary cancers together with cancers of the skin account for about 60% of the total cancers occurring in dogs. The veterinary options for therapeutic management of canine mammary cancer are limited and prognosis for such patients is poor. In this
Satoshi Inouye et al.
Protein expression and purification, 88(1), 150-156 (2013-01-01)
The cold-induced expression system in Escherichia coli is useful and we have applied this system to prepare the coelenterazine-utilizing luciferases including Renilla luciferase (RLase), a red-shifted variant of Renilla luciferase (RLase-547), the catalytic domain of Oplophorus luciferase (19kOLase) and Gaussia
M Sarah S Bovenberg et al.
Analytical chemistry, 84(2), 1189-1192 (2011-12-14)
Secreted Gaussia luciferase (Gluc) has been shown to be a useful tool for ex vivo monitoring of in vivo biological processes. The Gluc level in the blood was used to detect tumor growth, metastasis and response to therapy, gene transfer
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