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Merck
CN

C2230

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
NACRES:
NA.32
PubChem Substance ID:
24892477
UNSPSC Code:
12352200
MDL number:
MFCD00467176

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Product Name

Coelenterazine, native, solid

InChI key

YHIPILPTUVMWQT-UHFFFAOYSA-N

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

assay

≥95% (TLC)

form

solid

solubility

methanol and ethanol: soluble

storage temp.

−20°C

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 used to measure Ca2+ concentration.
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.

Disclaimer

Protect from exposure to light

General description

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCN6966
SLCJ2582
SLCH3617
SLCC5466
SLCC3993

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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)
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
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
Satoshi Inouye et al.
Analytical biochemistry, 407(2), 247-252 (2010-08-31)
Aequorin is a Ca(2+)-binding photoprotein and consists of an apoprotein (apoaequorin) and a 2-peroxide of coelenterazine. Eight new coelenterazine analogues modified at the C2-position were synthesized and incorporated into recombinant apoaequorin with O(2) to yield different semisynthetic aequorins. The luminescence
M L Dubuisson et al.
Biochemical pharmacology, 60(4), 471-478 (2000-06-30)
Coelenterazine (CLZn; 3, 7-dihydro-2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-8-benzylimidazolo++ +[1 ,2-a]pyrazin-3-one), the substrate for bioluminescence reactions in many marine animals, is endowed with high antioxidant properties. This work investigated the antioxidative properties of CLZn in primary cultures of rat hepatocytes subjected to the oxidant tert-butyl
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