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:
Molecular Weight:
423.46
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32
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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.[1]
Application
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.
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
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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
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
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
Miyuki Hasegawa et al.
Chemical communications (Cambridge, England), 49(3), 228-230 (2012-11-06)
Bioluminescence resonance energy transfer coupled near-infrared quantum dots using glutathione-s-transferase (GST) tagged luciferase were synthesized as luminescent probes for in vivo imaging.
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