Coelenterazine - CAS 55779-48-1
Molecular Formula:
C26H21N3O3
Molecular Weight:
423.5
COA:
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Application\Fluorophore:
Fluorescent Enzyme Substrates
Description:
Coelenterazine is a luciferin that serves as a substrate for luciferases. Coelenterazine can be used for probing superoxide anion and aequorin assays. Coelenterazine is also used to detect Ca2+ concentration in cells that have been transfected with apoaequorin cDNA.
Purity:
≥85%
Appearance:
Yellow Solid
Synonyms:
6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-8-(phenylmethyl)-imidazo[1,2-a]pyrazin-3(7H)-one
Storage:
Store at -20°C
MSDS:
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Melting Point:
>114°C (dec.)
Emission:
460-470 nm
InChIKey:
YHIPILPTUVMWQT-UHFFFAOYSA-N
InChI:
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
Canonical SMILES:
C1=CC=C(C=C1)CC2=C3N=C(C(=O)N3C=C(N2)C4=CC=C(C=C4)O)CC5=CC=C(C=C5)O
1.Expression, purification and luminescence properties of coelenterazine-utilizing luciferases from Renilla, Oplophorus and Gaussia: comparison of substrate specificity for C2-modified coelenterazines.
Inouye S1, Sahara-Miura Y, Sato J, Iimori R, Yoshida S, Hosoya T. Protein Expr Purif. 2013 Mar;88(1):150-6. doi: 10.1016/j.pep.2012.12.006. Epub 2012 Dec 27.
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 luciferase (GLase). The luminescence properties of the purified luciferases were characterized by using 10 kinds of C2-modified coelenterazine analogues as a substrate. The order of the maximal luminescence intensity for native coelenterazine was GLase (100%)>RLase (8.0%)>RLase-547 (0.73%)>19kOLase (0.09%) under our assay conditions. The substrate specificities of coelenterazine-utilizing luciferases for the C2-modified analogues showed significant differences, but the emission peaks catalyzed by coelenterazine-utilizing luciferases were not affected by the C2-substituted coelenterazine. These results suggest that the catalytic environment for the oxygenation process of coelenterazine and the excited species of coelenteramide might be different among coelenterazine-utilizing luciferases.
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Chemical Structure

CAS 55779-48-1 Coelenterazine

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