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HomeProduct name listCoelenterazine

Coelenterazine

Synonym(s):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;3,2-Dihydro-2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-8-benzylimidazolo[1,2-a]pyrazin-3-one;CLZN;Coelenterazine - CAS 122384-88-7 - Calbiochem

Coelenterazine Structural

What is Coelenterazine?

Description

Coelenterazine is a luciferin—the most prevalent bioluminescent molecule in sea life. It exists in many marine species, from protozoa to fish. Luciferase enzymes cause coelenterazine to oxidize, which triggers the luminescence.
In the mid-1970s, coelenterazine was discovered independently by two research teams: Milton J. Cormier et al. at the University of Georgia (Athens) and Osamu Shimamura and Frank Johnson at Princeton University (NJ). In both cases, the species investigated were in the phylum cnidaria: Renilla reniformis (sea pansy) and Aequorea victoria (crystal jelly). Shimamura was one of the recipients of the 2008 Nobel Prize in Chemistry.
Luciferins previously presented in Molecule of the Week were lucifer yellow (October 29, 2012) and firefly luciferin (October 26, 2015). Both were featured in anticipation of Halloween.

Chemical properties

Yellow Solid

The Uses of Coelenterazine

Coelenterazine is a luminophore of the aequorin complex which is oxidized by oxygen to illuminate at 465nm when Ca2+ binds to the complex. Used to measure Ca2+ concentration in cells with high sensitivity an dlarge dynamic range.

The Uses of Coelenterazine

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

What are the applications of Application

Coelenterazine is a chemiluminescent luciferin probe that can be used to detect changes in calcium level and redox status.

Definition

ChEBI: An imidazopyrazine that is imidazo[1,2-a]pyrazin-3(7H)-one in which positions 2, 6, and 8 are substituted by 4-hydroxybenzyl, 4-hydroxyphenyl, and benzyl groups, respectively.

General Description

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

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.

Properties of Coelenterazine

Melting point: 176–181 ℃ (decompose)
Boiling point: 641.4±65.0 °C(Predicted)
Density  1.32±0.1 g/cm3(Predicted)
storage temp.  -20°C
solubility  methanol and ethanol: soluble
appearance orange-yellow crystals
form  solid
pka 9.91±0.15(Predicted)
color  yellow
Sensitive  Moisture & Light Sensitive
λmax 429nm
Biological Applications Calciumindicator; detecting luciferase,protease,gene expression,nucleic acids,proteins,stem cells,quantum dot conjugates,superoxide; tracing protein dynamics; as a substrate for luciferase,alka
CAS DataBase Reference 55779-48-1(CAS DataBase Reference)

Safety information for Coelenterazine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H413:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P273:Avoid release to the environment.
P501:Dispose of contents/container to..…

Computed Descriptors for Coelenterazine

InChIKey YHIPILPTUVMWQT-UHFFFAOYSA-N

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