Coelenterazine is a luciferin, a light-emitting molecule, found in many aquatic organisms across eight phyla. It is the substrate of many luciferases such as Renilla reniformis luciferase (Rluc), Gaussia luciferase (Gluc), and photoproteins, including aequorin, and obelin. All these proteins catalyze the oxidation of this substance, an reaction catalogued EC 184.108.40.206.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||423.472 g·mol−1|
|Melting point||175 to 178 °C (347 to 352 °F; 448 to 451 K)|
|Absorbance||ε435 = 9800 M−1 cm−1 (methanol)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Coelenterazine was simultaneously isolated and characterized by two groups studying the luminescent organisms sea pansy (Renilla reniformis) and the cnidarian Aequorea victoria, respectively. Both groups unknowingly discovered that the same compound was used in both luminescent systems, however the name of the molecule was given after the now-obsolete phylum coelenterata. Likewise, the two main metabolites – coelenteramide and coelenteramine – were named after their respective functional groups. Despite being first discovered in Aequorea victoria, it was later shown that they do not synthesize coelenterazine, rather they obtain it through their diet, largely from crustaceans and copepods.
Coelenterazine is widely found in marine organisms including:
- cnidarians such as Aequorea victoria, Obelia geniculata and Renilla reniformis
- squid such as Watasenia scintillans and Vampyroteuthis infernalis
- shrimp such as Systellaspis debilis and Oplophorus gracilirostris
- copepods such as Pleuromamma xiphias and Gaussia princeps
- fish including some Neoscopelidae and Myctophidae
- echinoderms such as Amphiura filiformis
Biosynthesis of coelenterazine in Metridia starts from two molecules of tyrosine and one molecule of phenylalanine, and some researchers believe this comes in the form of a cyclized "Phe-Tyr-Tyr" (FYY) peptide.
Coelenterazine can be crystallized into orange-yellow crystals. The molecule absorbs light in the ultraviolet and visible spectrum, with peak absorption at 435 nm in methanol, giving the molecule a yellow color. The molecule spontaneously oxidizes in aerobic conditions or in some organic solvents such as dimethylformamide and DMSO and is preferentially stored in methanol or with an inert gas.
Synthetic coelenterazine derivativesEdit
To improve its biophysical properties, derivatives of coelenterazine have been synthesized by means of different procedures including multicomponent strategies.
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- Bioluminescence Page showing major luciferin types