Coelenterazine

Structural formula
General
Surname	Coelenterazine
other names	8-Benzyl-2- (4-hydroxybenzyl) -6- (4-hydroxyphenyl) imidazo [1,2- a ] pyrazin-3 (7 H ) -one
Molecular formula	C 26 H 21 N 3 O 3
Brief description	dark orange solid
External identifiers / databases
EC number	637-236-4
ECHA InfoCard	100.164.960
PubChem	2830
ChemSpider	2728
Wikidata	Q418878
properties
Molar mass	423.46 g · mol -1
Physical state	firmly
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: 413
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Coelenterazine is a natural product from the group of luciferins and serves as a substrate for the enzymes luciferase , aequorin and obelin in various organisms that generate light ( bioluminescence ). The name is derived from coelenterates ( Hohltiere ab), from whose representatives Aequorea victoria first was isolated coelenterazine. In addition, coelenterazine and analogous substances such as coelenterazine h, for example, have been detected in radiant animals , cnidarians , copepods , arrow worms and squids . In the presence of oxygen ( oxidation ), coelenterazine reacts with these enzymes and enables them to split off carbon dioxide and coelenteramide in an autocatalytic reaction with the release of energy in the form of a light quantum .

Coelenterazine is used in the biosciences together with the luciferase enzyme from the sea feather Renilla reniformis , whose gene acts as a reporter . It is mainly used in functional genetic research.

Aequorin catalyzes the oxidation of coelenterazine (left) to coelenteramide; when an energy-rich intermediate stage decays, light is created.

Individual evidence

↑ ^a ^b ^c Data sheet Coelenterazine, native from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
↑ Shimomura O, Johnson FH: Chemical Nature of Bioluminescence Systems in Coelenterates . In: Proc. Natl. Acad. Sci. USA . 72, 1975, pp. 1546-1549. PMID 236561 . PMC 432574 (free full text).
↑ promega.com: Dual-Luciferase® Reporter Assay System
↑ pjk-gmbh.de: Renilla Assays .

[sigma-1] Data sheet Coelenterazine, native from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).

[2] Shimomura O, Johnson FH: Chemical Nature of Bioluminescence Systems in Coelenterates . In: Proc. Natl. Acad. Sci. USA . 72, 1975, pp. 1546-1549. PMID 236561 . PMC 432574 (free full text).

[3] romega.com: Dual-Luciferase® Reporter Assay System

[4] -gmbh.de: Renilla Assays .