Coelenterazine

Coelenterazine
Names
	IUPAC name 6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-8-(phenylmethyl)-7H-imidazo[3,2-a]pyrazin-3-one
	Other names Coelenterazine, Renilla luciferin
Identifiers
CAS Number	55779-48-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:2311 ;
ChemSpider	2728 ;
ECHA InfoCard	100.164.960
PubChem CID	2830;
CompTox Dashboard (EPA)	DTXSID80204342 ;
	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 Key: YHIPILPTUVMWQT-UHFFFAOYSA-N ; 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;
	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;
Properties
Chemical formula	C26H21N3O3
Molar mass	423.463
Appearance	orange-yellow crystals
Melting point	175 to 178 °C (347 to 352 °F; 448 to 451 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Coelenterazine is the luciferin, the light-emitting molecule, found in many aquatic organisms across seven phyla.^[1] It is the substrate of many luciferases such as Renilla reniformis luciferase (Rluc), Gaussia luciferase (Gluc), and photoproteins, including aequorin, and obelin.

History

Coelenterazine was simultaneously isolated and characterized by two groups studying the luminescent organisms sea pansy (Renilla reniformis) and the coelenterate Aequorea victoria, respectively.^[2]^[3] Both groups unknowingly discovered that the same compound was used in both luminescent systems, however the name of the molecule was given after the coelenterate. 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.^[4]

Occurrence

Coelenterazine is widely found in marine organisms including:

radiolarians
ctenophores
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
chaetognaths^[5]
fish including some Neoscopelidae and Myctophidae
echinoderms such as Amphiura filiformis

The compound has also been isolated from organisms that are not luminescent, such as the Atlantic herring and several shrimp species including Pandalus borealis and Pandalus platyuros.

Properties

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 derivatives

To improve its biophysical properties, derivatives of Coelenterazine have been synthesized by means of different procedures including multicomponent strategies.^[6]

References

^ Shimomura, O. (2006). Bioluminescence: Chemical Principles and Methods. World Scientific Publishing. pp. 159–165. ISBN 978-981-256-801-4.
^ Hori K, Charbonneau H, Hart RC, and Cormier MJ (1977). "Structure of native Renilla reinformis luciferin". Proceedings of the National Academy of Sciences. 74 (10): 4285–4287. doi:10.1073/pnas.74.10.4285. PMC 431924. PMID 16592444.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Shimomura O, Johnson FH (1975). "Chemical nature of bioluminescence systems in coelenterates". Proceedings of the National Academy of Sciences. 72 (4): 1546–1549. doi:10.1073/pnas.72.4.1546. PMC 432574. PMID 236561.
^ Haddock, SH, Rivers, TJ, Robison, BH (2001). "Can coelenterates make coelenterazine? Dietary requirement for luciferin in cnidarian bioluminescence". Proceedings of the National Academy of Sciences. 98 (20): 11148–51. doi:10.1073/pnas.201329798. PMID 11572972.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Haddock SHD, Case JF (1994). "A bioluminescent chaetognath" (PDF). Nature. 367 (6460): 225–226. doi:10.1038/367225a0.
^ Vece V., Vuocolo G. (2015). "Multicomponent Synthesis of Novel Coelenterazine Derivatives Substituted at the C-3 Position". Tetrahedron. 71: 8781–8785. doi:10.1016/j.tet.2015.09.048.

External links

Bioluminescence Page showing major luciferin types

[1] Shimomura, O. (2006). Bioluminescence: Chemical Principles and Methods. World Scientific Publishing. pp. 159–165. ISBN 978-981-256-801-4.

[2] Hori K, Charbonneau H, Hart RC, and Cormier MJ (1977). "Structure of native Renilla reinformis luciferin". Proceedings of the National Academy of Sciences. 74 (10): 4285–4287. doi:10.1073/pnas.74.10.4285. PMC 431924. PMID 16592444.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] Shimomura O, Johnson FH (1975). "Chemical nature of bioluminescence systems in coelenterates". Proceedings of the National Academy of Sciences. 72 (4): 1546–1549. doi:10.1073/pnas.72.4.1546. PMC 432574. PMID 236561.

[4] Haddock, SH, Rivers, TJ, Robison, BH (2001). "Can coelenterates make coelenterazine? Dietary requirement for luciferin in cnidarian bioluminescence". Proceedings of the National Academy of Sciences. 98 (20): 11148–51. doi:10.1073/pnas.201329798. PMID 11572972.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[5] Haddock SHD, Case JF (1994). "A bioluminescent chaetognath" (PDF). Nature. 367 (6460): 225–226. doi:10.1038/367225a0.

[6] Vece V., Vuocolo G. (2015). "Multicomponent Synthesis of Novel Coelenterazine Derivatives Substituted at the C-3 Position". Tetrahedron. 71: 8781–8785. doi:10.1016/j.tet.2015.09.048.

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