Coelenterazine, native (Luciferin, Preluciferin)

Blue Ice

423, 46

Brownish/yellow to yellow/orange crystalline powder

Coelenterazine is a luciferin, a light-emitting biomolecule that serves as a substrate for luciferases or as a constituent of photoproteins, including aequorin.1 The oxidation of coelenterazine to coelenteramide is accompanied by emission of blue light (emission maximum, 460-470 nm). Luciferase-mediated oxidation of coelenterazine or a derivative is used as an energy donor, typically to a form of green or yellow fluorescent protein, in bioluminescent resonance energy transfer studies.2, 3 Alternatively, the calcium-mediated release of coelenterazine from aequorin, followed by non-enzymatic oxidation of this compound, results in bioluminescence. As light emission depends on both calcium and cellular redox status, this reaction is used to non-fluorescently detect changes in calcium level and redox status.4, 5

Synonyms:
3, 2-Dihydro-2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-8-benzylimidazolo[1, 2-a]pyrazin-3-one; CLZN; Preluciferin; Luciferin; 6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-8-(phenylmethyl)-imidazo[1, 2-a]pyrazin-3(7H)-one

CAS No:
55779-48-1

Molecular Formula:
C₂₆H₂₁N₃O₃

Molecular Weight:
423.46

Appearance:
Brownish/yellow to yellow/orange crystalline powder

Purity:
≥95%

Solubility (0.0125mg/ml in methanol:
Orange to yellow to brown liquid

Molar Extinction Coefficient (0.0125mg/ml in methanol, lambda max1):
>7800.0 L/(mol cm)

UV (0.0125mg/ml in methanol, lambda max1):
431-435nm

UV (0.0125mg/ml in methanol, lambda max2):
261-265nm

Storage and Stability:
Store at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap. Hygroscopic and light sensitive. Store in amber vial under inert atmosphere.

Note:
It is not recommended to store dissolved coelenterazine at -20°C or -70°C. Coelenterazine is a high energy dioxetanone ring structure that will spontaneously decompose even at low temperatures.