Coelenterazine
Name: Coelenterazine
CAS Registry Number: 55779-48-1
CA Index Name: Imidazo[1,2-a]pyrazin-3(7H)-one, 6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-8-(phe-nylmethyl)-
Other Names: 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hy-droxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one; CLZN; Coelenterazin; Coelenterazine; Coelenterazine native; 3,2-Dihydro-2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-8-benzylimidazolo[1,2-a]pyrazin-3-one; Luciferin; Lu-ciferin (Oplophorus); NanoFuel; Preluciferin; Prelucifer-in (Watasenia); Watasenia preluciferin
Merck Index Number: Not listed
Chemical / Dye Class: Heterocycle; Imidazo[1,2-α]pyrazin-3(7H)-one
Molecular Formula: C26H21N3O3
Molecular Weight: 423.46
Physical Form: Orange-yellow crystals or powder
Solubility: Soluble in ethanol, methanol
Melting Point: 176-181 °C (decompose)
Boiling Point: 641.4 ± 65.0 °C, pressure: 760 Torr
pKa: 9.91 ± 0.15, most acidic, temperature: 25 °C; 6.63 ± 0.60, most basic, temperature: 25 °C
Absorption (λmax): 429 nm
Emission (λmax): 466nm; 514nm
Synthesis: Synthetic methods
Staining Applications: Calcium ions; cells, erythrocytes
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, alkaline phosphatase, galactosidase; treating epilepsy, pain syndromes, hepatitis C virus (HCV) infections, herpes virus infection, Plasmodium falciparum infection, human immunodeficiency virus infection
Industrial Applications: Not reported
Safety / Toxicity: Fish toxicity; vascular toxicity
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