A bioluminescent luciferin
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Coelenterazine

Item No. 16123

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-8-(phenylmethyl)-imidazo[1,2-a]pyrazin-3(7H)-one
CAS Number
55779-48-1
Synonyms
  • Luciferin (Oplophorus)
  • Preluciferin (Watasenia)
Molecular Formula
C26H21N3O3
Formula Weight
423.5
Purity
≥85%
Emission
460-470 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Ethanol: 0.5 mg/mlMethanol: 0.5 mg/ml
SMILES
OC1=CC=C(C2=CN3C(N=C(CC4=CC=C(O)C=C4)C3=O)=C(CC5=CC=CC=C5)N2)C=C1
InChi Code
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
InChi Key
YHIPILPTUVMWQT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $72

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    1 mg

    $115

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    5 mg

    $501

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    Product Description

    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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sabnis, R.W. Handbook of biological dyes and stains: Synthesis and industrial applications. (2010).

    2. Pfleger, K.D., and Eidne, K.A. Illuminating insights into protein-protein interactions using bioluminescence resonance energy transfer (BRET). Nat. Methods 3(3), 165-174 (2006).

    3. Dacres, H., Dumancic, M.M., Horne, I., et al. Direct comparison of bioluminescence-based resonance energy transfer methods for monitoring of proteolytic cleavage. Anal. Biochem. 385(2), 194-202 (2009).

    4. Stables, J., Green, A., Marshall, F., et al. A bioluminescent assay for agonist activity at potentially any G-protein-coupled receptor. Anal. Biochem. 252(1), 115-126 (1997).

    5. Teranishi, K., and Shimomura, O. Coelenterazine analogs as chemiluminescent probe for superoxide anion. Anal. Biochem. 249(1), 37-43 (1997).