MilliporeSigma
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C2230

Sigma-Aldrich

Coelenterazine, native

solid

All Photos(1)
Synonym(s):
3,2-Dihydro-2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-8-benzylimidazolo[1,2-a]pyrazin-3-one, CLZN
Empirical Formula (Hill Notation):
C26H21N3O3
CAS Number:
55779-48-1
Molecular Weight:
423.46
MDL number:
MFCD00467176
PubChem Substance ID:
24892477
NACRES:
NA.32

assay

≥95% (TLC)

Quality Level

200

form

solid

solubility

methanol and ethanol: soluble

storage temp.

−20°C

SMILES string

Oc1ccc(CC2=NC3=C(Cc4ccccc4)NC(=CN3C2=O)c5ccc(O)cc5)cc1

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

General description

Coelenterazine is a luciferin molecule, which is utilized by several luciferases, such as Renilla, Oplophorus and Periphylla.

Application

Coelenterazine, native was used:-
  • For Aequorin assays
  • For measuring the intracellular calcium concentration in response to ionomycin or PMA using aequorin in COS-7 cells
  • In Bioluminescence imaging for analysing the presence of virus-dependent luciferase activity

Biochem/physiol Actions

Luminophore of the aequorin complex which is oxidized by oxygen to illuminate at 465 nm when Ca2+ binds to the complex; used to measure Ca2+ concentration in cells with high sensitivity and large dynamic range.

Caution

Protect from exposure to light

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

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Organic & Biomolecular Chemistry, 15(33), 7008-7018 (2017)
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Protein expression and purification, 88(1), 150-156 (2013-01-01)
The cold-induced expression system in Escherichia coli is useful and we have applied this system to prepare the coelenterazine-utilizing luciferases including Renilla luciferase (RLase), a red-shifted variant of Renilla luciferase (RLase-547), the catalytic domain of Oplophorus luciferase (19kOLase) and Gaussia
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The increase in atmospheric CO2 is causing a number of changes in plant growth such as increases in leaf area and number, branching, plant size and biomass, and growth rate. Despite the importance of stomatal responses to CO2, little is
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