COELENTERAZINE H Chemical Properties

Melting point:

>200℃

Boiling point:

593.5±60.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in methanol, ethanol

pka

10.50±0.30(Predicted)

form 

solid

color 

Yellow

Appearance

Yellow Solid

λmax

437nm

Stability:

Stable for 1 year from ate of purchase as supplied. Solutions in DMSO or methanol may be stored at -20°C for up to 1 month.

Biological Applications

Calcium indicator; assaying luminescent enzyme; measuring luciferase activity; as a substrate for luciferase; screening HIV-1 protease inhibitors; bioluminescence resonance energy transfer (BRET) detection system

InChI

InChI=1S/C26H21N3O2/c30-21-13-11-20(12-14-21)24-17-29-25(22(27-24)15-18-7-3-1-4-8-18)28-23(26(29)31)16-19-9-5-2-6-10-19/h1-14,17,27,30H,15-16H2

InChIKey

KAEGGIFPLJZUOZ-UHFFFAOYSA-N

SMILES

C12N=C(CC3=CC=CC=C3)C(=O)N1C=C(C1=CC=C(O)C=C1)NC=2CC1=CC=CC=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933998090

COELENTERAZINE H Usage And Synthesis

Description

Coelenterazine-h (50909-86-9) may be used as a substrate in gene reporter assays, live cell assays, and biochemical assays (ELISA, BRET etc). Renilla luciferase catalyzes coelenterazine oxidation by oxygen to produce light. Coelenterazine-h produces 10-fold higher light output than native coelenterazine. Coelenterazine-h also undergoes autoluminescence, which is enhanced by superoxide anion and peroxynitrite in cells.

Uses

Coelenterazine h, is a derivative of Coelenterazine (C636000), and iis more sensitive to Ca2+ than is the native complex, thus providing a valuable tool for measuring small changes in Ca2+ concentrations.

Definition

ChEBI: Renilla luciferin is a member of phenols and an imidazopyrazine. It has a role as a luciferin. It derives from a hydride of an imidazo[1,2-a]pyrazine.

General Description

Coelenterazine is an imidazopyrazinone derivative. It is a substrate for bioluminescence in many luminous marine organisms.

Biochem/physiol Actions

10 times higher luminescence intensity than native coelenterazine.

References

[1] O SHIMOMURA  Y K  B Musicki. Semi-synthetic aequorins with improved sensitivity to Ca2+ ions.[J]. Biochemical Journal, 1989, 261 3: 913-920. DOI:10.1042/bj2610913
[2] J NAKAJIMA-SHIMADA. Monitoring of intracellular calcium in Saccharomyces cerevisiae with an apoaequorin cDNA expression system.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1991, 88 15: 6878-6882. DOI:10.1073/pnas.88.15.6878
[3] SATOSHI INOUYE  Frederick I T. Monitoring gene expression in Chinese hamster ovary cells using secreted apoaequorin[J]. Analytical biochemistry, 1992, 201 1: Pages 114-118. DOI:10.1016/0003-2697(92)90182-7

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