COELENTERAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H21N3O3
Molecular Weight	423.4632
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(CC2=NC3=C(CC4=CC=CC=C4)NC(=CN3C2=O)C5=CC=C(O)C=C5)C=C1

InChI

InChIKey=YHIPILPTUVMWQT-UHFFFAOYSA-N

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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1332545 | https://www.ncbi.nlm.nih.gov/pubmed/10874121 | https://www.ncbi.nlm.nih.gov/pubmed/26873653

Coelenterazine is a cell-permeable aequorin luminophore that acts as a very sensitive and specific chemiluminescent probe for the superoxide anion. Coelenterazine can also be used for detecting changes in intracellular Ca2+ in cells that have been transfected with apoaequorin cDNA. Coelenterazine also acts as a powerful antioxidant. In vitro, coelenterazine enabled the dynamic monitoring of the RAW 264.7 cell oxidative burst. In vivo, there were early, preclinical, changes in the localization and magnitude of coelenterazine chemiluminescent foci. Coelenterazine offers a high-throughput method for assessing immune cell activation in culture and provides a means for the in vivo detection and localization of ROS during IBD disease progression.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
superoxide anion generation 11 Target ID: GO:0042554 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26420297 \| https://www.ncbi.nlm.nih.gov/pubmed/?10874121	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammatory bowel disease 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26873653	Diagnostic		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Coelenterazine is a superoxide anion-sensitive chemiluminescent probe: its usefulness in the assay of respiratory burst in neutrophils.	1992 Nov 1	1332545
Antioxidative properties of natural coelenterazine and synthetic methyl coelenterazine in rat hepatocytes subjected to tert-butyl hydroperoxide-induced oxidative stress.	2000 Aug 15	10874121

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Coelenterazine (5 mg/kg, intravenous administration) was a potential reporter of cancer-associated superoxide anion in the 4T1 breast adenocarcinoma mouse model.

Route of Administration: Intravenous

In Vitro Use Guide

Coelenterazine (3-10 uM) concentration-dependently increased survival and decreased lipid peroxidation in rat hepatocytes treated for 6 hr with t-BHP (250 uM)

Name

Type

Language

COELENTERAZINE

Common Name

English

PRELUCIFERIN (WATASENIA)

Common Name

English

OPLOPHORUS LUCIFERIN

Common Name

English

6-(4-HYDROXYPHENYL)-2-((4-HYDROXYPHENYL)METHYL)-8-(PHENYLMETHYL)-7H-IMIDAZO(3,2-A)PYRAZIN-3-ONE

Systematic Name

English

6-(4-HYDROXYPHENYL)-2-((4-HYDROXYPHENYL)METHYL)-8-(PHENYLMETHYL)IMIDAZO(1,2-A)PYRAZIN-3(7H)-ONE

Systematic Name

English

IMIDAZO(1,2-A)PYRAZIN-3(7H)-ONE, 6-(4-HYDROXYPHENYL)-2-((4-HYDROXYPHENYL)METHYL)-8-(PHENYLMETHYL)-

Systematic Name

English

COELENTERAZINE LUCIFERIN

Common Name

English

LUCIFERIN (OPLOPHORUS)

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID80204342