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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 of COELENTERAZINE

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

HIDE SMILES / InChI

Molecular Formula C26H21N3O3
Molecular Weight 423.4632
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment: Coelenterazine cannot cross the blood–brain barrier

Originator

Curator's Comment: Coelenterazine was simultaneously isolated and characterized by two groups studying the luminescent organisms sea pansy (Renilla reniformis) and the coelenterate Aequorea victoria, respectively.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

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
Coelenterazine (3-10 uM) concentration-dependently increased survival and decreased lipid peroxidation in rat hepatocytes treated for 6 hr with t-BHP (250 uM)
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:40:52 GMT 2023
Edited
by admin
on Fri Dec 15 19:40:52 GMT 2023
Record UNII
3O1CB88RRD
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 19:40:52 GMT 2023 , Edited by admin on Fri Dec 15 19:40:52 GMT 2023
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PUBCHEM
2830
Created by admin on Fri Dec 15 19:40:52 GMT 2023 , Edited by admin on Fri Dec 15 19:40:52 GMT 2023
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CHEBI
2311
Created by admin on Fri Dec 15 19:40:52 GMT 2023 , Edited by admin on Fri Dec 15 19:40:52 GMT 2023
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CAS
55779-48-1
Created by admin on Fri Dec 15 19:40:52 GMT 2023 , Edited by admin on Fri Dec 15 19:40:52 GMT 2023
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FDA UNII
3O1CB88RRD
Created by admin on Fri Dec 15 19:40:52 GMT 2023 , Edited by admin on Fri Dec 15 19:40:52 GMT 2023
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WIKIPEDIA
COELENTERAZINE
Created by admin on Fri Dec 15 19:40:52 GMT 2023 , Edited by admin on Fri Dec 15 19:40:52 GMT 2023
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