50909-86-9

Basic information

• Product Name: COELENTERAZINE H
• Synonyms: CLZ-H;CLZN-H;COELENTERAZINE H;COELENTERAZINE-H, SYNTHETIC;LUCIFERIN (RENILLA);2-(4-DEHYDROXY)COELENTERAZINE;2,8-DIBENZYL-6-(P-HYDROXYPHENYL)-IMIDAZO[1,2A]PYRAZIN-3-(7H)-ONE;2-BENZYL-6-(P-HYDROXYPHENYL)-8-BENZYLIMIDAZO[1,2-A]PYRAZIN-3-(7H)-ONE
• CAS NO: 50909-86-9
• Molecular Formula: C₂₆H₂₁N₃O₂
• Molecular Weight: 407.46
• Product Categories: Heterocycle;Imidazo[1,2-a]pyrazin-3(7H)-one
• Mol File: 50909-86-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: >200℃
• Boiling Point: 593.5 °C at 760 mmHg
• Flash Point: 312.7 °C
• Appearance: Yellow/solid
• Density: 1.26 g/cm³
• Vapor Pressure: 1.11E-14mmHg at 25°C
• Refractive Index: 1.675
• Storage Temp.: −20°C
• Solubility: Soluble in methanol, ethanol
• PKA: 10.50±0.30(Predicted)
• 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.
• CAS DataBase Reference: COELENTERAZINE H(CAS DataBase Reference)
• NIST Chemistry Reference: COELENTERAZINE H(50909-86-9)
• EPA Substance Registry System: COELENTERAZINE H(50909-86-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 50909-86-9(Hazardous Substances Data)

Usage

Description

Coelenterazine H, also known as Coelenterazine-h, is an imidazopyrazinone derivative and a derivative of Coelenterazine (C636000). It is a substrate for bioluminescence in many luminous marine organisms and is more sensitive to Ca2+ than the native complex, making it a valuable tool for measuring small changes in Ca2+ concentrations. Coelenterazine H produces a 10-fold higher light output than native Coelenterazine and undergoes autoluminescence, which is enhanced by superoxide anion and peroxynitrite in cells.

Uses

Used in Gene Reporter Assays:
COELENTERAZINE H is used as a substrate for Renilla luciferase in gene reporter assays for detecting and quantifying gene expression levels. The higher light output compared to native Coelenterazine allows for more sensitive and accurate measurements.
Used in Live Cell Assays:
COELENTERAZINE H is used as a Ca2+ indicator in live cell assays to measure small changes in intracellular Ca2+ concentrations. Its increased sensitivity to Ca2+ makes it an ideal tool for studying cellular processes that involve Ca2+ signaling.
Used in Biochemical Assays:
COELENTERAZINE H is used as a substrate in various biochemical assays, such as ELISA and BRET, to detect and quantify the activity of enzymes or other biomolecules. The enhanced light output and autoluminescence properties of Coelenterazine H improve the sensitivity and reliability of these assays.
Used in Analyzing Cellular Processes:
COELENTERAZINE H is used as a research tool for studying cellular processes that involve changes in Ca2+ concentrations or the activity of specific enzymes. Its unique properties make it a valuable asset in understanding the complex mechanisms underlying various biological phenomena.

Biochem/physiol Actions

10 times higher luminescence intensity than native coelenterazine.

References

1) Shimomura?et al. (1989),?Semi-synthetic aequorins with improved sensitivity to Ca2+ ions; Biochem. J.,?261?913 2) Nakajima-Shimada?et al.?(1991),?Monitoring of intracellular calcium in Saccharomyces cerevisiae with an apoaequorin cDNA expression system; Proc. Natl. Acad. Sci. USA,?88?6878 3) Inouye?et al. (1992),?Monitoring gene expression in Chinese hamster ovary cells using secreted apoaequorin; Anal. Biochem.,?201?114

InChI:InChI=1/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

Upstream product

• 56485-04-2 benzylglyoxal 
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• 1823-76-3 p-methoxy-isonitrosoacetophenone 
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• 40040-81-1 2-amino-3-benzyl-5-(4-methoxyphenyl)-pyrazine 
• 123437-73-0 3-benzyl-5-(4-methoxy-phenyl)-1-oxy-pyrazin-2-ylamine 
• 108-88-3 toluene 
• 19256-31-6 1,1-diethoxy-3-phenylpropane-2-one 
• 185148-51-0 3-benzyl-2-pyrazinamine 
• 174680-55-8 2-amino-5-bromo-3-phenylmethylpyrazine 

Downstream Products

• 50909-85-8 3-benzyl-5-(p-hydroxyphenyl)-2-(phenylacetamido)pyrazine 
• 1374040-42-2 C₃₄H₂₉N₃O₃ 
• 1374040-18-2 C₇₁H₈₄N₈O₁₄ 

Relevant articles and documents

Enzymatic conversion of dehydrocoelenterazine to coelenterazine using FMN-bound flavin reductase of NAD(P)H:FMN oxidoreductase

Coelenterazine (CTZ) is known as luciferin (a substrate) for the luminescence reaction with luciferase (an enzyme) in marine organisms and is unstable in aqueous solutions. The dehydrogenated form of CTZ (dehydrocoelenterazine, dCTZ) is stable and thought to be a storage form of CTZ and a recycling intermediate from the condensation reaction of coelenteramine and 4-hydroxyphenylpyruvic acid to CTZ. In this study, the enzymatic conversion of dCTZ to CTZ was successfully achieved using NAD(P)H:FMN oxidoreductase from the bioluminescent bacterium Vibrio fischeri ATCC 7744 (FRase) in the presence of NADH (the FRase–NADH reaction). CTZ reduced from dCTZ in the FRase–NADH reaction was identified by HPLC and LC/ESI-TOF-MS analyses. Thus, dCTZ can be enzymatically converted to CTZ in vitro. Furthermore, the concentration of dCTZ could be determined by the luminescence activity using the CTZ-utilizing luciferases (Gaussia luciferase or Renilla luciferase) coupled with the FRase–NADH reaction.

IMIDAZO[1,2-α]PYRAZIN-3(7H)-ONE DERIVATIVES BEARING A NEW ELECTRON-RICH STRUCTURE

The present invention relates to compound of formula I : and their use as chemiluminescent and/or bioluminescent reagents.