50909-86-9

Usage

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 
• 37156-84-6 4-(5-amino-6-benzyl-pyrazin-2-yl)-phenol 
• 1823-76-3 p-methoxy-isonitrosoacetophenone 
• 55379-75-4 2-amino-3-phenylpropanenitrile 
• 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

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

Relevant academic research and scientific papers

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.

Gram-scale synthesis of luciferins derived from coelenterazine and original insights into their bioluminescence properties

An original gram-scale synthesis of O-acetylated forms of coelenterazine, furimazine or hydroxy-bearing analogues of luciferins is described. The comparison over two hours of their bioluminescence, using the nanoKAZ/NanoLuc luciferase, provides remarkable insights useful for the selection of a substrate adapted for a given application.

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.

Chemi- and Bio-luminescence of Coelenterazine Analogues with Phenyl Homologues at the C-2 Position

A series of phenyl homologues of coelenterazine substituted at the C-2 position were synthesized and their bio- and chemi-luminescence properties were investigated including the measurement of chemiluminescence spectra in various media.The light emitting species of each analogue was found to be a neutral form of a coelenteramide derivative in diethylene glycol dimethyl ether (DGM) containing a trace amount of acetate buffer (pH 5.60), while a monoanion was found only in dimethyl sulfoxide (DMSO) and a dianion was observed in DMSO containing a trace amount of aqueous sodium hydroxide.Based on pseudo first-order reaction kinetics, chemiluminescence rate constants were obtained in DGM containing a trace amount of acetate buffer.Each of the synthetic coelenterazine analogues was incorporated into recombinant apoaequorin to obtain a series of semisynthetic aequorins.Measurements of bioluminescence activities of the aequorins revealed that a benzyl group in the C-2 position was essential for efficient luminescence activity.A two-step incubation procedure was used to determine why some analogues gave less luminescence activity than the benzyl analogue and natural coelenterazine.