70217-82-2

Basic information

• Product Name: COELENTERAZINE 400 A
• Synonyms: 2,8-DIBENZYL-6-PHENYL-IMIDAZO[1,2A]PYRAZIN-3-(7H)-ONE;BISDEOXYCOELENTERAZINE;COELENTERAZINE 400 A;DI-DEHYDRO COELENTERAZINE;DEEPBLUEC(TM);BlueSyn C;Coelenteramine 400a
• CAS NO: 70217-82-2
• Molecular Formula: C₂₆H₂₁N₃O
• Molecular Weight: 391.46
• Mol File: 70217-82-2.mol

Chemical Properties

• Boiling Point: 551.4°C at 760 mmHg
• Flash Point: 287.3°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 3.33E-12mmHg at 25°C
• Refractive Index: 1.661
• CAS DataBase Reference: COELENTERAZINE 400 A(CAS DataBase Reference)
• NIST Chemistry Reference: COELENTERAZINE 400 A(70217-82-2)
• EPA Substance Registry System: COELENTERAZINE 400 A(70217-82-2)

Safety Data

• Hazardous Substances Data: 70217-82-2(Hazardous Substances Data)

Usage

Uses

Used in Bioluminescence Research:
COELENTERAZINE 400 A is used as a substrate for the Aequorin protein to produce chemiluminescence in the presence of Ca2+. This property makes it an essential component in bioluminescence research, allowing scientists to study the behavior and interactions of calcium ions in various biological systems.
Used in Analytical Techniques:
COELENTERAZINE 400 A is used as a reagent in analytical techniques that measure calcium ion concentrations, such as bioluminescence resonance energy transfer (BRET) and fluorescence resonance energy transfer (FRET) assays. These assays are employed to monitor intracellular calcium levels, which are crucial for various cellular processes, including signal transduction and neurotransmission.
Used in Drug Screening and Development:
In the pharmaceutical industry, COELENTERAZINE 400 A is used as a tool for high-throughput screening of compounds that modulate calcium signaling pathways. This helps in the identification of potential drug candidates that can target calcium-related diseases, such as hypertension, heart disease, and neurological disorders.
Used in Environmental Monitoring:
COELENTERAZINE 400 A can be used in environmental monitoring applications to detect the presence of calcium ions in water samples. This is important for assessing water quality and understanding the impact of various pollutants on aquatic ecosystems.
Used in Diagnostics:
In the medical field, COELENTERAZINE 400 A can be employed in diagnostic assays to measure calcium ion levels in biological samples, such as blood or tissue extracts. This information can be valuable for diagnosing and monitoring various calcium-related disorders and conditions.

InChI:InChI=1/C26H21N3O/c30-26-23(17-20-12-6-2-7-13-20)28-25-22(16-19-10-4-1-5-11-19)27-24(18-29(25)26)21-14-8-3-9-15-21/h1-15,18,27H,16-17H2

Upstream product

• 19256-31-6 1,1-diethoxy-3-phenylpropane-2-one 
• 70217-86-6 2-amino-3-benzyl-5-phenyl-pyrazine 
• 960-16-7 tributylphenylstannane 
• 56485-04-2 benzylglyoxal 
• 6921-34-2 benzylmagnesium chloride 
• 174680-55-8 2-amino-5-bromo-3-phenylmethylpyrazine 
• 100-39-0 benzyl bromide 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 

Downstream Products

• 676460-47-2 2,8-dibenzyl-3-methoxy-6-phenyl-imidazo[1,2-a]pyrazine 

Relevant articles and documents

Efficient bioluminescence of bisdeoxycoelenterazine with the luciferase of a deep-sea shrimp Oplophorus

The luminescence of the bisdeoxy analogue of coelenterazine (1b : X=Y=H) catalyzed by Oplophorus luciferase was highly efficient (0.19 quanta/molecule), almost comparable to the luminescence of unmodified coelenterazine(1a : X=Y=OH), whereas the luminescence of 1b was very inefficient when catalyzed by apoaequorin or Renilla luciferase and when the arquorin regenerated with 1b was luminesced with Ca2+.

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.

IMIDAZOPYRAZINE DERIVATIVES, PROCESS FOR PREPARATION THEREOF, AND THEIR USES AS LUCIFERINS

The present invention is in the field of bioluminescence in biology and/or medicine. In particular, the invention provides imidazopyrazine derivatives, processes for preparation thereof, and their uses as luciferins.

New bioluminescent coelenterazine derivatives with various C-6 substitutions

A series of new coelenterazine analogs with varying substituents at the C-6 position of the imidazopyrazinone core have been designed and synthesized for the extension of bioluminescence substrates. Some of them display excellent bioluminescence properties compared to DeepBlueC or native coelenterazine with both in vitro and in vivo biological evaluations, thus placing these derivatives among the most ideal substrates for Renilla bioluminescence applications.

Luminescence of coelenterazine derivatives with C-8 extended electronic conjugation

Replacement of the methylene group at the C-8 position with an extended electronic conjugation is a new promising method to develop red-shifted coelenterazine derivatives. In this paper, we have described an oxygen-containing coelenterazine derivative with a significant red-shifted (63 nm) bioluminescence signal maximum relative to coelenterazine 400a (DeepBlueC, 1). In cell imaging, the sulfur-containing coelenterazine derivative displayed a significantly (1.77 ± 0.09; P ≤ 0.01) higher luminescence signal compared to coelenterazine 400a and the oxygen-containing coelenterazine derivative exhibited a slightly (0.74 ± 0.08; P ≤ 0.05) lower luminescence signal. It is beneficial to understand further the underlying mechanisms of bioluminescence.

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.

Luminescence-based methods and probes for measuring cytochrome P450 activity

The present invention provides methods, compositions, substrates, and kits useful for analyzing the metabolic activity in cells, tissue, and animals and for screening test compounds for their effect on cytochrome P450 activity. In particular, a one-step and two-step methods using luminogenic molecules, e.g. luciferin or coelenterazines, that are cytochrome P450 substrates and that are also bioluminescent enzyme, e.g., luciferase, pro-substrates are provided. Upon addition of the luciferin derivative or other luminogenic molecule into a P450 reaction, the P450 enzyme metabolizes the molecule into a bioluminescent enzyme substrate, e.g., luciferin and/or luciferin derivative metabolite, in a P450 reaction. The resulting metabolite(s) serves as a substrate of the bioluminescent enzyme, e.g., luciferase, in a second light-generating reaction. Luminescent cytochrome P450 assays with low background signals and high sensitivity are disclosed and isoform selectivity is demonstrated. The present invention also provides an improved method for performing luciferase reactions which employs added pyrophosphatase to remove inorganic pyrophosphate, a luciferase inhibitor which may be present in the reaction mixture as a contaminant or may be generated during the reaction. The present method further provides a method for stabilizing and prolonging the luminescent signal in a luciferase-based assay using luciferase stabilizing agents such as reversible luciferase inhibitors.

Bisdeoxycoelenterazine derivatives for improvement of bioluminescence resonance energy transfer assays

We report here syntheses of bisdeoxycoelenterazine derivatives that show significantly improved kinetics of the bioluminescent reaction. All derivatives contain a protecting group at the carbonyl group of the imidazopyrazinone moiety that ensures slower light signal decay. The longer lasting light signal offers the possibility of real-time imaging of protein-protein interactions. Copyright