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
• Article Data: 8

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

Description

COELENTERAZINE 400 A is a synthetic chemiluminescent molecule that serves as a substrate for the bioluminescent reaction involving the Aequorin protein in the presence of calcium ions (Ca2+). It is a derivative of the naturally occurring coelenterazine, which is found in certain bioluminescent organisms such as jellyfish. COELENTERAZINE 400 A is characterized by its ability to emit light upon interaction with the Aequorin protein, making it a valuable tool in various scientific applications.

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

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• 70217-86-6 2-amino-3-benzyl-5-phenyl-pyrazine 
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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+.

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.

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.