55779-48-1

Basic information

• Product Name: Coelenteramine
• Synonyms: 8-BENZYL-2-(4-HYDROXYBENZYL)-6-(4-HYDROXYPHENYL)IMIDAZO[1,2-A]PYRAZIN-3(7H)-ONE;2-[(4-HYDROXYPHENYL)METHYL]-6-(4-HYDROXYPHENYL)-8-(PHENYLMETHYL)-IMDAZO[1,2-A]PYRAZIN-3-(7H)-ONE;2-[(4-HYDROXYPHENYL)METHYL]-6-(4-HYDROXYPHENYL)-8-(PHENYLMETHYL)-IMIDAZO [1,2-A] PYRAZIN-3-(7H)-ONE;3,2-DIHYDRO-2-(P-HYDROXYBENZYL)-6-(P-HYDROXYPHENYL)-8-BENZYLIMIDAZOLO[1,2-A]PYRAZIN-3-ONE;2-(P-HYDROXYBENZYL)-6-(P-HYDROXYPHENYL)-8-BENZYLIMIDAZO[1,2-A]PYRAZIN-3-(7H)-ONE;2-(P-HYDROXYBENZYL)-6-(P-HYDROXYPHENYL)-8-BENZYL-IMIDAZOL[1,2-A]PYRAZIN-3-(7H)-ONE;2-(BETA-NAPHTHYLMETHYL)-6-(P-HYDROXYPHENYL)-8-BENZYLIMIDAZO[1,2-A]PYRAZIN-3-(7H)-ONE;2-(BETA-NAPHTHYLMETHYL)-6-(P-HYDROXYPHENYL)-8-BENZYLIMIDAZO[1,2-A]PYRAZINE-3-(7H)-ONE
• CAS NO: 55779-48-1
• Molecular Formula: C₂₆H₂₁N₃O₃
• Molecular Weight: 423.46
• Product Categories: Fluorescent Labels and Indicators;Fluorescent Labels & Indicators;Imidazo[1,2-a]pyrazin-3(7H)-one;Heterocycle
• Mol File: 55779-48-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 176–181 ℃ (decompose)
• Boiling Point: 641.4°Cat760mmHg
• Flash Point: 341.7°C
• Appearance: yellow/solid
• Density: 1.32g/cm³
• Vapor Pressure: 4.77E-17mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: −20°C
• Solubility: methanol and ethanol: soluble
• PKA: 9.91±0.15(Predicted)
• Sensitive: Moisture & Light Sensitive
• CAS DataBase Reference: Coelenteramine(CAS DataBase Reference)
• NIST Chemistry Reference: Coelenteramine(55779-48-1)
• EPA Substance Registry System: Coelenteramine(55779-48-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 55779-48-1(Hazardous Substances Data)

Usage

Description

Coelenterazine is a naturally occurring luciferin molecule that is utilized by various luciferases, such as Renilla, Oplophorus, and Periphylla. It is a yellow solid with the chemical structure of an imidazopyrazine, specifically an imidazo[1,2-a]pyrazin-3(7H)-one, where positions 2, 6, and 8 are substituted by 4-hydroxybenzyl, 4-hydroxyphenyl, and benzyl groups, respectively.

Uses

Used in Bioluminescence Applications:
Coelenterazine is used as a luminophore for the aequorin complex, which is oxidized by oxygen to emit light at 465 nm when Ca2+ binds to the complex. This property makes it useful for measuring Ca2+ concentration in cells with high sensitivity and a large dynamic range.
Used in Aequorin Assays:
Coelenterazine is used as a substrate in aequorin assays, which are employed to measure the intracellular calcium concentration in response to stimuli such as ionomycin or PMA using aequorin in COS-7 cells.
Used in Bioluminescence Imaging:
Coelenterazine is used in bioluminescence imaging for analyzing the presence of virus-dependent luciferase activity, which can be crucial in various research and diagnostic applications.
Used in Analyzing Calcium Concentration:
Coelenterazine is used as a reagent for measuring Ca2+ concentration in cells, providing valuable insights into cellular processes and functions.
Used in Pharmaceutical and Diagnostic Industries:
Coelenterazine is used as a key component in the development of various pharmaceutical and diagnostic tools, particularly those involving bioluminescence and calcium signaling.

Biochem/physiol Actions

Luminophore of the aequorin complex which is oxidized by oxygen to illuminate at 465 nm when Ca2+ binds to the complex; used to measure Ca2+ concentration in cells with high sensitivity and large dynamic range.

InChI:InChI=1/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

Upstream product

• 165330-28-9 3-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1,1-diethoxypropan-2-one 
• 37156-84-6 4-(5-amino-6-benzyl-pyrazin-2-yl)-phenol 
• 10589-27-2 3-(p-hydroxyphenyl)-2-oxopropanal 
• 156-39-8 4-hydroxyphenylpiruvic acid 
• 107503-09-3 watasenia preluciferyl β-D-glucopyranosiduronic acid 
• 1161931-09-4 coelenterazine hydroperoxide 
• 62541-09-7 Watasenia dehydropreluciferin 
• 836-42-0 4-benzyloxybenzyl chloride 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 625848-58-0 1,1-diethoxy-3-(4-hydroxyphenyl)-2-propan-2-one 
• 353497-17-3 3-benzyl-5-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-3-phenyl-2-pyrazinamine 
• 67963-68-2 t-butyldimethylsilyl-4-bromophenol 
• 174680-55-8 2-amino-5-bromo-3-phenylmethylpyrazine 
• 623-05-2 (4-hydroxyphenyl)methanol 

Downstream Products

• 65417-16-5 imidazo[1,2-a]pyrazin-3-ol,6-[4-(acetyloxy)phenyl]-2-[[4-(acetyloxy)phenyl]methyl]-8-(phenylmethyl)-3-acetate 
• 1189098-20-1 coelenteramide 
• 37156-84-6 4-(5-amino-6-benzyl-pyrazin-2-yl)-phenol 
• 67731-69-5 2-hydroperoxycoelenterazine 
• 1161931-09-4 coelenterazine hydroperoxide 
• 50611-86-4 coelenteramide 

Relevant articles and documents

A NEW SYNTHESIS OF WATASENIA PRELUCIFERIN BY CYCLIZATION OF 2-AMINO-3-BENZYL-5-(p-HYDROXYPHENYL)PYRAZINE WITH p-HYDROXYPHENYLPYRUVIC ACID

The reaction of 2-amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine with p-hydroxyphenylpyruvic acid gave directly Watasenia preluciferin in a satisfactory yield without any reductive treatment.

Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+-Binding Photoprotein Aequorin

Aequorin consists of apoprotein (apoAequorin) and (S)-2-peroxycoelenterazine (CTZ-OOH) and is considered to be a transient-state complex of an enzyme (apoAequorin) and a substrate (coelenterazine and molecular oxygen) in the enzymatic reaction. The degradation process of CTZ-OOH in aequorin was characterized under various conditions of protein denaturation. By acid treatment, the major product from CTZ-OOH was coelenteramine (CTM), but not coelenteramide (CTMD), and no significant luminescence was observed. The counterparts of CTM from CTZ-OOH were identified as 4-hydroxyphenylpyruvic acid (4HPPA) and 4-hydroxyphenylacetic acid (4HPAA) by liquid chromatography/electrospray ionization–time-of-flight mass spectrometry (LC/ESI-TOF-MS). In the luminescence reaction of aequorin with Ca2+, similar amounts of 4HPPA and 4HPAA were detected, indicating that CTM is formed by two pathways from CTZ-OOH through dioxetanone anion and not by hydrolysis from CTMD.

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.