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Coelenterazine

CAT: 0013-GTR19159019-07Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19159019-07Size:10 mg
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Description
Coelenterazine is the luciferin, the light-emitting molecule, found in many aquatic organisms across seven phyla. It is the substrate of many luciferases such as Renilla reniformis luciferase (Rluc), Gaussia luciferase (Gluc), and photoproteins, including aequorin, and obelin. Coelenterazine was used: (1) For Aequorin assays; (2) For measuring the intracellular calcium concentration in response to ionomycin or PMA using aequorin in COS-7 cells2; (3) . In Bioluminescence imaging for analysing the presence of virus-dependent luciferase activity. 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. (In Vitro) :HCT-8 control cells, transiently expressing Renilla luciferase (RLuc), showed low bioluminescence due to P-glycoprotein–mediated efflux transport of coelenterazine. By comparison, transiently expressing RLuc HCT-8 cells, wherein P-glycoprotein was down-regulated with shRNAi, showed high bioluminescence. (In Vivo) :The in vivo growth potential of HCC1806-RR was monitored by injecting animals with coelenterazine (2 mg/kg) i.v. and exposing them to a charged-coupled device (CCD) camera 5 minutes later. Rluc activity was detected as light emitted from the tumor cells and acquired as a pseudo-color image superimposed over a black and white photograph of the animal. All mice demonstrated very high Rluc activity at the primary site with the majority of mice simultaneously showing metastases to inguinal ILNs.
CAS Number
55779-48-1
Product Name Alternative
Oplophorus, luciferin | Coelenterazine | CLZN
Purity
>98% (HPLC)
Solubility
In Vitro: Ethanol : 1 mg/mL (2.36 mM)
Smiles
Oc1ccc (Cc2nc3c (Cc4ccccc4) [nH]c (cn3c2=O) c2ccc (O) cc2) cc1
Molecular Formula
C26H21N3O3
Molecular Weight
423.47
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
8-benzyl-2- (4-hydroxybenzyl) -6- (4-hydroxyphenyl) imidazo[1,2-a]pyrazin-3 (7H) -one

Chemical Information

Coelenterazine

Oplophorus luciferin is an imidazopyrazine that is imidazo[1,2-a]pyrazin-3(7H)-one in which positions 2, 6, and 8 are substituted by 4-hydroxybenzyl, 4-hydroxyphenyl, and benzyl groups, respectively. It has a role as a luciferin. It is a member of phenols and an imidazopyrazine. It derives from a hydride of an imidazo[1,2-a]pyrazine.

CAS Number55779-48-1
PubChem CID135445694
IUPAC Name8-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]imidazo[1,2-a]pyrazin-3-ol
Molecular FormulaC26H21N3O3
Molecular Weight423.5
XLogP5.5
Topological Polar Surface Area90.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Heavy Atom Count32
Formal Charge0
Complexity585
SMILES
C1=CC=C(C=C1)CC2=NC(=CN3C2=NC(=C3O)CC4=CC=C(C=C4)O)C5=CC=C(C=C5)O
InChI
InChI=1S/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/h1-13,16,30-32H,14-15H2
InChIKey
LNCOEGVEEQDKGX-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Coelenterazine
CAS: 55779-48-1
CID: 135445694
Formula: C26H21N3O3
MW: 423.5
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight423.5
XLogP35.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass423.15829154
Monoisotopic Mass423.15829154
Topological Polar Surface Area90.9 Ų
Heavy Atom Count32
Formal Charge0
Complexity585
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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