Coelenterazine

Modify Date: 2024-01-02 02:47:53

Coelenterazine Structure
Coelenterazine structure
 Common Name Coelenterazine
CAS Number 55779-48-1 Molecular Weight 423.463
Density 1.3±0.1 g/cm3 Boiling Point 641.4±65.0 °C at 760 mmHg
Molecular Formula C26H21N3O3 Melting Point N/A
MSDS Chinese USA Flash Point 341.7±34.3 °C

 Use of Coelenterazine


Coelenterazine is widely distributed among marine organisms which can produce bioluminescence by calcium-dependent oxidation mediated by the photoprotein aequorin.

 Names

Name Oplophorus luciferin
Synonym More Synonyms

 Coelenterazine Biological Activity

Description Coelenterazine is widely distributed among marine organisms which can produce bioluminescence by calcium-dependent oxidation mediated by the photoprotein aequorin.
Related Catalog
In Vitro On addition of Coelenterazine to the buffer, intact KB 3-1 Rluc cells show high bioluminescence, whereas intact KB 8-5-11 Rluc cells show low bioluminescence. A specific Pgp-mediated reduction in steady-state content of Coelenterazine exists in KB 8-5-11 Rluc cells compare to KB 3-1 Rluc cells. Bioluminescence signals from KB 3-1 Rluc cells, both in the absence and presence of GF120918 (300 nM), are readily detected with as little as 1 nM extracellular Coelenterazine and increase in a concentration-dependent manner to 1 μM extracellular Coelenterazine. In Pgp-expressing cells, there is evidence for a GF120918-reversible concentration-dependent saturation of bioluminescence with an EC50 of 257 nM Coelenterazine. The plateau in bioluminescence signal observed in KB 8-5-11 Rluc cells implies hat the capacity of Pgp to limit delivery of Coelenterazine to cytosolic Rluc is not exceeded within the concentration range test[1].
In Vivo At baseline, KB 3-1 Rluc tumors show a 4-fold higher bioluminescence signal in vivo than KB 8-5-11 Rluc tumors. Normalized bioluminescence signals arise from KB 3-1 Rluc tumors, signals emits from KB 8-5-11 Rluc tumors in vivo are consistently reduced by ≈75%[1] .
Cell Assay Cells are plated at a density of 5×104 cells per well into 24-well plates and grown to 80-100% confluency. Just before imaging, media are changed to a colorless solution containing (in mM): 2.7 KCl, 139 NaCl, 8.1 Na2HPO4, 0.7 H2O, 1.5 KH2PO4, 1.8 CaCl2, 1 MgCl2 and 5.5 d-glucose. Cells are preincubated for 15 min in the absence or presence of Pgp modulator, after which Coelenterazine (final concentration of 470 nM) is added directly to the cells[1].
Animal Admin Mice are anesthetized with metofane or isoflurane before tail vein injection of Coelenterazine (4 μg/g) formulated from an ethanol stock diluted in sodium phosphate buffer (50 mM). Bioluminescence imaging is performed on the in vivo imaging system at 2, 6, 8, and 11 min after injection. Anesthesia is maintained during imaging by nose cone delivery of 2.5% isoflurane. After imaging, animals are killed by cervical dislocation; tumors are then harvested and weighed[1].
References

[1]. Andrea Pichler, et al. Imaging reversal of multidrug resistance in living mice with bioluminescence: MDR1 P-glycoprotein transports coelenterazine. Proc Natl Acad Sci U S A. 2004 Feb 10; 101(6): 1702–1707.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 641.4±65.0 °C at 760 mmHg
Molecular Formula C26H21N3O3
Molecular Weight 423.463
Flash Point 341.7±34.3 °C
Exact Mass 423.158295
PSA 90.62000
LogP 3.87
Appearance of Characters solid | yellow
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.689
Storage condition −20°C
Water Solubility methanol and ethanol: soluble

 Safety Information

Hazard Statements H413
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3

 Synthetic Route

 Articles44

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 Synonyms

Coelenterazine, native
2-(4-Hydroxybenzyl)-6-(4-hydroxyphenyl)-8-benzyl-3,7-dihydroimidazo(1,2-a)pyrazin-3-one
Imidazo[1,2-a]pyrazin-3(7H)-one, 6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-8-(phenylmethyl)-
Coelenterazine
Imidazo(1,2-a)pyrazin-3(7H)-one, 6-(4-hydroxyphenyl)-2-((4-hydroxyphenyl)methyl)-8-(phenylmethyl)-
MFCD00467176
8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one
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Related Compounds: More...
Coelenterazine h
50909-86-9
COELENTERAZINE F
123437-16-1
coelenterazine-v
114496-03-6
Coelenterazine e
114496-02-5
coelenterazine-hh
70217-82-2
Coelenterazine cp
123437-25-2
COELENTERAZINE FCP
123437-33-2
Coelenterazine hcp
123437-32-1
Coelenterazine 400a (hydrochloride)
2320429-05-6
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