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Chemical Structure| 55779-48-1 Chemical Structure| 55779-48-1

Structure of Coelenterazine
CAS No.: 55779-48-1

Chemical Structure| 55779-48-1

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Coelenterazineis is the substrate of many luciferases, as a luciferin, light-emitting molecules, found in many aquatic organisms across eight phyla.

Synonyms: Luciferin (Oplophorus); Preluciferin (Watasenia); Coelenterazine, Coelenterazine

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Product Details of Coelenterazine

CAS No. :55779-48-1
Formula : C26H21N3O3
M.W : 423.46
SMILES Code : O=C1C(CC2=CC=C(O)C=C2)=NC3=C(CC4=CC=CC=C4)NC(C5=CC=C(O)C=C5)=CN31
Synonyms :
Luciferin (Oplophorus); Preluciferin (Watasenia); Coelenterazine, Coelenterazine
MDL No. :MFCD00467176
InChI Key :LNCOEGVEEQDKGX-UHFFFAOYSA-N
Pubchem ID :135445694

Safety of Coelenterazine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
MDA-MB231 cells 10 µM Evaluation of NIR-BRET signal of BBlue2.3 in cells stably expressing iRFP-RLuc8.6-535SG Theranostics. 2019 Apr 13;9(9):2646-2661.
HeLa cells 10 µM 2 seconds High-resolution bioluminescence imaging at single-cell level, BBlue2.3 rapidly diffused throughout the cell Theranostics. 2019 Apr 13;9(9):2646-2661.
COS-7 cells 10 µM Evaluation of the biophysical properties of new CTZ derivatives in intact cells, BBlue2.3 showed the highest membrane permeability and light output Theranostics. 2019 Apr 13;9(9):2646-2661.
HEK 293T cells 50 µM Evaluate the bioluminescence performance of new reporters, showing that the brightness of DTZ with teLuc or Antares2 was two to three orders of magnitude higher than that of FLuc/D-luciferin. Nat Methods. 2017 Oct;14(10):971-974.
293T cells 8.3 μM 24 hours Used for high-throughput screening of Hsp90 inhibitors, CP9 showed the ability to inhibit Hsp90(α/β)/p23 interactions Proc Natl Acad Sci U S A. 2012 Sep 11;109(37):E2476-85.
C6-Rluc cells 150 µg/ml 1 minute To check the crossreactivity of D-luciferin with RL, showing negligible bioluminescence from C6-Rluc cells exposed to D-luciferin. Proc Natl Acad Sci U S A. 2002 Jan 8;99(1):377-82.
C6-Fluc cells 2 µg/ml 1 minute To check the crossreactivity of coelenterazine with FL, showing minimal signal from C6-Fluc cells exposed to coelenterazine. Proc Natl Acad Sci U S A. 2002 Jan 8;99(1):377-82.
C6 rat glioma cells 0.1-200 µg/ml 10 seconds To determine the effects of coelenterazine dose on light yield, showing an approximately linear relationship between 0.1–10 µg/ml and peak signal at 50 µg/ml. Proc Natl Acad Sci U S A. 2002 Jan 8;99(1):377-82.
C6 rat glioma cells 50 µg/ml 10 seconds To determine the time kinetics of light production from RL with coelenterazine, showing the highest light intensity within the first 10 s of the reaction. Proc Natl Acad Sci U S A. 2002 Jan 8;99(1):377-82.
KB 8-5-11 Rluc cells 470 nM 6 seconds to 30 minutes To investigate Pgp-mediated transport of Coelenterazine, results showed low bioluminescence in KB 8-5-11 Rluc cells, which could be reversed by Pgp inhibitors. Proc Natl Acad Sci U S A. 2004 Feb 10;101(6):1702-7.
KB 3-1 Rluc cells 470 nM 6 seconds to 30 minutes To investigate Pgp-mediated transport of Coelenterazine, results showed high bioluminescence in KB 3-1 Rluc cells. Proc Natl Acad Sci U S A. 2004 Feb 10;101(6):1702-7.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Nude mice (BALB/c nude mice) Subcutaneous xenograft model Intraperitoneal injection 50 µg/100 µL Single injection Evaluation of autoluminescence and tumor imaging efficacy of BBlue2.3 in vivo, BBlue2.3 showed lower background signal and higher tumor-specific signal Theranostics. 2019 Apr 13;9(9):2646-2661.
Nude mice 293T tumor xenograft model Intraperitoneal injection 30 μg/150 μL Four doses, immediately after baseline imaging and at 16, 24, and 49 hours To monitor the inhibitory effect of CP9 on Hsp90(α/β)/p23 interactions in live mice, results showed CP9 selectively inhibited Hsp90α/p23 interactions Proc Natl Acad Sci U S A. 2012 Sep 11;109(37):E2476-85.
CD-1 mice Subcutaneously implanted C6-Rluc cells Tail-vein injection 0.07-3.5 mg/kg Single injection, lasting 10 minutes To determine the effects of coelenterazine dose on RL signal in vivo, showing a progressive increase in bioluminescence with increasing coelenterazine dose. Proc Natl Acad Sci U S A. 2002 Jan 8;99(1):377-82.
NCr nu/nu mice KB 3-1 and KB 8-5-11 cell xenograft models Tail vein injection 4 µg/g Single dose, imaging at 2, 6, 8, and 11 minutes post-injection To monitor Pgp transport activity and inhibition via bioluminescence imaging, results showed lower bioluminescence in KB 8-5-11 Rluc tumors compared to KB 3-1 Rluc tumors, which could be reversed by GF120918. Proc Natl Acad Sci U S A. 2004 Feb 10;101(6):1702-7.

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.36mL

0.47mL

0.24mL

11.81mL

2.36mL

1.18mL

23.61mL

4.72mL

2.36mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

[1]Pandey D, Fulton DJ, et al. Molecular regulation of NADPH oxidase 5 via the MAPK pathway. Am J Physiol Heart Circ Physiol. 2011 Apr;300(4):H1336-44.

[2]Ritsick DR, Edens WA, et al. Nox regulation of smooth muscle contraction. Free Radic Biol Med. 2007 Jul 1;43(1):31-8. Epub 2007 Mar 12.

[3]Gentschev I, Stritzker J, et al. Use of an oncolytic vaccinia virus for the treatment of canine breast cancer in nude mice: preclinical development of a therapeutic agent. Cancer Gene Ther. 2009 Apr;16(4):320-8.

[4]Bhaumik S, Gambhir SS, et al. Optical imaging of Renilla luciferase reporter gene expression in living mice. Proc Natl Acad Sci U S A. 2002 Jan 8;99(1):377-82. Epub 2001 Dec 18.

[5]Bronsart LL, Stokes C, et al. Chemiluminescence Imaging of Superoxide Anion Detects Beta-Cell Function and Mass. PLoS One. 2016 Jan 11;11(1):e0146601.

[6]Pandey D, Fulton DJ. Molecular regulation of NADPH oxidase 5 via the MAPK pathway. Am J Physiol Heart Circ Physiol. 2011 Apr;300(4):H1336-44. doi: 10.1152/ajpheart.01163.2010. Epub 2011 Feb 4. PMID: 21297032; PMCID: PMC3075021.

[7]Ritsick DR, Edens WA, Finnerty V, Lambeth JD. Nox regulation of smooth muscle contraction. Free Radic Biol Med. 2007 Jul 1;43(1):31-8. doi: 10.1016/j.freeradbiomed.2007.03.006. Epub 2007 Mar 12. PMID: 17561091; PMCID: PMC1989158.

[8]Gentschev I, Stritzker J, Hofmann E, Weibel S, Yu YA, Chen N, Zhang Q, Bullerdiek J, Nolte I, Szalay AA. Use of an oncolytic vaccinia virus for the treatment of canine breast cancer in nude mice: preclinical development of a therapeutic agent. Cancer Gene Ther. 2009 Apr;16(4):320-8. doi: 10.1038/cgt.2008.87. Epub 2008 Oct 24. PMID: 18949014.

 

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