Coelenterazine
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MedKoo CAT#: 317124

CAS#: 55779-48-1

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.


Chemical Structure

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Coelenterazine
CAS# 55779-48-1

Theoretical Analysis

MedKoo Cat#: 317124
Name: Coelenterazine
CAS#: 55779-48-1
Chemical Formula: C26H21N3O3
Exact Mass: 423.15829
Molecular Weight: 423.47
Elemental Analysis: C, 73.74; H, 5.00; N, 9.92; O, 11.33

Price and Availability

Size Price Availability Quantity
100.0mg USD 1250.0 2 Weeks
200.0mg USD 1950.0 2 Weeks
500.0mg USD 2950.0 2 Weeks
1.0g USD 3950.0 2 Weeks
2.0g USD 6850.0 2 Weeks
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Synonym: Oplophorus, luciferin; Coelenterazine; CLZN; Coelenterazine, Coelenterazine

IUPAC/Chemical Name: 8-benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

InChi Key: YHIPILPTUVMWQT-UHFFFAOYSA-N

InChi Code: 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/h1-13,16,27,30-31H,14-15H2

SMILES Code: C1=CC=C(C=C1)CC2=C3N=C(C(=O)N3C=C(N2)C4=CC=C(C=C4)O)CC5=CC=C(C=C5)O

Appearance: Yellow solid powder

Purity: >80% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 423.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Francis WR, Shaner NC, Christianson LM, Powers ML, Haddock SH. Occurrence of Isopenicillin-N-Synthase Homologs in Bioluminescent Ctenophores and Implications for Coelenterazine Biosynthesis. PLoS One. 2015 Jun 30;10(6):e0128742. doi: 10.1371/journal.pone.0128742. eCollection 2015. PubMed PMID: 26125183; PubMed Central PMCID: PMC4488382.

2: Nishihara R, Suzuki H, Hoshino E, Suganuma S, Sato M, Saitoh T, Nishiyama S, Iwasawa N, Citterio D, Suzuki K. Bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution. Chem Commun (Camb). 2015;51(2):391-4. doi: 10.1039/c4cc06886f. Epub 2014 Nov 18. PubMed PMID: 25407088.

3: Gealageas R, Malikova NP, Picaud S, Borgdorff AJ, Burakova LP, Brûlet P, Vysotski ES, Dodd RH. Bioluminescent properties of obelin and aequorin with novel coelenterazine analogues. Anal Bioanal Chem. 2014 Apr;406(11):2695-707. doi: 10.1007/s00216-014-7656-4. Epub 2014 Feb 20. PubMed PMID: 24553660.

4: Inouye S, Sahara-Miura Y. A Novel Catalytic Function of Synthetic IgG-Binding Domain (Z Domain) from Staphylococcal Protein A: Light Emission with Coelenterazine. Photochem Photobiol. 2013 Oct 19. doi: 10.1111/php.12192. [Epub ahead of print] PubMed PMID: 24138575.

5: Lindberg E, Mizukami S, Ibata K, Miyawaki A, Kikuchi K. Development of luminescent coelenterazine derivatives activatable by β-galactosidase for monitoring dual gene expression. Chemistry. 2013 Oct 25;19(44):14970-6. doi: 10.1002/chem.201302002. Epub 2013 Sep 17. PubMed PMID: 24105816.

6: Eremeeva EV, Markova SV, van Berkel WJ, Vysotski ES. Role of key residues of obelin in coelenterazine binding and conversion into 2-hydroperoxy adduct. J Photochem Photobiol B. 2013 Oct 5;127:133-9. doi: 10.1016/j.jphotobiol.2013.08.012. Epub 2013 Aug 28. PubMed PMID: 24041851.

7: Inouye S, Sato J, Sahara-Miura Y, Yoshida S, Kurakata H, Hosoya T. C6-Deoxy coelenterazine analogues as an efficient substrate for glow luminescence reaction of nanoKAZ: the mutated catalytic 19 kDa component of Oplophorus luciferase. Biochem Biophys Res Commun. 2013 Jul 19;437(1):23-8. doi: 10.1016/j.bbrc.2013.06.026. Epub 2013 Jun 18. PubMed PMID: 23792095.

8: Chan CM, Miller AL, Webb SE. Reconstitution of holo-aequorin with apoaequorin mRNA and coelenterazine in zebrafish embryos. Cold Spring Harb Protoc. 2013 May 1;2013(5):456-60. doi: 10.1101/pdb.prot072975. PubMed PMID: 23637361.

9: Eremeeva EV, Natashin PV, Song L, Zhou Y, van Berkel WJ, Liu ZJ, Vysotski ES. Oxygen activation of apo-obelin-coelenterazine complex. Chembiochem. 2013 Apr 15;14(6):739-45. doi: 10.1002/cbic.201300002. Epub 2013 Mar 12. PubMed PMID: 23494831.

10: Inouye S, Sahara-Miura Y, Sato J, Iimori R, Yoshida S, Hosoya T. Expression, purification and luminescence properties of coelenterazine-utilizing luciferases from Renilla, Oplophorus and Gaussia: comparison of substrate specificity for C2-modified coelenterazines. Protein Expr Purif. 2013 Mar;88(1):150-6. doi: 10.1016/j.pep.2012.12.006. Epub 2012 Dec 27. PubMed PMID: 23274053.

11: Morse D, Tannous BA. A water-soluble coelenterazine for sensitive in vivo imaging of coelenterate luciferases. Mol Ther. 2012 Apr;20(4):692-3. doi: 10.1038/mt.2012.38. PubMed PMID: 22472977; PubMed Central PMCID: PMC3321601.

12: Vassel N, Cox CD, Naseem R, Morse V, Evans RT, Power RL, Brancale A, Wann KT, Campbell AK. Enzymatic activity of albumin shown by coelenterazine chemiluminescence. Luminescence. 2012 May-Jun;27(3):234-41. doi: 10.1002/bio.2357. Epub 2012 Feb 24. PubMed PMID: 22362656.

13: Krasitskaya VV, Korneeva SI, Kudryavtsev AN, Markova SV, Stepanyuk GA, Frank LA. Ca(2+)-triggered coelenterazine-binding protein from Renilla as an enzyme-dependent label for binding assay. Anal Bioanal Chem. 2011 Nov;401(8):2573-9. doi: 10.1007/s00216-011-5343-2. Epub 2011 Sep 4. PubMed PMID: 21892640.

14: Huang R, Vider J, Serganova I, Blasberg RG. ATP-binding cassette transporters modulate both coelenterazine- and D-luciferin-based bioluminescence imaging. Mol Imaging. 2011 Jun;10(3):215-26. PubMed PMID: 21496450; PubMed Central PMCID: PMC4052835.

15: Jeon YH, Bae SA, Lee YJ, Lee YL, Lee SW, Yoon GS, Ahn BC, Ha JH, Lee J. Evaluation of the reversal of multidrug resistance by MDR1 ribonucleic acid interference in a human colon cancer model using a Renilla luciferase reporter gene and coelenterazine. Mol Imaging. 2010 Dec;9(6):343-50. PubMed PMID: 21084030.

16: Saleh L, Plieth C. A coelenterazine-based luminescence assay to quantify high-molecular-weight superoxide anion scavenger activities. Nat Protoc. 2010 Sep;5(10):1635-41. doi: 10.1038/nprot.2010.121. Epub 2010 Sep 16. PubMed PMID: 20885375.

17: Stepanyuk GA, Unch J, Malikova NP, Markova SV, Lee J, Vysotski ES. Coelenterazine-v ligated to Ca2+-triggered coelenterazine-binding protein is a stable and efficient substrate of the red-shifted mutant of Renilla muelleri luciferase. Anal Bioanal Chem. 2010 Oct;398(4):1809-17. doi: 10.1007/s00216-010-4106-9. Epub 2010 Aug 15. PubMed PMID: 20711766.

18: Oba Y, Kato S, Ojika M, Inouye S. Biosynthesis of coelenterazine in the deep-sea copepod, Metridia pacifica. Biochem Biophys Res Commun. 2009 Dec 18;390(3):684-8. doi: 10.1016/j.bbrc.2009.10.028. Epub 2009 Oct 13. PubMed PMID: 19833098.

19: Mosrin M, Bresser T, Knochel P. Regio- and chemoselective multiple functionalization of chloropyrazine derivatives. Application to the synthesis of coelenterazine. Org Lett. 2009 Aug 6;11(15):3406-9. doi: 10.1021/ol901275n. PubMed PMID: 19719188.

20: Eremeeva EV, Markova SV, Westphal AH, Visser AJ, van Berkel WJ, Vysotski ES. The intrinsic fluorescence of apo-obelin and apo-aequorin and use of its quenching to characterize coelenterazine binding. FEBS Lett. 2009 Jun 18;583(12):1939-44. doi: 10.1016/j.febslet.2009.04.043. Epub 2009 May 6. PubMed PMID: 19426732.