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MedKoo Cat#: 145576 | Name: Coelenteramide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Coelenteramide is produced from the coelenterazine oxidation via a series of complicated chemical reactions in protein. Coelenteramide is a fluorophore of discharged obelin. Coelenteramide is a photochemically active molecule.

Chemical Structure

Coelenteramide
Coelenteramide
CAS#50611-86-4

Theoretical Analysis

MedKoo Cat#: 145576

Name: Coelenteramide

CAS#: 50611-86-4

Chemical Formula: C25H21N3O3

Exact Mass: 411.1600

Molecular Weight: 411.46

Elemental Analysis: C, 72.98; H, 5.14; N, 10.21; O, 11.67

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Coelenteramide;
IUPAC/Chemical Name
N-(3-benzyl-5-(4-hydroxyphenyl)pyrazin-2-yl)-2-(4-hydroxyphenyl)acetamide
InChi Key
CJIIERPDFZUYPI-UHFFFAOYSA-N
InChi Code
1S/C25H21N3O3/c29-20-10-6-18(7-11-20)15-24(31)28-25-22(14-17-4-2-1-3-5-17)27-23(16-26-25)19-8-12-21(30)13-9-19/h1-13,16,29-30H,14-15H2,(H,26,28,31)
SMILES Code
OC1=CC=C(CC(=O)NC2=NC=C(N=C2CC3=CC=CC=C3)C4=CC=C(O)C=C4)C=C1
Appearance
To be determined
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 411.46 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
1: Gao M, Liu YJ. Photoluminescence Rainbow from Coelenteramide-A Theoretical Study. Photochem Photobiol. 2019 Mar;95(2):563-571. doi: 10.1111/php.12987. Epub 2018 Aug 20. PMID: 30059157. 2: Petrova AS, Lukonina AA, Badun GA, Kudryasheva NS. Fluorescent coelenteramide-containing protein as a color bioindicator for low-dose radiation effects. Anal Bioanal Chem. 2017 Jul;409(18):4377-4381. doi: 10.1007/s00216-017-0404-9. Epub 2017 May 19. PMID: 28527000. 3: Afonso ACP, González-Berdullas P, Esteves da Silva JCG, Pinto da Silva L. Combined Experimental and Theoretical Investigation into the Photophysical Properties of Halogenated Coelenteramide Analogs. Molecules. 2022 Dec 14;27(24):8875. doi: 10.3390/molecules27248875. PMID: 36558008; PMCID: PMC9781228. 4: Siniakova TS, Raikov AV, Kudryasheva NS. Water-Soluble Polymer Polyethylene Glycol: Effect on the Bioluminescent Reaction of the Marine Coelenterate Obelia and Coelenteramide-Containing Fluorescent Protein. Int J Mol Sci. 2023 Mar 28;24(7):6345. doi: 10.3390/ijms24076345. PMID: 37047313; PMCID: PMC10094403. 5: Xie JM, Cui XY, Liu H, Leng Y, Min CG, Ren AM. Theoretical investigation on triphenylamine coelenteramide for bioinspired OLED application using thiophene rings in π-bridge. Spectrochim Acta A Mol Biomol Spectrosc. 2024 Jan 5;304:123324. doi: 10.1016/j.saa.2023.123324. Epub 2023 Sep 1. PMID: 37678042. 6: Chen SF, Vysotski ES, Liu YJ. H2O-Bridged Proton-Transfer Channel in Emitter Species Formation in Obelin Bioluminescence. J Phys Chem B. 2021 Sep 23;125(37):10452-10458. doi: 10.1021/acs.jpcb.1c03985. Epub 2021 Sep 14. PMID: 34520210. 7: Alieva RR, Tomilin FN, Kuzubov AA, Ovchinnikov SG, Kudryasheva NS. Ultraviolet fluorescence of coelenteramide and coelenteramide-containing fluorescent proteins. Experimental and theoretical study. J Photochem Photobiol B. 2016 Sep;162:318-323. doi: 10.1016/j.jphotobiol.2016.07.004. Epub 2016 Jul 5. PMID: 27400455. 8: Alieva RR, Kudryasheva NS. Variability of fluorescence spectra of coelenteramide-containing proteins as a basis for toxicity monitoring. Talanta. 2017 Aug 1;170:425-431. doi: 10.1016/j.talanta.2017.04.043. Epub 2017 Apr 18. PMID: 28501192. 9: Min CG, Pinto da Silva L, Esteves da Silva JC, Yang XK, Huang SJ, Ren AM, Zhu YQ. A Computational Investigation of the Equilibrium Constants for the Fluorescent and Chemiluminescent States of Coelenteramide. Chemphyschem. 2017 Jan 4;18(1):117-123. doi: 10.1002/cphc.201600850. Epub 2016 Nov 23. PMID: 27806186. 10: Liu ZJ, Stepanyuk GA, Vysotski ES, Lee J, Markova SV, Malikova NP, Wang BC. Crystal structure of obelin after Ca2+-triggered bioluminescence suggests neutral coelenteramide as the primary excited state. Proc Natl Acad Sci U S A. 2006 Feb 21;103(8):2570-5. doi: 10.1073/pnas.0511142103. Epub 2006 Feb 8. PMID: 16467137; PMCID: PMC1413834. 11: Li ZS, Zhao X, Zou LY, Ren AM. The dynamics simulation and quantum calculation investigation about luminescence mechanism of coelenteramide. Photochem Photobiol. 2013 Jul-Aug;89(4):849-55. doi: 10.1111/php.12073. Epub 2013 Apr 17. PMID: 23495829. 12: Zhang H. NRluc-hER281-549-CRluc. 2008 Dec 29 [updated 2009 Jan 26]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004–2013. PMID: 20641444. 13: Larionova MD, Wu L, Eremeeva EV, Natashin PV, Gulnov DV, Nemtseva EV, Liu D, Liu ZJ, Vysotski ES. Crystal structure of semisynthetic obelin-v. Protein Sci. 2022 Feb;31(2):454-469. doi: 10.1002/pro.4244. Epub 2021 Nov 29. PMID: 34802167; PMCID: PMC8819848. 14: Inouye S, Hosoya T. Reconstitution of blue fluorescent protein from recombinant apoaequorin and synthetic coelenteramide. Biochem Biophys Res Commun. 2009 Sep 4;386(4):617-22. doi: 10.1016/j.bbrc.2009.06.094. Epub 2009 Jun 21. PMID: 19549504. 15: Chen SF, Navizet I, Roca-Sanjuán D, Lindh R, Liu YJ, Ferré N. Chemiluminescence of Coelenterazine and Fluorescence of Coelenteramide: A Systematic Theoretical Study. J Chem Theory Comput. 2012 Aug 14;8(8):2796-807. doi: 10.1021/ct300356j. Epub 2012 Jul 23. PMID: 26592121. 16: Li ZS, Zou LY, Min CG, Ren AM. The effect of micro-environment on luminescence of aequorin: the role of amino acids and explicit water molecules on spectroscopic properties of coelenteramide. J Photochem Photobiol B. 2013 Oct 5;127:94-9. doi: 10.1016/j.jphotobiol.2013.07.022. Epub 2013 Aug 3. PMID: 23973779. 17: Shimomura O. Bioluminescence in the sea: photoprotein systems. Symp Soc Exp Biol. 1985;39:351-72. PMID: 2871634. 18: Roca-Sanjuán D, Delcey MG, Navizet I, Ferré N, Liu YJ, Lindh R. Chemiluminescence and Fluorescence States of a Small Model for Coelenteramide and Cypridina Oxyluciferin: A CASSCF/CASPT2 Study. J Chem Theory Comput. 2011 Dec 13;7(12):4060-9. doi: 10.1021/ct2004758. Epub 2011 Nov 11. PMID: 26598351. 19: Inouye S, Nakamura M, Hosoya T. Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+ -Binding Photoprotein Aequorin. Photochem Photobiol. 2022 Sep;98(5):1068-1076. doi: 10.1111/php.13590. Epub 2022 Jan 12. PMID: 34971002. 20: Malikova NP, Eremeeva EV, Gulnov DV, Natashin PV, Nemtseva EV, Vysotski ES. Specific Activities of Hydromedusan Ca2+ -Regulated Photoproteins. Photochem Photobiol. 2022 Jan;98(1):275-283. doi: 10.1111/php.13556. Epub 2021 Nov 15. PMID: 34727376.