EFC
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MedKoo CAT#: 464989

CAS#: 115453-82-2

Description: EFC is a fluorogenic substrate for cytochrome P450s (CYPs). Upon O-deethylation by CYPs, EFC is released and its fluorescence can be used to quantify CYP activity. EFC displays excitation/emission maxima of 410/510 nm, respectively.


Chemical Structure

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EFC
CAS# 115453-82-2

Theoretical Analysis

MedKoo Cat#: 464989
Name: EFC
CAS#: 115453-82-2
Chemical Formula: C12H9F3O3
Exact Mass: 258.0504
Molecular Weight: 258.1962
Elemental Analysis: C, 55.82; H, 3.51; F, 22.07; O, 18.59

Price and Availability

Size Price Availability Quantity
5.0mg USD 210.0 2 Weeks
10.0mg USD 340.0 2 Weeks
25.0mg USD 540.0 2 Weeks
50.0mg USD 780.0 2 Weeks
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Synonym: EFC; 7-Ethoxy-4-(trifluoromethyl)coumarin;

IUPAC/Chemical Name: 7-ethoxy-4-(trifluoromethyl)-2H-chromen-2-one

InChi Key: OLHOIERZAZMHGK-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H9F3O3/c1-2-17-7-3-4-8-9(12(13,14)15)6-11(16)18-10(8)5-7/h3-6H,2H2,1H3

SMILES Code: O=C1OC2=C(C=CC(OCC)=C2)C(C(F)(F)F)=C1

Appearance: Solid powder

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

Preparing Stock Solutions

The following data is based on the product molecular weight 258.1962 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: Huo L, Liu J, Dearing MD, Szklarz GD, Halpert JR, Wilderman PR. Rational Re- Engineering of the O-Dealkylation of 7-Alkoxycoumarin Derivatives by Cytochromes P450 2B from the Desert Woodrat Neotoma lepida. Biochemistry. 2017 Apr 25;56(16):2238-2246. doi: 10.1021/acs.biochem.7b00097. Epub 2017 Apr 12. PMID: 28375626.

2: Vanduchova A, Tomankova V, Anzenbacher P, Anzenbacherova E. Influence of Sulforaphane Metabolites on Activities of Human Drug-Metabolizing Cytochrome P450 and Determination of Sulforaphane in Human Liver Cells. J Med Food. 2016 Dec;19(12):1141-1146. doi: 10.1089/jmf.2016.0063. Epub 2016 Oct 25. PMID: 27779894.

3: Liu J, Shah MB, Zhang Q, Stout CD, Halpert JR, Wilderman PR. Coumarin Derivatives as Substrate Probes of Mammalian Cytochromes P450 2B4 and 2B6: Assessing the Importance of 7-Alkoxy Chain Length, Halogen Substitution, and Non-Active Site Mutations. Biochemistry. 2016 Apr 5;55(13):1997-2007. doi: 10.1021/acs.biochem.5b01330. Epub 2016 Mar 24. PMID: 26982502; PMCID: PMC4864431.

4: Okamatsu G, Komatsu T, Ono Y, Inoue H, Uchide T, Onaga T, Endoh D, Kitazawa T, Hiraga T, Uno Y, Teraoka H. Characterization of feline cytochrome P450 2B6. Xenobiotica. 2017 Feb;47(2):93-102. doi: 10.3109/00498254.2016.1145754. Epub 2016 Mar 9. PMID: 26956662.

5: Shah MB, Liu J, Huo L, Zhang Q, Dearing MD, Wilderman PR, Szklarz GD, Stout CD, Halpert JR. Structure-Function Analysis of Mammalian CYP2B Enzymes Using 7-Substituted Coumarin Derivatives as Probes: Utility of Crystal Structures and Molecular Modeling in Understanding Xenobiotic Metabolism. Mol Pharmacol. 2016 Apr;89(4):435-45. doi: 10.1124/mol.115.102111. Epub 2016 Jan 29. PMID: 26826176; PMCID: PMC4809303.

6: Jang HH, Liu J, Lee GY, Halpert JR, Wilderman PR. Functional importance of a peripheral pocket in mammalian cytochrome P450 2B enzymes. Arch Biochem Biophys. 2015 Oct 15;584:61-9. doi: 10.1016/j.abb.2015.08.007. Epub 2015 Aug 28. PMID: 26319176; PMCID: PMC4599343.

7: Masek V, Starha P, Harvanova M, Michalova M, Milde D, Travnicek Z, Anzenbacherova E. Interaction of selected platinum(II) complexes containing roscovitine-based CDK inhibitors as ligands with human liver microsomal cytochrome P450. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2015 Sep;159(3):382-7. doi: 10.5507/bp.2014.031. Epub 2014 Jul 4. PMID: 25004912.

8: Jang HH, Davydov DR, Lee GY, Yun CH, Halpert JR. The role of cytochrome P450 2B6 and 2B4 substrate access channel residues predicted based on crystal structures of the amlodipine complexes. Arch Biochem Biophys. 2014 Mar 1;545:100-7. doi: 10.1016/j.abb.2014.01.008. Epub 2014 Jan 18. PMID: 24445070; PMCID: PMC4030592.

9: Wilderman PR, Jang HH, Malenke JR, Salib M, Angermeier E, Lamime S, Dearing MD, Halpert JR. Functional characterization of cytochromes P450 2B from the desert woodrat Neotoma lepida. Toxicol Appl Pharmacol. 2014 Feb 1;274(3):393-401. doi: 10.1016/j.taap.2013.12.005. Epub 2013 Dec 19. PMID: 24361551; PMCID: PMC3970846.

10: Mayumi K, Hanioka N, Masuda K, Koeda A, Naito S, Miyata A, Narimatsu S. Characterization of marmoset CYP2B6: cDNA cloning, protein expression and enzymatic functions. Biochem Pharmacol. 2013 Apr 15;85(8):1182-94. doi: 10.1016/j.bcp.2013.01.024. Epub 2013 Feb 5. PMID: 23395694.

11: Sridar C, Kenaan C, Hollenberg PF. Inhibition of bupropion metabolism by selegiline: mechanism-based inactivation of human CYP2B6 and characterization of glutathione and peptide adducts. Drug Metab Dispos. 2012 Dec;40(12):2256-66. doi: 10.1124/dmd.112.046979. Epub 2012 Aug 30. PMID: 22936314; PMCID: PMC3500550.

12: Jang HH, Kim SY, Kang JY, Park SH, Ryu SH, Ahn T, Yun CH. Increase of human CYP1B1 activities by acidic phospholipids and kinetic deuterium isotope effects on CYP1B1 substrate oxidation. J Biochem. 2012 Nov;152(5):433-42. doi: 10.1093/jb/mvs087. Epub 2012 Aug 9. PMID: 22888116.

13: Wilderman PR, Gay SC, Jang HH, Zhang Q, Stout CD, Halpert JR. Investigation by site-directed mutagenesis of the role of cytochrome P450 2B4 non-active-site residues in protein-ligand interactions based on crystal structures of the ligand-bound enzyme. FEBS J. 2012 May;279(9):1607-20. doi: 10.1111/j.1742-4658.2011.08411.x. Epub 2011 Nov 25. PMID: 22051155; PMCID: PMC3911823.

14: Lan SF, Safiejko-Mroczka B, Starly B. Long-term cultivation of HepG2 liver cells encapsulated in alginate hydrogels: a study of cell viability, morphology and drug metabolism. Toxicol In Vitro. 2010 Jun;24(4):1314-23. doi: 10.1016/j.tiv.2010.02.015. Epub 2010 Feb 18. PMID: 20171269.

15: Makaji E, Trambitas CS, Shen P, Holloway AC, Crankshaw DJ. Effects of cytochrome P450 inhibitors on the biotransformation of fluorogenic substrates by adult male rat liver microsomes and cDNA-expressed rat cytochrome P450 isoforms. Toxicol Sci. 2010 Feb;113(2):293-304. doi: 10.1093/toxsci/kfp255. Epub 2009 Oct 25. PMID: 19858067.

16: Lin HL, Zhang H, Hollenberg PF. Metabolic activation of mifepristone [RU486; 17beta-hydroxy-11beta-(4-dimethylaminophenyl)-17alpha-(1-propynyl)-estra-4,9-die n-3-one] by mammalian cytochromes P450 and the mechanism-based inactivation of human CYP2B6. J Pharmacol Exp Ther. 2009 Apr;329(1):26-37. doi: 10.1124/jpet.108.148536. Epub 2009 Jan 23. PMID: 19168709; PMCID: PMC2670597.

17: Oezguen N, Kumar S, Hindupur A, Braun W, Muralidhara BK, Halpert JR. Identification and analysis of conserved sequence motifs in cytochrome P450 family 2. Functional and structural role of a motif 187RFDYKD192 in CYP2B enzymes. J Biol Chem. 2008 Aug 1;283(31):21808-16. doi: 10.1074/jbc.M708582200. Epub 2008 May 21. PMID: 18495666; PMCID: PMC2490781.

18: Lin HL, Myshkin E, Waskell L, Hollenberg PF. Peroxynitrite inactivation of human cytochrome P450s 2B6 and 2E1: heme modification and site-specific nitrotyrosine formation. Chem Res Toxicol. 2007 Nov;20(11):1612-22. doi: 10.1021/tx700220e. Epub 2007 Oct 2. PMID: 17907788.

19: Kumar S, Zhao Y, Sun L, Negi SS, Halpert JR, Muralidhara BK. Rational engineering of human cytochrome P450 2B6 for enhanced expression and stability: importance of a Leu264->Phe substitution. Mol Pharmacol. 2007 Nov;72(5):1191-9. doi: 10.1124/mol.107.039693. Epub 2007 Aug 22. PMID: 17715394.

20: Kobayashi Y, Sridar C, Kent UM, Puppali SG, Rimoldi JM, Zhang H, Waskell L, Hollenberg PF. Structure-activity relationship and elucidation of the determinant factor(s) responsible for the mechanism-based inactivation of cytochrome P450 2B6 by substituted phenyl diaziridines. Drug Metab Dispos. 2006 Dec;34(12):2102-10. doi: 10.1124/dmd.106.011452. Epub 2006 Sep 22. PMID: 16997911.

EFC

5.0mg / USD 210.0