3-Cyano-7-ethoxycoumarin - CAS 117620-77-6
Molecular Formula:
C12H9NO3
Molecular Weight:
215.21
COA:
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Application\Fluorophore:
Fluorescent Enzyme Substrates
Description:
3-Cyano-7-ethoxycoumarin is a fluorogenic substrate used for determination of cytochrome P450.
Appearance:
Yellow Solid
Synonyms:
7-ethoxy-2-oxo-2h-chromene-3-carbonitrile; 7-Ethoxycoumarin-3-carbonitrile; 7-ethoxy-2-oxochromene-3-carbonitrile
Solubility:
15mg/mL in DMSO
MSDS:
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Shelf Life:
2 years
Boiling Point:
396.8ºC at 760 mmHg
Melting Point:
210-212°C
Density:
1.29 g/cm3
Excitation:
408 nm
Emission:
450 nm
InChIKey:
YAFGHMIAFYQSCF-UHFFFAOYSA-N
InChI:
InChI=1S/C12H9NO3/c1-2-15-10-4-3-8-5-9(7-13)12(14)16-11(8)6-10/h3-6H,2H2,1H3
Canonical SMILES:
CCOC1=CC2=C(C=C1)C=C(C(=O)O2)C#N
1.Fluorescence-based assays for screening nine cytochrome P450 (P450) activities in intact cells expressing individual human P450 enzymes.
Donato MT;Jiménez N;Castell JV;Gómez-Lechón MJ Drug Metab Dispos. 2004 Jul;32(7):699-706.
In this study we describe a battery of fluorescence assays for rapid measurement in intact cells of the activity of nine cytochromes P450 (P450s) involved in drug metabolism. The assays are based on the direct incubation of monolayers of cells expressing individual P450 enzymes with a fluorogenic substrate followed by fluorimetric quantification of the product formed and released into incubation medium. For each individual P450 activity, different fluorescence probes were examined, and the one showing the best properties (highest metabolic rates, lowest background fluorescence) was selected: 3-cyano-7-ethoxycoumarin for CYP1A2 and CYP2C19, coumarin for CYP2A6, 7-ethoxy-4-trifluoromethylcoumarin for CYP2B6, dibenzylfluorescein for CYP2C8, 7-methoxy-4-trifluoromethylcoumarin (MFC) for CYP2C9 and CYP2E1, 3-[2-(N,N-diethyl-N-methylammonium)ethyl]-7-methoxy-4-methylcoumarin for CYP2D6, and 7-benzyloxy-4-trifluoromethylcoumarin for CYP3A4. Fluorescence-based assays are highly sensitive and allow the simultaneous measurement of a large number of samples using plate readers, thus enhancing sample throughput. Major advantages over high-throughput assays in subcellular fractions are that, as living cells are used, manual handling and enzyme damage are minimized, the endoplasmic reticulum of the cells remains intact, exogenous cofactors or NADPH-regenerating systems are not required, and transport processes are maintained.
2.Assessment of cytochrome P450 fluorometric substrates with rainbow trout and killifish exposed to dexamethasone, pregnenolone-16alpha-carbonitrile, rifampicin, and beta-naphthoflavone.
Smith EM;Wilson JY Aquat Toxicol. 2010 May 10;97(4):324-33. doi: 10.1016/j.aquatox.2010.01.005. Epub 2010 Jan 25.
Cytochrome P450s (CYPs) are important xenobiotic metabolizing proteins. While their functions are well understood in mammals, CYP function in non-mammalian vertebrate systems is much less defined, with function often inferred from mammalian data, assuming similar function across vertebrate species. In this study, we investigate whether in vivo treatment with known mammalian CYP inducers can alter the in vitro catalytic activity of fish microsomes using eleven fluorescent CYP-mediated substrates. We investigate the basal metabolism and induction potential for hepatic CYPs in two fish species, rainbow trout (Oncorhynchus mykiss) and killifish (Fundulus heteroclitus). Species differences were found in the baseline metabolism of these substrates. Killifish have significantly higher metabolic rates for all tested substrates except 7-benzyloxyquinoline and 7-benzyloxy-4-trifluoromethylcoumarin (both mammalian CYP3A substrates); significant differences were also seen between male and female killifish. Treatment with dexamethasone, pregnenolone-16alpha-carbonitrile, and rifampicin did not cause broad, measurable CYP induction in either fish species. In trout, dexamethasone (100 mg kg(-1)) significantly induced 3-cyano-7-ethoxycoumarin metabolism and rifampicin (100 mg kg(-1)) induced the dealkylation of 7-methoxyresorufin, although both were highly variable.
3.Potent inhibition of CYP1A2 by Frutinone A, an active ingredient of the broad spectrum antimicrobial herbal extract from P. fruticosa.
Thelingwani RS;Dhansay K;Smith P;Chibale K;Masimirembwa CM Xenobiotica. 2012 Oct;42(10):989-1000. doi: 10.3109/00498254.2012.681077. Epub 2012 Apr 25.
1. Frutinone is an active ingredient extracted from the lipophilic fraction of the Polygala Fruticosa demonstrating various antibacterial and fungal properties. The aim of this study was to characterize its metabolism in an effort to understand metabolism based drug-herb interactions. 2. In vitro metabolic clearance and metabolite identification studies were done using cryopreserved hepatocytes. Reaction phenotyping and inhibition studies were done using human liver microsomes and recombinant cytochrome P450s (CYPs). Frutinone A-CYP1A2 interactions were rationalized using docking simulations. 3. Hepatic clearance was predicted to be low (7.17 mL/min/kg), with reaction phenotyping studies indicating no clearance by the enzymes tested. Frutinone was identified as a potent inhibitor of CYP1A2 with moderate effects on CYP2C19, 2C9, 2D6 and 3A4. CYP1A2 inhibition was reversible and characterised by an IC(50) of 0.56 µM. Inhibition was differential showing mixed (K(i) = 0.48 µM) and competitive (K(i) = 0.31 µM) inhibition with 3-cyano-7-ethoxycoumarin and ethoxyresorufin, respectively. Two binding sites, one for inhibitors and the other for substrates were identified in silico. 4. The potent CYP1A2 inhibition by Frutinone A could be predictive of the potential drug-herb interaction risk in the use of herbal extracts from P.
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CAS 117620-77-6 3-Cyano-7-ethoxycoumarin

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