129172-62-9Relevant academic research and scientific papers
Absolute Configuration of Epoxyeicosatrienoic Acids (EETs) Formed during Catalytic Oxygenation of Arachidonic Acid by Purified Rat Liver Microsomal Cytochrome P-450
Falck, J. R.,Manna, S.,Jacobson, Harry R.,Estabrook, R. W.,Chacos, N.,Capdevila, Jorge
, p. 3334 - 3336 (1984)
Incubation of arachidonic acid with a reconstituted enzymatic system containing a purified preparation of the major, phenobarbital-inducible form of rat liver microsomal cytochrome P-450, NADPH, cytochrome b5, and NADPH-cytochrome P-450 reductase affords as the principal products four regioisomeric cis-epoxides: 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs).Their absolute configurations were established by conversion to the corresponding hydroxyeicosatetraenoic acid (HETE) methyl esters, derivatization with dehydroabiethylisocyanate, and chromatographic analysis.Except for 5,6-EET, the cytochrome P-450 catalyzed epoxidation is highly enantioselective.
Analysis of epoxyeicosatrienoic acids by chiral liquid chromatography/ electron capture atmospheric pressure chemical ionization mass spectrometry using [13C]-analog internal standards
Mesaros, Clementina,Lee, Seon Hwa,Blair, Ian A.
experimental part, p. 3237 - 3247 (2012/01/06)
The metabolism of arachidonic acid (AA) to epoxyeicosatrienoic acids (EETs) is thought to be mediated primarily by the cytochromes P450 (P450s) from the 2 family (2C9, 2C19, 2D6, and 2J2). In contrast, P450s of the 4 family are primarily involved in omega oxidation of AA (4A11 and 4A22). The ability to determine enantioselective formation of the regioisomeric EETs is important in order to establish their potential biological activities and to asses which P450 isoforms are involved in their formation. It has been extremely difficult to analyze individual EET enantiomers in biological fluids because they are present in only trace amounts and they are extremely difficult to separate from each other. In addition, the deuterium-labeled internal standards that are commonly used for stable isotope dilution liquid chromatography/mass spectrometry (LC/MS) analyses have different LC retention times when compared with the corresponding protium forms. Therefore, quantification by LC/MS-based methodology can be compromised by differential suppression of ionization of the closely eluting isomers. We report the preparation of [13C20]-EET analog internal standards and the use of a validated high-sensitivity chiral LC/electron capture atmospheric pressure chemical ionization (ECAPCI)-MS method for the trace analysis of endogenous EETs as their pentafluorobenzyl (PFB) ester derivatives. The assay was then used to show the exquisite enantioselectivity of P4502C19-, P4502D6-, P4501A1-, and P4501B1-mediated conversion of AA into EETs and to quantify the enantioselective formation of EETs produced by AA metabolism in a mouse epithelial hepatoma (Hepa) cell line. Copyright
ARACHIDONATE EPOXXGENASE: TOTAL SYNTHESIS OF BOTH ENANTIOMERS OF 8,9- AND 11,12-EPOXYEICOSATRIENOIC ACID
Mosset, Paul,Yadagiri, Pendri,Lumin, Sun,Capdevila, Jorge,Falck, J. R.
, p. 6035 - 6038 (2007/10/02)
Both enantiomers of the epoxygenase metabolites 8,9- and 11,12-epoxyeicosatrienoic acid (EET) were synthesized by a convergent strategy utilizing dimethyl D- or L-malate and erythrospecific epoxidation.
