ArticleRapid communications in mass spectrometry : RCM2010
Analysis of epoxyeicosatrienoic acids by chiral liquid chromatography/electron capture atmospheric pressure chemical ionization mass spectrometry using [13C]-analog internal standards.
Article in Rapid communications in mass spectrometry : RCM, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 36 citations in OpenAlex.
- Unraveling enantioselective metabolism: Human cytochrome P450s in arachidonic acid biotransformation.Drug metabolism and disposition: the biological fate of chemicals · 2025Article
- Functional omics of ORP7 in primary endothelial cells.BMC biology · 2024Article
- Identification and validation of cortisol-related hub biomarkers and the related pathogenesis of biomarkers in Ischemic Stroke.Brain and behavior · 2024Article
- Identification of sex-specific genetic associations in response to opioid analgesics in a White, non-Hispanic cohort from Southeast Minnesota.The pharmacogenomics journal · 2022Article
- Vascular Damage, Thromboinflammation, Plasmablast Activation, T-Cell Dysregulation and Pathological Histiocytic Response in Pulmonary Draining Lymph Nodes of COVID-19.Frontiers in immunology · 2021Article
- Article
- Methods of the Analysis of Oxylipins in Biological Samples.Molecules (Basel, Switzerland) · 2020Review
- Modern Methods of Sample Preparation for the Analysis of Oxylipins in Biological Samples.Molecules (Basel, Switzerland) · 2019Review
- Chiral lipidomics of monoepoxy and monohydroxy metabolites derived from long-chain polyunsaturated fatty acids.Journal of lipid research · 2019Article
- Analysis of HETEs in human whole blood by chiral UHPLC-ECAPCI/HRMS.Journal of lipid research · 2018Article
- Expression and Functional Characterization of Breast Cancer-Associated Cytochrome P450 4Z1 inDrug metabolism and disposition: the biological fate of chemicals · 2017Article
- Novel liquid chromatography-mass spectrometry method shows that vitamin E deficiency depletes arachidonic and docosahexaenoic acids in zebrafish (Danio rerio) embryos.Redox biology · 2013Article
- Targeted chiral analysis of bioactive arachidonic Acid metabolites using liquid-chromatography-mass spectrometry.Metabolites · 2012Article
- Mass spectrometry strategies in metabolomics.The Journal of biological chemistry · 2011Review
- Stable isotope labeling by essential nutrients in cell culture for preparation of labeled coenzyme A and its thioesters.Analytical chemistry · 2011Article
- A new liquid chromatography/mass spectrometry method for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in urine.Rapid communications in mass spectrometry : RCM · 2011Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
Abstract
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 [(13)C(20)]-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.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.