Cytochrome P450 ω-Hydroxylases in Inflammation and Cancer

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Cytochrome P450 ω-Hydroxylases in Inflammation and Cancer is …
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review articleQ7318358
scholarly articleQ13442814

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P356DOI10.1016/BS.APHA.2015.05.002
P932PMC publication ID4667791
P698PubMed publication ID26233909

P2093author name stringAllan E Rettie
Amanda L Johnson
Rheem A Totah
Katheryne Z Edson
P2860cites workRole of human CYP4F2 in hepatic catabolism of the proinflammatory agent leukotriene B4Q22004251
Formation of 20-hydroxyeicosatetraenoic acid, a vasoactive and natriuretic eicosanoid, in human kidney. Role of Cyp4F2 and Cyp4A11Q22011198
Expression and characterization of CYP4V2 as a fatty acid omega-hydroxylaseQ24321523
CYP4F2 is a vitamin K1 oxidase: An explanation for altered warfarin dose in carriers of the V433M variantQ24322624
Metabolism of arachidonic acid to 20-hydroxy-5,8,11, 14-eicosatetraenoic acid by P450 enzymes in human liver: involvement of CYP4F2 and CYP4A11Q24322910
Cytochrome P450 omega hydroxylase (CYP4) function in fatty acid metabolism and metabolic diseasesQ24324593
A novel form of cytochrome P-450 family 4 in human polymorphonuclear leukocytes. cDNA cloning and expression of leukotriene B4 omega-hydroxylaseQ24329233
Cytochrome P450-dependent catabolism of vitamin K: ω-hydroxylation catalyzed by human CYP4F2 and CYP4F11Q24338572
Vascular endothelial growth factor and its receptor system: physiological functions in angiogenesis and pathological roles in various diseasesQ27004077
Resolution phase lipid mediators of inflammation: agonists of resolutionQ27687489
Tumor angiogenesis: therapeutic implicationsQ27860595
Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxidesQ28143376
Oxidation of prostaglandin H(2) and prostaglandin H(2) analogues by human cytochromes P450: analysis of omega-side chain hydroxy metabolites and four steroisomers of 5-hydroxyprostaglandin I(1) by mass spectrometryQ28205818
Prostaglandins and leukotrienes: advances in eicosanoid biologyQ28208246
Identification of the orphan G protein-coupled receptor GPR31 as a receptor for 12-(S)-hydroxyeicosatetraenoic acidQ28241946
Leukotriene E4 elimination and metabolism in normal human subjectsQ28243042
Expression of rabbit cytochromes P4504A which catalyze the omega-hydroxylation of arachidonic acid, fatty acids, and prostaglandins.Q36755658
Biosynthesis and metabolism of leukotrienesQ36876280
Human cytochrome p450 family 4 enzymes: function, genetic variation and regulationQ36929610
Catalytic characterization and cytokine mediated regulation of cytochrome P450 4Fs in rat hepatocytesQ36951768
PPARalpha: mechanism of species differences and hepatocarcinogenesis of peroxisome proliferatorsQ37002053
Vascular cytochrome p450 enzymes: physiology and pathophysiology.Q37060993
Expression of CYP4A1 in U251 human glioma cell induces hyperproliferative phenotype in vitro and rapidly growing tumors in vivoQ37085203
Contribution of iNOS/sGC/PKG pathway, COX-2, CYP4A1, and gp91(phox) to the protective effect of 5,14-HEDGE, a 20-HETE mimetic, against vasodilation, hypotension, tachycardia, and inflammation in a rat model of septic shockQ37138417
Prostanoids in health and diseaseQ37354582
Epoxyeicosatrienoic acids: formation, metabolism and potential role in tissue physiology and pathophysiologyQ37510865
20-HETE regulates the angiogenic functions of human endothelial progenitor cells and contributes to angiogenesis in vivoQ37603893
Endothelial precursors in vascular repairQ37698702
Esterified eicosanoids: generation, characterization and functionQ37971413
Analysis of eicosanoids by LC-MS/MS and GC-MS/MS: a historical retrospect and a discussionQ38205276
Cancer, inflammation, and therapy: effects on cytochrome p450-mediated drug metabolism and implications for novel immunotherapeutic agents.Q38225574
The gluconeogenicity of fatty acids in mammalsQ38767950
20-Hydroxyeicosatetraenoic acid stimulates nuclear factor-kappaB activation and the production of inflammatory cytokines in human endothelial cellsQ40065601
Cytochrome p450 epoxygenase promotes human cancer metastasisQ40105564
Activation of vascular endothelial growth factor through reactive oxygen species mediates 20-hydroxyeicosatetraenoic acid-induced endothelial cell proliferation.Q40185278
9L gliosarcoma cell proliferation and tumor growth in rats are suppressed by N-hydroxy-N'-(4-butyl-2-methylphenol) formamidine (HET0016), a selective inhibitor of CYP4A.Q40340300
Role of the peroxisome proliferator-activated receptor in cytochrome P450 4A gene regulation.Q41135351
20-Hydroxyeicosatetraenoic acid is formed in response to EGF and is a mitogen in rat proximal tubuleQ41264412
Cytochrome P-450 induction by clofibrate. Purification and properties of a hepatic cytochrome P-450 relatively specific for the 12- and 11-hydroxylation of dodecanoic acid (lauric acid)Q41834836
Arachidonic acid-metabolizing cytochrome P450 enzymes are targets of {omega}-3 fatty acidsQ42108073
Discovery, characterization, and significance of the cytochrome P450 omega-hydroxylase pathway of vitamin E catabolismQ36064383
Disruption of mouse cytochrome p450 4f14 (Cyp4f14 gene) causes severe perturbations in vitamin E metabolismQ36122179
CYP4F enzymes are the major enzymes in human liver microsomes that catalyze the O-demethylation of the antiparasitic prodrug DB289 [2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime].Q36143432
Bioactivation of 4-Ipomeanol by a CYP4B enzyme in bovine lung and inhibition by HET0016.Q36175877
CYP4V2 in Bietti's crystalline dystrophy: ocular localization, metabolism of ω-3-polyunsaturated fatty acids, and functional deficit of the p.H331P variantQ36294398
Liver microsomal cytochrome P-450 and the oxidative metabolism of arachidonic acidQ36366640
20-Hydroxyeicosatetraenoic acid mediates calcium/calmodulin-dependent protein kinase II-induced mitogen-activated protein kinase activation in vascular smooth muscle cellsQ36531189
Cytochrome P450 4F subfamily: at the crossroads of eicosanoid and drug metabolismQ36574121
Expression and purification of orphan cytochrome P450 4X1 and oxidation of anandamideQ36611878
Eicosanoids in inflammation: biosynthesis, pharmacology, and therapeutic frontiersQ36737986
Angiogenesis in cancerQ36746626
Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formationQ28244417
Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in diseaseQ28248677
Lipid mediators in the resolution of inflammationQ28250668
Inside epoxyeicosatrienoic acids and cardiovascular diseaseQ28252156
Cytochrome P450 eicosanoids in hypertension and renal diseaseQ28252210
Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acidQ28252674
Vascular actions of 20-HETEQ28259468
Comparison of cytochrome P450 (CYP) genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternative-splice variantsQ28260351
Purification and characterization of recombinant human neutrophil leukotriene B4 omega-hydroxylase (cytochrome P450 4F3)Q28277320
Omega-oxidation of cysteine-containing leukotrienes by rat-liver microsomes. Isolation and characterization of omega-hydroxy and omega-carboxy metabolites of leukotriene E4 and N-acetylleukotriene E4Q28280612
Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acidsQ28294130
Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids.Q28343514
HET0016, a potent and selective inhibitor of 20-HETE synthesizing enzymeQ28365824
Activation of the acute inflammatory response alters cytochrome P450 expression and eicosanoid metabolismQ28385509
The 2014 Bernard B. Brodie award lecture-epoxide hydrolases: drug metabolism to therapeutics for chronic painQ28392416
The CYP4A isoforms hydroxylate epoxyeicosatrienoic acids to form high affinity peroxisome proliferator-activated receptor ligandsQ28578924
Prostaglandin and leukotriene omega-hydroxylasesQ28620124
Cyclooxygenases 1 and 2Q29615645
Cyclooxygenases: structural, cellular, and molecular biologyQ29616510
Leukotrienes and lipoxins: structures, biosynthesis, and biological effectsQ29617543
Breast cancer metastasis: markers and modelsQ29618061
P-450 metabolites of arachidonic acid in the control of cardiovascular functionQ29620578
Expression and characterization of human cytochrome P450 4F11: Putative role in the metabolism of therapeutic drugs and eicosanoidsQ30482728
20-HETE contributes to the acute fall in cerebral blood flow after subarachnoid hemorrhage in the rat.Q30827044
Hepatic cytochrome P450 3A drug metabolism is reduced in cancer patients who have an acute-phase responseQ30843051
Omega oxidation of 3-hydroxy fatty acids by the human CYP4F gene subfamily enzyme CYP4F11.Q30981862
Characterization of human liver leukotriene B(4) omega-hydroxylase P450 (CYP4F2).Q31389061
Identification of a novel mammary-restricted cytochrome P450, CYP4Z1, with overexpression in breast carcinomaQ33200791
Altered inflammatory responses to Citrobacter rodentium infection, but not bacterial lipopolysaccharide, in mice lacking the Cyp4a10 or Cyp4a14 genesQ33671358
Vascular characterization of mice with endothelial expression of cytochrome P450 4F2.Q33775129
Expression of the CYP4F3 gene. tissue-specific splicing and alternative promoters generate high and low K(m) forms of leukotriene B(4) omega-hydroxylaseQ33868385
Promoter activity and regulation of the CYP4F2 leukotriene B(4) omega-hydroxylase gene by peroxisomal proliferators and retinoic acid in HepG2 cellsQ33906310
Regulation of CYP4F2 leukotriene B4 omega-hydroxylase by retinoic acids in HepG2 cellsQ33931951
Alterations in the regulation of androgen-sensitive Cyp 4a monooxygenases cause hypertensionQ33943987
Calibration of the channel that determines the omega-hydroxylation regiospecificity of cytochrome P4504A1: catalytic oxidation of 12-HALODOdecanoic acidsQ33947774
Eicosanoids and cancerQ33966203
Effects of 20-HETE and 19(S)-HETE on rabbit proximal straight tubule volume transportQ34014771
Alternative splicing determines the function of CYP4F3 by switching substrate specificityQ34084417
Lipoxins: revelations on resolutionQ34085413
Activation of mitogen-activated protein kinases by vascular endothelial growth factor and basic fibroblast growth factor in capillary endothelial cells is inhibited by the antiangiogenic factor 16-kDa N-terminal fragment of prolactinQ34121190
Profiling the expression of cytochrome P450 in breast cancerQ34131684
Cytochrome P450-derived eicosanoids: the neglected pathway in cancerQ34143118
Effects of 5,14-HEDGE, a 20-HETE mimetic, on lipopolysaccharide-induced changes in MyD88/TAK1/IKKβ/IκB-α/NF-κB pathway and circulating miR-150, miR-223, and miR-297 levels in a rat model of septic shock.Q34151380
Cytochrome P450 ω-hydroxylase promotes angiogenesis and metastasis by upregulation of VEGF and MMP-9 in non-small cell lung cancerQ34152658
The enzymology of prostaglandin endoperoxide H synthases-1 and -2.Q34159094
Omega-3 fatty acids in inflammation and autoimmune diseasesQ34164525
Prostaglandins and inflammationQ34179727
20-HETE-producing enzymes are up-regulated in human cancers.Q34288316
Increased expression of CYP4Z1 promotes tumor angiogenesis and growth in human breast cancer.Q34290867
Targeting 20-HETE producing enzymes in cancer - rationale, pharmacology, and clinical potentialQ34338086
Identification of a new P450 subfamily, CYP4F1, expressed in rat hepatic tumorsQ34359645
Conditional regulation of the human CYP4X1 and CYP4Z1 genesQ34407244
Cytochrome p450 profile of colorectal cancer: identification of markers of prognosisQ34419306
Metabolism of 20-hydroxyeicosatetraenoic acid by cyclooxygenase. Formation and identification of novel endothelium-dependent vasoconstrictor metabolitesQ34428688
Human U251 glioma cell proliferation is suppressed by HET0016 [N-hydroxy-N'-(4-butyl-2-methylphenyl)formamidine], a selective inhibitor of CYP4A.Q34440503
Profiling cytochrome P450 expression in ovarian cancer: identification of prognostic markersQ34462038
Regulation of human cytochrome P450 4F2 expression by sterol regulatory element-binding protein and lovastatinQ34586649
Temporal changes of cytochrome P450 (Cyp) and eicosanoid-related gene expression in the rat brain after traumatic brain injuryQ34705038
Genistein, resveratrol, and 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside induce cytochrome P450 4F2 expression through an AMP-activated protein kinase-dependent pathwayQ34715847
Human CYP4Z1 catalyzes the in-chain hydroxylation of lauric acid and myristic acid.Q34906403
20-Hydroxylation is the CYP-dependent and retinoid-inducible leukotriene B4 inactivation pathway in human and mouse skin cellsQ34982901
Biochemical and molecular properties of the cytochrome P450 arachidonic acid monooxygenases.Q34997982
Down-regulation of 20-HETE synthesis and signaling inhibits renal adenocarcinoma cell proliferation and tumor growth.Q35008976
Finding homes for orphan cytochrome P450s: CYP4V2 and CYP4F22 in disease states.Q35030324
Identification of amino acid determinants in CYP4B1 for optimal catalytic processing of 4-ipomeanol.Q35032512
The cytochrome P450 4A/F-20-hydroxyeicosatetraenoic acid system: a regulator of endothelial precursor cells derived from human umbilical cord bloodQ35122891
Mass spectrometry based lipidomics: an overview of technological platformsQ35193597
Resolvins and protectins in inflammation resolution.Q35332873
Epoxyeicosanoids stimulate multiorgan metastasis and tumor dormancy escape in miceQ35640579
CYP4Fs expression in rat brain correlates with changes in LTB4 levels after traumatic brain injuryQ42128844
Identification and biological activity of novel omega-oxidized metabolites of leukotriene B4 from human leukocytesQ42257673
Effects of a 20-HETE antagonist and agonists on cerebral vascular toneQ42457671
Western blots versus selected reaction monitoring assays: time to turn the tables?Q42595907
Smooth muscle--specific expression of CYP4A1 induces endothelial sprouting in renal arterial microvesselsQ42833184
Suppression of hepatocyte nuclear factor-4alpha by acyl-CoA thioesters of hypolipidemic peroxisome proliferatorsQ43574299
Discovery of a N'-hydroxyphenylformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitorQ43803513
Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomesQ43830180
CYP4A metabolites of arachidonic acid and VEGF are mediators of skeletal muscle angiogenesisQ44274467
Differential expression of cytochrome P450 omega-hydroxylase isoforms and their association with clinicopathological features in pancreatic ductal adenocarcinoma.Q44362268
Regulation of renal CYP4A expression and 20-HETE synthesis by nitric oxide in pregnant ratsQ44396063
Urinary metabolites of leukotriene B4 in the human subjectQ44412878
Pyrazole and isoxazole derivatives as new, potent, and selective 20-hydroxy-5,8,11,14-eicosatetraenoic acid synthase inhibitorsQ44670150
Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxidesQ44897935
Ketoconazole increases fingolimod blood levels in a drug interaction via CYP4F2 inhibitionQ46178229
Characterization of the active site properties of CYP4F12.Q46431804
Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolismQ46520416
WY-14 643 rapidly activates nuclear factor kappaB in Kupffer cells before hepatocytesQ47770934
Effects of fenofibrate on plasma cytokine concentrations in patients with atherosclerosis and hyperlipoproteinemia IIb.Q47862536
Activation of human aortic smooth-muscle cells is inhibited by PPARalpha but not by PPARgamma activatorsQ47877643
Tumor-specific expression of cytochrome P450 CYP1B1.Q48657856
Randomized placebo-controlled intervention with n-3 LC-PUFA-supplemented yoghurt: effects on circulating eicosanoids and cardiovascular risk factors.Q50496603
Functional aspects of eicosanoid hydroxylation by lung and kidney cytochromes P450. Expression of cDNAs in mammalian cells and E. coli.Q54661547
Oxidation of prostaglandin H2 and prostaglandin H2 analogues by human cytochromes P450: analysis of ω-side chain hydroxy metabolites and four steroisomers of 5-hydroxyprostaglandin I1 by mass spectrometry11Abbreviations: CYP, cytochrome P450; HHT, (Q56594078
Effects of 17-octadecynoic acid, a suicide-substrate inhibitor of cytochrome P450 fatty acid omega-hydroxylase, on renal function in ratsQ57222889
Hypolipidaemic hepatic peroxisome proliferators form a novel class of chemical carcinogensQ59072082
Metabolic Inactivation of Resolvin E1 and Stabilization of Its Anti-inflammatory ActionsQ61632740
Expression of glutathione S-transferases and cytochrome P450 in normal and tumor breast tissueQ64445223
Clofibrate-inducible rat hepatic P450s IVA1 and IVA3 catalyze the omega- and (omega-1)-hydroxylation of fatty acids and the omega-hydroxylation of prostaglandins E1 and F2 alphaQ68664961
Role of hemoprotein P-450 in fatty acid omega-hydroxylation in a soluble enzyme system from liver microsomesQ68726619
Conversion of arachidonic acid to two novel products by a cytochrome P450-dependent mixed-function oxidase in polymorphonuclear leukocytesQ70500858
Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytesQ72389890
Segregated coupling of phospholipases A2, cyclooxygenases, and terminal prostanoid synthases in different phases of prostanoid biosynthesis in rat peritoneal macrophagesQ74336632
Distribution of COX-1 and COX-2 in normal and inflamed tissuesQ74454815
OMEGA-OXIDATION OF LONG CHAIN FATTY ACIDS IN RAT LIVERQ76707110
Transcellular regulation of eicosanoid biosynthesisQ77796361
Kupffer cell oxidant production is central to the mechanism of peroxisome proliferatorsQ77958214
The cytochromes P450 (CYP) response to allergic inflammation of the lungQ79325392
P450 CYP2C epoxygenase and CYP4A omega-hydroxylase mediate ciprofibrate-induced PPARalpha-dependent peroxisomal proliferationQ79596635
Studies on omega-oxidation of fatty acids in vitro. I. Overall reaction and intermediateQ79703158
Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid productionQ79838379
Inflammation resolved by retinoid X receptor-mediated inactivation of leukotriene signaling pathwaysQ81331990
LeukotrienesQ81542824
Cytochrome P4504f, a potential therapeutic target limiting neuroinflammationQ83785218
A search for reliable molecular markers of prognosis in prostate cancer: a study of 240 casesQ84131673
Immunochemical and mass-spectrometry-based serum hepcidin assays for iron metabolism disordersQ84805975
Molecular modelling of CYP4A subfamily members based on sequence homology with CYP102Q93927609
P407language of work or nameEnglishQ1860
P921main subjectinflammationQ101991
P304page(s)223-62
P577publication date2015-01-01
P1433published inAdvances in PharmacologyQ15753809
P1476titleCytochrome P450 ω-Hydroxylases in Inflammation and Cancer
P478volume74

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