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Journal articles on the topic 'CYP4A11'

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Published: 11 March 2023

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1

Muller, Dominik N., Cosima Schmidt, Eduardo Barbosa-Sicard, Maren Wellner, Volkmar Gross, Hantz Hercule, Marija Markovic, Horst Honeck, Friedrich C. Luft, and Wolf-Hagen Schunck. "Mouse Cyp4a isoforms: enzymatic properties, gender- and strain-specific expression, and role in renal 20-hydroxyeicosatetraenoic acid formation." Biochemical Journal 403, no. 1 (March 13, 2007): 109–18. http://dx.doi.org/10.1042/bj20061328.

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AA (arachidonic acid) hydroxylation to 20-HETE (20-hydroxyeicosatetraenoic acid) influences renal vascular and tubular function. To identify the CYP (cytochrome P450) isoforms catalysing this reaction in the mouse kidney, we analysed the substrate specificity of Cyp4a10, 4a12a, 4a12b and 4a14 and determined sex- and strain-specific expressions. All recombinant enzymes showed high lauric acid hydroxylase activities. Cyp4a12a and Cyp4a12b efficiently hydroxylated AA to 20-HETE with Vmax values of approx. 10 nmol·nmol−1·min−1 and Km values of 20–40 μM. 20-Carboxyeicosatetraenoic acid occurred as a secondary metabolite. AA hydroxylase activities were approx. 25–75-fold lower with Cyp4a10 and not detectable with Cyp4a14. Cyp4a12a and Cyp4a12b also efficiently converted EPA (eicosapentaenoic acid) into 19/20-OH- and 17,18-epoxy-EPA. In male mice, renal microsomal AA hydroxylase activities ranged between approx. 100 (NMRI), 45–55 (FVB/N, 129 Sv/J and Balb/c) and 25 pmol·min−1·mg−1 (C57BL/6). The activities correlated with differences in Cyp4a12a protein and mRNA levels. Treatment with 5α-dihydrotestosterone induced both 20-HETE production and Cyp4a12a expression more than 4-fold in male C57BL/6 mice. All female mice showed low AA hydroxylase activities (15–25 pmol·min−1·mg−1) and very low Cyp4a12a mRNA and protein levels, but high Cyp4a10 and Cyp4a14 expression. Renal Cyp4a12b mRNA expression was almost undetectable in both sexes of all strains. Thus Cyp4a12a is the predominant 20-HETE synthase in the mouse kidney. Cyp4a12a expression determines the sex- and strain-specific differences in 20-HETE generation and may explain sex and strain differences in the susceptibility to hypertension and target organ damage.

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2

HENG, Yee M., C. W. Sharon KUO, Paul S. JONES, Richard SAVORY, Ruth M. SCHULZ, Simon R. TOMLINSON, Tim J. B. GRAY, and David R. BELL. "A novel murine P-450 gene, Cyp4a14, is part of a cluster of Cyp4a and Cyp4b, but not of CYP4F, genes in mouse and humans." Biochemical Journal 325, no. 3 (August 1, 1997): 741–49. http://dx.doi.org/10.1042/bj3250741.

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Genomic clones for Cyp4a12 and a novel member of the murine Cyp4a gene family were isolated. The novel gene, designated Cyp4a14, has a GC rich sequence immediately 5′ of the transcription start site, and is similar to the rat CYP4A2 and CYP4A3 genes. The Cyp4a14 gene spans approximately 13 kb, and contains 12 exons; sequence similarity to the rat CYP4A2 gene sequence falls off 300 bp upstream from the start site. In view of the known sex-specific expression of the rat CYP4A2 gene, the expression and inducibility of Cyp4a14 was examined. The gene was highly inducible in the liver when mice were treated with the peroxisome proliferator, methylclofenapate; induction levels were low in control animals and no sex differences in expression were observed. By contrast, the Cyp4a12 RNA was highly expressed in liver and kidney of control male mice but was expressed at very low levels in liver and kidney of female mice. Testosterone treatment increased the level of this RNA in female liver slightly, and to a greater extent in the kidney of female mice. In agreement with studies on the cognate RNA, expression of Cyp4a12 protein was male-specific in the liver of control mice and extremely high inducibility of Cyp4a10 protein, with no sex differences, was also demonstrated. In view of the overlapping patterns of inducibility of the three Cyp4a genes, we investigated whether the three genes were co-localized in the genome. Two overlapping yeast artificial chromosome (YAC) clones were isolated, and the three Cyp4a genes were shown to be present on a single YAC of 220 kb. The Cyp4a genes are adjacent to the Cyp4b1 gene, with Cyp4a12 most distant from Cyp4b1. The clustering of these two gene subfamilies in the mouse was replicated in the human, where the CYPA411 and CYP4B1 genes were present in a single YAC clone of 440 kb. However, the human CYP4F2 gene was mapped to chromosome 19. Phylogenetic analysis of the CYP4 gene families demonstrated that CYP4A and CYP4B are more closely related than CYP4F.

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3

Savas, Üzen, Daniel E. W. Machemer, Mei-Hui Hsu, Pryce Gaynor, Jerome M. Lasker, Robert H. Tukey, and Eric F. Johnson. "Opposing Roles of Peroxisome Proliferator-activated Receptor α and Growth Hormone in the Regulation of CYP4A11 Expression in a Transgenic Mouse Model." Journal of Biological Chemistry 284, no. 24 (April 14, 2009): 16541–52. http://dx.doi.org/10.1074/jbc.m902074200.

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CYP4A11 transgenic mice (CYP4A11 Tg) were generated to examine in vivo regulation of the human CYP4A11 gene. Expression of CYP4A11 in mice yields liver and kidney P450 4A11 levels similar to those found in the corresponding human tissues and leads to an increased microsomal capacity for ω-hydroxylation of lauric acid. Fasted CYP4A11 Tg mice exhibit 2–3-fold increases in hepatic CYP4A11 mRNA and protein, and this response is absent in peroxisome proliferator-activated receptor α (PPARα) null mice. Dietary administration of either of the PPARα agonists, fenofibrate or clofibric acid, increases hepatic and renal CYP4A11 levels by 2–3-fold, and these responses were also abrogated in PPARα null mice. Basal liver CYP4A11 levels are reduced differentially in PPARα−/− females (>95%) and males (<50%) compared with PPARα−/+ mice. Quantitative and temporal differences in growth hormone secretion are known to alter hepatic lipid metabolism and to underlie sexually dimorphic gene expression, respectively. Continuous infusion of low levels of growth hormone reduced CYP4A11 expression by 50% in PPARα-proficient male and female transgenic mice. A larger decrease was observed for the expression of CYP4A11 in PPARα−/− CYP4A11 Tg male mice to levels similar to that of female PPARα-deficient mice. These results suggest that PPARα contributes to the maintenance of basal CYP4A11 expression and mediates CYP4A11 induction in response to fibrates or fasting. In contrast, increased exposure to growth hormone down-regulates CYP4A11 expression in liver.

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4

LUNDELL, Kerstin. "Cloning and expression of two novel pig liver and kidney fatty acid hydroxylases [cytochrome P450 (CYP)4A24 and CYP4A25]." Biochemical Journal 363, no. 2 (April 8, 2002): 297–303. http://dx.doi.org/10.1042/bj3630297.

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A new member of the cytochrome P450 (CYP) 4A subfamily (CYP4A21) was recently cloned by PCR from pig liver [Lundell, Hansson, and Wikvall (2001) J. Biol. Chem. 276, 9606–9612]. This enzyme does not catalyse ω- or (ω-1)-hydroxylation of lauric acid, the model substrate for CYP4A enzymes. Instead, CYP4A21 participates in bile acid biosynthesis in the pig. Extensive studies, primarily conducted to verify the aberrant amino acids found in CYP4A21 within a normally conserved CYP4A motif, revealed that besides CYP4A21 two additional sequences were co-amplified by PCR. These two sequences (designated CYP4A24 and CYP4A25), generated from both pig liver and kidney, were characterized by restriction-enzyme analysis and were subsequently cloned. The deduced amino acid sequences of CYP4A24 and CYP4A25 share extensive sequence identity (97%). Both enzymes, expressed in yeast cells, exhibit ω-and (ω-1)-hydroxylase activities towards lauric acid and palmitic acid. The positions of the variable regions between CYP4A24 and CYP4A25, which are confined to β-sheets 1 and 4, indicate a possible difference in substrate specificity or regioselectivity. The porcine CYP4A21, CYP4A24 and CYP4A25 enzymes, with an overall identity of 94%, have probably evolved from a common ancestral gene, perhaps in conjunction with species-specific habits.

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5

Wang, Mong-Heng, Hui Guan, Xuandai Nguyen, Barbara A. Zand, Alberto Nasjletti, and Michal Laniado-Schwartzman. "Contribution of cytochrome P-450 4A1 and 4A2 to vascular 20-hydroxyeicosatetraenoic acid synthesis in rat kidneys." American Journal of Physiology-Renal Physiology 276, no. 2 (February 1, 1999): F246—F253. http://dx.doi.org/10.1152/ajprenal.1999.276.2.f246.

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20-Hydroxyeicosatetraenoic acids (20-HETE), a biologically active cytochrome P-450 (CYP) metabolite of arachidonic acid in the rat kidney, can be catalyzed by CYP4A isoforms including CYP4A1, CYP4A2, and CYP4A3. To determine the contribution of CYP4A isoforms to renal 20-HETE synthesis, specific antisense oligonucleotides (ODNs) were developed, and their specificity was examined in vitro in Sf9 cells expressing CYP4A isoforms and in vivo in Sprague-Dawley rats. Administration of CYP4A2 antisense ODNs (167 nmol ⋅ kg body wt−1 ⋅ day−1iv for 5 days) decreased vascular 20-HETE synthesis by 48% with no effect on tubular synthesis, whereas administration of CYP4A1 antisense ODNs inhibited vascular and tubular 20-HETE synthesis by 52 and 40%, respectively. RT-PCR of microdissected renal microvessel RNA indicated the presence of CYP4A1, CYP4A2, and CYP4A3 mRNAs, and a CYP4A1-immunoreactive protein was detected by Western analysis of microvessel homogenates. Blood pressure measurements revealed a reduction of 17 ± 6 and 16 ± 4 mmHg in groups receiving CYP4A1 and CYP4A2 antisense ODNs, respectively. These studies implicate CYP4A1 as a major 20-HETE synthesizing activity in the rat kidney and further document the feasibility of using antisense ODNs to specifically inhibit 20-HETE synthesis and thereby investigate its role in the regulation of renal function and blood pressure.

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6

Nguyen, Xuandai, Mong-Heng Wang, Komandla M. Reddy, John R. Falck, and Michal Laniado Schwartzman. "Kinetic profile of the rat CYP4A isoforms: arachidonic acid metabolism and isoform-specific inhibitors." American Journal of Physiology-Regulatory, Integrative and Comparative Physiology 276, no. 6 (June 1, 1999): R1691—R1700. http://dx.doi.org/10.1152/ajpregu.1999.276.6.r1691.

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20-Hydroxyeicosatetraenoic acid (HETE), the cytochrome P-450 (CYP) 4A ω-hydroxylation product of arachidonic acid, has potent biological effects on renal tubular and vascular functions and on the control of arterial pressure. We have expressed high levels of the rat CYP4A1, -4A2, -4A3, and -4A8 cDNAs, using baculovirus and Sf 9 insect cells. Arachidonic acid ω- and ω-1-hydroxylations were catalyzed by three of the CYP4A isoforms; the highest catalytic efficiency of 947 nM−1 ⋅ min−1for CYP4A1 was followed by 72 and 22 nM−1 ⋅ min−1for CYP4A2 and CYP4A3, respectively. CYP4A2 and CYP4A3 exhibited an additional arachidonate 11,12-epoxidation activity, whereas CYP4A1 operated solely as an ω-hydroxylase. CYP4A8 did not catalyze arachidonic or linoleic acid but did have a detectable lauric acid ω-hydroxylation activity. The inhibitory activity of various acetylenic and olefinic fatty acid analogs revealed differences and indicated isoform-specific inhibition. These studies suggest that CYP4A1, despite its low expression in extrahepatic tissues, may constitute the major source of 20-HETE synthesis. Moreover, the ability of CYP4A2 and -4A3 to catalyze the formation of two opposing biologically active metabolites, 20-HETE and 11,12-epoxyeicosatrienoic acid, may be of great significance to the regulation of vascular tone.

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7

Cho, Byeong Hoon, Byung Lae Park, Lyoung Hyo Kim, Hyun Sub Chung, and Hyoung Doo Shin. "Highly polymorphic human CYP4A11 gene." Journal of Human Genetics 50, no. 5 (May 2005): 259–63. http://dx.doi.org/10.1007/s10038-005-0245-9.

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8

Bell, D. R., N. J. Plant, C. G. Rider, L. Na, S. Brown, I. Ateitalla, S. K. Acharya, et al. "Species-specific induction of cytochrome P-450 4A RNAs: PCR cloning of partial guinea-pig, human and mouse CYP4A cDNAs." Biochemical Journal 294, no. 1 (August 15, 1993): 173–80. http://dx.doi.org/10.1042/bj2940173.

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PCR was used to demonstrate the presence of a conserved region and to clone novel members of the cytochrome P-450 4A gene family from guinea pig, human and mouse cDNAs. This strategy is based on the sequences at nucleotides 925-959 and at the haem binding domain (nucleotides 1381-1410) of the rat CYP4A1 gene. Murine Cyp4a clones showed high sequence identity with members of the rat gene family, but CYP4A clones from human and guinea pig were equally similar to the rat/mouse genes, suggesting that the rat/mouse line had undergone gene duplication events after divergence from human and guinea-pig lines. The mouse Cyp4a-12 clone was localized to chromosome 4 using interspecific backcross mapping, in a region of synteny with human chromosome 1. The assignment of the human CYP4A11 gene to chromosome 1 was confirmed by somatic cell hybridization. An RNAase protection assay was shown to discriminate between the murine Cyp4a-10 and Cyp4a-12 cDNAs. Treatment of mice with the potent peroxisome proliferator methylclofenapate (25 mg/kg) induced Cyp4a-10 RNA in liver, and to a lesser extent in kidney; there was no sex difference in this response. Cyp4a-12 RNA was present at high levels in male control liver and kidney samples, and was not induced by treatment with methylclofenapate. However, Cyp4a-12 RNA was present at low levels in control female liver and kidney RNA, and was greatly induced in both organs by methylclofenapate. Guinea pigs were exposed to methylclofenapate (50 mg/kg), but there was no significant induction of the guinea-pig CYP4A13 RNA. These findings are consistent with a species difference in response to peroxisome proliferators between the rat/mouse and the guinea pig.

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9

Elijovich, Fernando, and Cheryl L. Laffer. "The relationship between CYP4A11 and human hypertension." Journal of Hypertension 26, no. 8 (August 2008): 1712–14. http://dx.doi.org/10.1097/hjh.0b013e3283000504.

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10

Yamaori, Satoshi, Noriyuki Araki, Kurumi Ikehata, Shigeru Ohmori, and Kazuhito Watanabe. "Epalrestat potently and selectively inhibits CYP4A11 activity." Drug Metabolism and Pharmacokinetics 32, no. 1 (January 2017): S55. http://dx.doi.org/10.1016/j.dmpk.2016.10.224.

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11

Shekhar, Shashank, Kevin Varghese, Man Li, Letao Fan, George Booz, Richard Roman, and Fan Fan. "Conflicting Roles of 20-HETE in Hypertension and Stroke." International Journal of Molecular Sciences 20, no. 18 (September 11, 2019): 4500. http://dx.doi.org/10.3390/ijms20184500.

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Hypertension is the most common modifiable risk factor for stroke, and understanding the underlying mechanisms of hypertension and hypertension-related stroke is crucial. 20-hydroxy-5, 8, 11, 14-eicosatetraenoic acid (20-HETE), which plays an important role in vasoconstriction, autoregulation, endothelial dysfunction, angiogenesis, inflammation, and blood-brain barrier integrity, has been linked to hypertension and stroke. 20-HETE can promote hypertension by potentiating the vascular response to vasoconstrictors; it also can reduce blood pressure by inhibition of sodium transport in the kidney. The production of 20-HETE is elevated after the onset of both ischemic and hemorrhagic strokes; on the other hand, subjects with genetic variants in CYP4F2 and CYP4A11 that reduce 20-HETE production are more susceptible to stroke. This review summarizes recent genetic variants in CYP4F2, and CYP4A11 influencing 20-HETE production and discusses the role of 20-HETE in hypertension and the susceptibility to the onset, progression, and prognosis of ischemic and hemorrhagic strokes.

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12

Wang, Mong-Heng, Jishi Wang, Hsin-Hsin Chang, Barbara A. Zand, Miao Jiang, Alberto Nasjletti, and Michal Laniado-Schwartzman. "Regulation of renal CYP4A expression and 20-HETE synthesis by nitric oxide in pregnant rats." American Journal of Physiology-Renal Physiology 285, no. 2 (August 2003): F295—F302. http://dx.doi.org/10.1152/ajprenal.00065.2003.

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20-Hydroxyeicosatetraenoic acid (20-HETE), which promotes renal vasoconstriction, is formed in the rat kidney primarily by cytochrome P-450 (CYP) 4A isoforms (4A1, 4A2, 4A3, 4A8). Nitric oxide (NO) has been shown to bind to the heme moiety of the CYP4A2 protein and to inhibit 20-HETE synthesis in renal arterioles of male rats. However, it is not known whether NO interacts with and affects the activity of CYP4A1 and CYP4A3, the major renal CYP4A isoforms in female rats. Incubation of recombinant CYP4A1 and 4A3 proteins with sodium nitroprusside (SNP) shifted the absorbance at 440 nm, indicating the formation of a ferric-nitrosyl-CYP4A complex. The absorbance for CYP4A3 was about twofold higher than that of CYP4A1. Incubation of SNP or peroxynitrite (PN; 0.01–1 mM) with CYP4A recombinant membranes caused a concentration-dependent inhibition of 20-HETE synthesis, with both chemicals having a greater inhibitory effect on CYP4A3-catalyzed activity. Moreover, incubation of CYP4A1 and 4A3 proteins with PN (1 mM) resulted in nitration of tyrosine residues in both proteins. In addition, PN and SNP inhibited 20-HETE synthesis in renal microvessels from female rats by 65 and 59%, respectively. We previously showed that microvessel CYP4A1/CYP4A3 expression and 20-HETE synthesis are decreased in late pregnancy. Therefore, we investigated whether such a decrease is dependent on NO, the synthesis of which has been shown to increase in late pregnancy. Administration of NG-nitro-l-arginine methyl ester (l-NAME) to pregnant rats for 6 days ( days 15- 20 of pregnancy) caused a significant increase in systolic blood pressure, which was prevented by concurrent treatment with the CYP4A inhibitor 1-aminobenzotriazole (ABT). Urinary NO2/NO3 excretion decreased by 40 and 52% in l-NAME- and l-NAME + ABT-treated groups, respectively. Interestingly, renal microvessel 20-HETE synthesis showed a marked increase following l-NAME treatment, and this increase was diminished with coadministration of ABT. These results demonstrate that NO interacts with CYP4A proteins in a distinct manner and it interferes with renal microvessel 20-HETE synthesis, which may play an important role in the regulation of blood pressure and renal function during pregnancy.

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13

Marji, Jackleen S., Mong-Heng Wang, and Michal Laniado-Schwartzman. "Cytochrome P-450 4A isoform expression and 20-HETE synthesis in renal preglomerular arteries." American Journal of Physiology-Renal Physiology 283, no. 1 (July 1, 2002): F60—F67. http://dx.doi.org/10.1152/ajprenal.00265.2001.

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20-Hydroxyeicosatetraenoic acid (20-HETE), a potent vasoconstrictor and mediator of the myogenic response, is a major arachidonic acid metabolite in the microvasculature of the rat kidney formed primarily by the cytochrome P-450 (CYP) 4A isoforms, CYP4A1, CYP4A2, and CYP4A3. We examined CYP4A isoform expression and 20-HETE synthesis in microdissected interlobar, arcuate, and interlobular arteries; mRNA for all CYP4A isoforms was identified by RT-PCR. Western blot analysis indicated that the levels of CYP4A2/4A3-immunoreactive protein increased with decreased arterial diameter, whereas those of CYP4A1-immunoreactive protein remained unchanged. 20-HETE synthesis was the highest in the interlobular arteries (17 ± 1.62 nmol · mg−1 · h−1) and, like CYP4A2/4A3-immunoreactive protein, decreased with increasing vessel diameter (4.5 ± 1.21, 2.65 ± 0.58, and 0.81 ± 0.14 nmol · mg−1 · h−1 in the arcuate, interlobar, and segmental arteries, respectively). 20-HETE synthesis in the renal artery and the abdominal aorta was undetectable. The observed decreased immunoreactivity of NADPH-cytochrome P-450 ( c) oxidoreductase with increased arterial diameter provided a possible explanation for the decreased capacity to generate 20-HETE in the large arteries. The increase in CYP4A isoform expression and 20-HETE synthesis with decreasing diameter along the preglomerular arteries and the potent biological activity of 20-HETE underscore the significance of 20-HETE as a modulator of renal hemodynamics.

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14

Yamaori, Satoshi, Noriyuki Araki, Mio Shionoiri, Kurumi Ikehata, Shinobu Kamijo, Shigeru Ohmori, and Kazuhito Watanabe. "A Specific Probe Substrate for Evaluation of CYP4A11 Activity in Human Tissue Microsomes and a Highly Selective CYP4A11 Inhibitor: Luciferin-4A and Epalrestat." Journal of Pharmacology and Experimental Therapeutics 366, no. 3 (July 5, 2018): 446–57. http://dx.doi.org/10.1124/jpet.118.249557.

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15

Lino Cardenas, Christian L., Nicolas Renault, Amaury Farce, Christelle Cauffiez, Delphine Allorge, Jean-Marc Lo-Guidice, Michel Lhermitte, Philippe Chavatte, Franck Broly, and Dany Chevalier. "Genetic polymorphism of CYP4A11 and CYP4A22 genes and in silico insights from comparative 3D modelling in a French population." Gene 487, no. 1 (November 2011): 10–20. http://dx.doi.org/10.1016/j.gene.2011.07.015.

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16

Williams, Jonathan S., Paul N. Hopkins, Xavier Jeunemaitre, and Nancy J. Brown. "CYP4A11 T8590C polymorphism, salt-sensitive hypertension, and renal blood flow." Journal of Hypertension 29, no. 10 (October 2011): 1913–18. http://dx.doi.org/10.1097/hjh.0b013e32834aa786.

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17

Chang, Yan-Tyng, and Gilda H. Loew. "Homology modeling and substrate binding study of human CYP4A11 enzyme." Proteins: Structure, Function, and Genetics 34, no. 3 (February 15, 1999): 403–15. http://dx.doi.org/10.1002/(sici)1097-0134(19990215)34:3<403::aid-prot12>3.0.co;2-d.

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18

Antoun, Joseph, Yolande Amet, Brigitte Simon, Yvonne Dréano, Anne Corlu, Laurent Corcos, Jean Pierre Salaun, and Emmanuelle Plée-Gautier. "CYP4A11 is repressed by retinoic acid in human liver cells." FEBS Letters 580, no. 14 (May 11, 2006): 3361–67. http://dx.doi.org/10.1016/j.febslet.2006.05.006.

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19

Choi, Seunghye, Songhee Han, Hwayoun Lee, Young-Jin Chun, and Donghak Kim. "Evaluation of Luminescent P450 Analysis for Directed Evolution of Human CYP4A11." Biomolecules and Therapeutics 21, no. 6 (November 30, 2013): 487–92. http://dx.doi.org/10.4062/biomolther.2013.086.

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20

Gainer, James V., Michael S. Lipkowitz, Chang Yu, Michael R. Waterman, Elliott P. Dawson, Jorge H. Capdevila, and Nancy J. Brown. "Association of a CYP4A11 Variant and Blood Pressure in Black Men." Journal of the American Society of Nephrology 19, no. 8 (April 2, 2008): 1606–12. http://dx.doi.org/10.1681/asn.2008010063.

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21

Fu, Zhenyan, Tomohiro Nakayama, Naoyuki Sato, Yoichi Izumi, Yuji Kasamaki, Atsushi Shindo, Masakatsu Ohta, et al. "Haplotype-based case-control study of CYP4A11 gene and myocardial infarction." Hereditas 149, no. 3 (June 2012): 91–98. http://dx.doi.org/10.1111/j.1601-5223.2012.02247.x.

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White, C. C., Q. Feng, L. A. Cupples, J. V. Gainer, E. P. Dawson, R. A. Wilke, and N. J. Brown. "CYP4A11 variant is associated with high-density lipoprotein cholesterol in women." Pharmacogenomics Journal 13, no. 1 (September 13, 2011): 44–51. http://dx.doi.org/10.1038/tpj.2011.40.

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23

Dierks, Elizabeth A., Zhoupeng Zhang, Eric F. Johnson, and Paul R. Ortiz de Montellano. "The Catalytic Site of Cytochrome P4504A11 (CYP4A11) and Its L131F Mutant." Journal of Biological Chemistry 273, no. 36 (September 4, 1998): 23055–61. http://dx.doi.org/10.1074/jbc.273.36.23055.

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24

Bellamine, Aouatef, Yarong Wang, Michael R. Waterman, James V. Gainer III, Elliot P. Dawson, Nancy J. Brown, and Jorge H. Capdevila. "Characterization of the CYP4A11 gene, a second CYP4A gene in humans." Archives of Biochemistry and Biophysics 409, no. 1 (January 2003): 221–27. http://dx.doi.org/10.1016/s0003-9861(02)00545-3.

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Laniado-Schwartzman, Michal, Mong-Heng Wang, Jackleen Marji, Fan Zhang, Jun-Ichi Kaide, and Alberto Nasjletti. "Synthesis and Function of Cytochrome P450 4A1-Derived 20-Hydroxyeicosatetraenoic Acid in Rat Renal Arteries." Hypertension 36, suppl_1 (October 2000): 681–82. http://dx.doi.org/10.1161/hyp.36.suppl_1.681-e.

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22 20-hydroxyeicosatetraenoic acid (20-HETE) is the principal arachidonic acid metabolite in tubular and vascular structures of the rat kidney. In the tubules it inhibits sodium reabsorption, while in the renal microcirculation it is a vasoconstrictor and a regulator of myogenic tone. 20-HETE synthesis is catalyzed by the cytochrome P450 (CYP) 4A isoforms (4A1, 4A2, 4A3 and 4A8). Our studies indicated that despite the high homology, these isoforms display distinct catalytic properties. CYP4A1 is the low Km isoform and thus, by far, the most efficient 20-HETE synthesizing enzyme. Whereas CYP4A1 is solely an ω-hydroxylase, CYP4A2 and CYP4A3 also catalyze arachidonate 11,12-epoxidation. Systemic administration of CYP4A1 antisense oligodeoxynucleotides reduced the level of CYP4A proteins and 20-HETE synthesis in renal vessels by 50%, and decreased blood pressure in SHR from 137±3 to 121±4 mmHg (p < 0.05). Immunoblot analysis and inhibitor studies indicated that within the renal vasculature CYP4A1 is primarily localized to the interlobar arteries. Transfection of CYP4A1 cDNA, cloned into the expression plasmid pcDNA3.1, to renal interlobar arteries increased CYP4A immunoreactivity by 3-fold and 20-HETE synthesis from 92±10 to 239±71 pg 20-HETE/mg/h. CYP4A1-transfected arteries demonstrated a marked increase in the constrictor responses to phenylephrine (EC 50 = 0.07±0.02 vs 0.37±0.04 μM). The increased constrictor responses to phenylephrine were greatly attenuated by DDMS, a selective inhibitor of 20-HETE synthesis (EC 50 from 0.07±0.01 to 0.74±0.11 μM) and by 20-HEDE, a specific 20-HETE antagonist (to 0.54±0.05 μM) without affecting the maximal response. The inhibitory effect of DDMS was reversed by addition of 20-HETE further substantiating the notion that increased endogenous levels of 20-HETE contributed to the increased vascular reactivity to phenylephrine in vessels expressing the CYP4A1 cDNA. Thus, 20-HETE of vascular origin serves as a stimulatory regulator of vascular responses to phenylephrine.

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26

Kim, Sup, Jin Man Kim, Hyo Jin Lee, Jae Sung Lim, In-Ock Seong, and Kyung-Hee Kim. "Alteration of CYP4A11 expression in renal cell carcinoma: diagnostic and prognostic implications." Journal of Cancer 11, no. 6 (2020): 1478–85. http://dx.doi.org/10.7150/jca.36438.

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27

Lee, Hye-Ja, Mi-Kyung Park, Young-Ran Park, Dong-Hak Kim, Chul-Ho Yun, Young-Jin Chun, Hee-Jung Shin, Han-Sung Na, Myeon-Woo Chung, and Chang-Hoon Lee. "Expression of CYP2A6, CYP2D6 and CYP4A11 Polymorphisms in COS7 Mammalian Cell Line." Toxicological Research 27, no. 1 (March 1, 2011): 25–29. http://dx.doi.org/10.5487/tr.2011.27.1.025.

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Fu, Z. Y., T. Nakayama, N. Sato, Y. Izumi, Y. Kasamaki, A. Shindo, M. Ohta, et al. "P374 Haplotype-based case—control study of CYP4A11 gene and myocardial infarction." International Journal of Cardiology 125 (February 2008): S72. http://dx.doi.org/10.1016/s0167-5273(08)70285-7.

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29

Laffer, Cheryl L., James V. Gainer, Michael R. Waterman, Jorge H. Capdevila, Michal Laniado-Schwartzman, Alberto Nasjletti, Nancy J. Brown, and Fernando Elijovich. "The T8590C Polymorphism of CYP4A11 and 20-Hydroxyeicosatetraenoic Acid in Essential Hypertension." Hypertension 51, no. 3 (March 2008): 767–72. http://dx.doi.org/10.1161/hypertensionaha.107.102921.

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30

Han, Songhee, Gun-Su Cha, Young-Jin Chun, Chang Hoon Lee, Donghak Kim, and Chul-Ho Yun. "Biochemical analysis of recombinant CYP4A11 allelic variant enzymes: W126R, K276T and S353G." Drug Metabolism and Pharmacokinetics 31, no. 6 (December 2016): 445–50. http://dx.doi.org/10.1016/j.dmpk.2016.09.003.

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LUNDELL, Kerstin. "The porcine taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21) gene: evolution by gene duplication and gene conversion." Biochemical Journal 378, no. 3 (March 15, 2004): 1053–58. http://dx.doi.org/10.1042/bj20031657.

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Porcine taurochenodeoxycholic acid 6α-hydroxylase, cytochrome P450 4A21 (CYP4A21), differs from other members of the CYP4A subfamily in terms of structural features and catalytic activity. CYP4A21 participates in the formation of hyocholic acid, a species-specific primary bile acid in the pig. The CYP4A21 gene was investigated and found to be approx. 13 kb in size and split into 12 exons. The intron–exon organization of the CYP4A21 gene corresponds to that of CYP4A fatty acid hydroxylase genes in other species. Comparison with a genomic segment of a pig CYP4A fatty acid hydroxylase gene (CYP4A24) revealed a sequence identity with CYP4A21 that extends beyond the exons, indicating a common origin by gene duplication. A pronounced sequence identity was found also within the proximal 5´-flanking regions, whereas the patterns of mRNA expression of CYP4A21 and CYP4A fatty acid hydroxylases in pig liver differ. Sequence comparison aiming to elucidate the origin of the unique features of CYP4A21 revealed a region of decreased sequence identity from exon 6 to exon 8, strongly suggesting that gene conversion could have contributed to the evolution of CYP4A21.

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32

Sukkasem, Nadta, Waranya Chatuphonprasert, and Kanokwan Jarukamjorn. "Cytochrome P450 expression-associated multiple-hit pathogenesis of non-alcoholic fatty liver disease (NAFLD) in HepG2 cells." Tropical Journal of Pharmaceutical Research 19, no. 4 (May 14, 2020): 707–14. http://dx.doi.org/10.4314/tjpr.v19i4.5.

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Purpose: To establish a free fatty acid (FFA)-induced non-alcoholic fatty liver disease (NAFLD) model in HepG2 cells.Methods: HepG2 cells were incubated with 0.1, 1, or 5 mM oleic acid (OA) or palmitic acid (PA) for 24 h. Histological features were examined by oil-red-O staining. Expression levels of metabolic genes (peroxisome proliferator activated receptors α/γ, sterol regulatory element binding proteins 1a/1c, acetyl-CoA carboxylase, acyl-CoA oxidase, and fatty acid synthase), antioxidative genes (catalase and superoxide dismutases 1/2), and cytochrome P450 genes (CYP1A2, CYP2C19, CYP2D6, CYP2E1, CYP3A4, and CYP4A11) were determined by reverse transcription-real time polymerase chain reaction (RT-qPCR).Results: Intracellular lipid storage was observed in cells treated with 1 mM OA or PA while cell shrinkage was present at 5 mM concentrations of both. Expression of all metabolic genes were elevated by 1 mM PA and 5 mM OA and PA. Expression of all antioxidative genes were diminished by 5 mM OA whereas 5 mM PA only reduced superoxide dismutase-2 expression. Expression of CYP1A2, CYP2D6, and CYP3A4 genes were down-regulated by both FFAs, CYP2C19 was induced by PA, while CYP2E1 and CYP4A11 were up-regulated in a concentration-dependent manner.Conclusion: PA was the more potent steatogenic agent in an OA- or PA- induced NAFLD model in HepG2 cells. Increase in intracellular hepatic lipid and expression of metabolic genes, suppression of antioxidative genes, suppression of CYP1A2, CYP2D6, and CYP3A4, and induction of CYP2E1 andCYP4A11 correlated with the multiple-hit pathogenesis model of NAFLD. These findings suggest that PA-induced NAFLD model in HepG2 cells is a suitable in vitro model for studying novel therapeutic approaches to NAFLD treatment. Keywords: NAFLD, Multiple-hit pathogenesis, Free fatty acid, Oleic acid, Palmitic acid

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Gainer, James V., Aouatef Bellamine, Elliott P. Dawson, Kristie E. Womble, Sarah W. Grant, Yarong Wang, L. Adrienne Cupples, et al. "Functional Variant of CYP4A11 20-Hydroxyeicosatetraenoic Acid Synthase Is Associated With Essential Hypertension." Circulation 111, no. 1 (January 4, 2005): 63–69. http://dx.doi.org/10.1161/01.cir.0000151309.82473.59.

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Fu, Zhenyan, Tomohiro Nakayama, Naoyuki Sato, Yoichi Izumi, Yuji Kasamaki, Atsushi Shindo, Masakatsu Ohta, et al. "A haplotype of the CYP4A11 gene associated with essential hypertension in Japanese men." Journal of Hypertension 26, no. 3 (March 2008): 453–61. http://dx.doi.org/10.1097/hjh.0b013e3282f2f10c.

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35

Baker, Jason R., Soisungwan Satarug, Supanee Urbenjapol, Robert J. Edwards, David J. Williams, Michael R. Moore, and Paul E. B. Reilly. "Associations between human liver and kidney cadmium content and immunochemically detected CYP4A11 apoprotein." Biochemical Pharmacology 63, no. 4 (February 2002): 693–96. http://dx.doi.org/10.1016/s0006-2952(01)00905-4.

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36

Balabanidou, Vasileia, Anastasia Kampouraki, Marina MacLean, Gary J. Blomquist, Claus Tittiger, M. Patricia Juárez, Sergio J. Mijailovsky, et al. "Cytochrome P450 associated with insecticide resistance catalyzes cuticular hydrocarbon production in Anopheles gambiae." Proceedings of the National Academy of Sciences 113, no. 33 (July 20, 2016): 9268–73. http://dx.doi.org/10.1073/pnas.1608295113.

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The role of cuticle changes in insecticide resistance in the major malaria vector Anopheles gambiae was assessed. The rate of internalization of 14C deltamethrin was significantly slower in a resistant strain than in a susceptible strain. Topical application of an acetone insecticide formulation to circumvent lipid-based uptake barriers decreased the resistance ratio by ∼50%. Cuticle analysis by electron microscopy and characterization of lipid extracts indicated that resistant mosquitoes had a thicker epicuticular layer and a significant increase in cuticular hydrocarbon (CHC) content (∼29%). However, the CHC profile and relative distribution were similar in resistant and susceptible insects. The cellular localization and in vitro activity of two P450 enzymes, CYP4G16 and CYP4G17, whose genes are frequently overexpressed in resistant Anopheles mosquitoes, were analyzed. These enzymes are potential orthologs of the CYP4G1/2 enzymes that catalyze the final step of CHC biosynthesis in Drosophila and Musca domestica, respectively. Immunostaining indicated that both CYP4G16 and CYP4G17 are highly abundant in oenocytes, the insect cell type thought to secrete hydrocarbons. However, an intriguing difference was indicated; CYP4G17 occurs throughout the cell, as expected for a microsomal P450, but CYP4G16 localizes to the periphery of the cell and lies on the cytoplasmic side of the cell membrane, a unique position for a P450 enzyme. CYP4G16 and CYP4G17 were functionally expressed in insect cells. CYP4G16 produced hydrocarbons from a C18 aldehyde substrate and thus has bona fide decarbonylase activity similar to that of dmCYP4G1/2. The data support the hypothesis that the coevolution of multiple mechanisms, including cuticular barriers, has occurred in highly pyrethroid-resistant An. gambiae.

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Yu, Kuiying, Tao Zhang, and Xuhua Li. "Genetic role of CYP4A11 polymorphisms in the risk of developing cardiovascular and cerebrovascular diseases." Annals of Human Genetics 82, no. 6 (August 22, 2018): 370–81. http://dx.doi.org/10.1111/ahg.12280.

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38

Fu, Zhenyan, Tomohiro Nakayama, Naoyuki Sato, Yoichi Izumi, Yuji Kasamaki, Atsushi Shindo, Masakatsu Ohta, et al. "Haplotype-based case study of human CYP4A11 gene and cerebral infarction in Japanese subject." Endocrine 33, no. 2 (April 2008): 215–22. http://dx.doi.org/10.1007/s12020-008-9078-6.

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39

Zhang, Rong, Jingyi Lu, Cheng Hu, Congrong Wang, Weihui Yu, Xiaojing Ma, Yuqian Bao, Kunsan Xiang, Youfei Guan, and Weiping Jia. "A common polymorphism of CYP4A11 is associated with blood pressure in a Chinese population." Hypertension Research 34, no. 5 (February 17, 2011): 645–48. http://dx.doi.org/10.1038/hr.2011.8.

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40

Powell, Pnina K., Imre Wolf, and Jerome M. Lasker. "Identification of CYP4A11 as the Major Lauric Acid ω-Hydroxylase in Human Liver Microsomes." Archives of Biochemistry and Biophysics 335, no. 1 (November 1996): 219–26. http://dx.doi.org/10.1006/abbi.1996.0501.

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41

Liang, J. Q., M. R. Yan, L. Yang, Q. Suyila, H. W. Cui, and X. L. Su. "Association of a CYP4A11 polymorphism and hypertension in the Mongolian and Han populations of China." Genetics and Molecular Research 13, no. 1 (2014): 508–17. http://dx.doi.org/10.4238/2014.january.21.20.

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42

Ding, Hu, Guanglin Cui, Lan Zhang, Yujun Xu, Xunna Bao, Yuanchao Tu, Bin Wu, et al. "Association of common variants of CYP4A11 and CYP4F2 with stroke in the Han Chinese population." Pharmacogenetics and Genomics 20, no. 3 (March 2010): 187–94. http://dx.doi.org/10.1097/fpc.0b013e328336eefe.

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43

Fu, Z. Y., T. Nakayama, N. Sato, Y. Izumi, Y. Kasamaki, A. Shindo, M. Ohta, et al. "P375 Haplotype-based case study of human CYP4A11 gene and cerebral infarction in Japanese subjects." International Journal of Cardiology 125 (February 2008): S73. http://dx.doi.org/10.1016/s0167-5273(08)70286-9.

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44

Sugimoto, Ken, Hiroshi Akasaka, Tomohiro Katsuya, Koichi Node, Tomomi Fujisawa, Izumi Shimaoka, Osamu Yasuda, et al. "A Polymorphism Regulates CYP4A11 Transcriptional Activity and Is Associated With Hypertension in a Japanese Population." Hypertension 52, no. 6 (December 2008): 1142–48. http://dx.doi.org/10.1161/hypertensionaha.108.114082.

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45

Mayer, Bjoern, Wolfgang Lieb, Anika Götz, Inke R. König, Zouhair Aherrahrou, Annett Thiemig, Stephan Holmer, et al. "Association of the T8590C Polymorphism of CYP4A11 With Hypertension in the MONICA Augsburg Echocardiographic Substudy." Hypertension 46, no. 4 (October 2005): 766–71. http://dx.doi.org/10.1161/01.hyp.0000182658.04299.15.

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46

Xu, Meijuan, Lifeng Jiang, Wenzheng Ju, Haiping Hao, Guangji Wang, and Ping Li. "Inhibitory effects of dihydrotanshinone I on CYP4A11 and CYP4F3A mediated ω-hydroxylation of arachidonic acid." European Journal of Integrative Medicine 6, no. 6 (December 2014): 735. http://dx.doi.org/10.1016/j.eujim.2014.09.110.

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DING, HU, YUJUN XU, BIN WU, LAN ZHANG, and DAO WEN WANG. "Association of common variants of CYP4A11 and CYP4F2 with stroke in the Chinese Han population." International Journal of Cardiology 137 (October 2009): S109. http://dx.doi.org/10.1016/j.ijcard.2009.09.367.

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Yang, Hong, Zhenyan Fu, Yitong Ma, Ding Huang, Qing Zhu, Cha Erdenbat, Xiang Xie, Fen Liu, and Yingying Zheng. "CYP4A11 gene T8590C polymorphism is associated with essential hypertension in the male western Chinese Han population." Clinical and Experimental Hypertension 36, no. 6 (October 28, 2013): 398–403. http://dx.doi.org/10.3109/10641963.2013.846353.

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Hermann, M., J. P. Hellermann, K. Quitzau, M. M. Hoffmann, T. Gasser, T. Meinertz, T. Münzel, I. Fleming, and T. F. Lüscher. "CYP4A11 polymorphism correlates with coronary endothelial dysfunction in patients with coronary artery disease—The ENCORE Trials." Atherosclerosis 207, no. 2 (December 2009): 476–79. http://dx.doi.org/10.1016/j.atherosclerosis.2009.06.009.

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Han, Liujun, Heng Zhang, Yan Zeng, Yehui Lv, Li Tao, Jianlong Ma, Hongmei Xu, et al. "Identification of the miRNA-3185/CYP4A11 axis in cardiac tissue as a biomarker for mechanical asphyxia." Forensic Science International 311 (June 2020): 110293. http://dx.doi.org/10.1016/j.forsciint.2020.110293.

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