Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Editor

Personal info

View

About

Terms

Javascript disabled

Please enable Javascript support in your browser to use this application.

Instructions on how to enable JavaScript on different browsers can be found here: http://www.google.com/support/bin/answer.py?answer=23852.

[edit this page]

Chemical Compound Review:

AC1NSO0N (5E,8Z,11Z,13Z)-15- hydroxyicosa-5,8,11,13...

Synonyms: LMFA03060066, 15-Hete, 15-Hydroxyeicosa-5,8,11,13-tetraenoic acid

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of 15-Hete

In contrast, the exposure of mastocytoma cells to 0.1-3 micrograms/ml of 15-hydroxyeicosatetraenoic acid (15-HETE) stimulates selectively the generation of leukotrienes, in the absence of histamine release, while 0.1-1 micrograms/ml of compound 48/80 releases histamine without enhancing the generation of leukotrienes [1].
Analyses of BS-C-1 cells infected with cowpox virus or vaccinia virus detected enhanced arachidonate product formation from both the cyclooxygenase (specifically prostaglandins E2 and F2 alpha) and lipoxygenase (specifically 15-hydroxyeicosatetraenoic acid and 12-hydroxyeicosatetraenoic acid) pathways [2].
IL-4 induces apoptosis in A549 lung adenocarcinoma cells: evidence for the pivotal role of 15-hydroxyeicosatetraenoic acid binding to activated peroxisome proliferator-activated receptor gamma transcription factor [3].
BACKGROUND: Although the mechanisms of aspirin-induced rhinosinusitis-asthma appear to be related to arachidonic acid abnormalities, only recently has a specific aspirin-triggered enhancement of 15-hydroxyeicosatetraenoic acid (15-HETE) generation in nasal polyp epithelial cells from aspirin-sensitive patients been demonstrated [4].
Finally, we demonstrate that this receptor may be functional since stimulation of the cells with the antibody to the alpha chain of Fcepsilon RI results in the liberation of 15-hydroxyeicosatetraenoic acid from epithelial cells of asthmatic, but not control, subjects or subjects suffering from chronic bronchitis [5].

High impact information on 15-Hete

Our findings suggest that orbital connective tissues may represent a site of localized 15-hydroxyeicosatetraenoic acid generation resulting from cell type-specific 15-LOX-1 mRNA stabilization by IL-4 [6].
Cellular oxygenation of 12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid by 5-lipoxygenase is stimulated by 5-lipoxygenase-activating protein [7].
The expression of 15-LO and 15-hydroxyeicosatetraenoic acid or 13(S)-hydroxyoctadecadienoic acid formation correlates with cell differentiation or apoptosis in Caco-2 cells induced by NaBT [8].
15-Hydroxyeicosatetraenoic acid inhibits neutrophil migration across cytokine-activated endothelium [9].
We found that aspirin treatment of cultured ovine tracheal epithelial cells blocked PGH synthase-catalyzed formation of PG as expected but also caused a dose-dependent increase in 15-hydroxyeicosatetraenoic acid (15-HETE) production from arachidonic acid [10].

Chemical compound and disease context of 15-Hete

Overexpression of human prostaglandin G/H synthase-1 and -2 by recombinant vaccinia virus: inhibition by nonsteroidal anti-inflammatory drugs and biosynthesis of 15-hydroxyeicosatetraenoic acid [11].
The aspirin effects on prostaglandin H synthase synthesis and 15-hydroxyeicosatetraenoic acid release in trophoblast suggest that the mechanisms of action for aspirin in the prophylaxis of preeclampsia may be more diverse than simply altering platelet thromboxane production [12].
LDL from patients suffering from intermittent claudication due to atherosclerosis was analyzed using HPLC and gas chromatography/mass spectrophotometry and found to contain 9-hydroxy and 13-hydroxyoctadecadienoic acid (9- and 13-HODE), as well as 5-hydroxy-, 12-hydroxy- and 15-hydroxyeicosatetraenoic acid (5-, 12- and 15-HETE respectively) [13].
Eicosapentaenoic acid (EPA) is effective in attenuating the increased protein catabolism in muscle in cancer cachexia, possibly due to inhibition of 15-hydroxyeicosatetraenoic acid (15-HETE) formation [14].

Biological context of 15-Hete

Defective apoptotic cell phagocytosis attenuates prostaglandin E2 and 15-hydroxyeicosatetraenoic acid in severe asthma alveolar macrophages [15].
5-, 12-, and 15-hydroxyeicosatetraenoic acid (HETE), lipoxygenase metabolites of arachidonic acid that may modulate cell proliferation, were examined for their ability to affect the [3H]thymidine incorporation of human umbilical artery smooth muscle cells [16].
Increase in ovarian 15-hydroxyeicosatetraenoic acid during ovulation in the gonadotropin-primed immature rat [17].
Enzymatically synthesized 12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid inhibited the muscarinic receptor [3H]cyclic GMP response, with IC50 values of 17 and 8 microM respectively [18].
Addition of PPAR-gamma ligand 15-hydroxyeicosatetraenoic acid in the presence of PPAR-gamma expression caused further down-regulation of 15-lipoxygenase-2 [19].

Anatomical context of 15-Hete

New role for 15-hydroxyeicosatetraenoic acid. Activator of leukotriene biosynthesis in PT-18 mast/basophil cells [20].
However, when the cells were preincubated with the lymphocyte product 15-hydroxyeicosatetraenoic acid (15-HETE), addition of [14C]arachidonic acid consistently resulted in a dose-dependent synthesis of large amounts of both [14C]leukotriene B4 and [14C]5-HETE [20].
Small bowel mucosa from celiac patients generates 15-hydroxyeicosatetraenoic acid (15-HETE) after in vitro challenge with gluten [21].
Bovine aortic endothelial cells cultured in Se-deficient media and stimulated with tumor necrosis factor alpha or H2O2 produced significantly less prostacyclin (PGI(2)) and more 15-hydroxyeicosatetraenoic acid, 15-hydroperoxyeicosatetraenoic acid (15-HPETE), and thromboxane than Se-supplemented BAEC [22].
omega-Hydroxylation of 15-hydroxyeicosatetraenoic acid by lung microsomes from pregnant rabbits [23].

Associations of 15-Hete with other chemical compounds

After incubation was performed, cell supernatants were removed, and the release of 15-hydroxyeicosatetraenoic acid, prostaglandin2 leukotriene B4, and fibronectin was measured [24].
Similarly, 15-hydroperoxyeicosatetraenoic acid and its hydroxy derivative, 15-hydroxyeicosatetraenoic acid, at somewhat higher molar concentrations (10(-6) M) also reduced basal renin [25].
Differential effects of aspirin and misoprostol on 15-hydroxyeicosatetraenoic acid generation by leukocytes from aspirin-sensitive asthmatic patients [4].
The product of 15-lipoxygenase-2, 15-hydroxyeicosatetraenoic acid, may be a ligand for the nuclear receptor peroxisome proliferator activated receptor-gamma, which is expressed in sebocytes, and contribute to secretory differentiation in androgen regulated tissues such as prostate and sebaceous glands [26].
The iv bolus of prednisolone caused a significant decrease in 15-hydroxyeicosatetraenoic acid (acid-saline group 1027 +/- 43 pg/mL; acid-prednisolone group 514 +/- 62 pg/mL; p less than .01) and cell counts of bronchoalveolar lavage fluid 48 hrs after intratracheal injection of acid, while there was no significant change in 11-dehydro-TxB2 [27].

Gene context of 15-Hete

RESULTS: Interleukin-1 beta (IL-1 beta)-primed A549 cells showed selective elevation in the levels of PGHS-2 mRNA and generated 15-hydroxyeicosatetraenoic acid (15-HETE) [28].
Enhanced epithelial cAMP levels, induced by forskolin and PDE4 inhibition, increased formation of prostaglandin E2 (PGE2), but not of interleukin (IL)-8 or 15-hydroxyeicosatetraenoic acid (15-HETE) in airway epithelial cells [29].
Arachidonic acid metabolism in a cloned strain of rat pituitary tumor cells: correlation between 15 hydroxyeicosatetraenoic acid release and the prolactin secretory process [30].
RTMGL1 synthesize multiple cyclooxygenase (COX) products including 11- and 15-hydroxyeicosatetraenoic acid (HETE) and express COX-2 [31].
Role of 15-hydroxyeicosatetraenoic acid in phosphorylation of ERK1/2 and caldesmon in pulmonary arterial smooth muscle cells [32].

Analytical, diagnostic and therapeutic context of 15-Hete

Levels of 15-hydroxyeicosatetraenoic acid, which may also have a role in the pulmonary allergic response, were detectable in lavage fluid before challenge and increased after provocation with the antigen in four of the five patients [33].
The glomerulosa cells produced the lipoxygenase products 12- and 15-hydroxyeicosatetraenoic acid (HETE) in the basal state, as measured by high pressure liquid chromatography and RIA [34].
Light microscope immunocytochemistry using polyclonal antibodies has demonstrated the presence of immunoreactive 15-LO protein and 15-hydroxyeicosatetraenoic acid (15-HETE), the primary product of the 15-LO pathway [35].
HPLC analysis showed that [(14)C]AA was metabolized by mesenteric arteries to PGI(2), PGE(2), THETAs, hydroxyepoxyeicosatrienoic acids (HEETAs), and 15-hydroxyeicosatetraenoic acid (15-HETE) [36].
RESULTS: The concentration of 15-hydroxyeicosatetraenoic acid in bronchoalveolar lavage fluid of either acid-saline group (804 +/- 129 pg/mL) or acid-prednisolone group (748 +/- 112 pg/mL) was significantly greater than that of the control group (143 +/- 27 pg/mL, p less than .01) 1 hr after the administration [27].

References

Stimulus specificity of the generation of leukotrienes by dog mastocytoma cells. Goetzl, E.J., Phillips, M.J., Gold, W.M. J. Exp. Med. (1983) [Pubmed]
Poxvirus-induced alteration of arachidonate metabolism. Palumbo, G.J., Glasgow, W.C., Buller, R.M. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
IL-4 induces apoptosis in A549 lung adenocarcinoma cells: evidence for the pivotal role of 15-hydroxyeicosatetraenoic acid binding to activated peroxisome proliferator-activated receptor gamma transcription factor. Shankaranarayanan, P., Nigam, S. J. Immunol. (2003) [Pubmed]
Differential effects of aspirin and misoprostol on 15-hydroxyeicosatetraenoic acid generation by leukocytes from aspirin-sensitive asthmatic patients. Kowalski, M.L., Ptasinska, A., Bienkiewicz, B., Pawliczak, R., DuBuske, L. J. Allergy Clin. Immunol. (2003) [Pubmed]
Expression of the high-affinity receptor for IgE on bronchial epithelial cells of asthmatics. Campbell, A.M., Vachier, I., Chanez, P., Vignola, A.M., Lebel, B., Kochan, J., Godard, P., Bousquet, J. Am. J. Respir. Cell Mol. Biol. (1998) [Pubmed]
Interleukin-4 induces 15-lipoxygenase-1 expression in human orbital fibroblasts from patients with Graves disease. Evidence for anatomic site-selective actions of Th2 cytokines. Chen, B., Tsui, S., Boeglin, W.E., Douglas, R.S., Brash, A.R., Smith, T.J. J. Biol. Chem. (2006) [Pubmed]
Cellular oxygenation of 12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid by 5-lipoxygenase is stimulated by 5-lipoxygenase-activating protein. Mancini, J.A., Waterman, H., Riendeau, D. J. Biol. Chem. (1998) [Pubmed]
Expression of 15-lipoxygenase by human colorectal carcinoma Caco-2 cells during apoptosis and cell differentiation. Kamitani, H., Geller, M., Eling, T. J. Biol. Chem. (1998) [Pubmed]
15-Hydroxyeicosatetraenoic acid inhibits neutrophil migration across cytokine-activated endothelium. Takata, S., Papayianni, A., Matsubara, M., Jimenez, W., Pronovost, P.H., Brady, H.R. Am. J. Pathol. (1994) [Pubmed]
Identification of a pharmacologically distinct prostaglandin H synthase in cultured epithelial cells. Holtzman, M.J., Turk, J., Shornick, L.P. J. Biol. Chem. (1992) [Pubmed]
Overexpression of human prostaglandin G/H synthase-1 and -2 by recombinant vaccinia virus: inhibition by nonsteroidal anti-inflammatory drugs and biosynthesis of 15-hydroxyeicosatetraenoic acid. O'Neill, G.P., Mancini, J.A., Kargman, S., Yergey, J., Kwan, M.Y., Falgueyret, J.P., Abramovitz, M., Kennedy, B.P., Ouellet, M., Cromlish, W. Mol. Pharmacol. (1994) [Pubmed]
Aspirin induces increased expression of both prostaglandin H synthase-1 and prostaglandin H synthase-2 in cultured human placental trophoblast. Johnson, R.D., Polakoski, K., Everson, W.V., Nelson, D.M. Am. J. Obstet. Gynecol. (1997) [Pubmed]
Differential recruitment of the coactivator proteins CREB-binding protein and steroid receptor coactivator-1 to peroxisome proliferator-activated receptor gamma/9-cis-retinoic acid receptor heterodimers by ligands present in oxidized low-density lipoprotein. Wigren, J., Surapureddi, S., Olsson, A.G., Glass, C.K., Hammarström, S., Söderström, M. J. Endocrinol. (2003) [Pubmed]
Downregulation of ubiquitin-dependent proteolysis by eicosapentaenoic acid in acute starvation. Whitehouse, A.S., Tisdale, M.J. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
Defective apoptotic cell phagocytosis attenuates prostaglandin E2 and 15-hydroxyeicosatetraenoic acid in severe asthma alveolar macrophages. Huynh, M.L., Malcolm, K.C., Kotaru, C., Tilstra, J.A., Westcott, J.Y., Fadok, V.A., Wenzel, S.E. Am. J. Respir. Crit. Care Med. (2005) [Pubmed]
Selective conversion and esterification of monohydroxyeicosatetraenoic acids by human vascular smooth muscle cells: relevance to smooth muscle cell proliferation. Brinkman, H.J., van Buul-Wortelboer, M.F., van Mourik, J.A. Exp. Cell Res. (1991) [Pubmed]
Increase in ovarian 15-hydroxyeicosatetraenoic acid during ovulation in the gonadotropin-primed immature rat. Tanaka, N., Espey, L.L., Okamura, H. Endocrinology (1989) [Pubmed]
Blockade of N1E-115 murine neuroblastoma muscarinic receptor function by agents that affect the metabolism of arachidonic acid. McKinney, M., Richelson, E. Biochem. Pharmacol. (1986) [Pubmed]
Differential peroxisome proliferator-activated receptor-gamma isoform expression and agonist effects in normal and malignant prostate cells. Subbarayan, V., Sabichi, A.L., Kim, J., Llansa, N., Logothetis, C.J., Lippman, S.M., Menter, D.G. Cancer Epidemiol. Biomarkers Prev. (2004) [Pubmed]
New role for 15-hydroxyeicosatetraenoic acid. Activator of leukotriene biosynthesis in PT-18 mast/basophil cells. Vanderhoek, J.Y., Tare, N.S., Bailey, J.M., Goldstein, A.L., Pluznik, D.H. J. Biol. Chem. (1982) [Pubmed]
Small bowel mucosa from celiac patients generates 15-hydroxyeicosatetraenoic acid (15-HETE) after in vitro challenge with gluten. Krilis, S.A., Macpherson, J.L., de Carle, D.J., Daggard, G.E., Talley, N.A., Chesterman, C.N. J. Immunol. (1986) [Pubmed]
Increased 15-HPETE production decreases prostacyclin synthase activity during oxidant stress in aortic endothelial cells. Weaver, J.A., Maddox, J.F., Cao, Y.Z., Mullarky, I.K., Sordillo, L.M. Free Radic. Biol. Med. (2001) [Pubmed]
omega-Hydroxylation of 15-hydroxyeicosatetraenoic acid by lung microsomes from pregnant rabbits. Okita, R.T., Soberman, R.J., Bergholte, J.M., Masters, B.S., Hayes, R., Murphy, R.C. Mol. Pharmacol. (1987) [Pubmed]
Stimulation of dispersed nasal polyp cells by hyperosmolar solutions. Souques, F., Crampette, L., Mondain, M., Vignola, A.M., Chanez, P., Bousquet, J., Campbell, A.M. J. Allergy Clin. Immunol. (1995) [Pubmed]
The inhibitory role of 12- and 15-lipoxygenase products on renin release. Antonipillai, I., Nadler, J.L., Robin, E.C., Horton, R. Hypertension (1987) [Pubmed]
15-Lipoxygenase-2 expression in benign and neoplastic sebaceous glands and other cutaneous adnexa. Shappell, S.B., Keeney, D.S., Zhang, J., Page, R., Olson, S.J., Brash, A.R. J. Invest. Dermatol. (2001) [Pubmed]
Intravenous bolus of prednisolone decreases 15-hydroxyeicosatetraenoic acid formation in the rat model of acid aspiration. Nagase, T., Fukuchi, Y., Teramoto, S., Jo, C., Uejima, Y., Yamaoka, M., Ishida, K., Shimizu, T., Orimo, H. Crit. Care Med. (1991) [Pubmed]
Aspirin-triggered lipoxins (15-epi-LX) are generated by the human lung adenocarcinoma cell line (A549)-neutrophil interactions and are potent inhibitors of cell proliferation. Clària, J., Lee, M.H., Serhan, C.N. Mol. Med. (1996) [Pubmed]
Identification and function of cyclic nucleotide phosphodiesterase isoenzymes in airway epithelial cells. Fuhrmann, M., Jahn, H.U., Seybold, J., Neurohr, C., Barnes, P.J., Hippenstiel, S., Kraemer, H.J., Suttorp, N. Am. J. Respir. Cell Mol. Biol. (1999) [Pubmed]
Arachidonic acid metabolism in a cloned strain of rat pituitary tumor cells: correlation between 15 hydroxyeicosatetraenoic acid release and the prolactin secretory process. Rabier, M., Chavis, C., Crastes de Paulet, A., Damon, M. Prostaglandins, leukotrienes, and medicine. (1987) [Pubmed]
Production of hydroxyeicosatetraenoic acids and prostaglandins by a novel rat microglial cell line. Rademacher, D.J., Kearn, C.S., Carrier, E.J., Patel, S., Delgado, M.A., Barkmeier, A., Klick, D.E., Breese, N.M., Pfister, S.L., Nithipatikom, K., Campbell, W.B., Hillard, C.J. J. Neuroimmunol. (2004) [Pubmed]
Role of 15-hydroxyeicosatetraenoic acid in phosphorylation of ERK1/2 and caldesmon in pulmonary arterial smooth muscle cells. Lu, C., Liu, Y., Tang, X., Ye, H., Zhu, D. Can. J. Physiol. Pharmacol. (2006) [Pubmed]
Release of prostaglandin D2 into human airways during acute antigen challenge. Murray, J.J., Tonnel, A.B., Brash, A.R., Roberts, L.J., Gosset, P., Workman, R., Capron, A., Oates, J.A. N. Engl. J. Med. (1986) [Pubmed]
Role of the lipoxygenase pathway in angiotensin II-mediated aldosterone biosynthesis in human adrenal glomerulosa cells. Natarajan, R., Stern, N., Hsueh, W., Do, Y., Nadler, J. J. Clin. Endocrinol. Metab. (1988) [Pubmed]
The expression of 15-lipoxygenase gene and the presence of functional enzyme in cytoplasm and nuclei of pregnancy human myometria. Lei, Z.M., Rao, C.V. Endocrinology (1992) [Pubmed]
Cyclooxygenase- and lipoxygenase-dependent relaxation to arachidonic acid in rabbit small mesenteric arteries. Zhang, D.X., Gauthier, K.M., Chawengsub, Y., Holmes, B.B., Campbell, W.B. Am. J. Physiol. Heart Circ. Physiol. (2005) [Pubmed]

Contributions to this collaborative article are from individual authors of WikiGenes or mined by the WikiGenes Data Mining Engine from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.About WikiGenes Open Access Licence Privacy Policy Terms of Use apsburg

The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.