71030-39-2Relevant academic research and scientific papers
Repurposing Resveratrol and Fluconazole to Modulate Human Cytochrome P450-Mediated Arachidonic Acid Metabolism
El-Sherbeni, Ahmed A.,El-Kadi, Ayman O. S.
, p. 1278 - 1288 (2016/04/26)
Cytochrome P450 (P450) enzymes metabolize arachidonic acid (AA) to several biologically active epoxyeicosatrienoic acids (EETs) and hydroxyeicosatetraenoic acids (HETEs). Repurposing clinically-approved drugs could provide safe and readily available means
COX-2-dependent and -independent biosynthesis of dihydroxy-arachidonic acids in activated human leukocytes
Tejera, Noemi,Boeglin, William E.,Suzuki, Takashi,Schneider, Claus
scheme or table, p. 87 - 94 (2012/03/26)
Biosynthesis of 5,15-dihydroxyeicosatetraenoic acid (5,15-diHETE) in leukocytes involves consecutive oxygenation of arachidonic acid by 5-lipoxygenase (LOX) and 15-LOX in either order. Here, we analyzed the contribution of cyclooxygenase (COX)-2 to the biosynthesis of 5,15-di-HETE and 5,11-diHETE in isolated human leukocytes activated with lipopolysaccharide and calcium ionophore A23187. Transformation of arachidonic acid was initiated by 5-LOX providing 5 S -HETE as a substrate for COX-2 forming 5 S,15 S -diHETE, 5 S,15 R -diHETE, and 5 S,11 R -di-HETE as shown by LC/MS and chiral phase HPLC analyses. The levels of 5,15-diHETE were 0.45 ± 0.2 ng/106 cells (mean ± SEM, n = 6), reaching about half the level of LTB 4 (1.3 ± 0.5 ng/106 cells, n = 6). The COX-2 specific inhibitor NS-398 reduced the levels of 5,15-diHETE to below 0.02 ng/106 cells in four of six samples. Similar reduction was achieved by MK-886, an inhibitor of 5-LOX activating protein but the above differences were not statistically significant. Aspirin treatment of the activated cells allowed formation of 5,15-diHETE (0.1 ± 0.05 ng/106 cells, n = 6) but, as expected, abolished formation of 5,11-diHETE. The mixture of activated cells also produced 5 S,12 S -diHETE with the unusual 6 E,8 Z,10 E double bond configuration, implicating biosynthesis by 5-LOX and 12-LOX activity rather than by hydrolysis of the leukotriene A 4 -epoxide. Exogenous octadeuterated 5 S -HETE and 15 S -HETE were converted to 5,15-diHETE, implicating that multiple oxygenation pathways of arachidonic acid occur in activated leukocytes. The contribution of COX-2 to the biosynthesis of dihydroxylated derivatives of arachidonic acid provides evidence for functional coupling with 5-LOX in activated human leukocytes. Copyright
METHOD OF SYNTHESIZING A 5-OXO-CONJUGATED FATTY ACID
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, (2011/11/06)
There is provided a novel chemical synthetic method for the preparation of a 5-oxo-ETE and related compounds. The method is based on a short and efficient synthesis of 5-oxo-ETE from commercially available Arachidonic acid. The method is based on the surprising discovery that a 5-oxo-conjugated fatty acid may be efficiently converted into the corresponding 5-oxo-conjugated fatty acid by reaction with the Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one)in the presence of pyridine or a substituted pyridine.
Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways
Anterola, Aldwin,G?bel, Cornelia,Hornung, Ellen,Sellhorn, George,Feussner, Ivo,Grimes, Howard
experimental part, p. 40 - 52 (2009/07/11)
Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 α-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering p
Preparation of high specific activity tritium-labelled leukotriene B 4 suitable for radioligand binding assay
Schramm, Stanislav I.,Nagaev, Igor Yu.,Sabirsh, Alan,Shevchenko, Valeriy P.,Arkhipova, Anastasiya S.,Haeggstroem, Jesper Z.,Myasoedov, Nikolay F.
, p. 101 - 105 (2008/09/20)
We describe a method of preparation of high specific activity tritium-labelled leukotriene (LT) B4 from [5,6,8,9,11,12, 14,15- 3H] arachidonic acid (AA; 6.66 TBq/mmol) utilizing a LTB 4-synthesizing enzyme system from rat basophilic leukemia (RBL-1) cells. It was shown that both cyclooxygenase inhibitor indomethacin and adenosine 5′-triphosphate induced [3H] AA transformation to [3H] LTB4. In optimized conditions up to 15% of total radioactivity of the incubation mixture was present in [3H] LTB 4. A separation of [3H] LTB4 from other labelled C20:4 products was achieved by a three-step reverse phase-high-performance liquid chromatography in methanol- and acetonitrile-based solvent systems. [3H] LTB4 was confirmed to be identical to the naturally occurring LTB4 by a radioligand binding assay using a culture of HF1 cells that express a BLT1 receptor. Copyright
Synthesis of polyconjugated fatty acids
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Page 3; 12, (2010/02/10)
The present invention relates to fatty acids. In particular, the present invention provides polyconjugated fatty acids, and methods of their synthesis and their use.
Synthesis of long chain n-3 and n-6 fatty acids having a photoactive conjugated tetraene group
Kuklev, Dmitry V.,Smith, William L.
, p. 145 - 158 (2007/10/03)
Fatty acids of the n-3 and n-6 families containing a photoactive conjugated tetraene group near the carboxylate were prepared from several naturally occurring fatty acids by sequential iodolactonization and treatment with excess 1,8-diazabicyclo[5.4.0]undec-7-ene. The new conjugated fatty acids include 5E,7E,9E,11Z,14Z- and 5E,7E,9E,11E,14Z-eicosapentaenoic acids derived from arachidonic acid; 5E,7E,9E,11Z,14Z,17Z- and 5E,7E,9E,11E,14Z,17Z-eicosahexaenoic acids from eicosapentaenoic acid; and 4E,6E,8E,10Z,13Z,16Z,19Z- and 4E,6E,8E,10E,13Z,16Z,19Z-docosaheptaenoic acids from docosahexaenoic acid. All of the newly synthesized fatty acids were characterized by UV, 1H NMR and mass spectroscopy. These new products represent the first examples of directed conjugation of methylene interrupted double bond systems. The products can be synthesized in gram quantities and in high yields (>50%). Interestingly, it did not prove possible to synthesize fatty acids having a triene group near the carboxyl group even using mild conditions and different synthetic approaches. Once initiated, the isomerization always continued until a tetraene group was formed. Because of the sensitivity of the tetraene group to light, these fatty acids have the potential for being used in tracking fatty acid movements in cells employing fluorescence techniques and in UV light-induced cross linking to membrane proteins.
5-HETE congeners as modulators of cell proliferation
Miller, Thomas A.,Ghosh, Jagadananda,Myers, Charles E.,Macdonald, Timothy L.
, p. 1913 - 1916 (2007/10/03)
The synthesis and assessment of the mitogenic properties of 5-HETE congeners are reported. These studies represent an effort to develop a structure-activity profile for ligands of the 5-HETE/5-oxoETE G-protein coupled receptor(s). Many of these agents possess mitogenic activity that equals or exceeds that of racemic 5-HETE family constituents in prostate cancer cell lines. (C) 2000 Elsevier Science Ltd.
Stereospecific Total Synthesis of Dimorphecolic Acid, 5(S)-HETE, and 12(S)-Hete
Shimazaki, Toshiyuki,Kobayashi, Yuichi,Sato, Fumie
, p. 1785 - 1788 (2007/10/02)
First enantiospecific synthesis of dimorphecolic acid is accomplished via an efficient and stereocontrolled route.The convenient synthesis of 5(S)-HETE and 12(S)-HETE is also described.
