70968-99-9Relevant academic research and scientific papers
5-HETE congeners as modulators of cell proliferation
Miller, Thomas A.,Ghosh, Jagadananda,Myers, Charles E.,Macdonald, Timothy L.
, p. 1913 - 1916 (2000)
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.
A PRACTICAL PROCESS FOR LARGE-SCALE SYNTHESIS OF (S)-5-HYDROXY-6-TRANS-8,11,14-CIS-EICOSATETRAENOIC ACID (5-HETE)
Corey, E. J.,Hashimoto, Shun-ichi
, p. 299 - 302 (1981)
(S)-5-hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid (5-HETE) (1) and its enantiomer are readily available by a chemical synthesis from arachidonic acid which includes a chromatographic separation of diastereomeric urethanes (3) made from (+/-)-5-HETE methyl ester and the isocyanate 4 derived from dehydroabietylamine.
Synthesis, molecular modelling studies and biological evaluation of new oxoeicosanoid receptor 1 agonists
Stepniewski, Tomasz Maciej,Torrens-Fontanals, Mariona,Rodríguez-Espigares, Ismael,Giorgino, Toni,Primdahl, Karoline G.,Vik, Anders,Stenstr?m, Yngve,Selent, Jana,Hansen, Trond Vidar
, p. 3580 - 3587 (2018/06/06)
The oxoeicosanoid receptor 1 (OXER1) is a member of the G-protein coupled receptors (GPCR) family, and is involved in inflammatory processes and oncogenesis. As such it is an attractive target for pharmacological intervention. The present study aimed to shed light on the molecular fundaments of OXER1 modulation using chemical probes structurally related to the natural agonist 5-oxo-ETE. In a first step, 5-oxo-ETE and its closely related derivatives (5-oxo-EPE and 4-oxo-DHA) were obtained by conducting concise and high-yielding syntheses. The biological activity of obtained compounds was assessed in terms of potency (EC50) and efficacy (Emax) for arrestin recruitment. Finally, molecular modelling and simulation were used to explore binding characteristics of 5-oxo-ETE and derivatives with the aim to rationalize biological activity. Our data suggest that the tested 5-oxo-ETE derivatives (i) insert quickly into the membrane, (ii) access the receptor via transmembrane helices (TMs) 5 and 6 from the membrane side and (iii) drive potency and efficacy by differential interaction with TM5 and 7. Most importantly, we found that the methyl ester of 5-oxo-ETE (1a) showed even a higher maximum response than the natural agonist (1). In contrast, shifting the 5-oxo group into position 4 results in inactive compounds (4-oxo DHA compounds (3) and (3a)). All in all, our study provides relevant structural data that help understanding better OXER1 functionality and its modulation. The structural information presented herein will be useful for designing new lead compounds with desired signalling profiles.
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.
Absolute Configuration of Epoxyeicosatrienoic Acids (EETs) Formed during Catalytic Oxygenation of Arachidonic Acid by Purified Rat Liver Microsomal Cytochrome P-450
Falck, J. R.,Manna, S.,Jacobson, Harry R.,Estabrook, R. W.,Chacos, N.,Capdevila, Jorge
, p. 3334 - 3336 (2007/10/02)
Incubation of arachidonic acid with a reconstituted enzymatic system containing a purified preparation of the major, phenobarbital-inducible form of rat liver microsomal cytochrome P-450, NADPH, cytochrome b5, and NADPH-cytochrome P-450 reductase affords as the principal products four regioisomeric cis-epoxides: 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs).Their absolute configurations were established by conversion to the corresponding hydroxyeicosatetraenoic acid (HETE) methyl esters, derivatization with dehydroabiethylisocyanate, and chromatographic analysis.Except for 5,6-EET, the cytochrome P-450 catalyzed epoxidation is highly enantioselective.
A new general method for the synthesis of lipoxygenase products: Preparation of ±5-HETE
Rokach,Adams,Perry
, p. 5185 - 5188 (2007/10/02)
Recognizing 3 as the basic common unit in the structures of all HETEs, a general synthetic approach is proposed. As an illustration of this method, the synthesis of ±5-HETE was accomplished using the marked diene 8.
FORMATION AND STRUCTURE DETERMINATION OF 5,6-EPOXY-8,11,14-Z-EICOSATRIENOIC ACID AND 5-OXO-8,11,14-Z-EICOSATRIENOIC ACID
Spur, Bernd,Crea, Attilio,Peters, Wilfried
, p. 1755 - 1758 (2007/10/02)
The formation of 5,6-epoxy-8,11,14-Z-eicosatrienoic acid and 5-oxo-8,11,14-Z-eicosatrienoic acid as by-products in the synthesis of 5-hydroxy-6-E-8,11,14-Z-eicosatetraenoic acid is described.
