197508-63-7Relevant academic research and scientific papers
Synthesis of a radioactive photoaffinity arachidonic acid analog
Perrier, Helene,Prasit, Petpiboon,Wang, Zhaoyin
, p. 1501 - 1502 (1994)
A novel photoaffinity probe based of arachidonic acid was synthesized by coupling 20-hydroxyarachidonic acid and 2-azido-5-iodobenzoic acid. The key epoxide required for the formation of 20-hydroxyarachidonic acid was obtained using a new mild and safe me
Synthesis of 15N-, 13C-, and 2H-labeled methanandamide analogs
Yao, Fen-Mei,Palmer, Sonya L.,Khanolkar, Atmaram D.,Tian, Xiaoyu,Guo, Jianxin,Makriyannis, Alexandros
, p. 115 - 129 (2003)
Four isotopically labeled, metabolically stable analogs of arachidonylethanolamide (anandamide), an endogenous cannabinoid ligand, were synthesized via a five-step reaction sequence starting from arachidonic acid. These stable methanandamide derivatives will serve as probes for studying the conformational properties of anandamide in model membrane systems using solid-state NMR spectroscopy. The synthetic methods described can be applied to the preparations of other anandamide analogs with isotopic labeling in different positions of the molecule, which could be utilized in biochemical and pharmacological experiments. Copyright
New Alkoxy- Analogues of Epoxyeicosatrienoic Acids Attenuate Cisplatin Nephrotoxicity in Vitro via Reduction of Mitochondrial Dysfunction, Oxidative Stress, Mitogen-Activated Protein Kinase Signaling, and Caspase Activation
Hammock, Bruce D.,Lybrand, Daniel B.,Morisseau, Christophe,Singh, Nalin,Vik, Anders
, (2021/12/09)
The usage of cisplatin, a highly potent chemotherapeutic, is limited by its severe nephrotoxicity. Arachidonic acid (ARA)-derived epoxyeicosatrienoic acids (EETs) and soluble epoxide hydrolase (sEH) inhibitors were shown to ameliorate this dose-limiting side effect, but both approaches have some pharmacological limitations. Analogues of EETs are an alternative avenue with unique benefits, but the current series of analogues face concerns regarding their structure and mimetic functionality. Hence, in this study, regioisomeric mixtures of four new ARA alkyl ethers were synthesized, characterized, and assessed as EET analogues against the concentration- and time-dependent toxicities of cisplatin in porcine proximal tubular epithelial cells. All four ether groups displayed bioisostere activity, ranging from marginal for methoxy- (1), good for n-propoxy- (4), and excellent for ethoxy- (2) and i-propoxy- (3). Compounds 2 and 3 displayed cytoprotective effects comparable to that of an EET regioisomeric mixture (5) against high, acute cisplatin exposures but were more potent against low to moderate, chronic exposures. Compounds 2 and 3 (and 5) acted through stabilization of the mitochondrial transmembrane potential and attenuation of reactive oxygen species, leading to reduced phosphorylation of mitogen-activated protein kinases p38 and JNK and decreased activation of caspase-9 and caspase-3. This study demonstrates that alkoxy- groups are potent and more metabolically stable bioisostere alternatives to the epoxide within EETs that enable sEH-independent activity. It also illustrates the potential of ether-based mimics of EETs and other epoxy fatty acids as promising nephroprotective agents to tackle the clinically relevant side effect of cisplatin without compromising its antineoplastic function.
SYNTHESIS OF FLUOROARACHIDONIC ACID AND METHODS OF USE THEREOF
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Paragraph 0061, (2013/11/19)
There are provided, inter alia, methods for diagnosis of the extent of neuroinflammation in a subject. The methods include administering an 18F-labeled arachidonic acid to a subject in need thereof, obtaining a positron emission tomography (PET
CANNABINERGIC LIPID LIGANDS
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Page/Page column 38, (2008/06/13)
One aspect of this disclosure relates generally to lipid compounds that exert diverse effects in the endocannabinoid system, such as regulating CB1 and CB2 receptor or moderating other bio-macromolecules within the endocannabinoid system. Some of the compounds showed improved receptor binding affinity, and/or improved receptor subtype selectivity, and improved bio-stability. Some of the compounds exhibit activities to regulate the enzymes that moderate the bio-disposal of endogenous cannabinoids, such as the fatty acid amide hydrolase (FAAH). Some of the compounds exhibit activities to inhibit the anandamide transporter. Other aspects of the invention are pharmaceutical preparations employing these ligands and methods of administering therapeutically effective amounts of the preparations to provide a physiological effect.
Epoxidation of polyunsaturated fatty acid double bonds by dioxirane reagent: Regioselectivity and lipid supramolecular organization
Grabovskiy, Stanislav A.,Kabal'nova, Natalia N.,Chatgilialoglu, Chryssostomos,Ferreri, Carla
, p. 2243 - 2253 (2007/10/03)
The use of dimethyldioxirane (DMD) as the epoxidizing agent for polyunsaturated fatty acids was investigated. With fatty acid methyl esters, this is a convenient method for avoiding acidic conditions, using different solvents, and simplifying the isolation procedures, with less contamination due to by-products. The reagent was also tested with free fatty acids in water. In this case, the supramolecular organization of fatty acids influenced the reaction outcome, and the epoxidation showed interesting regioselective features. The C=C bonds closest to the aqueous-micelle interface is the most favored for the interaction with dimethyldioxirane. The preferential epoxidation of linoleic acid (=(9Z,12Z)-octadeca-9,12-dienoic acid) to the 9,10-monoepoxy derivative was achieved, with a high yield and 65% regioselectivity. In case of arachidonic acid (=(5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoic acid) micelles, the regioselective outcome with formation of the four possible monoepoxy isomers was studied under different conditions. It resulted to be a convenient synthesis of 'cis-5,6-epoxyeicosatrienoic acid' (=3-[(2Z,5Z,8Z)-tetradeca-2,5,8- trienyl]oxiran-2-butanoic acid), whereas in reverse micelles, epoxidation mostly gave 'cis-14,15-epoxyeicosatrienoic acid (= (5Z,8Z,11Z)-13-(3-pentyloxiran-2- yl)trideca-5,8,11-trienoic acid).
Use of cis-Epoxyeicosantrienoic acids and inhibitors of soluble epoxide hydrolase to reduce pulmonary infiltration by neutrophils
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Page/Page column 12, (2008/06/13)
It has now been discovered that inhibitors of soluble epoxide hydrolase (“sEH”) are useful in reducing the severity of or inhibiting the progression of obstructive pulmonary diseases, restrictive airway diseases, and asthma. Administering a cis-epoxyeicosantrienoic acid (“EET”) in addition to the inhibitor is at least additive, and may be synergistic, in reducing or inhibiting these conditions and diseases, as measured by reduced numbers of neutrophils present in the lung. The inhibitor of sEH may be a nucleic acid, such as a small interfering RNA.
9,11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma
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Page/Page column 5-6, (2010/11/30)
9,11-Cycloendoperoxide derivatives of biologically active prostaglandin analogs, and particularly of the ocular hypotensive drugs Bimatoprost, Latanaprost, Unoprostone, Travoprost and prostaglandin H2 1-ethanolamide or of structurally closely related analogs, are pro-drugs which hydrolyze under physiological conditions to provide prostaglandin analogues that are capable of providing sustained ocular and other in vivo concentrations of the respective drugs. The compounds of the invention have the formula shown below where the variables have the meaning defined in the specification.
Synthesis of 15N and 13C selectively labeled anandamide
Xie, Xiang-Qun,Yang, Hongqin,Choi, Greg,Lin, Sunyuan,Makriyannis, Alexandros
, p. 775 - 784 (2007/10/03)
Anandamide (Figure 1a) (arachidonyl ethanolamide, AEA), (5Z,8Z, 11Z, 14Z)-N-(2-hydroxyethyl)-5,8,11,14-Eicosatetraenamide, is an endogenous cannabinoid ligand possessing important biological activity. The conformation of AEA in its native receptor binding
Biosynthesis of the algal pheromone fucoserratene by the freshwater diatom Asterionella formosa (Bacillariophyceae)
Hombeck, Marc,Boland, Wilhelm
, p. 11033 - 11042 (2007/10/03)
The freshwater diatom Asterionella formosa (Bacillariophyceae) produces octa-1,3E,5Z-triene (6) (fucoserratene), previously identified as the sexual pheromone of the brown seaweed Fucus serratus. Fucoserratene is biosynthesised from eicosa-5,8,11,14,17-pentaenoic acid (7) by oxidative cleavage of the corresponding 12-hydroperoxy intermediate 8. The biosynthetic sequence was established using eicosa5,8,11,14-tetraen-17-ynoic acid (18), a structural analogue of 7, which was converted to octa-1,3E-dien-5-yne (21), a structural analogue of 6, by homogenates of Asterionella formosa. In addition, a general approach to highly unsaturated eicosanoids from arachidonic acid is described.
