21308-79-2Relevant academic research and scientific papers
Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists
Schiano Moriello, Aniello,López Chinarro, Silvia,Novo Fernández, Olalla,Eras, Jordi,Amodeo, Pietro,Canela-Garayoa, Ramon,Vitale, Rosa Maria,Di Marzo, Vincenzo,De Petrocellis, Luciano
, p. 8255 - 8281 (2018/09/25)
The transient receptor potential vanilloid type-2 (TRPV2) protein is a nonselective Ca2+ permeable channel member of the TRPV subfamily, still considered an orphan TRP channel due to the scarcity of available selective and potent pharmacological tools and endogenous modulators. Here we describe the discovery of novel synthetic long-chain capsaicin derivatives as potent TRPV2 antagonists in comparison to the totally inactive capsaicin, the role of their hydrophobic chain, and how the structure-activity relationships of such derivatives led, through a ligand-based approach, to the identification of endogenous long-chain fatty acid ethanolamides or primary amides acting as TRPV2 antagonists. Both synthetic and endogenous antagonists exhibited differential inhibition against known TRPV2 agonists characterized by distinct kinetic profiles. These findings represent the first example of both synthetic and naturally occurring TRPV2 modulators with efficacy in the submicromolar/low-micromolar range, which will be useful for clarifying the physiopathological roles of this receptor, its regulation, and its targeting in pathological conditions.
Isomerization of methyl (9Z)-12-Oxooctadec-9-enoate
Davletbakova,Baibulatova,Dokichev,Yunusova,Yunusov
, p. 781 - 783 (2007/10/03)
Methyl (9Z)-12-oxooctadec-9-enoate isomerizes stereoselectively in 86% yield into methyl (10E)-12-octadec-10-enoate in the presence of a complex H2O2-BF3-Et2O.
Stereochemistry of Olefin and Fatty Acid Oxidation. Part 3. The Allylic Hydroperoxides from the Autoxidation of Methyl Oleate
Frankel, Edwin N.,Garwood, Robert F.,Khambay, Bhupinder P. S.,Moss, Gerard P.,Weedon, Basil C. L.
, p. 2233 - 2240 (2007/10/02)
Methods have been developed, using 13C n.m.r. spectroscopy and mass spectrometry, for the analysis of all eight cis and trans allylic 8-, 9-, 10-, and 11-hydroperoxides formed on autoxidation of methyl oleate.
