ArticleBioorganic & medicinal chemistry letters2017
Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids.
Article in Bioorganic & medicinal chemistry letters, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 20 citations in OpenAlex.
- Expedited access to polyunsaturated fatty acids and biofunctional analogues by full solid-phase synthesis.Nature chemistry · 2025Article
- Synthesis of 19-Hydroxyarachidonic Acid by Fungal Peroxygenases: An Experimental and Computational Study.ChemSusChem · 2025Article
- Effects of molecular interactions between the exposome and oxylipin metabolism on healthspan.Frontiers in physiology · 2025Review
- Oxylipins Derived from PUFAs in Cardiometabolic Diseases: Mechanism of Actions and Possible Nutritional Interactions.Nutrients · 2024Review
- Synthesis and Preclinical Evaluation of 22-[ACS chemical neuroscience · 2023Article
- Radiosynthesis of 20-[Prostaglandins, leukotrienes, and essential fatty acids · 2022Article
- Novel Unspecific Peroxygenase fromMicroorganisms · 2022Article
- TRPV1: Structure, Endogenous Agonists, and Mechanisms.International journal of molecular sciences · 2020Review
- Asymmetric Total Synthesis of 19,20-Epoxydocosapentaenoic Acid, a Bioactive Metabolite of Docosahexaenoic Acid.The Journal of organic chemistry · 2019Article
- Adaptive thermogenesis by dietary n-3 polyunsaturated fatty acids: Emerging evidence and mechanisms.Biochimica et biophysica acta. Molecular and cell biology of lipids · 2019Review
Corrections and comments
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Authors and funding
9 authors at 3 institutions in 2 countries.
Funding
Abstract
ω-Hydroxy polyunsaturated fatty acids (PUFAs), natural metabolites from arachidonic acid (ARA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) were prepared via convergent synthesis approach using two key steps: Cu-mediated CC bond formation to construct methylene skipped poly-ynes and a partial alkyne hydrogenation where the presence of excess 2-methyl-2-butene as an additive that is proven to be critical for the success of partial reduction of the poly-ynes to the corresponding cis-alkenes without over-hydrogenation. The potential biological function of ω-hydroxy PUFAs in pain was evaluated in naive rats. Following intraplantar injection, 20-hydroxyeicosatetraenoic acid (20-HETE, ω-hydroxy ARA) generated an acute decrease in paw withdrawal thresholds in a mechanical nociceptive assay indicating pain, but no change was observed from rats which received either 20-hydroxyeicosapentaenoic acid (20-HEPE, ω-hydroxy EPA) or 22-hydroxydocosahexaenoic acid (22-HDoHE, ω-hydroxy DHA). We also found that both 20-HEPE and 22-HDoHE are more potent than 20-HETE to activate murine transient receptor potential vanilloid receptor1 (mTRPV1).
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