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Chemical synthesis and biological evaluation of ?-hydroxy polyunsaturated fatty acids.


ABSTRACT: ?-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 ?-hydroxy PUFAs in pain was evaluated in naive rats. Following intraplantar injection, 20-hydroxyeicosatetraenoic acid (20-HETE, ?-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, ?-hydroxy EPA) or 22-hydroxydocosahexaenoic acid (22-HDoHE, ?-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).

SUBMITTER: Hwang SH 

PROVIDER: S-EPMC5584617 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids.

Hwang Sung Hee SH   Wagner Karen K   Xu Jian J   Yang Jun J   Li Xichun X   Cao Zhengyu Z   Morisseau Christophe C   Lee Kin Sing Stephen KS   Hammock Bruce D BD  

Bioorganic & medicinal chemistry letters 20161202 3


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  ...[more]

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