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• W2525930159 abstract "Leukotrienes (LTs) are a class of lipid mediators implicated in numerous inflammatory disorders. Caffeic acid phenethyl ester (CAPE) possesses potent anti-LTs activity through the inhibition of 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of LTs. In this study, we describe the design and synthesis of CAPE analogs as radical scavengers and 5-LO inhibitors. Caffeic esters bearing propargyl and allyl linkers between the caffeoyl and aryl moieties (4a-i and 5a-i, respectively) were synthesized by Sonogashira and Heck cross-coupling reactions to probe the effects of flexibility and aryl substitution on 5-LO inhibition. Caffeoyl alcohol and ethers (6, 7a-b) as well as caffeoyl aldehyde and ketones (8a-e) were synthesized to elucidate the importance of the ester linkage for inhibitory activity. All tested compounds proved to be good radical scavengers (IC50 of 10-30 μm). After preliminary anti-LTs activity screening in HEK293 cell models, 5-LO inhibition potential of selected compounds was determined in human polymorphonuclear leukocytes (PMNL). Most screened compounds outperformed CAPE 3 in concentration-dependent assays on PMNL, with ester dimers 4i and 5i along with caffeoyl ethers 7a-b being roughly eight-, seven-, and 16-fold more potent than Zileuton, with IC50 values of 0.36, 0.43, and 0.18 μm, respectively." @default.
• W2525930159 created "2016-10-07" @default.
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• W2525930159 date "2016-11-15" @default.
• W2525930159 modified "2023-10-05" @default.
• W2525930159 title "Structure-activity relationship of caffeic acid phenethyl ester analogs as new 5-lipoxygenase inhibitors" @default.
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• W2525930159 doi "https://doi.org/10.1111/cbdd.12874" @default.
• W2525930159 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/27717142" @default.
• W2525930159 hasPublicationYear "2016" @default.
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