Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 16, Issue 2, Pages 890-901Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2007.10.016
Keywords
4-allyl-2-methoxyphenol; 15-HLOa; 15-HLOb; protein modeling; soybean lipoxygenasel; docking
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A group of 4-allyl-2-methoxyphenol (eugenol) esters were designed, synthesized, and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO). Compounds 4c, 4d 4f, 4p, and 4q showed the best IC50 in SLO inhibition (IC50 = 1.7, 2.3, 2.1, 2.2, and 0.017 mu M respectively). All compounds were docked into SLO active site and showed that ally) group of compounds is oriented toward the iron atom in the active site of SLO. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of eugenol derivatives in inhibiting 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques. (C) 2007 Elsevier Ltd. All rights reserved.
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