Journal of Enzyme Inhibition and Medicinal Chemistry p. 238 - 244 (2011)
Update date:2022-07-30
Topics:
Sadeghian, Hamid
Seyedi, Seyed Mohammad
Attaran, Neda
Jabbari, Atena
Jafari, Zeinab
A group of 2-alkoxy-5-methoxyallylbenzene were designed, synthesised and evaluated as potential inhibitors of the soybean 15-lipoxygenase (SLO) on the basis of the eugenol and esteragol structures. Compound 4d showed the best half maximal inhibitory concentration (IC50) for SLO inhibition (IC 50=5.9±0.6 μM). All the compounds were docked in the SLO active site retrieved from the Research Collaboratory for Structural Bioinformatics (RCSB) Protein Data Bank (PDB entry: 1IK3) and showed that the allyl group of the synthetic compounds similar to the linoleic acid double bond, were oriented toward the Fe3+-OH moiety in the active site of the enzyme and this conformation was especially fixed by the hydrophobic interaction of the 2-alkoxy group with Leu515, Trp519, Val 566 and Ile572. It was concluded that the molecular volume and shape of the alkoxy moiety was a major factor in the inhibitory potency variation of the synthetic compounds.
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