Elsevier, Bioorganic and Medicinal Chemistry, 17(17), p. 6166-6172
DOI: 10.1016/j.bmc.2009.07.064
Full text: Unavailable
Recent reports show that the natural β-diketone curcumin displays important biological properties regarding the intercellular adhesion molecule-1 (ICAM-1), which plays a critical role in the immune responses and inflammation. In this study the ICAM-1 inhibitory activity of β-diketone compounds, which are curcumin models lacking aromatic peripheral hydroxyl and methoxy groups, along with some metal derivatives is investigated. β-Diketones are systematically more active than metal complexes and the best obtained inhibition is 75% for both groups. The best inhibitors are 4-benzoyl-3-methyl-1-phenyl-pyrazol-5-one (HQ Ph ) among the ligands, and sodium benzoylacetonato among metal derivatives. These results appear in line with the reported antitumor activity of related species. Since 4-acyl-5-pyrazolones posses four tautomeric forms, those corresponding to HQ Ph were investigated using density functional theory. Docking of all HQ Ph tautomers on ICAM-1 protein was performed suggesting one keto-enol form favored to act in biological environment.