Abstract
Through two unequivalent oxygen donor atoms of the hinokitiol (Hhino; C10H12O2; 4-isopropyltropolone) ligand that showed noteworthy biological activities, the dimeric, silver(I)-oxygen bonding complex [Ag(hino)]21, the monomeric aluminium(III) complex [Al(hino)3]·0.5H2O 4 and the cobalt(II) complex “[Co(hino)2]2 ·H2O” 6 were synthesized and characterized with elemental analysis, thermogravimetric and differential thermal analysis (TG/DTA), FTIR and solution (1H and 13C) NMR spectroscopy. The crystal structure of 1 was determined by Rietveld analysis based on X-ray powder diffraction (XPD) data and those of [Al(hino)3]·MeOH 4a and [Co(hino)2(EtOH)]26a, being obtained as yellow block crystals and red platelet crystals, respectively, by crystallization of 4 and 6, were determined by single-crystal X-ray analysis. The antimicrobial activities of 1, 4 and 6, evaluated with minimum inhibitory concentration (MIC; μg ml−1), were compared with those of other metal complexes (M=Na, Li, Cs, Ca, V, Zn) with the hino− ligand. The antimicrobial activities observed in the alkali-metal salts strongly suggested that they were attributed to the effect of the anionic hino− species. The antimicrobial activities of 1 were significantly enhanced, whereas those of other metal complexes were suppressed, compared with those of the neutral Hhino and anionic hino− molecules. The antimicrobial activities observed in 1 were comparable with those of other recently found silver(I)-oxygen bonding complexes, the ligands of which had no activity. Thus, it is proposed that the antimicrobial activities of the silver(I)-oxygen bonding complexes are due to a direct interaction or complexation of the silver(I) ion with biological ligands such as protein, enzyme and membrane, and the coordinating ligands of the silver(I) complexes play the role of a carrier of the silver(I) ion to the biological system.
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