DEVELOPMENT OF ANTIFUNGAL GLYCOSIDE COMPLEX AGAINST PATHADINAC EAST CANDIDA ALBICANS

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Nickel(II) complexes containing N-glycosides derived from D-glucosamine (D-GlcN) and ethylenediamine (en) and trimethylenediamine (tn), [Ni(D-GlcN-en)ィイD22ィエD2] ClィイD22ィエD2・HィイD22ィエD2O (1)(D-GlcN-en = 1-{(2-aminoethyl)amino}-2-amino-1, 2-dideoxy-D-glucose) and [Ni(D-GlcN-tn)ィイD22ィエD2] ClィイD22ィエD2・4HィイD22ィエD2O (2)(D-GlcN-tn = 1-{(3-aminopropyl)amino}-2-amino-1, 2-dideoxy-D-Glucose), are fairly stable in water at room temperature and showed effective antifungal activity against pathogenic yeast, Candida albicans, with the MIC(minimal concentration of inhibition) values of the complexes being 0.25 mM. The results obtained enzyme assays by using preparations of C.albicans chitinase fraction suggested that the sugar complexes 1 and 2 played a role of novel chitinase (chitin-degradation enzyme) inhibitor, where the modes of inhibition were competitive (Ki = 1.3 mM for 1, Ki = 1.8 mM for 2). Zinc(II) complexes containing N-glycosides derived from D-glucosamine (D-GlcN) and ethylenediamine (en), [Zn(D-GlcN-en)ィイD22ィエD2]XィイD22ィエD2(1a.X = Cl, 1b.XィイD22ィエD2 = SOィイD24ィエD2ィイD12-ィエD1), were prepared and characterized by elemental analysis and nuclear magnetic resonance spectroscopy involving X-ray crystallography, where D-GlcN-en = 1-{(2-aminoethyl)amino}-2-amino-1, 2-dideoxy-D-glucose. The complex cation of 1a has a nearly C2 symmetry and the central nickel atom is octahedrally coordinated by two tridentate N-glycoside ligands from D-glucosamine and ethylenediamine in a meridional mode. The result of n.m.r. measurements of 1a confirmed the similar structure of complex cation orevealed by X-ray crystallography. The 1, 3-propanediamine derivatives having a sugar unit (2-sugar-pn) have been prepared and characterized, where the structures of two paracetylated diazides which are intermediate compounds for the syntheses of two diamines have been determined by X-ray crystallography. Bioactivity of metal complexes of 2-sugar-pn have been examined.