Abstract
A series of metallosupramolecular [Fe2L3](BF4)4 “click” cylinders have been synthesized in excellent yields (90%–95%) from [Fe(H2O)6](BF4)2 and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, 1H-, 13C- and DOSY-NMR spectroscopies and, in four cases, the structures confirmed by X-ray crystallography. Molecular modeling indicated that some of these “click” complexes were of similar size and shape to related biologically active pyridylimine-based iron(II) helicates and suggested that the “click” complexes may bind both duplex and triplex DNA. Cell-based agarose diffusion assays showed that the metallosupramolecular [Fe2L3](BF4)4 “click” cylinders display no antifungal activity against S. cerevisiae. This observed lack of antifungal activity appears to be due to the poor stability of the “click” complexes in DMSO and biological media.
Highlights
Helicates [1,2,3,4,5,6] are one of the most studied types of discrete metallosupramolecular architectures.With judicious choice of the metal ion and linker ligand cyclic, doubly, triply- or quadruply-stranded helicates can be generated
The control compound at 7 nmol per disk gave an inhibition zone of 9 mm. These results indicate that Hannon’s metallosupramolecular cylinders, 1 and 8 have modest antifungal activity compared with amphotericin B under the conditions of the experiment
These results suggest that suitably designed metallosupramolecular cylinders have potential as a novel class of antifungal agents
Summary
With judicious choice of the metal ion and linker ligand cyclic-, doubly-, triply- or quadruply-stranded helicates can be generated These systems display interesting electronic [7,8,9], optical [10,11,12,13], catalytic [14] and molecular recognition [15,16,17,18,19,20] properties. Pioneering work by Hannon and co-workers [22] showed that the triply stranded [Fe2L3]4+ helicate 1 (Figure 1) displays unique biological properties [23,24] This tetracationic diiron(II) cylinder binds strongly and non-covalently to the major groove of duplex DNA [25,26,27] and, even more remarkably, can bind at the center of threeway (Y-shaped) DNA junctions [28,29].
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