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Molecules 2013, 18(6), 6383-6407; doi:10.3390/molecules18066383

[Fe2L3]4+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity

1
Department of Chemistry, University of Otago, P. O. Box 56, Dunedin 9054, New Zealand
2
National School of Pharmacy, University of Otago, Dunedin 9054, New Zealand
3
Sir John Walsh Research Institute, P.O. Box 647, Dunedin 9054, New Zealand
4
Faculty of Dentistry, University of Otago, Dunedin 9054, New Zealand
5
Department of Chemistry, College of Science, University of Canterbury, Christchurch 8140, New Zealand
*
Author to whom correspondence should be addressed.
Received: 12 April 2013 / Revised: 16 May 2013 / Accepted: 17 May 2013 / Published: 29 May 2013
(This article belongs to the Special Issue Advances in Click Chemistry)
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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.
Keywords: iron(II); CuAAC; metallosupramolecular cylinders; biological activity iron(II); CuAAC; metallosupramolecular cylinders; biological activity
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Vellas, S.K.; Lewis, J.E.M.; Shankar, M.; Sagatova, A.; Tyndall, J.D.A.; Monk, B.C.; Fitchett, C.M.; Hanton, L.R.; Crowley, J.D. [Fe2L3]4+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity. Molecules 2013, 18, 6383-6407.

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