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

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

1, 1, 2,3, 3, 2, 3,4, 5, 1 and 1,*
Received: 12 April 2013; in revised form: 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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Vellas SK, Lewis JEM, Shankar M, Sagatova A, Tyndall JDA, Monk BC, Fitchett CM, Hanton LR, Crowley JD. [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(6):6383-6407.

Chicago/Turabian Style

Vellas, Sreedhar K.; Lewis, James E.M.; Shankar, Madhu; Sagatova, Alia; Tyndall, Joel D.A.; Monk, Brian C.; Fitchett, Christopher M.; Hanton, Lyall R.; Crowley, James D. 2013. "[Fe2L3]4+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity." Molecules 18, no. 6: 6383-6407.


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