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

Molecules

Sreedhar K. Vellas²  James E. M. Lewis²  Madhu Shankar¹  Alia Sagatova⁴  Joel D. A. Tyndall¹  Brian C. Monk⁴  Christopher M. Fitchett³  Lyall R. Hanton² 

[1] National School of Pharmacy, University of Otago, Dunedin 9054, New Zealand;Department of Chemistry, University of Otago, P. O. Box 56, Dunedin 9054, New Zealand;Department of Chemistry, College of Science, University of Canterbury, Christchurch 8140, New Zealand;Sir John Walsh Research Institute, P.O. Box 647, Dunedin 9054, New Zealand

关键词: iron(II);    CuAAC;    metallosupramolecular cylinders;    biological activity;   

DOI  :  10.3390/molecules18066383

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.