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Molecules 2016, 21(11), 1548;

Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies

Department of Chemistry, University of Otago, P.O. Box 56, Dunedin 9016, Otago, New Zealand
Department of Microbiology and Immunology, University of Otago, P.O. Box 56, 720 Cumberland Street, Dunedin 9054, Otago, New Zealand
Department of Chemistry and Biochemistry, California State University, Long Beach, 1250 Bellflower Boulevard, Long Beach, CA 90840-9507, USA
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 30 September 2016 / Revised: 4 November 2016 / Accepted: 10 November 2016 / Published: 16 November 2016
(This article belongs to the Special Issue Recent Advances in CuAAC Click Chemistry)
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A small family of [Co2(Lpytrz)3]6+ cylinders was synthesised from bis(bidentate) 2-pyridyl-1,2,3-triazole “click” ligands (Lpytrz) through an “assembly-followed-by-oxidation” method. The cylinders were characterised using 1H, 13C, and DOSY NMR, IR, and UV-Vis spectroscopies, along with electrospray ionisation mass spectrometry (ESMS). Stability studies were conducted in dimethyl sulfoxide (DMSO) and D2O. In contrast to similar, previously studied, [Fe2(Lpytrz)3]4+ helicates the more kinetically inert [Co2(Lpytrz)3]6+ systems proved stable (over a period of days) when exposed to DMSO and were even more stable in D2O. The triply stranded [Co2(Lpytrz)3]6+ systems and the corresponding “free” ligands were tested for antimicrobial activity in vitro against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) microorganisms. Agar-based disk diffusion and Mueller–Hinton broth micro-dilution assays showed that the [Co2(Lpytrz)3]6+ cylinders were not active against either strain of bacteria. It is presumed that a high charge of the [Co2(Lpytrz)3]6+ cylinders is preventing them from crossing the bacterial cell membranes, rendering the compounds biologically inactive. View Full-Text
Keywords: cobalt(III); metallosupramolecular; cylinders; antimicrobial agents cobalt(III); metallosupramolecular; cylinders; antimicrobial agents

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Vasdev, R.A.S.; Preston, D.; Scottwell, S.Ø.; Brooks, H.J.L.; Crowley, J.D.; Schramm, M.P. Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies. Molecules 2016, 21, 1548.

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