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The toxicity (IC 50 ) of a series of mononuclear ruthenium complexes containing bis[4(4′-methyl-2,2′-bipyridyl)]-1, n -alkane (bb n ) as a tetradentate ligand against three eukaryotic cell lines—BHK (baby hamster kidney), Caco-2 (heterogeneous human epithelial colorectal adenocarcinoma) and Hep-G2 (liver carcinoma)—have been determined. The results demonstrate that  cis -α-[Ru(Me 4 phen)(bb 7 )] 2+  (designated as α-Me 4 phen-bb 7 , where Me 4 phen = 3,4,7,8-tetramethyl-1,10-phenanthroline) showed little toxicity toward the three cell lines, and was considerably less toxic than  cis -α-[Ru(phen)(bb 12 )] 2+  (α-phen-bb 12 ) and the dinuclear complex [{Ru(phen) 2 } 2 {μ-bb 12 }] 4+ . Fluorescence spectroscopy was used to study the binding of the ruthenium complexes with human serum albumin (HSA). The binding of α-Me 4 phen-bb 7  to the macrocyclic host molecule cucurbit[10]uril (Q[10]) was examined by NMR spectroscopy. Large upfield  1 H NMR chemical shift changes observed for the methylene protons in the bb 7  ligand upon addition of Q[10], coupled with the observation of several intermolecular ROEs in ROESY spectra, indicated that α-Me 4 phen-bb 7  bound Q[10] with the bb 7  methylene carbons within the cavity and the metal center positioned outside one of the portals. Simple molecular modeling confirmed the feasibility of the binding model. An α-Me 4 phen-bb 7 -Q[10] binding constant of 9.9 ± 0.2 × 10 6  M −1  was determined by luminescence spectroscopy. Q[10]-encapsulation decreased the toxicity of α-Me 4 phen-bb 7  against the three eukaryotic cell lines and increased the binding affinity of the ruthenium complex for HSA. Confocal microscopy experiments indicated that the level of accumulation of α-Me 4 phen-7 in BHK cells is not significantly affected by Q[10]-encapsulation. Taken together, the combined results suggest that α-Me 4 phen-7 could be a good candidate as a new antimicrobial agent, and Q[10]-encapsulation could be a method to improve the pharmacokinetics of the ruthenium complex.

Eukaryotic Cell Toxicity and HSA Binding of [Ru(Me4phen)(bb7)]2+ and the Effect of Encapsulation in Cucurbit[10]uril