Institut de Chimie, Université de Neuchâtel, Avenue de Bellevaux 51, 2000 Neuchâtel, Switzerland.
Chemistry. 2011 Feb 7;17(6):1966-71. doi: 10.1002/chem.201002634. Epub 2011 Jan 5.
The self-assembly of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (tpt) triangular panels with p-cymene-ruthenium building blocks and 5,8-dioxido-1,4-naphthoquinonato (donq) bridges, in the presence of pyrenyl-containing dendrimers of different generations (P(0), P(1) and P(2)), affords the triangular prismatic host-guest compounds P(n)⊂Ru(6)(p-cymene)(6)(tpt)(2)(donq)(3) (P(n)⊂1). The host-guest nature of these systems, with the pyrenyl moiety being encapsulated in the hydrophobic cavity of the cage and the dendritic functional group pointing outwards, was confirmed by NMR spectroscopy ((1)H, 2D and DOSY). The host-guest properties of these systems were studied in solution by NMR and UV/Vis spectroscopic methods, allowing the determination of their affinity constants (K(a)). Moreover, the ability of these water-soluble host-guest systems to carry the pyrenyl-containing dendrimers into cancer cells was evaluated on human ovarian cancer cells. The host-guest systems are all more cytotoxic than the empty cage [1]CF(3)SO(3) (IC(50)≈4 μM), with the most active compound, [P(0)⊂1]CF(3)SO(3), being an order of magnitude more cytotoxic.
2,4,6-三(4-吡啶基)-1,3,5-三嗪(tpt)三角形单元与 p-枯烯钌构筑块和 5,8-二氧代-1,4-萘醌(donq)桥的自组装，在含有不同代的吡喃基树枝状大分子(P(0)、P(1)和 P(2))的存在下，提供了三角形棱柱形主客体化合物P(n)⊂Ru(6)(p-枯烯)(6)(tpt)(2)(donq)(3)P(n)⊂1。这些体系的主客体性质，由于吡喃基部分被包裹在笼状的疏水性空腔中，而树枝状官能团指向外部，通过 NMR 光谱((1)H、2D 和 DOSY)得到了证实。通过 NMR 和 UV/Vis 光谱方法在溶液中研究了这些体系的主客体性质，允许确定它们的亲和常数(K(a))。此外，还评估了这些水溶性主客体体系将含吡喃基的树枝状大分子带入癌细胞的能力，在人卵巢癌细胞上进行了研究。这些主客体体系的细胞毒性均高于空笼[1]CF(3)SO(3)(IC(50)≈4 μM)，最活跃的化合物[P(0)⊂1]CF(3)SO(3)的细胞毒性高出一个数量级。
