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Double Targeting of Tumours with Pyrenyl‐Modified Dendrimers Encapsulated in an Arene–Ruthenium Metallaprism
Author(s) -
PittoBarry Anaïs,
Barry Nicolas P. E.,
Zava Olivier,
Deschenaux Robert,
Dyson Paul J.,
Therrien Bruno
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002634
Subject(s) - ruthenium , dendrimer , moiety , chemistry , triazine , host (biology) , stereochemistry , nuclear magnetic resonance spectroscopy , polymer chemistry , organic chemistry , ecology , biology , catalysis
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 ] 6+ ([P n ⊂ 1 ] 6+ ). 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 ] 6 (IC 50 ≈4 μ M ), with the most active compound, [P 0 ⊂ 1 ][CF 3 SO 3 ] 6 , being an order of magnitude more cytotoxic.