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Excellent Correlation between Drug Release and Portal Size in Metalla‐Cage Drug‐Delivery Systems
Author(s) -
Barry Nicolas P. E.,
Zava Olivier,
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.201003530
Subject(s) - ruthenium , cationic polymerization , chemistry , pyrene , molecule , drug delivery , triazine , host (biology) , combinatorial chemistry , stereochemistry , medicinal chemistry , nuclear chemistry , polymer chemistry , organic chemistry , catalysis , ecology , biology
A series of large cationic hexanuclear metalla‐prisms, [Ru 6 ( p ‐ i PrC 6 H 4 Me) 6 (tpt) 2 (donq) 3 ] 6+ , [Ru 6 ( p ‐ i PrC 6 H 4 Me) 6 (tpt) 2 (doaq) 3 ] 6+ and [Ru 6 ( p ‐ i PrC 6 H 4 Me) 6 (tpt) 2 (dotq) 3 ] 6+ , composed of p ‐cymene–ruthenium building blocks bridged by OO ∩ OO ligands (donq=5,8‐dioxido‐1,4‐naphthoquinonato; doaq=5,8‐dioxido‐1,4‐anthraquinonato, dotq=6,11‐dioxido‐5,12‐naphthacenedionato) and connected by two 2,4,6‐tripyridin‐4‐yl‐1,3,5‐triazine (tpt) panels, which encapsulate the guest molecules 1‐(4,6‐dichloro‐1,3,5‐triazin‐2‐yl)pyrene and Pd(acac) 2 , have been prepared. The host–guest properties of these water‐soluble delivery systems were studied in solution by NMR and fluorescence spectroscopy, providing the stability constants ( K ) for these host–guest systems. Moreover, the ability of the hosts to deliver the guests into cancer cells was evaluated and the uptake mechanism studied; the rate of release of the guest molecule was found to depend on the portal size of the host.