Excellent Correlation between Drug Release and Portal Size in Metalla-Cage Drug-Delivery Systems

Barry, Nicolas P.E.; Zava, Olivier; Dyson, Paul J.; Therrien, Bruno

doi:10.1002/chem.201003530

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

Institut de chimie

Date issued

2011

In

Chemistry - A European Journal, Wiley, 2011/17/35/9669-9677

Subjects

bioorganometallic chemistry drug delivery endocytosis host–guest systems ruthenium

Abstract

A series of large cationic hexanuclear metalla-prisms, [Ru6(p-iPrC6H4Me)6(tpt)2(donq)3]6+, [Ru6(p-iPrC6H4Me)6(tpt)2(doaq)3]6+ and [Ru6(p-iPrC6H4Me)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.