Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 41, Pages 13068-13078Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200787
Keywords
azo compounds; drug delivery; enzymes; mesoporous materials; polyesters
Categories
Funding
- Spanish Government [MAT2009-14564-C04, CTQ2007-64735-AR07, SAF2010-15512]
- Generalitat Valencia [PROMETEO/2009/016, PROMETEO/2010/005]
- Universidad Politecnica de Valencia
- Generalitat Valenciana
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The synthesis and characterisation of new capped silica mesoporous nanoparticles for on-command delivery applications is reported. Functional capped hybrid systems consist of MCM-41 nanoparticles functionalised on the external surface with polyesters bearing azobenzene derivatives and rhodamine B inside the mesopores. Two solid materials, Rh-PAzo8-S and Rh-PAzo6-S, containing two closely related polymers, PAzo8 and PAzo6, in the pore outlets have been prepared. Materials Rh-PAzo8-S and Rh-PAzo6-S showed an almost zero release in water due to steric hindrance imposed by the presence of anchored bulky polyesters, whereas a large delivery of the cargo was observed in the presence of an esterase enzyme due to the progressive hydrolysis of polyester chains. Moreover, nanoparticles Rh-PAzo8-S and Rh-PAzo6-S were used to study the controlled release of the dye in intracellular media. Nanoparticles were not toxic for HeLa cells and endocytosis-mediated cell internalisation was confirmed by confocal microscopy. Furthermore, the possible use of capped materials as a drug-delivery system was demonstrated by the preparation of a new mesoporous silica nanoparticle functionalised with PAzo6 and loaded with the cytotoxic drug camptothecin (CPT-PAzo6-S). Following cell internalisation and lysosome resident enzyme-dependent gate opening, CPT-PAzo6-S induced CPT-dependent cell death in HeLa cells.
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