Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems

Publication: Research - peer-reviewJournal article – Annual report year: 2012

  • Author: Bernardos, Andrea

    Departamento de Química, Universidad Politécnica de Valencia, Spain

  • Author: Mondragón, Laura

    Departamento de Química, Universidad Politécnica de Valencia, Spain

  • Author: Javakhishvili, Irakli

    The Danish Polymer Centre, Department of Chemical and Biochemical Engineering, Technical University of Denmark, Søltofts Plads, 2800, Kgs. Lyngby, Denmark

  • Author: Mas, Núria

    Departamento de Química, Universidad Politécnica de Valencia, Spain

  • Author: de la Torre, Cristina

    Departamento de Química, Universidad Politécnica de Valencia, Spain

  • Author: Martínez‐Máñez, Ramón

    Departamento de Química, Universidad Politécnica de Valencia, Spain

  • Author: Sancenón, Félix

    Departamento de Química, Universidad Politécnica de Valencia, Spain

  • Author: Barat, José M.

    Departamento de Tecnología de Alimentos, Universidad Politécnica de Valencia, Spain

  • Author: Hvilsted, Søren

    The Danish Polymer Centre, Department of Chemical and Biochemical Engineering, Technical University of Denmark, Søltofts Plads, 2800, Kgs. Lyngby, Denmark

  • Author: Orzaez, Mar

    Laboratorio Péptidos y Proteínas, Centro de Investigación Príncipe Felipe, Spain

  • Author: Pérez‐Payá, Enríque

    Laboratorio Péptidos y Proteínas, Centro de Investigación Príncipe Felipe, Spain

  • Author: Amorós, Pedro

    Institut de Ciència del Materials (ICMUV), Universitat de València, Spain

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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.
Original languageEnglish
JournalChemistry: A European Journal
Publication date2012
Volume18
Issue41
Pages13068-13078
ISSN0947-6539
DOIs
StatePublished
CitationsWeb of Science® Times Cited: 5

Keywords

  • Azo compounds, Drug delivery, Enzymes, Mesoporous materials, Polyesters
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