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

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

Standard

Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems. / Bernardos, Andrea; Mondragón, Laura; Javakhishvili, Irakli; Mas, Núria; de la Torre, Cristina; Martínez‐Máñez, Ramón; Sancenón, Félix; Barat, José M.; Hvilsted, Søren; Orzaez, Mar; Pérez‐Payá, Enríque; Amorós, Pedro.

In: Chemistry: A European Journal, Vol. 18, No. 41, 2012, p. 13068-13078.

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

Harvard

Bernardos, A, Mondragón, L, Javakhishvili, I, Mas, N, de la Torre, C, Martínez‐Máñez, R, Sancenón, F, Barat, JM, Hvilsted, S, Orzaez, M, Pérez‐Payá, E & Amorós, P 2012, 'Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems' Chemistry: A European Journal, vol 18, no. 41, pp. 13068-13078., 10.1002/chem.201200787

APA

Bernardos, A., Mondragón, L., Javakhishvili, I., Mas, N., de la Torre, C., Martínez‐Máñez, R., ... Amorós, P. (2012). Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems. Chemistry: A European Journal, 18(41), 13068-13078. 10.1002/chem.201200787

CBE

Bernardos A, Mondragón L, Javakhishvili I, Mas N, de la Torre C, Martínez‐Máñez R, Sancenón F, Barat JM, Hvilsted S, Orzaez M, Pérez‐Payá E, Amorós P. 2012. Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems. Chemistry: A European Journal. 18(41):13068-13078. Available from: 10.1002/chem.201200787

MLA

Vancouver

Bernardos A, Mondragón L, Javakhishvili I, Mas N, de la Torre C, Martínez‐Máñez R et al. Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems. Chemistry: A European Journal. 2012;18(41):13068-13078. Available from: 10.1002/chem.201200787

Author

Bernardos, Andrea; Mondragón, Laura; Javakhishvili, Irakli; Mas, Núria; de la Torre, Cristina; Martínez‐Máñez, Ramón; Sancenón, Félix; Barat, José M.; Hvilsted, Søren; Orzaez, Mar; Pérez‐Payá, Enríque; Amorós, Pedro / Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems.

In: Chemistry: A European Journal, Vol. 18, No. 41, 2012, p. 13068-13078.

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

Bibtex

@article{ed6c0553cc684820896720f200b37bc3,
title = "Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems",
keywords = "Azo compounds, Drug delivery, Enzymes, Mesoporous materials, Polyesters",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
author = "Andrea Bernardos and Laura Mondragón and Irakli Javakhishvili and Núria Mas and {de la Torre}, Cristina and Ramón Martínez‐Máñez and Félix Sancenón and Barat, {José M.} and Søren Hvilsted and Mar Orzaez and Enríque Pérez‐Payá and Pedro Amorós",
year = "2012",
doi = "10.1002/chem.201200787",
volume = "18",
number = "41",
pages = "13068--13078",
journal = "Chemistry: A European Journal",
issn = "0947-6539",

}

RIS

TY - JOUR

T1 - Azobenzene Polyesters Used as Gate‐Like Scaffolds in Nanoscopic Hybrid Systems

A1 - Bernardos,Andrea

A1 - Mondragón,Laura

A1 - Javakhishvili,Irakli

A1 - Mas,Núria

A1 - de la Torre,Cristina

A1 - Martínez‐Máñez,Ramón

A1 - Sancenón,Félix

A1 - Barat,José M.

A1 - Hvilsted,Søren

A1 - Orzaez,Mar

A1 - Pérez‐Payá,Enríque

A1 - Amorós,Pedro

AU - Bernardos,Andrea

AU - Mondragón,Laura

AU - Javakhishvili,Irakli

AU - Mas,Núria

AU - de la Torre,Cristina

AU - Martínez‐Máñez,Ramón

AU - Sancenón,Félix

AU - Barat,José M.

AU - Hvilsted,Søren

AU - Orzaez,Mar

AU - Pérez‐Payá,Enríque

AU - Amorós,Pedro

PB - Wiley - V C H Verlag GmbH & Co. KGaA

PY - 2012

Y1 - 2012

N2 - 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.

AB - 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.

KW - Azo compounds

KW - Drug delivery

KW - Enzymes

KW - Mesoporous materials

KW - Polyesters

U2 - 10.1002/chem.201200787

DO - 10.1002/chem.201200787

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 41

VL - 18

SP - 13068

EP - 13078

ER -