Efficient γ-amino-proline-derived cell penetrating peptide–superparamagnetic iron oxide nanoparticle conjugates via aniline-catalyzed oxime chemistry as bimodal imaging nanoagents

Silvia Cavalli; Daniel Carbajo; Milena Acosta; Silvia Lope-Piedrafita; Ana Paula Candiota; Carles Arús; Miriam Royo; Fernando Albericio

doi:10.1039/C2CC17937G

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Chemical Communications

Issue 43, 2012

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Efficient γ-amino-proline-derived cell penetrating peptide–superparamagnetic iron oxide nanoparticle conjugates via aniline-catalyzed oxime chemistry as bimodal imaging nanoagents

Silvia Cavalli,*^a^b Daniel Carbajo,^c Milena Acosta,^a^d Silvia Lope-Piedrafita,^e^a Ana Paula Candiota,^a^d^f Carles Arús,^d^a^f Miriam Royo^a^c and Fernando Albericio*^a^b^g

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CIBER-BBN, Networking Centre on Bioengineering, Biomaterials, and Nanomedicine, 08028 Barcelona, Spain
E-mail: silviacavalliIRB@gmail.com ;
Fax: +34 93403 7126 ;
Tel: +34 93403 7088

Institute for Research in Biomedicine, 08028 Barcelona, Spain

Combinatorial Chemistry Unit, Barcelona Science Park, 08028 Barcelona, Spain

Department of Biochemistry and Molecular Biology, Universitat Autònoma de Barcelona (UAB), 08193 Cerdanyola del Vallès, Spain

Nuclear Magnetic Resonance Service, Universitat Autònoma de Barcelona (UAB), 08193 Cerdanyola del Vallès, Spain

Institute of Biotechnology and Biomedicine, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Spain

Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain

Chem. Commun., 2012,48, 5322-5324

DOI: 10.1039/C2CC17937G
Received 19 Dec 2011, Accepted 03 Apr 2012
First published online 04 Apr 2012

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Aniline-catalyzed oxime chemistry was employed to conjugate a γ-amino-proline-derived cell penetrating peptide to superparamagnetic iron oxide nanoparticles (SPIONs). Internalization of the novel nanoconjugate into HeLa cells was found to be remarkably higher compared to the analogous TAT–SPION conjugate.

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Silvia Cavalli
Daniel Carbajo
Milena Acosta
Silvia Lope-Piedrafita
Ana Paula Candiota
Carles Arús
Miriam Royo
Fernando Albericio

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Chemical Communications

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Efficient γ-amino-proline-derived cell penetrating peptide–superparamagnetic iron oxide nanoparticle conjugates via aniline-catalyzed oxime chemistry as bimodal imaging nanoagents

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