title: Iron oxide nanoparticles functionalized with novel hydrophobic and hydrophilic porphyrins as potential agents for photodynamic therapy.
abstract: The preparation of novel porphyrin derivatives and their immobilization onto iron oxide nanoparticles to build up suitable nanotools for potential use in photodynamic therapy (PDT) has been explored. To achieve this purpose, a zinc porphyrin derivative, ZnPR-COOH, has been synthesized, characterized at the molecular level and immobilized onto previously synthesized iron oxide nanoparticles covered with oleylamine. The novel nanosystem (ZnPR-IONP) has been thoroughly characterized by a variety of techniques such as UV-Vis absorption spectroscopy, fluorescence spectroscopy, X-ray photoloectron spectroscopy (XPS) and transmission electron microscopy (TEM). In order to probe the capability of the photosensitizer for PDT, the singlet oxygen production of both ZnPR-IONP and the free ligand ZnPR-COOH have been quantified by measuring the decay in absorption of the anthracene derivative 9,10-anthracenedipropionic acid (ADPA), showing an important increase on singlet oxygen production when the porphyrin is incorporated onto the IONP (ZnPR-IONP). On the other hand, the porphyrin derivative PR-TRIS3OH, incorporating several polar groups (TRIS), was synthesized and immobilized with the intention of obtaining water soluble nanosystems (PR-TRIS-IONP). When the singlet oxygen production ability was evaluated, the values obtained were similar to ZnPR-COOH/ZnPR-IONP, again much higher in the case of the nanoparticles PR-TRIS-IONP, with more than a twofold increase. The efficient singlet oxygen production of PR-TRIS-IONP together with their water solubility, points to the great promise that these new nanotools represent for PDT.
authors.affiliation: Departament de Farmacologia i Química Terapèutica, Avda. Joan XXIII s/n, 08028 Barcelona, Spain; Institut de Nanociència i Nanotecnologia UB (IN2UB), Universitat de Barcelona, 08028 Barcelona, Spain.
authors.forename: Oriol
authors.initials: O
authors.lastname: Penon
authors.affiliation: School of Chemistry, University of East Anglia, Norwich Research Park, Norwich NR4 7TJ, UK.
authors.forename: María J
authors.initials: MJ
authors.lastname: Marín
authors.affiliation: Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus Universitari de Bellaterra, 08193 Cerdanyola del Vallès, Spain.
authors.forename: David B
authors.initials: DB
authors.lastname: Amabilino
authors.affiliation: School of Chemistry, University of East Anglia, Norwich Research Park, Norwich NR4 7TJ, UK.
authors.forename: David A
authors.initials: DA
authors.lastname: Russell
authors.affiliation: Departament de Farmacologia i Química Terapèutica, Avda. Joan XXIII s/n, 08028 Barcelona, Spain; Institut de Nanociència i Nanotecnologia UB (IN2UB), Universitat de Barcelona, 08028 Barcelona, Spain. Electronic address: mlperez@ub.edu.
authors.forename: Lluïsa
authors.initials: L
authors.lastname: Pérez-García
mesh_terms: D005290:Ferric Compounds / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D053758:Nanoparticles / Q000737:chemistry*; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000627:therapeutic use*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D005290:Ferric Compounds; D017319:Photosensitizing Agents; D011166:Porphyrins; C000499:ferric oxide
keywords: Iron oxide nanoparticles (IONPs); Photodynamic therapy (PDT); Singlet oxygen production; Water soluble photosensitizers; Zn-porphyrins