title: A new porphyrin for the preparation of functionalized water-soluble gold nanoparticles with low intrinsic toxicity.
abstract: A potential new photosensitizer based on a dissymmetric porphyrin derivative bearing a thiol group was synthesized. 5-[4-(11-Mercaptoundecyloxy)-phenyl-10,15,20-triphenylporphyrin (PR-SH) was used to functionalize gold nanoparticles in order to obtain a potential drug delivery system. Water-soluble multifunctional gold nanoparticles GNP-PR/PEG were prepared using the Brust-Schiffrin methodology, by immobilization of both a thiolated polyethylene glycol (PEG) and the porphyrin thiol compound (PR-SH). The nanoparticles were fully characterized by transmission electron microscopy and (1)H nuclear magnetic resonance spectroscopy, UV/Vis absorption spectroscopy, and X-ray photoelectron spectroscopy. Furthermore, the ability of GNP-PR/PEGs to induce singlet oxygen production was analyzed to demonstrate the activity of the photosensitizer. Cytotoxicity experiments showed the nanoparticles are nontoxic. Finally, cellular uptake experiments demonstrated that the functionalized gold nanoparticles are internalized. Therefore, this colloid can be considered to be a novel nanosystem that could potentially be suitable as an intracellular drug delivery system of photosensitizers for photodynamic therapy.
authors.affiliation: Departament de Farmacologia i Química Terapèutica, and Institut de Nanociència i Nanotecnologia UB (IN2UB), Universitat de Barcelona Avda. Joan XXIII s/n, 08028, Barcelona, (Spain).
authors.forename: Oriol
authors.initials: O
authors.lastname: Penon
authors.affiliation: Departament de Biologia Cellular, Fisiologia i Immunologia, Universitat Autònoma de Barcelona Campus de la UAB, 08193, Bellaterra, Spain.
authors.forename: Tania
authors.initials: T
authors.lastname: Patiño
authors.affiliation: Departament de Biologia Cellular, Fisiologia i Immunologia, Universitat Autònoma de Barcelona Campus de la UAB, 08193, Bellaterra, Spain.
authors.forename: Lleonard
authors.initials: L
authors.lastname: Barrios
authors.affiliation: Departament de Biologia Cellular, Fisiologia i Immunologia, Universitat Autònoma de Barcelona Campus de la UAB, 08193, Bellaterra, Spain.
authors.forename: Carme
authors.initials: C
authors.lastname: Nogués
authors.affiliation: Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus de la UAB 08193, Bellaterra, (Spain).
authors.forename: David B
authors.initials: DB
authors.lastname: Amabilino
authors.affiliation: Institut für Anorganische Chemie Innrain 80/82, 6020, Innsbruck, (Austria).
authors.forename: Klaus
authors.initials: K
authors.lastname: Wurst
authors.affiliation: Departament de Farmacologia i Química Terapèutica, and Institut de Nanociència i Nanotecnologia UB (IN2UB), Universitat de Barcelona Avda. Joan XXIII s/n, 08028, Barcelona, (Spain).
authors.forename: Lluïsa
authors.initials: L
authors.lastname: Pérez-García
keywords: drug delivery; gold nanoparticles; photodynamic therapy; photosensitizers; porphyrins