A New Porphyrin for the Preparation of Functionalized Water‐Soluble Gold Nanoparticles with Low Intrinsic Toxicity

ChemistryOpen

Dr. Oriol Penon²  Tania Patiño⁴  Prof. Lleonard Barrios⁴  Prof. Carme Nogués⁴  Prof. David B. Amabilino&thinsp¹  Prof. Klaus Wurst³ 

[1] Institut de Ciència de Materials de Barcelona (ICMAB-CSIC, Campus de la UAB, Bellaterra, (Spain;Departament de Farmacologia i Química Terapèutica, and Institut de Nanociència i Nanotecnologia UB (IN2UB, Universitat de Barcelona, Barcelona, (Spain;Institut für Anorganische Chemie, Innsbruck, (Austria;Departament de Biologia Cellular, Fisiologia i Immunologia, Universitat Autònoma de Barcelona, Bellaterra, Spain

关键词: drug delivery;    gold nanoparticles;    photodynamic therapy;    photosensitizers;    porphyrins;   

DOI  :  10.1002/open.201402092

来源: Wiley

【 摘 要 】

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 ¹H 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.

【 授权许可】

CC BY-NC-ND   
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

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