A new porphyrin for the preparation of functionalized water-soluble gold nanoparticles with low intrinsic toxicity

Oriol Penon, Tania Patiño, Lleonard Barrios, Carme Nogués, David B. Amabilino, Klaus Wurst, Lluïsa Pérez-García

Research output: Contribution to journalArticleResearchpeer-review

31 Citations (Scopus)

Abstract

© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. 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 <sup>1</sup>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.
Original languageEnglish
Pages (from-to)127-136
JournalChemistryOpen
Volume4
DOIs
Publication statusPublished - 1 Apr 2015

Keywords

  • drug delivery
  • gold nanoparticles
  • photodynamic therapy
  • photosensitizers
  • porphyrins

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