A New Porphyrin for the Preparation of Functionalized Water‐Soluble Gold Nanoparticles with Low Intrinsic Toxicity. Issue 2 (1st December 2014)

• Record Type: Journal Article
• Authors: Penon, Oriol; Patiño, Tania; Barrios, Lleonard; Nogués, Carme; Amabilino , David B.; Wurst, Klaus; Pérez-García, Lluïsa
• Is Part Of: ChemistryOpen. Volume 4:Issue 2(2015:Apr.)
• Page Start: 127
• Page End: 136
• Publication Date: 2014-12-01
• Subjects: Chemistry -- Periodicals; 540; 540.5
• DOI: 10.1002/open.201402092
• Languages: English
• ISSNs: 2191-1363

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 (<bold>PR‐SH)</bold> was used to functionalize gold nanoparticles in order to obtain a potential drug delivery system. Water‐soluble multifunctional gold nanoparticles <bold>GNP‐PR/PEG</bold> were prepared using the Brust–Schiffrin methodology, by immobilization of both a thiolated polyethylene glycol (PEG) and the porphyrin thiol compound (<bold>PR‐SH)</bold>. 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 <bold>GNP‐PR/PEGs</bold> 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.</p> </abstract>