A New Porphyrin for the Preparation of Functionalized Water-Soluble Gold Nanoparticles with Low Intrinsic Toxicity
نویسندگان
چکیده
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.
منابع مشابه
Entrapment of hydrophobic drugs in nanoparticle monolayers with efficient release into cancer cells.
Gold nanoparticles functionalized with water-soluble zwitterionic ligands form kinetically stable complexes with hydrophobic drugs and dyes. These drugs and dyes are efficiently released into cells, as demonstrated through fluorescence microscopy and cytotoxicity assays. Significantly, there is little or no cellular uptake of particle, making these low toxicity particles promising for delivery ...
متن کاملPREPARATION AND EVALUATION OF PROPERTIES OF PSEUDOMONAS AERUGINOSA EXOTOXIN A CONJUGATE WITH GOLD NANOPARTICLES
Background & Aims: Pseudomonas aeruginosa is an opportunistic pathogen and most important cause of hospital infections, which causes septicemia and death through various virulence factors such as exotoxin A. In the present study, P. aeruginosa exotoxin A (as a toxic factor) was prepared with the aim of obtaining a new recombinant vaccine candidate and conjugated with gold nanoparticles and its ...
متن کاملThermodynamic of Interaction between Some Water-Soluble Porphyrins and DNA by Titration Microcalorimetry
In the present work, the interaction of three water soluble porphyrins, tetra (p-trimethyle) ammoniumphenyl porphyrin iodide (TAPP) as a cationic porphyrin, tetra sodium meso-tetrakis (p-sulphonatophenyle) porphyrin (TSPP) as an anionic porphyrin and manganese tetrakis (p-sulphonato phenyl)porphinato acetate (MnTSPP) as a metal porphyrin, with DNA have been studied by isothermaltitration microc...
متن کاملEffect of Some Synthetic Parameters on Size and Polydispersity Index of Gelatin Nanoparticles Cross-Linked by CDI/NHS System
In our previous work, the effect of use of a water soluble CDI/NHS system as nontoxic cross-linking agent on fabrication of gelatin nanoparticles was investigated. In this research, the effect of variation in some synthetic parameters of gelatin nanoparticles cross-linked by CDI/NHS system such as type of gelatin and formulation of cross- linking agent on their size and distribution was examine...
متن کاملSi-Imidazole-HSO4 Functionalized Magnetic Fe3O4 Nanoparticles as an Efficient and Reusable Catalyst for the Regioselective Ring Opening of Epoxides in Water
An efficient and simple method for the preparation of Si-Imidazole-HSO4 functionalized magnetic Fe3O4 nanoparticles (Si-Im-HSO4 MNPs) and used as an efficient and reusable magnetic catalysts for the regioselective ring opening of epoxides under green conditions in water. This catalyst was used for the ring opening of epoxide corresponding to the thiocyanohydrins and azidohydrines. Compared to t...
متن کامل