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Fluorinated and Charged Hydrogenated Alkanethiolates Grafted on Gold: Expanding the Diversity of Mixed-Monolayer Nanoparticles for Biological Applications

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Department of Chemical and Pharmaceutical Sciences, University of Trieste and INSTM Trieste Unit, via L. Giorgieri 1, 34127 Trieste, Italy
Dipartimento di Scienze Molecolari e Nanosistemi and Centro di Microscopia Elettronica R. Stevanato, Università Ca’ Foscari Venezia, Via Torino 155/b, 30172 Venezia-Mestre, Italy
§ NanoMed lab, Fondazione IRCCS, Istituto Neurologico “Carlo Besta”, IFOM-IEO-campus, via Adamello, 20133 Milan, Italy
Institute of Materials, École Polytecnique Fédérale de Lausanne, Lausanne CH-1015, Switzerland
Cite this: Bioconjugate Chem. 2017, 28, 1, 43–52
Publication Date (Web):November 16, 2016
https://doi.org/10.1021/acs.bioconjchem.6b00585
Copyright © 2016 American Chemical Society

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    Abstract

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    Low intrinsic toxicity, high solubility, and stability are important and necessary features of gold nanoparticles to be used in the biomedical field. In this context, charged nanoparticles proved to be very versatile, and among them charged mixed-monolayer gold nanoparticles, displaying monolayers with well-defined morphologies, represent a paradigm. By using mixtures of hydrogenated and fluorinated thiols, the formation of monolayer domains may be brought to an extreme because of the immiscibility of fluorinated and hydrogenated chains. Following this rationale, mixed monolayer gold nanoparticles featuring ammonium, sulfonate, or carboxylic groups on their surface were prepared by using amphiphilic hydrogenated thiols and 1H,1H,2H,2H-perfluoro-alkanethiols. The toxicity of these systems was assessed in HeLa cells and was found to be, in general, low even for the cationic nanoparticles which usually show a high cytotoxicity and is comparable to that of homoligand gold nanoparticles displaying amphiphilic—charge neutral—hydrogenated or fluorinated thiolates in their monolayer. These properties make the mixed ligand monolayer gold nanoparticles an interesting new candidate for medical application.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.bioconjchem.6b00585.

    • Synthetic and characterization details of the ligands HMDDS, HMDA, HTMDA, NP-MUS/F8, NP-MDDS/F8, NP-C8TEG, NP-F8PEG. Characterization data for the nanoparticles NP-MDDS/F6, NP-MDA/F6, and NP-TMDA/F6. Results of the red blood assay for the nanoparticle systems NP-MDDS/F6/Bodipy, NP-TMDA/F6/Bodipy, NP-C8TEG/Bodipy, and NP-F8PEG/Bodipy. FACS analysis of HeLa cells incubated with 0.2 mL/mL of the nanoparticle systems. (PDF)

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