Title
Enantiopure polythiophene nanoparticles. Chirality dependence of cellular uptake, intracellular distribution and antimicrobial activity
Author
Ilaria Elena Palamà, Francesca Di Maria, Mattia Zangoli, Stefania D'Amone, Giovanni Manfredi, Jonathan Barsotti, Guglielmo Lanzani, Luca Ortolani, Elisabetta Salatelli, Giuseppe Giglia, Giovanna Barbarella
Year
2019
Journal
RSC Advances
Abstract
The use of intrinsic chiral molecules opens the door to bio-imaging specific tools and to the development of target-therapy. In this work the synthesis and characterization of polythiophenes with alkyl side chains containing one R or S chiral carbon is reported. Enantiopure chiral nanoparticles (R or S NPs) were prepared from the polymers by a reprecipitation method. UV-vis, photoluminescence and circular dichroism spectroscopy of the NPs are described. In vitro analysis and metabolic assays show that both R and S NPs are efficiently taken-up by fibroblast cells without signs of toxicity. SDS-PAGE experiments show that formation of hard protein ‘corona’ enhances the chirality difference between nanoparticles. Co-localization experiments demonstrate that the cells are able to discriminate between the enantiomeric R and S nanoparticles. Finally, experiments carried out on Gram negative and Gram positive bacteria show that the enantiomeric NPs display different antibacterial activity.
Instrument
J-715
Keywords
Circular dichroism, Polymers, Stereochemistry, Nanostructures, Materials