Issue 40, 2019

Enantiopure polythiophene nanoparticles. Chirality dependence of cellular uptake, intracellular distribution and antimicrobial activity

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.

Graphical abstract: Enantiopure polythiophene nanoparticles. Chirality dependence of cellular uptake, intracellular distribution and antimicrobial activity

Supplementary files

Article information

Article type
Paper
Submitted
25 iyn 2019
Accepted
19 iyl 2019
First published
25 iyl 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 23036-23044

Enantiopure polythiophene nanoparticles. Chirality dependence of cellular uptake, intracellular distribution and antimicrobial activity

I. E. Palamà, F. Di Maria, M. Zangoli, S. D'Amone, G. Manfredi, J. Barsotti, G. Lanzani, L. Ortolani, E. Salatelli, G. Gigli and G. Barbarella, RSC Adv., 2019, 9, 23036 DOI: 10.1039/C9RA04782D

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