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Guanidinium-Functionalized Photodynamic Antibacterial Oligo(Thiophene)s

Published online by Cambridge University Press:  20 September 2019

Zhe Zhou,
Cansu Ergene and
Edmund F. PalermoOpen the ORCID record for Edmund F. Palermo[Opens in a new window]
Zhe Zhou
Affiliation:
Materials Science and Engineering, Rensselaer Polytechnic Institute, 110 8th St., Troy, NY12180
Cansu Ergene
Affiliation:
Materials Science and Engineering, Rensselaer Polytechnic Institute, 110 8th St., Troy, NY12180
Edmund F. Palermo*
Affiliation:
Materials Science and Engineering, Rensselaer Polytechnic Institute, 110 8th St., Troy, NY12180
*
*(Email: palere@rpi.edu)
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Abstract

We synthesized precision oligomers of thiophene with cationic and hydrophobic side chains to mimic the charge, hydrophobicity, and molecular size of antibacterial host defense peptides (HDPs). In this study, the source of cationic charge was a guanidinium salt moiety intended to reflect the structure of arginine-rich HDPs. Due to the pi-conjugated oligo(thiophene) backbone structure, these compounds absorb visible light in aqueous solution and react with dissolved oxygen to produce highly biocidal reactive oxygen species (ROS). Thus, the compounds exert bactericidal activity in the dark with dramatically enhanced potency upon visible light illumination. We find that guanylation of primary amine groups enhanced the activity of the oligomers in the dark but also mitigated their light-induced activity enhancement. In addition, we also quantified their toxicity to mammalian cell membranes using a hemolysis assay with red blood cells, in the light and dark conditions.

Keywords

polymerbiomimeticbiomaterial

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Type
Articles
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MRS Advances , Volume 4 , Issue 59-60: International Materials Research Congress XXVIII , 2019, pp. 3223 - 3231
Copyright
Copyright © Materials Research Society 2019 

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