4-[(E)-2-(1-Pyrenyl)Vinyl]Pyridine Complexes: How to Modulate the Toxicity of Heavy Metal Ions to Target Microbial Infections

Author:

Schwarte Justine V.1ORCID,Crochet Aurélien12ORCID,Fromm Katharina M.123ORCID

Affiliation:

1. Department of Chemistry, University of Fribourg, Chemin du Musée 9, 1700 Fribourg, Switzerland

2. Fribourg Center for Nanomaterials, 1700 Fribourg, Switzerland

3. NCCR Bio-Inspired Materials, University of Fribourg, 1700 Fribourg, Switzerland

Abstract

Pyrene derivatives are regularly proposed for use in biochemistry as dyes due to their photochemical characteristics. Their antibacterial properties are, however, much less well understood. New complexes based on 4-[(E)-2-(1-pyrenyl)vinyl]pyridine (PyPe) have been synthesized with metal ions that are known to possess antimicrobial properties, such as zinc(II), cadmium(II), and mercury(II). The metal ion salts, free ligand, combinations thereof, and the coordination compounds themselves were tested for their antibacterial properties through microdilution assays. We found that the ligand is able to modulate the antibacterial properties of transition metal ions, depending on the complex stability, the distance between the ligand and the metal ions, and the metal ions themselves. The coordination by the ligand weakened the antibacterial properties of heavy metal ions (Cd(II), Hg(II), Bi(III)), allowing the bacteria to survive higher concentrations thereof. Mixing the ligand and the metal ion salts without forming the complex beforehand enhanced the antibacterial properties of the cations. Being non-cytotoxic itself, the ligand therefore balances the biological consequences of heavy metal ions between toxicity and therapeutic weapons, depending on its use as a coordinating ligand or simple adjuvant.

Funder

Swiss National Science Foundation

FriMat

NCCR Bioinspired Material

University of Fribourg

Publisher

MDPI AG

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