Polyradical PROXYL/TEMPO-Derived Amides: Synthesis, Physicochemical Studies, DFT Calculations, and Antimicrobial Activity
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Updated: Dec 30, 2025

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Patrik Poprac1, Peter Poliak1, Miroslav Kavala1
1Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovakia.
Abstract:
A series of polynitroxide amides possessing 2,2,5,5-tetramethyl-1-pyrrolidinyloxy (PROXYL) and/or 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) units connected through various bridges were synthesized and their properties were analyzed. EPR spectroscopy provided detailed insight into their paramagnetic character and related properties. A thorough examination of the EPR spectra of dinitroxides in organic solvents provided valuable information on the intramolecular motions, thermodynamics, and spin-exchange mechanisms. Analysis of low-temperature X- and Q-band EPR spectra of the dissolved dinitroxides provided spin-spin distances that were comparable with the theoretical values obtained by DFT. Cyclic voltammetry investigations revealed (quasi)reversible electrochemical behavior for PROXYL-derived biradicals, whereas significant loss of the reversibility was found for TEMPO-containing bi- and polyradicals. The inhibitory activities of the nitroxides against model bacteria, yeasts, and filamentous fungi were assessed.
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