One-Electron Reduction of Penicillins in Relation to the Oxidative Stress Phenomenon

Int J Mol Sci. 2015 Dec 11;16(12):29673-81. doi: 10.3390/ijms161226130.

Abstract

Certain bactericidal antibiotics target mitochondrial components and, due to the leakage of electrons from the electron transport chain, one-electron reduction might occur that can lead to intermediates passing the electron to suitable acceptors. This study aimed at investigating the one-electron reduction mechanism of selected penicillin derivatives using pulse radiolysis techniques. Penicillins can accommodate the electron on each of their carbonyl carbon. Ketyl radicals are thus produced, which are reducing agents with possibility to interact with suitable biomolecules. A detailed mechanism of the reduction is reported.

Keywords: antibiotic; hydrated electron; ketyl radical; oxidative stress; penicillin; pulse radiolysis; reactive oxygen species; reduction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Kinetics
  • Oxidation-Reduction
  • Oxidative Stress
  • Penicillins / chemistry*
  • Pulse Radiolysis
  • Reactive Oxygen Species / chemistry

Substances

  • Anti-Bacterial Agents
  • Penicillins
  • Reactive Oxygen Species