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

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.

Mechanistic study on thiacloprid transformation: Free radical reactions

“…The initial build-up, which is assigned to the formation of species o, is followed by a fast firstorder decay with k = 2.4 × 10 4 s -1 that represents the transformation process into species p ( Figure 5B). Decrease in absorbance upon protonation has already been observed in our previous study [59] and it is a frequently observed phenomenon in the literature. Assuming that the absorption band at 285 nm represents the only transient in the system molar absorption coefficients of 1360 mol -1 L cm -1 and 684 mol -1 L cm -1 are calculated for species o and p, respectively.…”

A Mitocentric View of the Main Bacterial and Parasitic Infectious Diseases in the Pediatric Population

“…Of note, the bactericides oxacillin, cloxacillin, dicloxacillin, and nafcillin, belonging to the beta-lactam family, which prevent the formation of the bacterial cell wall [ 109 , 110 ] as well as the bacteriostatic clindamycin, belonging to the lincosamide family, have not been considered in the table due to the lack of pediatric studies (neither has clindamycin been associated with mitochondria in the literature). However, it should be mentioned that the former promote mitochondrial oxidative impairment through ROS overproduction [ 138 ] via the disruption of the TCA cycle and ETC [ 139 ], as well as decrease Δψm [ 139 ]. Daptomycin is another antibiotic from the lipopeptic family, which has been demonstrated to present high clinical success rates against a wide variety of infections and is well tolerated in children and adolescents [ 140 ].…”

“…Specific mitochondrial interactions derived from these antibiotics are provided (Table 6). • Promotes ROS overproduction [138] Ampicillin is a "broad-spectrum penicillin" used as therapy for suspected bacterial meningitis. Penetrates the blood-brain barrier sufficiently with an adequate dose and inflamed meninges.…”

Electron Transfer in Electro-Oxidation of Amoxicillin Using Platinum Electrode and Platinum Modified Cobalt Electrodes

“…Laszlo Szabo outlining the phenomenon of the one-electron reduction mechanism of oxidative damage from selected penicillin (amoxicillin, ampicillin, cloxacillin, and their general 6-aminopenicillins acid) was studied using pulse radiolysis techniques to investigate the presence of reactive intermediates that can damage the biological system. Besides, the oxidation of one amoxicillin electron was previously studied by the method of pulse radiolysis techniques [7] [8].…”

“…The mechanism for the reduction of one electron penicillin derivative has been reported before [7], but the transfer of electro-oxidation amoxicillin by voltammetry has not been widely reported. This work aims to test the oxidation of amoxicillin on platinum electrodes and platinum modified cobalt electrodes in phosphate buffer solutions with a pH range of 2-11 to develop a new direct voltammetry method for the determination of compounds in pharmaceutical preparations.…”