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

被引:6
作者
Szabo, Laszlo [1 ,2 ]
Toth, Tuende [2 ]
Takacs, Erzsebet [1 ,3 ]
Wojnarovits, Laszlo [1 ]
机构
[1] Hungarian Acad Sci, Energy Res Ctr, Inst Energy Secur & Environm Safety, H-1121 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1111 Budapest, Hungary
[3] Obuda Univ, Sandor Rejto Fac Light Ind & Environm Engn, H-1034 Budapest, Hungary
关键词
antibiotic; penicillin; oxidative stress; reactive oxygen species; reduction; hydrated electron; ketyl radical; pulse radiolysis; BETA-LACTAM ANTIBIOTICS; PULSE-RADIOLYSIS; AQUEOUS-SOLUTION; HYDRATED ELECTRONS; BACTERICIDAL ANTIBIOTICS; AMINO-ACIDS; PEPTIDES; PROTEINS; RADICALS; CONFORMATION;
D O I
10.3390/ijms161226130
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
引用
收藏
页码:29673 / 29681
页数:9
相关论文
共 30 条
[1]   A MULTIFACETED APPROACH TO THE STUDY OF THE SIDE-CHAIN CONFORMATION IN BETA-LACTAMASE-RESISTANT PENICILLINS [J].
BLANPAIN, PC ;
NAGY, JB ;
LAURENT, GH ;
DURANT, FV .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (12) :1283-1292
[2]   REEVALUATION OF THE THIOCYANATE DOSIMETER FOR PULSE-RADIOLYSIS [J].
BUXTON, GV ;
STUART, CR .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1995, 91 (02) :279-281
[3]  
Chain E. B., 1964, THE CHEMICAL STRUCTU, P110
[4]   REACTION OF HYDRATED ELECTRON WITH AMINO-ACIDS, PEPTIDES, AND PROTEINS IN AQUEOUS-SOLUTION .2. FORMATION OF RADICALS AND ELECTRON-TRANSFER REACTIONS [J].
FARAGGI, M ;
TAL, Y .
RADIATION RESEARCH, 1975, 62 (02) :347-356
[5]   A COMPUTER-CONTROLLED PULSE-RADIOLYSIS LABORATORY [J].
FOLDIAK, G ;
HARGITTAI, P ;
KASZANYICZKI, L ;
WOJNAROVITS, L .
JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY-ARTICLES, 1988, 125 (01) :19-28
[6]   REACTION-MECHANISMS IN THE RADIOLYSIS OF PEPTIDES, POLYPEPTIDES, AND PROTEINS [J].
GARRISON, WM .
CHEMICAL REVIEWS, 1987, 87 (02) :381-398
[7]   REACTIONS OF CARBONYLIC COMPOUNDS WITH HYDRATED ELECTRONS [J].
HART, EJ ;
FIELDEN, EM ;
ANBAR, M .
JOURNAL OF PHYSICAL CHEMISTRY, 1967, 71 (12) :3993-&
[8]   Diagnosing oxidative stress in bacteria: not as easy as you might think [J].
Imlay, James A. .
CURRENT OPINION IN MICROBIOLOGY, 2015, 24 :124-131
[9]   DIRECT OBSERVATION OF THE PROTONATION OF ACETONE KETYL RADICAL BY CONDUCTOMETRIC PULSE-RADIOLYSIS [J].
JANATA, E ;
SCHULER, RH .
JOURNAL OF PHYSICAL CHEMISTRY, 1980, 84 (25) :3351-3353
[10]   Bactericidal Antibiotics Induce Mitochondrial Dysfunction and Oxidative Damage in Mammalian Cells [J].
Kalghatgi, Sameer ;
Spina, Catherine S. ;
Costello, James C. ;
Liesa, Marc ;
Morones-Ramirez, J. Ruben ;
Slomovic, Shimyn ;
Molina, Anthony ;
Shirihai, Orian S. ;
Collins, James J. .
SCIENCE TRANSLATIONAL MEDICINE, 2013, 5 (192)