Inhibition of ATP synthesis by fenbufen and its conjugated metabolites in rat liver mitochondria

Toxicology in Vitro - Tập 31 - Trang 23-29 - 2016
Muzeeb Syed1, Christian Skonberg2, Steen Honoré Hansen1
1Section of Analytical Biosciences, Department of Pharmacy, School of Pharmaceutical Sciences, Faculty of Health and Medical Sciences, University of Copenhagen, Copenhagen, Denmark
2ADME Department, Discovery Biology and Technology, Novo Nordisk A/S, Måløv, Copenhagen, Denmark

Tài liệu tham khảo

Agundez, 2011, Assessment of nonsteroidal anti-inflammatory drug-induced hepatotoxicity, Expert Opin. Drug Metab. Toxicol., 7, 817, 10.1517/17425255.2011.574613 Amacher, 2012, The primary role of hepatic metabolism in idiosyncratic drug-induced liver injury, Expert Opin. Drug Metab. Toxicol., 8, 335, 10.1517/17425255.2012.658041 Benet, 1993, Predictability of the covalent binding of acidic drugs in man, Life Sci., 53, PL141, 10.1016/0024-3205(93)90279-C Boelsterli, 2002, Xenobiotic acyl glucuronides and acyl CoA thioesters as protein-reactive metabolites with the potential to cause idiosyncratic drug reactions, Curr. Drug Metab., 3, 439, 10.2174/1389200023337315 Chan, 2005, Drug-induced mitochondrial toxicity, Expert Opin. Drug Metab. Toxicol., 1, 655, 10.1517/17425255.1.4.655 Chiccarelli, 1980, Disposition and metabolism of fenbufen in several laboratory animals, Arzneimittelforschung, 30, 707 Chiccarelli, 1980, Metabolic and pharmacokinetic studies with fenbufen in man, Arzneimittelforschung, 30, 728 Choi, 2008, Mitochondrial complex I inhibition is not required for dopaminergic neuron death induced by rotenone, MPP+, or paraquat, Proc. Natl. Acad. Sci. U. S. A., 105, 15136, 10.1073/pnas.0807581105 Deavall, 2012, Drug-induced oxidative stress and toxicity, J. Toxicol., 2012, 645460, 10.1155/2012/645460 Friis, 1992, Drug-induced hepatic injury: an analysis of 1100 cases reported to the Danish Committee on Adverse Drug Reactions between 1978 and 1987, J. Intern. Med., 232, 133, 10.1111/j.1365-2796.1992.tb00562.x Grillo, 2001, Interaction of gamma-glutamyltranspeptidase with clofibryl-S-acyl-glutathione in vitro and in vivo in rat, Chem. Res. Toxicol., 14, 1033, 10.1021/tx010039x Grillo, 2003, Studies on the chemical reactivity of diclofenac acyl glucuronide with glutathione: identification of diclofenac-S-acyl-glutathione in rat bile, Drug Metab. Dispos., 31, 1327, 10.1124/dmd.31.11.1327 Grillo, 2003, Mechanistic studies on the bioactivation of diclofenac: identification of diclofenac-S-acyl-glutathione in vitro in incubations with rat and human hepatocytes, Chem. Res. Toxicol., 16, 1410, 10.1021/tx034038b Hadi, 2012, Mouse precision-cut liver slices as an ex vivo model to study idiosyncratic drug-induced liver injury, Chem. Res. Toxicol., 25, 1938, 10.1021/tx300248j Hadi, 2013, Human precision-cut liver slices as an ex vivo model to study idiosyncratic drug-induced liver injury, Chem. Res. Toxicol., 26, 710, 10.1021/tx300519p Hargus, 1995, Covalent modification of rat liver dipeptidyl peptidase IV (CD26) by the nonsteroidal anti-inflammatory drug diclofenac, Chem. Res. Toxicol., 8, 993, 10.1021/tx00050a001 Hu, 2015, Characterizing the mechanism of thiazolidinedione-induced hepatotoxicity: an in vitro model in mitochondria, Toxicol. Appl. Pharmacol., 284, 134, 10.1016/j.taap.2015.02.018 Husain, 2009, Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents, Eur. J. Med. Chem., 44, 3798, 10.1016/j.ejmech.2009.04.009 Jones, 1967, Properties of substituted 2-trifluoromethylbenzimidazoles as uncouplers of oxidative phosphorylation, Biochem. J., 102, 564, 10.1042/bj1020564 Kass, 2006, Mitochondrial involvement in drug-induced hepatic injury, Chem. Biol. Interact., 163, 145, 10.1016/j.cbi.2006.06.007 Kitz, 1962, Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase, J. Biol. Chem., 237, 3245, 10.1016/S0021-9258(18)50153-8 Kretz-Rommel, 1993, Diclofenac covalent protein binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes, Toxicol. Appl. Pharmacol., 120, 155, 10.1006/taap.1993.1097 Labbe, 2008, Drug-induced liver injury through mitochondrial dysfunction: mechanisms and detection during preclinical safety studies, Fundam. Clin. Pharmacol., 22, 335, 10.1111/j.1472-8206.2008.00608.x Lacroix, 2004, Nonsteroidal anti-inflammatory drug-induced liver injury: a case–control study in primary care, Fundam. Clin. Pharmacol., 18, 201, 10.1111/j.1472-8206.2004.00224.x Luz, 2015, Seahorse Xf(e) 24 Extracellular Flux AnalyzerbasedAnalysis of Cellular Respiration in Caenorhabditis elegans, Current protocols intoxicology/editorial board, 66, 10.1002/0471140856.tx2507s66 Mahmud, 1996, Nonsteroidal antiinflammatory drugs and uncoupling of mitochondrial oxidative phosphorylation, Arthritis Rheum., 39, 1998, 10.1002/art.1780391208 Masubuchi, 1998, Structural requirements for the hepatotoxicity of nonsteroidal anti-inflammatory drugs in isolated rat hepatocytes, J. Pharmacol. Exp. Ther., 287, 208 Masubuchi, 1999, Diphenylamine as an important structure of nonsteroidal anti-inflammatory drugs to uncouple mitochondrial oxidative phosphorylation, Biochem. Pharmacol., 58, 861, 10.1016/S0006-2952(99)00163-X Olinga, 1997, Liver slices in in vitro pharmacotoxicology with special reference to the use of human liver tissue, Toxicol. In Vitro, 12, 77, 10.1016/S0887-2333(97)00097-0 Pessayre, 2012, Central role of mitochondria in drug-induced liver injury, Drug Metab. Rev., 44, 34, 10.3109/03602532.2011.604086 Polasek, 2004, Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro, J. Pharmacol. Exp. Ther., 311, 996, 10.1124/jpet.104.071803 Robinson, 1987, An enzymatic approach to the study of the krebs tricarboxylic acid cycle, 153 Rogers, 2011, High throughput microplate respiratory measurements using minimal quantities of isolated mitochondria, PLoS One, 6, 10.1371/journal.pone.0021746 Schneider, 1950, Intracellular distribution of enzymes V. Further studies on the distribution of cytochrome c in rat liver homogenates, J. Biol. Chem., 183, 123, 10.1016/S0021-9258(18)56449-8 Skonberg, 2005 Skonberg, 2008, Metabolic activation of carboxylic acids, Expert Opin. Drug Metab. Toxicol., 4, 425, 10.1517/17425255.4.4.425 Somasundaram, 1997, Mitochondrial damage: a possible mechanism of the “topical” phase of NSAID induced injury to the rat intestine, Gut, 41, 344, 10.1136/gut.41.3.344 Stadtman, 1957, [137] Preparation and assay of acyl coenzyme A and other thiol esters; use of hydroxylamine, 931, 10.1016/S0076-6879(57)03481-3 Syed, 2013, Effect of some organic solvents on oxidative phosphorylation in rat liver mitochondria: choice of organic solvents, Toxicol. In Vitro, 27, 2135, 10.1016/j.tiv.2013.09.010 Wallace, 2000, Mitochondrial targets of drug toxicity, Annu. Rev. Pharmacol. Toxicol., 40, 353, 10.1146/annurev.pharmtox.40.1.353