Valproic acid metabolites inhibit dihydrolipoyl dehydrogenase activity leading to impaired 2-oxoglutarate-driven oxidative phosphorylation

Biochimica et Biophysica Acta - Bioenergetics

Volumn 1767, Issue 9, 2007, Pages 1126-1133

  Luís, Paula B M ^a   Ruiter, Jos P N ^b   Aires, Cátia C P ^a   Soveral, Graça ^a,c   Tavares de Almeida, Isabel ^a   Duran, Marinus ^b   Wanders, Ronald J A ^b   Silva, Margarida F B ^a  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

^c UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

Dihydrolipoyl dehydrogenase; Drug induced hepatotoxicity; Mitochondrial dysfunction; Oxidative phosphorylation; Valproic acid; Valproyl CoA

Indexed keywords

2 OXOGLUTARIC ACID; 2 PROPYL 4 PENTENOIC ACID; ACETYL COENZYME A; ADENOSINE TRIPHOSPHATE; DELTA 2 VALPROIC ACID; DIGITONIN; DIHYDROLIPOAMIDE DEHYDROGENASE; DRUG METABOLITE; ROTENONE; SUCCINIC ACID; UNCLASSIFIED DRUG; VALPROIC ACID; VALPROYLCOENZYME A; VALPROYLDEPHOSPHOCOENZYME A;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CELL MEMBRANE PERMEABILITY; CONTROLLED STUDY; DRUG INHIBITION; DRUG MECHANISM; DRUG TARGETING; ENZYME ACTIVITY; ENZYME SUBSTRATE; IN VITRO STUDY; LIVER CELL; LIVER MITOCHONDRION; MALE; NONHUMAN; OXIDATIVE PHOSPHORYLATION; OXYGEN CONSUMPTION; POLAROGRAPHY; PRIORITY JOURNAL; RAT; RESPIRATORY CHAIN;

ADENOSINE TRIPHOSPHATE; ANIMALS; ANTICONVULSANTS; DIHYDROLIPOAMIDE DEHYDROGENASE; HEPATOCYTES; KETOGLUTARIC ACIDS; MALE; MITOCHONDRIA; MITOCHONDRIA, LIVER; OXIDATIVE PHOSPHORYLATION; OXYGEN; OXYGEN CONSUMPTION; RATS; RATS, WISTAR; VALPROIC ACID;

RATTUS;

EID: 34548187167     PISSN: 00052728     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbabio.2007.06.007     Document Type: Article

References (35)

1. Bryant III A.E., and Dreifuss F.E. Valproic acid hepatic fatalities. III U.S. experience since 1986. Neurology 46 (1996) 465-469
2. Lee W.M. Drug-induced hepatotoxicity. N. Engl. J. Med. 349 (2003) 474-485
3. Watkins P.B., and Seeff L.B. Drug-induced liver injury: summary of a single topic clinical research conference. Hepatology 43 (2006) 618-631
4. Björnsson E., and Olsson R. Suspected drug-induced liver fatalities reported to the WHO database. Dig. Liver Dis. 38 (2006) 33-38
5. Begriche K., Igoudjil A., Pessayre D., and Fromenty B. Mitochondrial dysfunction in NASH: causes, consequences and possible means to prevent it. Mitochondrion 6 (2006) 1-28
6. Fromenty B., and Pessayre D. Impaired mitochondrial function in microvesicular steatosis: effects of drugs, ethanol, hormones and cytokines. J. Hepatol. 26 (1997) 43-53
7. Haas R., Stumpf D.A., Parks J.K., and Eguren L. Inhibitory effects of sodium valproate on oxidative phosphorylation. Neurology 31 (1981) 1473-1476
8. Becker C.M., and Harris R.A. Influence of valproic acid on hepatic carbohydrate and lipid metabolism. Arch. Biochem. Biophys. 223 (1983) 381-392
9. Ponchaut S., van Hoof F., and Veitch K. In vitro effects of valproate and valproate metabolites on mitochondrial oxidations. Biochem. Pharmacol. 43 (1992) 2435-2442
10. Rumbach L., Warter J.M., Rendon A., Marescaux C., Micheletti G., and Waksman A. Inhibition of oxidative phosphorylation in hepatic and cerebral mitochondria of sodium valproate-treated rats. J. Neurol. Sci. 61 (1983) 417-423
11. Hayasaka K., Takahashi I., Kobayashi Y., Iinuma K., Narisawa K., and Tada K. Effects of valproate on biogenesis and function of liver mitochondria. Neurology 36 (1986) 351-356
12. Ponchaut S., and Veitch K. Valproate and mitochondria. Biochem. Parmacol. 46 (1993) 199-204
13. Silva M.F.B., Ruiter J.P.N., IJlst L., Jakobs C., Duran M., de Almeida I.T., and Wanders R.J.A. Valproate inhibits the mitochondrial pyruvate-driven oxidative phosphorylation in vitro. J. Inherit. Metab. Dis. 20 (1997) 397-400
14. Williams Jr. C.H. Lipoamide dehydrogenase, glutathione reductase, thioredoxin reductase and mercuric reductase. In: Müller F. (Ed). Chemistry and Biochemistry of Flavoenzymes vol. 3 (1992), CRC Press, Boca Raton 121-211
15. Silva M.F.B., Ruiter J.P.N., IJlst L., Allers P., Ten Brink H., Jakobs C., Duran M., de Almeida I.T., and Wanders R.J.A. Synthesis and intramitochondrial levels of valproyl-CoA metabolites. Anal. Biochem. 290 (2001) 60-67
16. Mortensen P.B., Kølvraa S., and Christensen E. Inhibition of the glycine cleavage system: hyperglycinemia and hyperglycinuria caused by valproic acid. Epilepsia 21 (1980) 563-569
17. Martin-Gallardo A., Rodriguez P., Lopez M., Benavides J., and Ugarte M. Effects of dipropylacetate on the glycine cleavage system and glycine levels. Biochem. Pharmacol. 34 (1985) 2877-2882
18. Silva M.F.B., IJlst L., Allers P., Jakobs C., Duran M., de Almeida I.T., and Wanders R.J.A. Valproyl-dephosphoCoA: a novel metabolite of valproate formed in vitro in rat liver mitochondria. Drug Metab. Dispos. 32 (2004) 1304-1310
19. Berry M.N., and Friend D.S. High yield preparation of isolated rat liver parenchymal cells: a biochemical and fine structure study. J. Cell Biol. 43 (1969) 506-520
20. Smith P.K., Krohn R.I., Hermanson G.T., Malliu A.K., Gartner F.H., Provenzano M.D., Fugimoto E.K., Goede N.M., Olson B.J., and Klenk D.C. Measurement of protein using bicinchoninic acid. Anal. Biochem. 150 (1985) 76-85
21. Wanders R.J.A., Ruiter J.P.N., and Wijburg F.A. Studies on mitochondrial oxidative phosphorylation in permeabilized human skin fibroblasts: application to mitochondrial encephalomyopathies. Biochim. Biophys. Acta 1181 (1993) 219-222
22. Williamson J.R., and Corkey B.E. Assays of intermediates of the citric acid cycle and related compounds by fluorimetric enzyme methods. Methods Enzymol. 13 (1969) 434-513
23. Estabrook R.W. Mitochondrial respiratory control and the polarographic measurement of ADP:O ratios. Methods Enzymol. 10 (1967) 41-47
24. Reed L.J., and Willms C.R. Purification and resolution of the pyruvate dehydrogenase complex. Methods Enzymol. 9 (1966) 247-277
25. Cornish-Bowden A.C. Fundamentals of Enzyme Kinetics (1995), Portland Press, London
26. Dixon M. The determination of enzyme inhibitor constants. Biochem. J. 55 (1953) 170
27. Luder A.S., Parks J.K., Frerman F., and Parker Jr. W.D. Inactivation of beef brain ketoglutarate dehydrogenase complex by valproic acid and valproic acid metabolites. J. Clin. Invest. 86 (1990) 1574-1581
28. Anderson G.D., Acheampong A.A., and Levy R.H. Interaction between valproate and branched-chain amino acid metabolism. Neurology 44 (1994) 742-744
29. Turnbull D.M., Bone A.J., Bartlett K., Koundakjian P.P., and Sherratt H.A.S. The effects of valproate on intermediary metabolism in isolated rat hepatocytes and intact rats. Biochem. Pharmacol. 32 (1983) 1887-1892
30. Grafakou O., Oexle K., Heuvel L., Smeets R., Trijbels F., Goebel H.H., Bosshard N., Superti-Furga A., Steinmann B., and Smeitink J. Leigh syndrome due to compound heterozygosity of dihydrolipoamide dehydrogenase gene mutations: description of the first E3 splice site mutation. Eur. J. Pediatr. 162 (2003) 714-718
31. Aptowitzer I., Saada A., Faber J., Kleid D., and Elpeleg O.N. Liver disease in the Ashkenazi-Jewish lipoamide dehydrogenase deficiency. J. Pediatr. Gastroenterol. Nutr. 24 (1997) 599-601
32. Shaag A., Saada A., Berger I., Mandel H., Joseph A., Feigenbaum A., and Elpeleg O.N. Molecular basis of lipoamide dehydrogenase deficiency in the Ashkenazi-Jews. Am. J. Med. Genet. 82 (1999) 177-182
33. Barak N., Huminer D., Segal T., Ari Z.B., Halevy J., and Kaspa R.T. Lipoamide dehydrogenase deficiency: a newly discovered cause of acute hepatitis in adults. J. Hepatol. 29 (1998) 482-484
34. König S.A., Schenk M., Sick C., Holm E., Weiss A., Konog I., and Hehlmann R. Fatal liver failure associated with valproate therapy in a patient with Friedreich's disease: a review of valproate hepatotoxicity in adults. Epilepsia 40 (1999) 1036-1040
35. Saada A., Aptowitzwer I., Link G., and Elpeleg O.N. ATP synthesis in lipoamide dehydrogenase deficiency. Biochem. Biophys. Res. Commun. 269 (2000) 382-386