Multiscale modelling approach combining a kinetic model of glutathione metabolism with PBPK models of paracetamol and the potential glutathione-depletion biomarkers ophthalmic acid and 5-oxoproline in humans and rats

Integrative Biology (United Kingdom)

Volumn 5, Issue 6, 2013, Pages 877-888

  Geenen, Suzanne ^a,b   Yates, James W T ^b   Kenna, J Gerry ^b   Bois, Frederic Y ^c,d   Wilson, Ian D ^b,e   Westerhoff, Hans V ^a,f,g  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITÉ DE TECHNOLOGIE DE COMPIÈGNE   (France)

^d INSTITUT NATIONAL DE L ENVIRONNEMENT INDUSTRIEL ET DES RISQUES INERIS   (France)

^e IMPERIAL COLLEGE LONDON   (United Kingdom)

^f VU UNIVERSITY AMSTERDAM   (Netherlands)

^g UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL MARKER; GLUTATHIONE; GLUTATHIONE DERIVATIVE; METHIONINE; OPHTHALMIC ACID; PARACETAMOL; PYROGLUTAMIC ACID; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG DISPOSITION; DRUG EFFECT; DRUG METABOLISM; GLUTATHIONE METABOLISM; HUMAN; HUMAN EXPERIMENT; LIVER LEVEL; NONHUMAN; PRIORITY JOURNAL; RAT; URINE LEVEL;

RATTUS;

EID: 84878754200     PISSN: 17579694     EISSN: 17579708     Source Type: Journal    
DOI: 10.1039/c3ib20245c     Document Type: Article

References (41)

1. B. K. Park A. Boobis S. Clarke C. E. Goldring D. Jones J. G. Kenna C. Lambert H. G. Laverty D. J. Naisbitt S. Nelson D. A. Nicoll-Griffith R. S. Obach P. Routledge D. A. Smith D. J. Tweedie N. Vermeulen D. P. Williams I. D. Wilson T. A. Baillie Managing the challenge of chemically reactive metabolites in drug development Nat. Rev. Drug Discovery 2011 10 4 292 306
2. T. Nguyen P. Nioi C. B. Pickett The Nrf2-antioxidant response element signaling pathway and its activation by oxidative stress J. Biol. Chem. 2009 284 20 13291 13295
3. J. A. Hinson D. W. Roberts L. P. James Mechanisms of acetaminophen- induced liver necrosis Handb. Exp. Pharmacol. 2010 196 369 405
4. N. J. Waters C. J. Waterfield R. D. Farrant E. Holmes J. K. Nicholson Integrated metabonomic analysis of bromobenzene-induced hepatotoxicity: novel induction of 5-oxoprolinosis J. Proteome Res. 2006 5 1448 1459
5. F. Ghauri A. McLean D. Beales I. Wilson J. Nicholson Induction of 5-oxoprolinuria in the rat following chronic feeding with N-acetyl 4-aminophenol (paracetamol) Biochem. Pharmacol. 1993 46 5 953 957
6. K. Macé F. Aguilar J. S. Wang P. Vautravers M. Gómez-Lechón F. J. Gonzalez J. Groopman C. C. Harris A. M. Pfeifer Aflatoxin B1-induced DNA adduct formation and p53 mutations in CYP450-expressing human liver cell lines Carcinogenesis 1997 18 1291 1297
7. S. Geenen C. Guallar-Hoyas F. Michopoulos J. G. Kenna K. L. Kolaja H. V. Westerhoff P. Thomas I. D. Wilson HPLC-MS/MS methods for the quantitative analysis of 5-oxoproline (pyroglutamate) in rat plasma and hepatic cell line culture medium J. Pharm. Biomed. Anal. 2011 56 655 663
8. T. Soga R. Baran M. Suematsu Y. Ueno S. Ikeda T. Sakurakawa Y. Kakazu T. Ishikawa M. Robert T. Nishioka M. Tomita Differential metabolomics reveals ophthalmic acid as an oxidative stress biomarker indicating hepatic glutathione consumption J. Biol. Chem. 2006 281 16768 16776
9. P. Armenian R. R. Gerona P. D. Blanc A. H. B. Wu S. Mookherjee 5-Oxoprolinemia causing elevated anion gap metabolic acidosis in the setting of acetaminophen use J. Emerg. Med. 2012 43 1 54 57
10. G. Brooker J. Jeffery T. Nataraj M. Sair R. Ayling High anion gap metabolic acidosis secondary to pyroglutamic aciduria (5-oxoprolinuria): association with prescription drugs and malnutrition Ann. Clin. Biochem. 2007 44 406 409
11. A. Z. Fenves H. M. Kirkpatrick V. V. Patel L. Sweetman M. Emmett Increased anion gap metabolic acidosis as a result of 5-oxoproline (Pyroglutamic Acid): a role for acetaminophen Clin. J. Am. Soc. Nephrol. 2006 1 441 447
12. B. D. Humphreys J. P. Forman K. Zandi-Nejad H. Bazari J. Seifter C. C. Magee Acetaminophen-induced anion gap metabolic acidosis and 5-oxoprolinuria (Pyroglutamic Aciduria) acquired in hospital Am. J. Kidney Dis. 2005 46 143 146
13. D. T. Lawrence L. K. Bechtel N. P. Charlton C. P. Holstege 5-Oxoproline-induced anion gap metabolic acidosis after an acute acetaminophen overdose J. Am. Osteopath. Assoc. 2010 110 545 551
14. P. Leung S. Tsui T. Siu S. Tam Acquired 5-oxoprolinuria (Pyroglutamic acidaemia) as a cause of early high anion gap metabolic acidosis in acute massive paracetamol overdose Hong Kong Journal of Emergency Medicine 2011 18 264 270
15. J. J. Pitt S. Hauser Transient 5-oxoprolinuria and high anion gap metabolic acidosis: clinical and biochemical findings in eleven subjects Clin. Chem. 1998 44 1497 1503
16. S. Geenen F. B. du Preez J. L. Snoep A. J. Foster S. Sarda J. G. Kenna I. D. Wilson H. V. Westerhoff Glutathione metabolism modeling: a mechanism for liver drug-robustness and a new biomarker strategy Biochim. Biophys. Acta, Gen. Subj. 2013 10.1016/j.bbagen.2013.04.014
17. S. Geenen F. B. du Preez M. Reed H. F. Nijhout J. G. Kenna I. D. Wilson H. V. Westerhoff J. L. Snoep A mathematical modelling approach to assessing the reliability of biomarkers of glutathione metabolism Eur. J. Pharm. Sci. 2012 46 233 243
18. I. Nestorov Whole body pharmacokinetic models Clin. Pharmacokinet. 2003 42 883 908
19. S. R. B. Allerheiligen Next-generation model-based drug discovery and development: quantitative and systems pharmacology Clin. Pharmacol. Ther. 2010 88 135 137
20. A. J. Atkinson P. M. Lyster Systems clinical pharmacology Clin. Pharmacol. Ther. 2010 88 3 6
21. J. M. Berg M. E. Rogers P. M. Lyster Systems biology and pharmacology Clin. Pharmacol. Ther. 2010 88 17 19
22. B. National Institute of General Medical Sciences, MD Final report of the Quantitative and Systems Pharmacology Workshop; 〈 http://www.nigms.nih. gov/News/Reports/PharmacologyConference20080925.htm 〉: 2008
23. P. van der Graaf N. Benson Systems pharmacology: bridging systems biology and pharmacokinetics-pharmacodynamics (PKPD) in drug discovery and development Pharm. Res. 2011 28 1460 1464
24. B. Rodriguez K. Burrage D. Gavaghan V. Grau P. Kohl D. Noble The systems biology approach to drug development: application to toxicity assessment of cardiac drugs Clin. Pharmacol. Ther. 2010 88 130 134
25. T. Rodgers M. Rowland Mechanistic approaches to volume of distribution predictions: understanding the processes Pharm. Res. 2007 24 918 933
26. A. A. Jackson C. Persaud M. Hall S. Smith N. Evans N. Rutter Urinary excretion of 5-l-oxoproline (pyroglutamic acid) during early life in term and preterm infants Arch. Dis. Child. 1997 76 F152 F157
27. Y.-M. Yu C. M. Ryan Z.-W. Fei X.-M. Lu L. Castillo J. T. Schultz R. G. Tompkins V. R. Young Plasma l-5-oxoproline kinetics and whole blood glutathione synthesis rates in severely burned adult humans Am. J. Physiol. 2002 282 E247 E258
28. L. Eldjarn E. Jellum O. Stokke Pyroglutamic aciduria: studies on the enzymic block and on the metabolic origin of pyroglutamic acid Clin. Chim. Acta 1972 40 461 476
29. R. Hahn A. Wendel L. Flohé The fate of extracellular glutathione in the rat Biochim. Biophys. Acta, Gen. Subj. 1978 539 324 337
30. M. Orlowski S. Wilk Synthesis of ophthalmic acid in liver and kidney in vivo Biochem. J. 1978 170 415 419
31. M. Orlowski S. Wilk Metabolism of γ-glutamyl amino acids and peptides in mouse liver and kidney in vivo Eur. J. Biochem. 1976 71 549 555
32. N. Gregoire L. Hovsepian V. Gualano E. Evene G. Dufour A. Gendron Safety and pharmacokinetics of paracetamol following intravenous administration of 5 g during the first 24 h with a 2 g starting dose Clin. Pharmacol. Ther. 2007 81 401 405
33. W. M. Johannessen I. M. Tyssebotn J. Aarbakke Antipyrine and acetaminophen kinetics in the rat: comparison of data based on blood samples from the cut tail and a cannulated femoral artery J. Pharm. Sci. 1982 71 1352 1356
34. N. Watari M. Iwai N. Kaneniwa Pharmacokinetic study of the fate of acetaminophen and its conjugates in rats J. Pharmacokinet. Biopharm. 1983 11 28
35. S. Hoops S. Sahle R. Gauges C. Lee J. Pahle N. Simus M. Singhal L. Xu P. Mendes U. Kummer COPASI-a COmplex PAthway Simulator Bioinformatics 2006 22 3067 3074
36. S. Geenen F. Michopoulos J. G. Kenna K. L. Kolaja H. V. Westerhoff I. Wilson HPLC-MS/MS methods for the quantitative analysis of ophthalmic acid in rodent plasma and hepatic cell line culture medium J. Pharm. Biomed. Anal. 2011 54 1128 1135
37. P. Poulin F.-P. Theil Prediction of pharmacokinetics prior to in vivo studies. 1. Mechanism-based prediction of volume of distribution J. Pharm. Sci. 2002 91 129 156
38. D. H. Calam S. G. Waley Some derivatives of glutathione Biochem. J. 1962 85 417 419
39. P. J. Kilford M. Gertz J. B. Houston A. Galetin Hepatocellular binding of drugs: correction for unbound fraction in hepatocyte incubations using microsomal binding or drug lipophilicity data Drug Metab. Dispos. 2008 36 1194 1197
40. R. Brown M. Delp S. Lindstedt L. Rhomberg R. Beliles Physiological parameter values for physiologically based pharmacokinetic models Toxicol. Ind. Health 1997 13 407 484
41. M. D. Delp M. V. Evans C. Duan Effects of aging on cardiac output, regional blood flow, and body composition in Fischer-344 rats J. Appl. Physiol. 1998 85 1813 1822