Acyclovir-induced nephrotoxicity: The role of the acyclovir aldehyde metabolite

Translational Research

Volumn 158, Issue 5, 2011, Pages 290-301

  Gunness, Patrina ^a,b   Aleksa, Katarina ^a,c   Bend, John ^d   Koren, Gideon ^a,b  

^a HOSPITAL FOR SICK CHILDREN   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c UNIVERSITY OF WATERLOO   (Canada)

^d WESTERN UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

9 CARBOXYMETHOXYMETHYLGUANINE; ACICLOVIR; ACYCLOVIR ALDEHYDE; ALCOHOL DEHYDROGENASE; ALDEHYDE DEHYDROGENASE ISOENZYME 2; DRUG METABOLITE; GUANINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL DEATH; CELL VIABILITY; COLORIMETRY; CYTOTOXICITY; ENZYME ACTIVITY; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; KIDNEY TUBULE CELL; NEPHROTOXICITY; PRIORITY JOURNAL; PROTEIN EXPRESSION; WESTERN BLOTTING;

EID: 80054693283     PISSN: 19315244     EISSN: 18781810     Source Type: Journal    
DOI: 10.1016/j.trsl.2011.07.002     Document Type: Article

References (67)

1. D. Brigden, and P. Whiteman The clinical pharmacology of acyclovir and its prodrugs Scand J Infect Dis 47 1985 33 39 (Pubitemid 16211579)
2. G.B. Elion The biochemistry and mechanism of action of acyclovir J Antimicrob Chemother 12 1983 9 17 (Pubitemid 14227995)
3. M.G. Bianchetti, C. Roduit, and O.H. Oetliker Acyclovir-induced renal failure: course and risk factors Pediatr Nephrol 5 1991 238 239
4. D. Brigden, A.E. Rosling, and N.C. Woods Renal function after acyclovir intravenous injection Am J Med 3 1982 182 185 (Pubitemid 12067781)
5. C.V. Fletcher, J.A. Englund, and B. Bean Continuous infusion of high-dose acyclovir for serious herpesvirus infections Antimicrob Agents Chemother 33 1989 1375 1378 (Pubitemid 19191990)
6. M. Hintz, J.D. Connor, and S.A. Spector Neonatal acyclovir pharmacokinetics in patients with herpes virus infections Am J Med 73 1982 210 214 (Pubitemid 12067787)
7. R.E. Keeney, L.E. Kirk, and D. Brigden Acyclovir tolerance in humans Am J Med 73 1982 176 181 (Pubitemid 12067780)
8. P. Vachvanichsanong, P. Patamasucon, M. Malagon, and E.S. Moore Acute renal failure in a child associated with acyclovir Pediatr Nephrol 9 1995 346 347
9. T. Ahmad, M. Simmonds, A.G. McIver, and M.E. McGraw Reversible renal failure in renal transplant patients receiving oral acyclovir prophylaxis Pediatr Nephrol 8 1994 489 491 (Pubitemid 24228647)
10. G. Genc, O. Ozkaya, and Y. Acikgoz Acute renal failure with acyclovir treatment in a child with leukemia Drug Chem Toxicol 33 2010 217 219
11. R. Schreiber, J. Wolpin, and G. Koren Determinants of aciclovir-induced nephrotoxicity in children Paediatr Drugs 10 2008 135 139 (Pubitemid 351414761)
12. A.W. Lyon, A. Mansoor, and M.J. Trotter Urinary gems: acyclovir crystalluria Arch Pathol Lab Med 126 2002 753 754 (Pubitemid 34602588)
13. W.J. Mason, and H.H. Nickols Crystalluria from acyclovir use N Engl J Med 358 2008 e14
14. N.A. Peterslund, M.L. Larsen, and H. Mygind Acyclovir crystalluria Scand J Infect Dis 20 1988 225 228
15. J.L. Potter, and C.E. Krill Jr. Acyclovir crystalluria Pediatr Infect Dis 5 1986 710 712 (Pubitemid 17196623)
16. M.H. Sawyer, D.E. Webb, J.E. Balow, and S.E. Straus Acyclovir-induced renal failure. Clinical course and histology Am J Med 84 1988 1067 1071
17. G. Vomiero, B. Carpenter, I. Robb, and G. Filler Combination of ceftriaxone and acyclovir - an underestimated nephrotoxic potential? Pediatr Nephrol 17 2002 633 637 (Pubitemid 36097338)
18. P. Gunness, K. Aleksa, K. Kosuge, S. Ito, and G. Koren Comparison of the novel HK-2 human renal proximal tubular cell line with the standard LLC-PK1 cell line in studying drug-induced nephrotoxicity Can J Physiol Pharmacol 88 2010 448 455
19. P. de Miranda, S.S. Good, H.C. Kransy, J.D. Connor, and O.L. Laskin Metabolic fate of radioactive acyclovir in humans Am J Med 73 1982 215 220 (Pubitemid 12067788)
20. P. de Miranda, and S.S. Good Biotransformation of acyclovir to 9-carboxymethoxymethylguanine Fed Proc 41 1982 1733
21. P. de Miranda, and S.S. Good Species differences in the metabolism and disposition of antiviral nucleoside analogues 1. Acyclovir. Antivir Chem Chemother 3 1992 1 8
22. P. de Miranda, and T.C. Burnette Metabolic fate and pharmacokinetics of the acyclovir prodrug valaciclovir in cynomolgus monkeys Drug Metab Dispos 22 1994 55 59 (Pubitemid 24045380)
23. P.J. O'Brien, A.G. Siraki, and N. Shangari Aldehyde sources, metabolism, molecular toxicity mechanisms, and possible effects on human health Crit Rev Toxicol 35 2005 609 662 (Pubitemid 41693601)
24. D. Walker, J.P. Flinois, and S.C. Monkman Identification of the major human hepatic cytochrome P450 involved in activation and N-dechloroethylation of ifosfamide Biochem Pharmacol 47 1994 1157 1163
25. L. Dubourg, C. Michoudet, P. Cochat, and G. Baverel Human kidney tubules detoxify chloroacetaldehyde, a presumed nephrotoxic metabolite of ifosfamide J Am Soc Nephrol 12 2001 1615 1623 (Pubitemid 32674423)
26. D.U. Silverthorn The kidneys D.K. Brake, Human physiology an integrated approach 1998 Prentice Hall Upper Saddle River, NJ 518 542
27. M.W. Anders Metabolism of drugs by the kidney Kidney Int 18 1980 636 647 (Pubitemid 11204064)
28. J.W. Lohr, G.R. Willsky, and M.A. Acara Renal drug metabolism Pharmacol Rev 50 1998 107 141 (Pubitemid 28158844)
29. K. Aleksa, S. Ito, and G. Koren Enantioselective metabolism of ifosfamide by the kidney Chirality 18 2006 398 405 (Pubitemid 43855623)
30. G.L. Diamond, and A.J. Quebbemann In vivo quantification of renal sulfate and glucuronide conjugation in the chicken Drug Metab Dispos 9 1981 402 409 (Pubitemid 12201233)
31. K. Engeland, and W. Maret Extrahepatic, differential expression of four classes of human alcohol dehydrogenase Biochem Biophys Res Commun 193 1993 47 53 (Pubitemid 23199911)
32. M. Nishimura, and S. Naito Tissue-specific mRNA expression profiles of human phase I metabolizing enzymes except for cytochrome P450 and phase II metabolizing enzymes Drug Metab Pharmacokinet 21 2006 357 374
33. S. Harada, D.P. Agarwal, and H.W. Goedde Electrophoretic and biochemical studies of human aldehyde dehydrogenase isozymes in various tissues Life Sci 26 1980 1773 1780 (Pubitemid 10060685)
34. M. Estonius, S. Svensson, and J.O. Hoog Alcohol dehydrogenase in human tissues: localisation of transcripts coding for five classes of the enzyme FEBS Lett 397 1996 338 342 (Pubitemid 26414045)
35. K. Hara, K. Suyama, H. Itoh, and S. Nagashima Influence of ALDH2 genetic polymorphisms on aciclovir pharmacokinetics following oral administration of valaciclovir in Japanese end-stage renal disease patients Drug Metab Pharmacokinet 23 2008 306 312
36. Millipore Technical Publications. RIPA Buffer - Preparation of modified radioimmunoprecipitation (RIPA) buffer. 2007; http://www.millipore.com/ userguides/tech1/mcproto402.
37. U.K. Laemmli Cleavage of structural proteins during the assembly of the head of bacteriophage T4 Nature 227 1970 680 685
38. H. Towbin, T. Staehelin, and J. Gordon Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications Proc Natl Acad Sci U S A 76 1979 4350 4354 (Pubitemid 9256559)
39. D.L. Clemens, C.M. Halgard, R.R. Miles, M.F. Sorrell, and D.J. Tuma Establishment of a recombinant hepatic cell line stably expressing alcohol dehydrogenase Arch Biochem Biophys 321 1995 311 318
40. G.L. Pawan Metabolism of alcohol (ethanol) in man Proc Nutr Soc 31 1972 83 89
41. J.R.L. Walker Spectrophotometric determination of enzyme activity: alcohol dehydrogenase (ADH) Biochemical Education 20 1992 42 43
42. M.A. Gyamfi, and Y.J. Wan The effect of ethanol, ethanol metabolizing enzyme inhibitors, and vitamin E on regulating glutathione, glutathione S-transferase, and S-adenosylmethionine in mouse primary hepatocyte Hepatol Res 35 2006 53 61
43. D.W. Crabb, M. Matsumoto, D. Chang, and M. You Overview of the role of alcohol dehydrogenase and aldehyde dehydrogenase and their variants in the genesis of alcohol-related pathology Proc Nutr Soc 63 2004 49 63 (Pubitemid 38543873)
44. M.S. Quesenberry, and Y.C. Lee A rapid formaldehyde assay using purpald reagent: application under periodation conditions Anal Biochem 234 1996 50 55 (Pubitemid 26051488)
45. M.J. Ryan, G. Johnson, J. Kirk, S.M. Fuerstenberg, R.A. Zager, and B. Torok-Storb HK-2: an immortalized proximal tubule epithelial cell line from normal adult human kidney Kidney Int 45 1994 48 57 (Pubitemid 24045991)
46. P. de Miranda, H.C. Krasny, D.A. Page, and G.B. Elion Species differences in the disposition of acyclovir Am J Med 73 1982 31 35 (Pubitemid 12067753)
47. R.G. Schnellmann Toxic responses of the kidney C.D. Klaassen, Casarett and Doull's toxicology: the basic science of poisons 2001 McGraw-Hill New York 491 500
48. J.C. Davila, R.J. Rodriguez, R.B. Melchert, and D. Acosta Jr. Predictive value of in vitro model systems in toxicology Annu Rev Pharmacol Toxicol 38 1998 63 96 (Pubitemid 28231489)
49. A. Hellden, I. Odar-Cederlof, and P. Diener High serum concentrations of the acyclovir main metabolite 9-carboxymethoxymethylguanine in renal failure patients with acyclovir-related neuropsychiatric side effects: an observational study Nephrol Dial Transplant 18 2003 1135 1141 (Pubitemid 36722515)
50. A. Hellden, J. Lycke, and T. Vander The aciclovir metabolite CMMG is detectable in the CSF of subjects with neuropsychiatric symptoms during aciclovir and valaciclovir treatment J Antimicrob Chemother 57 2006 945 949
51. K. Ramu, L.H. Fraiser, B. Mamiya, T. Ahmed, and J.P. Kehrer Acrolein mercapturates: synthesis, characterization, and assessment of their role in the bladder toxicity of cyclophosphamide Chem Res Toxicol 8 1995 515 524
52. I.M. Kapetanovic, C.D. Torchin, and J.M. Strong Reactivity of atropaldehyde, a felbamate metabolite in human liver tissue in vitro Chem Biol Interact 142 2002 119 134 (Pubitemid 35238045)
53. S. Shaw, and E. Jayatilleke Acetaldehyde-mediated hepatic lipid peroxidation: role of superoxide and ferritin Biochem Biophys Res Commun 143 1987 984 990 (Pubitemid 17048366)
54. N. Shangari, and P.J. O'Brien The cytotoxic mechanism of glyoxal involves oxidative stress Biochem Pharmacol 68 2004 1433 1442 (Pubitemid 39185861)
55. J.L. Maggs, and B.K. Park Drug-protein conjugates-XVI. Studies of sorbinil metabolism: formation of 2-hydroxysorbinil and unstable protein conjugates Biochem Pharmacol 37 1988 743 748 (Pubitemid 18053755)
56. M. Wang, E.J. McIntee, and G. Cheng Identification of DNA adducts of acetaldehyde Chem Res Toxicol 13 2000 1149 1157
57. J.A. Doorn, T.D. Hurley, and D.R. Petersen Inhibition of human mitochondrial aldehyde dehydrogenase by 4-hydroxynon-2-enal and 4-oxonon-2-enal Chem Res Toxicol 19 2006 102 110 (Pubitemid 43185467)
58. Z. Gregus, and C.D. Klaassen Mechanisms of toxicity C.D. Klaassen, Casarett and Doull's toxicology: the basic science of poisons 2001 McGraw-Hill New York 35 82
59. P. Meier, and H.K. Seitz Age, alcohol metabolism and liver disease Curr Opin Clin Nutr Metab Care 11 2008 21 26 (Pubitemid 350295221)
60. L. Chrostek, W. Jelski, M. Szmitkowski, and Z. Puchalski Gender-related differences in hepatic activity of alcohol dehydrogenase isoenzymes and aldehyde dehydrogenase in humans J Clin Lab Anal 17 2003 93 96 (Pubitemid 36523414)
61. C.J. Brown, L. Zhang, and H.J. Edenberg Gene expression in a young multigene family: tissue-specific differences in the expression of the human alcohol dehydrogenase genes ADH1, ADH2, and ADH3 DNA Cell Biol 15 1996 187 196 (Pubitemid 26109135)
62. W.F. Bosron, and T.K. Li Genetic polymorphism of human liver alcohol and aldehyde dehydrogenases, and their relationship to alcohol metabolism and alcoholism Hepatology 6 1986 502 510 (Pubitemid 16086644)
63. C.J. Mulligan, R.W. Robin, and M.V. Osier Allelic variation at alcohol metabolism genes (ADH1B, ADH1C, ALDH2) and alcohol dependence in an American Indian population Hum Genet 113 2003 325 336 (Pubitemid 37059115)
64. Y. Mizoi, K. Yamamoto, Y. Ueno, T. Fukunaga, and S. Harada Involvement of genetic polymorphism of alcohol and aldehyde dehydrogenases in individual variation of alcohol metabolism Alcohol Alcohol 29 1994 707 710
65. F. Stickel, and C.H. Osterreicher The role of genetic polymorphisms in alcoholic liver disease Alcohol Alcohol 41 2006 209 224
66. S. Matsuzaki, and C.S. Sieber Increased susceptibility of hepatic mitochondria to the toxicity of acetaldehyde after chronic ethanol consumption Biochem Biophys Res Commun 75 1977 1059 1065 (Pubitemid 8099437)
67. S. Zakhari Overview: how is alcohol metabolized by the body? Alcohol Res Health 29 2006 245 254