Aldo-keto reductase 1C2 fails to metabolize doxorubicin and daunorubicin in vitro

Drug Metabolism and Disposition

Volumn 36, Issue 6, 2008, Pages 991-994

  Takahashi, Ryan H ^a   Bains, Onkar S ^a   Pfeifer, Tom A ^a   Grigliatti, Thomas A ^a   Reid, Ronald E ^a   Riggs, K Wayne ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDOKETO REDUCTASE 1A1; ALDOKETO REDUCTASE 1C2; CARBONYL REDUCTASE; DAUNORUBICIN; DAUNORUBICINOL; DOXORUBICIN; DOXORUBICINOL; OXIDOREDUCTASE;

ARTICLE; CATALYSIS; DRUG METABOLISM; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REDUCTION;

ALCOHOL OXIDOREDUCTASES; ANTIBIOTICS, ANTINEOPLASTIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DAUNORUBICIN; DOXORUBICIN; FLUORESCENCE; HUMANS; HYDROXYSTEROID DEHYDROGENASES; RECOMBINANT PROTEINS;

EID: 44149115224     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.020388     Document Type: Article

References (23)

1. Bains OS, Takahashi RH, Pfeifer TA, Grigliatti TA, Reid RE, and Riggs KW (2008) Two allelic variants of aldo-keto reductase 1A1 exhibit reduced in vitro metabolism of daunorubicin. Drug Metab Dispos 5:904-910.
2. Behnia K and Boroujerdi M (1999) Inhibition of aldo-keto reductases by phenobarbital alters metabolism, pharmacokinetics and toxicity of doxorubicin in rats. J Pharm Pharmacol 51:1275-1282.
3. Berggren K, Chernokalskaya E, Steinberg TH, Kemper C, Lopez MF, Diwu Z, Haugland RP, and Patton WF (2000) Background-free, high sensitivity staining of proteins in one- and two-dimensional sodium dodecyl sulfate-polyacrylamide gels using a luminescent ruthenium complex. Electrophoresis 21:2509-2521.
4. Boucek RJ Jr, Olson RD, Brenner DE, Ogunbunmi EM, Inui M, and Fleischer S (1987) The major metabolite of doxorubicin is a potent inhibitor of membrane-associated ion pumps: a correlative study of cardiac muscle with isolated membrane fractions. J Biol Chem 262:15851-15856.
5. Burczynski ME, Harvey RG, and Penning TM (1998) Expression and characterization of four recombinant human dihydrodiol dehydrogenase isoforms: oxidation of trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene to the activated o-quinone metabolite benzo[a]pyrene-7,8-dione. Biochemistry 37:6781-6790.
6. Cusack BJ, Mushlin PS, Voulelis LD, Li X, Boucek RJ Jr, and Olson RD (1993) Daunorubicin-induced cardiac injury in the rabbit: a role for daunorubicinol? Toxicol Appl Pharmacol 118:177-185.
7. Del Tacca M, Danesi R, Ducci M, Bernardini C, and Romanini A (1985) Might adriamycinol contribute to adriamycin-induced cardiotoxicity? Pharmacol Res Commun 17:1073-1084.
8. Jin Y and Penning TM (2007) Aldo-keto reductases and bioactivation/ detoxication. Annu Rev Pharmacol Toxicol 47:263-292.
9. Licata S, Saponiero A, Mordente A, and Minotti G (2000) Doxorubicin metabolism and toxicity in human myocardium: role of cytoplasmic deglycosidation and carbonyl reduction. Chem Res Toxicol 13:414-420.
10. Martin HJ, Breyer-Pfaff U, Wsol V, Venz S, Block S, and Maser E (2006) Purification and characterization of akr1b10 from human liver: role in carbonyl reduction of xenobiotics. Drug Metab Dispos 34:464-470.
11. Mordente A, Minotti G, Martorana GE, Silvestrini A, Giardina B, and Meucci E (2003) Anthracycline secondary alcohol metabolite formation in human or rabbit heart: biochemical aspects and pharmacologic implications. Biochem Pharmacol 66:989-998.
12. O'Connor T, Ireland LS, Harrison DJ, and Hayes JD (1999) Major differences exist in the function and tissue-specific expression of human aflatoxin B1 aldehyde reductase and the principal human aldo-keto reductase AKR1 family members. Biochem J 343 Pt 2:487-504.
13. Ohara H, Miyabe Y, Deyashiki Y, Matsuura K, and Hara A (1995) Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver. Biochem Pharmacol 50:221-227.
14. Olson LE, Bedja D, Alvey SJ, Cardounel AJ, Gabrielson KL, and Reeves RH (2003) Protection from doxorubicin-induced cardiac toxicity in mice with a null allele of carbonyl reductase 1. Cancer Res 63:6602-6606.
15. Olson RD and Mushlin PS (1990) Doxorubicin cardiotoxicity: analysis of prevailing hypotheses. FASEB J 4:3076-3086.
16. Oppermann U (2007) Carbonyl reductases: the complex relationships of mammalian carbonyland quinone-reducing enzymes and their role in physiology. Annu Rev Pharmacol Toxicol 47:293-322.
17. Palackal NT, Burczynski ME, Harvey RG, and Penning TM (2001) The ubiquitous aldehyde reductase (AKR1A1) oxidizes proximate carcinogen trans-dihydrodiols to o-quinones: potential role in polycyclic aromatic hydrocarbon activation. Biochemistry 40:10901-10910.
18. Penning TM (2004) Aldo-keto reductases and formation of polycyclic aromatic hydrocarbon o-quinones. Methods Enzymol 378:31-67.
19. Sacco G, Giampietro R, Salvatorelli E, Menna P, Bertani N, Graiani G, Animati F, Goso C, Maggi CA, Manzini S, et al. (2003) Chronic cardiotoxicity of anticancer anthracyclines in the rat: role of secondary metabolites and reduced toxicity by a novel anthracycline with impaired metabolite formation and reactivity. Br J Pharmacol 139:641-651.
20. Singal PK and Iliskovic N (1998) Doxorubicin-induced cardiomyopathy. N Engl J Med 339:900-905.
21. Stewart DJ, Grewaal D, Green RM, Mikhael N, Goel R, Montpetit VA, and Redmond MD (1993) Concentrations of doxorubicin and its metabolites in human autopsy heart and other tissues. Anticancer Res 13:1945-1952.
22. Takanashi S and Bachur NR (1976) Adriamycin metabolism in man: evidence from urinary metabolites. Drug Metab Dispos 4:79-87.
23. Weiss RB (1992) The anthracyclines: will we ever find a better doxorubicin? Semin Oncol 19:670-686.