Identification of a novel glucosylsulfate conjugate as a metabolite of 3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione (ARQ 501, β-lapachone) in mammals

Drug Metabolism and Disposition

Volumn 36, Issue 4, 2008, Pages 753-758

  Savage, Ronald E ^a   Tyler, Andrew N ^a,b   Miao, Xiu Sheng ^a,c   Chan, Thomas C K ^a  

^a ARQULE INC   (United States)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ARQ 501; BETA LAPACHONE; GLUCOSYLSULFATE; PESTICIDE; PYRENE; PYRENE DERIVATIVE; SULFATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; COTTON; CRUSTACEA; DRUG BLOOD LEVEL; DRUG CONJUGATION; DRUG STRUCTURE; HUMAN; MASS SPECTROMETRY; MOUSE; NONHUMAN; NUDE MOUSE; PRIORITY JOURNAL; RAT; SERUM; TABEBUIA;

ANIMALS; GLUCOSE; HUMANS; METABOLIC NETWORKS AND PATHWAYS; MICE; MICE, NUDE; NAPHTHOQUINONES; SULFATES;

CRUSTACEA; GOSSYPIUM HIRSUTUM; MAMMALIA; MUS; RATTUS; TABEBUIA AVELLANEDAE; TABEBUIA IMPETIGINOSA;

EID: 41549101628     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.018655     Document Type: Article

References (29)

1. Abreu FC, Goulart MOF, and Brett AMO (2002) Reduction of lapachones in aqueous media at a glassy carbon electrode. Electroanalysis 14:29-34.
2. Boberg M, Angerbauer R, Kanhai WK, Karl W, Kern A, Radtke M, and Steinke W (1998) Biotransformation of cerivastatin in mice, rats, and dogs in vivo. Drug Metab Dispos 26:640-652.
3. Capps TM, Barringer VM, Eberle WJ, Brown DR, and Sanson DR (1996) Identification of a unique glucosylsulfate conjugate metabolite of profenofos in cotton. J Agric Food Chem 44:2408-2411.
4. Chang Y, Moody DE, and McCance-Katz EF (2006) Novel metabolites of buprenorphine detected in human liver microsomes and human urine. Drug Metab Dispos 34:440-448.
5. Chau YP, Shiah SG, Don MJ, and Kuo ML (1998) Involvement of hydrogen peroxide in topoisomerase inhibitor β-lapachone-induced apoptosis and differentiation in human leukemia cells. Free Radic Biol Med 24:660-670.
6. Chmela Z, Vesely J, Lemr K, Rypka M, Hanus J, Havlicek L, Krystof V, Michnova L, Fuksova K, and Lukes J (2001) In vivo metabolism of 2,6,9-trisubstituted purine-derived cylin-dependent kinase inhibitor bohemine in mice: glucosidation as the principal metabolic route. Drug Metab Dispos 29:326-334.
7. Coughtrie MWH and Fisher MB (2003) Drug metabolizing enzymes: cytochrome P450 and other enzymes, in Drug Discovery and Development (Lee SJ, Obach RS, and Fisher MB eds) pp 541-575, CRC Press, Taylor and Francis Group, Boca Raton.
8. Docampo R, Cruz FS, Boveris A, Muniz RP, and Esquivel DM (1979) β-Lapachone enhancement of lipid peroxidation and superoxide anion and hydrogen peroxide formation by sarcoma 180 ascites tumor cells. Biochem Pharmacol 28:723-728.
9. Duggan DE, Baldwin JJ, Arison BH, and Rhodes RE (1974) N-glucoside formation as a detoxification mechanism in mammals. J Pharmacol Exp Ther 190:563-569.
10. Endo T, Ban M, Hirata K, Yamamoto A, Hara Y, and Momose Y (2007) Involvement of CYP2A6 in the formation of a novel metabolite, 3-chydroxypilocarpine, from pilocarpine in human liver microsomes. Drug Metab Dispos 35:476-483.
11. Fernández Villamil S, Stoppani AOM, and Dubin M (2004) Redox cycling of β-lapachone and structural analogues in microsomal and cytosol liver preparations. Methods Enzymol 378:67-87.
12. Ikenaka I, Ishizaka M, Eun H, and Miyabara Y (2007) Glucose-sulfate conjugates as a new phase II metabolite formed by aquatic crustaceans. Biochem Biophys Res Commun 360:490-495.
13. Jaggi R, Addison RS, King AR, Suthers BD, and Dickinson RG (2002) Conjugation of desmethylnaproxen in the rat - a novel acyl glucuronide-sulfate diconjugate as a major biliary metabolite. Drug Metab Dispos 30:161-166.
14. Kostiainen R, Kotiaho T, Kuuranne T, and Auriola S (2003) Liquid chromatography/atmospheric pressure ionization-mass spectrometry in drug metabolism studies. J Mass Spectrom 38:357-372.
15. Kuuranne T, Mikko V, Leinonen A, and Kostiainen R (2000) Electrospray and atmospheric pressure chemical ionization tandem mass spectrometric behavior of eight anabolic steroid glucuronides. J Am Soc Mass Spectrom 11:722-730.
16. Lamoureux GL (1989) Plant metabolism of herbicides in relation to detoxification, selectivity, antidosing, and synergism, in Xenobiotic Metabolism and Disposition (Kato R, Estabrook RW, and Gayen MN eds) pp 267-274, Taylor and Francis, Bristol.
17. Laurent F, Debrauwer L, Rathahao E, and Scalla R (2000) 2,4-Dichlorophenoxyacetic acid metabolism in transgenic tolerant cotton (Gossypium hirsutum). J Agric Food Chem 48:5307-5311.
18. Levsen K, Schiebel H-M, Behnke B, Dotzer R, Dreher W, Elend M, and Thiele H (2005) Structure elucidation of phase II metabolites by tandem mass spectrometry: an overview. J Chromatogr A 1067:55-72.
19. Li CJ, Li Y-Z, Pinto AV, and Pardee AB (1999) Potent inhibition of tumor survival in vivo by β-lapachone plus taxol: combining drugs imposes different artificial checkpoints. Proc Natl Acad Sci U S A 96:13369-13374.
20. Li Y, Li CJ, Yu D, and Pardee AB (2000) Potent induction of apoptosis by beta-lapachone in human multiple myeloma cell lines and patient cells. Mol Med 6:1008-1015.
21. Miao Z, Kamel A, and Prakash C (2005) Characterization of a novel metabolite intermediate of ziprasidone in hepatic cytosolic fractions of rat, dog, and human by ESI-MS/MS, hydrogen/ deuterium exchange, and chemical derivatization. Drug Metab Dispos 33:879-883.
22. Nakano K, Ohashi M, and Harigaya S (1986) The β-glucosidation and β-glucuronidation of pantothenic acid compared with p-nitrophenol in dog liver microsomes. Chem Pharm Bull 34:3949-3952.
23. Oliveira-Brett AM, Goulart MO, and Abreu FC (2002) Reduction of lapachones and their reaction with L-cysteine and mercaptoethanol on glassy carbon electrodes. Bioelectrochemistry 56:53-55.
24. Ough M, Lewis A, Bey EA, Gao J, Ritchie JM, Bornmann W, Boothman DA, Oberley LW, and Cullen JJ (2005) Efficacy of β-lapachone in pancreatic cancer treatment. Cancer Biol Ther 4:95-102.
25. Schaffner-Sabba K, Schmidt-Ruppin KH, Wehrli W, Schuerch AR, and Wasley JW (1984) β-Lapachone: synthesis of derivatives and activities in tumor models. J Med Chem 27:990-994.
26. Strott CA (2002) Sulfonation and molecular action. Endocr Rev 23:703-732.
27. A receptor antagonist in human liver microsomes. Drug Metab Dispos 31:37-45.
28. 1H-NMR. Drug Metab Dispos 31:215-223.
29. Zhen Y, Slanar O, Krausz KW, Chen C, Slavik J, Mcphail K, Zabriskie TM, Perlik F, Gonzalez FJ, and Idle JR (2006) 3,4-Dehydrodebrisoquine, a novel debrisoquine metabolite formed from 4-hydroxydebrisquine that affects the CYP2D6 metabolic ratio. Drug Metab Dispos 34:1563-1574.