Metabolic profile, enzyme kinetics, and reaction phenotyping of β-lapachone metabolism in human liver and intestine in vitro

Molecular Pharmaceutics

Volumn 9, Issue 12, 2012, Pages 3476-3485

  Cheng, Xuefang ^a   Liu, Fang ^a   Yan, Tingting ^a   Zhou, Xueyan ^a   Wu, Liang ^a   Liao, Ke ^a   Wang, Guangji ^a   Hao, Haiping ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

beta; lapachone; enzyme kinetics; glucuronidation; reaction phenotyping; UGT

Indexed keywords

BETA LAPACHONE; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A7; GLUCURONOSYLTRANSFERASE 1A8; GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B7; ISOENZYME;

ARTICLE; DRUG CLEARANCE; DRUG CONJUGATION; DRUG METABOLISM; ENZYME KINETICS; ENZYME MECHANISM; GLUCURONIDATION; HUMAN; HUMAN TISSUE; IN VITRO STUDY; INTESTINE; LIVER; PHENOTYPE; PRIORITY JOURNAL;

GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; INTESTINES; ISOENZYMES; KINETICS; METABOLOME; MICROSOMES, LIVER; NAD(P)H DEHYDROGENASE (QUINONE); NAPHTHOQUINONES; PHENOTYPE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84870554107     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300296m     Document Type: Article

References (29)

1. Schaffner-Sabba, K.; Schmidt-Ruppin, K. H.; Wehrli, W.; Schuerch, A. R.; Wasley, J. W. beta-Lapachone: synthesis of derivatives and activities in tumor models J. Med. Chem. 1984, 27 (8) 990-4 (Pubitemid 14057359)
2. Cruz, F. S.; Docampo, R.; Boveris, A. Generation of superoxide anions and hydrogen peroxide from beta-lapachone in bacteria Antimicrob. Agents Chemother. 1978, 14 (4) 630-3 (Pubitemid 9028433)
3. Medeiros, C. S.; Pontes-Filho, N. T.; Camara, C. A.; Lima-Filho, J. V.; Oliveira, P. C.; Lemos, S. A.; Leal, A. F.; Brandao, J. O.; Neves, R. P. Antifungal activity of the naphthoquinone beta-lapachone against disseminated infection with Cryptococcus neoformans var. neoformans in dexamethasone- immunosuppressed Swiss mice Braz. J. Med. Biol. Res. 2010, 43 (4) 345-9
4. Boveris, A.; Docampo, R.; Turrens, J. F.; Stoppani, A. O. Effect of beta-lapachone on superoxide anion and hydrogen peroxide production in Trypanosoma cruzi Biochem. J. 1978, 175 (2) 431-9 (Pubitemid 9060101)
5. Bourguignon, S. C.; Cavalcanti, D. F.; de Souza, A. M.; Castro, H. C.; Rodrigues, C. R.; Albuquerque, M. G.; Santos, D. O.; da Silva, G. G.; da Silva, F. C.; Ferreira, V. F.; de Pinho, R. T.; Alves, C. R. Trypanosoma cruzi: insights into naphthoquinone effects on growth and proteinase activity Exp. Parasitol. 2011, 127 (1) 160-6
6. Pardee, A. B.; Li, Y. Z.; Li, C. J. Cancer therapy with beta-lapachone Curr. Cancer Drug Targets 2002, 2 (3) 227-42
7. Planchon, S. M.; Wuerzberger, S.; Frydman, B.; Witiak, D. T.; Hutson, P.; Church, D. R.; Wilding, G.; Boothman, D. A. Beta-lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells: a p53-independent response Cancer Res. 1995, 55 (17) 3706-11
8. Wuerzberger, S. M.; Pink, J. J.; Planchon, S. M.; Byers, K. L.; Bornmann, W. G.; Boothman, D. A. Induction of apoptosis in MCF-7:WS8 breast cancer cells by beta-lapachone Cancer Res. 1998, 58 (9) 1876-85 (Pubitemid 28217462)
9. Huang, L.; Pardee, A. B. beta-lapachone induces cell cycle arrest and apoptosis in human colon cancer cells Mol. Med. 1999, 5 (11) 711-20 (Pubitemid 32937031)
10. Bey, E. A.; Bentle, M. S.; Reinicke, K. E.; Dong, Y.; Yang, C. R.; Girard, L.; Minna, J. D.; Bornmann, W. G.; Gao, J.; Boothman, D. A. An NQO1- and PARP-1-mediated cell death pathway induced in non-small-cell lung cancer cells by beta-lapachone Proc. Natl. Acad. Sci. U.S.A. 2007, 104 (28) 11832-7 (Pubitemid 47175098)
11. Rich, T.; Allen, R. L.; Wyllie, A. H. Defying death after DNA damage Nature 2000, 407 (6805) 777-83
12. Miao, X. S.; Zhong, C.; Wang, Y.; Savage, R. E.; Yang, R. Y.; Kizer, D.; Volckova, E.; Ashwell, M. A.; Chan, T. C. In vitro metabolism of beta-lapachone (ARQ 501) in mammalian hepatocytes and cultured human cells Rapid Commun. Mass Spectrom. 2009, 23 (1) 12-22
13. Pink, J. J.; Planchon, S. M.; Tagliarino, C.; Varnes, M. E.; Siegel, D.; Boothman, D. A. NAD(P)H:Quinone oxidoreductase activity is the principal determinant of beta-lapachone cytotoxicity J. Biol. Chem. 2000, 275 (8) 5416-24 (Pubitemid 30115173)
14. Bentle, M. S.; Reinicke, K. E.; Bey, E. A.; Spitz, D. R.; Boothman, D. A. Calcium-dependent modulation of poly(ADP-ribose) polymerase-1 alters cellular metabolism and DNA repair J. Biol. Chem. 2006, 281 (44) 33684-96 (Pubitemid 46036747)
15. Miao, X. S.; Song, P.; Savage, R. E.; Zhong, C.; Yang, R. Y.; Kizer, D.; Wu, H.; Volckova, E.; Ashwell, M. A.; Supko, J. G.; He, X.; Chan, T. C. Identification of the in vitro metabolites of 3,4-dihydro-2,2-dimethyl-2H- naphthol[1,2-b]pyran-5,6-dione (ARQ 501; beta-lapachone) in whole blood Drug Metab. Dispos. 2008, 36 (4) 641-8 (Pubitemid 351468368)
16. Savage, R. E.; Tyler, A. N.; Miao, X. S.; Chan, T. C. 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, beta-lapachone) in mammals Drug Metab. Dispos. 2008, 36 (4) 753-8 (Pubitemid 351468383)
17. Wang, Q.; Hao, H.; Zhu, X.; Yu, G.; Lai, L.; Liu, Y.; Wang, Y.; Jiang, S.; Wang, G. Regioselective glucuronidation of tanshinone iia after quinone reduction: identification of human UDP-glucuronosyltransferases, species differences, and interaction potential Drug Metab. Dispos. 2010, 38 (7) 1132-40
18. Talcott, R. E.; Rosenblum, M.; Levin, V. A. Possible role of DT-diaphorase in the bioactivation of antitumor quinones Biochem. Biophys. Res. Commun. 1983, 111 (1) 346-51 (Pubitemid 13125167)
19. Reber, P.; Brenneisen, R.; Flogerzi, B.; Batista, C.; Netzer, P.; Scheurer, U. Effect of naloxone-3-glucuronide and N-methylnaloxone on the motility of the isolated rat colon after morphine Dig. Dis. Sci. 2007, 52 (2) 502-7 (Pubitemid 46202827)
20. Belinsky, M.; Jaiswal, A. K. NAD(P)H:quinone oxidoreductase1 (DT-diaphorase) expression in normal and tumor tissues Cancer Metastasis Rev. 1993, 12 (2) 103-17 (Pubitemid 23220675)
21. Smitskamp-Wilms, E.; Giaccone, G.; Pinedo, H. M.; van der Laan, B. F.; Peters, G. J. DT-diaphorase activity in normal and neoplastic human tissues; an indicator for sensitivity to bioreductive agents? Br. J. Cancer 1995, 72 (4) 917-21
22. Malkinson, A. M.; Siegel, D.; Forrest, G. L.; Gazdar, A. F.; Oie, H. K.; Chan, D. C.; Bunn, P. A.; Mabry, M.; Dykes, D. J.; Harrison, S. D. Elevated DT-diaphorase activity and messenger RNA content in human non-small cell lung carcinoma: relationship to the response of lung tumor xenografts to mitomycin Cl Cancer Res. 1992, 52 (17) 4752-7
23. Liu, F.; Yu, G.; Wang, G.; Liu, H.; Wu, X.; Wang, Q.; Liu, M.; Liao, K.; Wu, M.; Cheng, X.; Hao, H. An NQO1-initiated and p53-independent apoptotic pathway determines the anti-tumor effect of tanshinone IIA against non-small cell lung cancer PLoS One 2012, 7 (7) e42138
24. Hao, H.; Wang, G.; Cui, N.; Li, J.; Xie, L.; Ding, Z. Identification of a novel intestinal first pass metabolic pathway: NQO1 mediated quinone reduction and subsequent glucuronidation Curr. Drug Metab. 2007, 8 (2) 137-49 (Pubitemid 46218680)
25. Choi, E. K.; Terai, K.; Ji, I. M.; Kook, Y. H.; Park, K. H.; Oh, E. T.; Griffin, R. J.; Lim, B. U.; Kim, J. S.; Lee, D. S.; Boothman, D. A.; Loren, M.; Song, C. W.; Park, H. J. Upregulation of NAD(P)H:quinone oxidoreductase by radiation potentiates the effect of bioreductive beta-lapachone on cancer cells Neoplasia 2007, 9 (8) 634-42 (Pubitemid 47328082)
26. Harbourt, D. E.; Fallon, J. K.; Ito, S.; Baba, T.; Ritter, J. K.; Glish, G. L.; Smith, P. C. Quantification of human uridine-diphosphate glucuronosyl transferase 1A isoforms in liver, intestine, and kidney using nanobore liquid chromatography-tandem mass spectrometry Anal. Chem. 2012, 84 (1) 98-105
27. Tukey, R. H.; Strassburg, C. P. Human UDP-glucuronosyltransferases: metabolism, expression, and disease Annu. Rev. Pharmacol. Toxicol. 2000, 40, 581-616 (Pubitemid 30340694)
28. Nakamura, A.; Nakajima, M.; Yamanaka, H.; Fujiwara, R.; Yokoi, T. Expression of UGT1A and UGT2B mRNA in human normal tissues and various cell lines Drug Metab. Dispos. 2008, 36 (8) 1461-4
29. Ohno, S.; Nakajin, S. Determination of mRNA expression of human UDP-glucuronosyltransferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction Drug Metab. Dispos. 2009, 37 (1) 32-40