Evaluation of the effect of oxygen exposure on human liver microsomal metabolism of mitomycin C in the presence of glutathione using liquid chromatography-quadrupole time of flight mass spectrometry

Analytical Biochemistry

Volumn 343, Issue 2, 2005, Pages 268-276

  Lang, Wensheng ^a   Caldwell, Gary W ^a   Masucci, John A ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Glutathione; Human liver microsomes; LC Q TOF MS; Metabolism; Mitomycin C

Indexed keywords

BIOMOLECULES; DRUG PRODUCTS; LIQUIDS; MASS SPECTROMETRY; METABOLISM; METABOLITES; OXYGEN; PEPTIDES;

GLUTATHIONES; HUMAN LIVER MICROSOMES; INTERMEDIATE METABOLITES; LC/Q-TOF-MS; LIQUID CHROMATOGRAPHY-QUADRUPOLE TIME-OF-FLIGHT MASS SPECTROMETRIES; METABOLITE PROFILING; MITOMYCIN C; QUADRUPOLE TIME OF FLIGHT MASS SPECTROMETRY;

LIQUID CHROMATOGRAPHY;

2,7 DIAMINOMITOSENE; 2,7 DIAMINOMITOSENE 10 GLUTATHIONE; AMINO ACID DERIVATIVE; AZIRIDINE DERIVATIVE; CYTOCHROME P450 REDUCTASE; DRUG METABOLITE; GLUTATHIONE; GLUTATHIONE DERIVATIVE; HELIUM; LEUCOAZIRIDINOMITOSENE; MITOMYCIN C; OXYGEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ANALYTIC METHOD; ARTICLE; DRUG METABOLISM; ELECTRON; ENZYME PURIFICATION; GLUTATHIONE METABOLISM; HUMAN; HUMAN TISSUE; HYPEROXIA; INCUBATION TIME; LIQUID CHROMATOGRAPHY; LIVER ISCHEMIA; LIVER MICROSOME METABOLISM; METABOLIC ACTIVATION; PRIORITY JOURNAL; QUADRUPOLE MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; ULTRAVIOLET RADIATION;

EID: 23044433584     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2005.05.036     Document Type: Article

References (37)

1. B.G. Haffty, Y.H. Son, C.T. Sasaki, R.J. Papac, D.B. Fischer, S. Rockwell, A.C. Sartorelli, and J.J. Fischer Mitomycin C as an adjunct to postoperative radiation therapy in squamous cell carcinoma of the head and neck: results from two randomized clinical trials Int. J. Radiat. Oncol. Biol. Phys. 27 1996 241 250
2. B.G. Haffty, L.D. Wilson, Y.H. Son, E.I. Cho, R.J. Papac, D.B. Fischer, S. Rockwell, A.C. Sartorelli, D.A. Ross, C.T. Sasaki, and J.J. Fischer Concurrent chemo-radiotherapy with mitomycin C compared with porfiromycin in squamous cell cancer of the head and neck: final results of a randomized clinical trial Int. J. Radiat. Oncol., Biol. Phys. 61 2005 119 128
3. M. Tomasz, R. Lipman, D. Chowdary, J. Pawlak, G.L. Verdine, and K. Nakanishi Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA Science 235 1987 1204 1208
4. M. Tomasz, D. Chowdary, R. Lipman, S. Shimotakahara, D. Veiro, V. Walker, and G.L. Verdine Reaction of DNA with chemically or enzymatically activated mitomicin C: isolation and structure of the major covalent adduct Proc. Natl. Acad. Sci. USA 83 1986 6702 6706
5. A.A. Clarke, N.J. Philpott, E.C. Gordon-Smith, and T.R. Rutherford The sensitivity of Fanconi anaemia group C cells to apoptosis induced by mitomycin C is due to oxygen radical generation, not DNA crosslinking Br. J. Haematol. 96 1997 240 247
6. G. Pagano Mitomycin C and diepoxybutane action mechanisms and FANCC protein functions: further insights into the role for oxidative stress in Fanconi's anaemia phenotype Carcinogenesis 21 2000 1067 1068
7. C.A. Pritsos, and A.C. Sartorelli Generation of reactive oxygen radicals through bioactivation of mitomycin antibiotics Cancer Res. 46 1986 3528 3532
8. J.H. Doroshow Mitomycin C-enhanced superoxide and hydrogen peroxide formation in rat heart J. Pharmacol. Exp. Ther. 218 1981 206 211
9. C.S. Lee, S.Y. Park, H.H. Ko, and E.S. Han Effect of change in cellular GSH levels on mitochondrial damage and cell viability loss due to mitomycin C in small cell lung cancer cells Biochem. Pharmacol. 68 2004 1857 1867
10. C.S. Lee Effect of depletion and oxidation of cellular GSH on cytotoxicity of mitomycin C in small cell lung cancer cells J. Appl. Pharmacol. 12 2004 92 100
11. O.P. Jurma, D.G. Hom, and J.K. Andersen Decreased glutathione results in calcium-mediated cell death in PC12 Free Radic. Biol. Med. 23 1997 1055 1066
12. E. Bousquet, N.A. Santagati, and T. Lancetta Determination of glutathione in biological tissues by high-performance liquid chromatography with electrochemical detection J. Pharm. Biomed. Anal. 7 1989 643 647
13. A. Pastore, G. Federici, E. Bertini, and F. Piemonte Analysis of glutathione: implication in redox and detoxification Clin. Chim. Acta 333 2003 19 39
14. M. Sharma, and M. Tomasz Conjugation of glutathione and other thiols with bioreductively activated mitomycin C: effect of thiols on the reductive activation rate Chem. Res. Toxicol. 7 1994 390 400
15. M. Sharma, Q.Y. He, and M. Tomasz Effects of glutathione on alkylation and cross-linking of DNA by mitomycin C: isolation of a ternary glutathione-mitomycin DNA adduct Chem. Res. Toxicol. 7 1994 401 407
16. H.F.J. Bligh, A. Bartoszek, C.N. Robson, I.D. Hickson, C.B. Kasper, J.D. Beggs, and C.R. Wolf Activation of mitomycin C by NADPH:cytochrome P-450 reductase Cancer Res. 50 1990 7789 7792
17. S. Pan, P.A. Andrew, and C.J. Glover Reductive activation of mitomycin C and mitomycin C metabolites catalyzed by NADPH-cytochrome P-450 reductase and xanthine oxidase J. Biol. Chem. 259 1984 959 966
18. W.F. Hodnick, and A.C. Sartorelli Reductive activation of mitomycin by NADH:cytochrome b5 reductase Cancer Res. 53 1993 4907 4912
19. D. Siegel, H. Beall, C. Senekowitsch, M. Kasai, H. Arai, N.W. Gibson, and D. Ross Bioreductive activation of mitomycin C by DT-diaphorase Biochemistry 31 1992 7879 7885
20. S. Pan, G.L. Forrest, S.A. Akman, and L. Hu NAD(P)H:quinone oxidoreductase expression and mitomycin C resistance developed by human colon cancer HCT116 cells Cancer Res. 55 1995 330 335
21. S. Pan, S.A. Akman, G.L. Forrest, C. Hipsher, and R. Johnson The role of NAD(P)H:quinone oxidoreductase in mitomycin C- and porfiromycin-resistant HCT 116 human colon-cancer cell Cancer Chemother. Pharmacol. 31 1992 23 31
22. H.D. Beall, R.T. Mulcahy, D. Siegel, R.D. Traver, N.W. Gibson, and D. Ross Metabolism of bioreductive antitumor compounds by purified rat and human DT-diaphorases Cancer Res. 54 1994 3196 3201
23. M. Tomasz, and R. Lipman Reductive metabolism and alkylating activity of mitomycin C induced by rat liver microsomes Biochemistry 20 1981 5056 5061
24. K.A. Kennedy, S.G. Sligar, L. Polomski, and A.C. Sartorelli Metabolic activation of mitomycin C by liver microsomes and nuclei Biochem. Pharmacol. 31 1982 2011 2016
25. W. Lang, J. Mao, Q. Wang, C. Niu, T.W. Doyle, and B. Almassian Isolation and identification of metabolites of porfiromycin formed in a rat liver preparation J. Pharm. Sci. 89 2000 191 198
26. W. Lang, J. Mao, T.W. Doyle, and B. Almassian Isolation and identification of urinary metabolites of porfiromycin in dogs and humans Drug Metab. Dispos. 28 2000 899 904
27. F. Chung, D. Komninou, L. Zhang, R. Nath, J. Pan, S. Amin, and J. Richie Glutathione depletion enhances the formation of endogenous cyclic DNA adducts derived from t-4-hydroxy-2-nonenal in rat liver Chem. Res. Toxicol. 18 2005 24 27
28. I.J. Stratford, and P. Workman Bioreductive drugs into the next millennium Anticancer Drug Des. 13 1998 519 528
29. J.H. Lee, M. Naito, and T. Tsuruo Nonenzymatic reductive activation of 7-N-((2-([2-(gamma-l-glutamylamino)ethyl]dithio)ethyl))mitomycin C by thiol molecules: a novel mitomycin C derivative effective on mitomycin C-resistant tumor cells Cancer Res. 54 1994 2398 2403
30. S. Kobayashi, J. Ushiki, K. Takai, S. Okumura, M. Kono, M. Kasai, K. Gomi, M. Morimoto, H. Ueno, and T. Hirata Disposition and metabolism of KW-2149, a novel anticancer agent Cancer Chemother. Pharmacol. 32 1993 143 150
31. Q. He, H. Maruenda, and M. Tomasz Novel bioreductive activation mechanism of mitomycin C derivatives bearing a disulfide substituent in their quinone J. Am. Chem. Soc. 116 1994 9349 9350
32. M. Kono, Y. Saitoh, M. Kasai, and K. Shirahata Isolation of albomitomycins from solutions of 7-amino substituted mitomycins: mitomycin C and KW-2149 J. Antibiot. 48 1995 179 181
33. W. Wu, and L.A. McKown In vitro drug metabolite profiling using hepatic S9 and human liver microsomes Z. Yan G.W. Caldwell Optimization in Drug Discovery: In Vitro Methods 2004 Humana Totowa, NJ 163 184
34. N. Cotelle, S. Moreau, P. Cotelle, J.P. Catteau, J.L. Bernier, and J.P. Henichart Generation of free radicals by simple prenylated hydroquinone derivatives, natural antitumor agents from the marine urochordate Aplidium californicum Chem. Res. Toxicol. 4 1991 300 305
35. G.S. Kumar, S.M. Musser, J. Cummings, and M. Tomasz 2,7-Diaminomitosene, a monofunctional mitomycin C derivative, alkylates DNA in the major groove: structure and base-sequence specificity of the DNA adduct and mechanism of the alkylation J. Am. Chem. Soc. 118 1996 9209 9217
36. Y. Palom, M.F. Belcourt, G.S. Kumar, H. Arai, M. Kasai, A.C. Sartorelli, S. Rockwell, and M. Tomasz Formation of a major DNA adduct of the mitomycin metabolite 2,7-diaminomitosene in EMT6 mouse mammary tumor cells treated with mitomycin C Oncol. Res. 10 1998 509 521
37. Y. Palom, M.F. Belcourt, L.-Q. Tang, S.S. Mehta, A.C. Sartorelli, C.A. Pritsos, K.L. Pritsos, S. Rockwell, and M. Tomasz Bioreductive metabolism of mitomycin C in EMT6 mouse mammary tumor cells: cytotoxic and non-cytotoxic pathways, leading to different types of DNA adducts: the effect of dicumarol Biochem. Pharmacol. 61 2001 1517 1529