Pharmacological determinants of the antitumour activity of mitomycin C

Biochemical Pharmacology

Volumn 56, Issue 11, 1998, Pages 1497-1503

  Spanswick, Victoria J ^a   Cummings, Jeffrey ^a   Ritchie, Alison A ^a   Smyth, John F ^a  

^a WESTERN GENERAL HOSPITAL   (United Kingdom)

Author keywords

2,7 Diaminomitosene; Antitumour activity; MAC tumours; Metabolic activation; Mitomycin C; Pharmacokinetics

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; DRUG METABOLITE; MITOMYCIN C; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ARTICLE; COLON ADENOCARCINOMA; DRUG CLEARANCE; DRUG METABOLISM; DRUG SENSITIVITY; INTRATUMORAL DRUG ADMINISTRATION; NONHUMAN; PRIORITY JOURNAL;

ADENOCARCINOMA; ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; BIOTRANSFORMATION; COLONIC NEOPLASMS; METABOLIC CLEARANCE RATE; MICE; MICE, INBRED STRAINS; MITOMYCIN;

EID: 0031770452     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(98)00164-6     Document Type: Article

References (52)

1. Moore H.W. Bioactivation as a model for drug design bioreductive alkylation. Science (Washington DC). 197:1977;527-532.
2. Kennedy K.A., Teicher B.A., Rockwell S., Sartorelli A.C. The hypoxic tumor cell: A target for selective cancer chemotherapy. Biochem Pharmacol. 29:1980;1-8.
3. Malkinson A.M., Siegel D., Forrest G.L., Gadzar A.F., Oie H.K., Chan D.C., Bunn P.A., Mabry M., Dykes D.J., Harrison S.D. Jr, Ross 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 C. Cancer Res. 52:1992;4752-4757.
4. Schlager J.J., Powis G. Cytosolic NAD(P)H, quinone acceptor oxidoreductase in human normal tissue. Effects of cigarette smoking and alcohol. Int J Cancer. 45:1990;403-409.
5. Cresteil T., Jaiswel A.K. High levels of the NAD(P)H:quinone oxidoreductase (NQO1) gene in tumour cells compared to normal cells of the same origin. Biochem Pharmacol. 42:1991;1021-1027.
6. Workman P. Enzyme-directed bioreductive drug development revisited: A commentary on recent progress and future prospects with emphasis on quinone anticancer drugs and quinone metabolising enzymes, particularly DT-diaphorase. Oncol Res. 6:1994;461-475.
7. Workman P., Walton M.I. Enzyme-directed bioreductive drug development. Adams G.E., Breccia A., Fielden E.M., Wardman P. Selective Activation of Drugs by Redox Processes. 1990;73-191 Plenum, New York.
8. Fitzsimmons S.A., Workman P., Grever M., Paull K., Camalier R., Lewis A.D. The differential expression of reductase enzymes in the NCI human tumour cell line panel: correlation with sensitivity to mitomycin C and the investigational indoloquinone EO9. J Natl Cancer Inst. 88:1996;259-269.
9. Sartorelli A.C. Therapeutic attack of hypoxic cells of solid tumours: Presidential address. Cancer Res. 48:1988;775-778.
10. Cummings J., Spanswick V.J., Tomasz M., Smyth J.F. Enzymology of mitomycin C metabolic activation in tumour tissue - implications for enzyme directed bioreductive drug development. Biochem Pharmacol. 56:1998;405-414.
11. Nishiyama M., Saeki S., Aogi K., Hirabayashi N., Toge T. Relevance of DT-diaphorase activity to mitomycin C (MMC) efficacy on human cancer cells differences in in vitro and in vivo systems. In J Cancer. 53:1993;1013-1016.
12. Plumb J.A., Gerritsen M., Workman P. DT-diaphorase protects cells from the hypoxic cytotoxicity of indoloquinone EO9. Br J Cancer. 70:1994;1136-1143.
13. Plumb J.A., Workman P. Unusually marked hypoxic sensitisation to indoloquinone EO9 and mitomycin C in a human colon-tumour cell line that lacks DT-diaphorase activity. Int J Cancer. 56:1995;134-139.
14. Cummings J., Chirrey L., Willmott N., Halbert G.W., Smyth J.F. Determination of mitomycin C, 2,7-diaminomitosene, 1,2-cis- and 1,2-trans-1-hydroxy-2,7-diaminomitosene in tumour tissue by high-performance liquid chromatography. J Chromatogr. 612:1993;105-113.
15. Cummings J., Spanswick V.J., Smyth J.F. Re-evaluation of the molecular pharmacology of mitomycin C. Eur J Cancer. 31A:1995;1928-1933.
16. Spanswick V.J., Cummings J., Smyth J.F. Enzymology of mitomycin C metabolic activation in tumour tissue: Characterisation of a novel mitochondrial reductase. Biochem Pharmacol. 51:1996;1623-1630.
17. Allan L., Cummings J., Willmott N., Whateley T.L., Smyth J.F. Incorporation and release of chemically intact mitomycin C from albumin microspheres: A high-performance liquid chromatography evaluation. J Drug Target. 1:1993;317-332.
18. Chirrey L., Cummings J., Halbert G.W., Smyth J.F. Conversion of mitomycin C to 2,7-diaminomitosene and 10-decarbamoyl 2,7-diaminomitosene in tumour tissue in vivo. Cancer Chemother Pharmacol. 35:1995;318-322.
19. Cummings J., Spanswick V.J., Gardiner J., Ritchie A., Smyth J.F. Pharmacological and biochemical determinants of the antitumour activity of the indoloquinone EO9. Biochem Pharmacol. 55:1998;253-260.
20. Malviya V.K., Young J.D., Boike G., Gove N., Deppe G. Pharmacokinetics of mitomycin-C in plasma and tumour tissue of cervical cancer patients and selected tissues of female rats. Gynecol Oncol. 25:1986;160-170.
21. Verweij J., den Hartigh J., Stuurman M., de Vries J., Pinedo H.M. Relationship between clinical parameters and pharmacokinetics of mitomycin C. J Cancer Res Clin Oncol. 113:1987;91-94.
22. Pan S.-S., Andrews P.A., Glover C.J., Bachur N.R. Reductive activation of mitomycin C and mitomycin C metabolites by NADPH-cytochrome P-450 and xanthine oxidase. J Biol Chem. 259:1984;959-966.
23. Pan S.-S., Iracki T., Bachur N.R. DNA alkylation by enzyme-activated mitomycin C. Mol Pharmacol. 29:1986;622-628.
24. Double J., Bibby M.C. Therapeutic index: A vital component in selection of anticancer agents for clinical trial. J Natl Cancer Inst. 81:1989;988-994.
25. Bibby M.C., Double J.A., Loadman P.M. Unique chemosensitivity of MAC 16 tumours to flavone acetic acid (LM975, NSC 347512). Br J Cancer. 58:1988;341-344.
26. Walton M.I., Bibby M.C., Double J.A., Plumb J.A., Workman P. DT-diaphorase activity correlates with sensitivity to the indoloquinone EO9 in mouse and human colon carcinomas. Eur J Cancer. 28A:1992;1597-1600.
27. Double J.A., Ball C.R., Cowen P.M. Transplantation of adenocarcinoma of the colon in mice. J Natl Cancer Inst. 54:1975;271-275.
28. Kerpel-Fronius S., Verwey J., Stuurman M., Kanyar B., Lelieveld P., Pinedo H.M. Pharmacokinetics and toxicity of mitomycin C in rodents, given alone, in combination, or after induction of microsomal drug metabolism. Cancer Chemother Pharmacol. 22:1988;104-108.
29. Dorr R.T., Alberts D.S., Liddil J.D. Mitomycin C toxicity and pharmacokinetics in mice given sulphur nucleophiles. Anticancer Res. 8:1988;733-738.
30. Beijnen J.H., Fokkens R.H., Rosing H., Underberg W.J.M. Degradation of mitomycin C in acid phosphate and acetate buffer solutions. Int J Pharmaceut. 32:1986;111-121.
31. Den Hartigh J, Analysis, electrochemistry and pharmacokinetics of mitomycin C. PhD Thesis, Amsterdam, 1986.
32. Hoey B.M., Butler J., Swallow A.J. Reductive activation of mitomycin C. Biochemistry. 27:1988;2608-2614.
33. Dorr R.T., Bowden T., Alberts D.S., Liddil J.D. Interactions of mitomycin C with mammalian DNA detected by alkaline elution. Cancer Res. 45:1985;3510-3516.
34. Kumar G.S., Lipman R., Cummings J., Tomasz M. Mitomycin C-DNA adducts generated by DT-diaphorase. Mechanism of the enzymatic reductive activation of mitomycin C. Biochemistry. 36:1997;14128-14136.
35. Kumar G.S., Musser S.M., Cummings J., Tomasz M. 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. Siegel D., Gibson N.W., Preusch P.C., Ross D. Metabolism of mitomycin C by DT-diaphorase: Role in mitomycin C-induced DNA damage and cytotoxicity in human colon-carcinoma cells. Cancer Res. 50:1990;7483-7489.
37. Cummings J., Allan L., Smyth J.F. Encapsulation of mitomycin C in albumin microspheres markedly alters pharmacokinetics, drug quinone bioreduction in tumour tissue and antitumour activity implications for the drugs in vivo mechanism of action . Biochem Pharmacol. 47:1994;1345-1356.
38. Ross D., Siegel D., Beall H., Prakash A.S., Mulcahy R.T., Gibson N.W. DT-diaphorase in activation and detoxification of quinones. Bioreductive activation of mitomycin C. Cancer Met Rev. 12:1993;83-101.
39. Marshall R.S., Paterson M.C., Rauth A.M. Studies on the mechanism of resistance to mitomycin C and porfiromycin in a human cell strain derived from a cancer prone individual. Biochem Pharmacol. 41:1991;1351-1360.
40. Dulhanty A.M., Whitmore G.F. Chinese hamster ovary cell lines resistant to mitomycin C under aerobic but not hypoxic conditions are deficient in DT-diaphorase. Cancer Res. 51:1991;1860-1865.
41. Pan S.-S., Akman S.A., Forrest G.L., Hipsher C., Johnson R. The role of NAD(P)H: Quinone oxidoreductase in mitomycin C and porfiromycin-resistant HCT 116 human colon-cancer cells. Cancer Chemother Pharmacol. 31:1992;23-31.
42. Pritsos C.A., Pardini I.L., Elliot A.J., Pardini R.S. Relationship between antioxidant enzyme DT-diaphorase and tumour responses to mitomycin C treatment. Simic M.G., Taylor K.A. Oxygen Radicals in Biology and Medicine. 1987;713-716 Plenum Press, New York.
43. Bizanek R., Chowdray D., Arai H., Kasai M., Hughes C.S., Sartorelli C., Rockwell S., Tomasz M. Adducts of mitomycin C and DNA in EMT6 mouse mammary tumour cells: Effects of hypoxia and dicoumarol on adduct formation. Cancer Res. 53:1993;5127-5134.
44. Iyer V.N., Szybalski W. Mitomycins and porfiromycin, chemical mechanism of activation and cross-linking of DNA. Science (Washington DC). 145:1964;55-58.
45. Kennedy K.A., Rockwell S., Sartorelli A.C. Preferential activation of mitomycin C to cytotoxic metabolites by hypoxic tumour cells. Cancer Res. 40:1980;2356-2360.
46. Pritsos C. Re: Reductase enzyme expression across the national cancer institute tumour cell panel: Correlation with sensitivity to mitomycin C and EO9. J Natl Cancer Inst. 88:1996;1161.
47. Cummings J., Langdon S.P., Ross D., Butler J. Antitumour activity of the novel bioreductive MeDZQ against human non-small cell lung cancer xenografts. Annal Oncol. 7:(Supp1):1996;39.
48. Walton M.I., Suggest N., Workman P. The role of human and rodent DT-diaphorase in the reductive metabolism of hypoxic cell cytotoxins. Int J Radiat Oncol Biol Phys. 22:1992;643-647.
49. Beall H.D., Mulcahy R.M., Siegel D., Traver R.D., Gibson N.W., Ross D. Metabolism of bioreductive antitumour compounds by purified rat and human DT-diaphorase. Cancer Res. 54:1994;3196-3201.
50. Gustafson D.L., Beall H.D., Bolton E.M., Ross D., Waldren C.A. Expression of human NAD(P)H: Quinone oxidoreductase (DT-diaphorase) in Chinese hamster ovary cells: effect on the toxicity of antitumour quinones. Mol Pharmacol. 50:1996;728-735.
51. Muscarella D.E., Bloom S.E. Involvement of gene specific DNA damage and apoptosis in the differential toxicity of mitomycin C analogs toward B-lineage versus T-lineage lymphoma cells. Biochem Pharmacol. 53:1997;811-822.
52. lyn Tyrosine kinase activation in mammalian cells treated with mitomycin C. Oncogene. 9:1994;3005-3011.