Pharmacological and biochemical determinants of the antitumour activity of the indoloquinone EO9

Biochemical Pharmacology

Volumn 55, Issue 3, 1998, Pages 253-260

  Cummings, Jeffrey ^a   Spanswick, Victoria J ^a,b   Gardiner, Jill ^a   Ritchie, Alison ^a   Smyth, John F ^a  

^a WESTERN GENERAL HOSPITAL   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Antitumour activity; Bioreductive enzymes; Drug metabolites; DT diaphorase; Indoloquinone EO9; Xenografts

Indexed keywords

5 (1 AZIRIDINYL) 3 HYDROXYMETHYL 2 (3 HYDROXY 1 PROPENYL) 1 METHYL 4,7 INDOLEDIONE; CYTOCHROME B5 REDUCTASE; CYTOCHROME P450 REDUCTASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMOSENSITIVITY; COLON ADENOCARCINOMA; COLON CANCER; CONTROLLED STUDY; DRUG METABOLISM; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; IN VITRO STUDY; INTRATUMORAL DRUG ADMINISTRATION; NONHUMAN; PRIORITY JOURNAL; ULTRAVIOLET SPECTROPHOTOMETRY; XENOGRAFT;

EID: 0032007820     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00265-7     Document Type: Article

References (41)

1. Oostveen EA, Speckamp WN. Mitomycin C analogs I Indoloquinones as (potential) bisalkylation agents . Tetrahedron. 43:1987;255-262.
2. Smitskamp-Wilms E, Hendriks HR, Peters GJ. Development, pharmacology, role of DT-diaphorase and prospects of the indoloquinone EO9. Gen Pharmac. 27:1996;421-429.
3. Bailey SM, Lohmeyer M, Castaner J. EO9. Drugs Fut. 21:1996;143-151.
4. Ross D, Beall HD, Siegel D, Traver RD, Gustafson DL. Enzymology of bioreductive drug activation. Br J Cancer. 74:1996;S1-S8.
5. Butler J, Spanswick VJ, Cummings J. The autoxidation of the reduced forms of EO9. Free Radic Res. 25:1996;141-148.
6. Hendriks HR, Pizao PE, Berger DP, Kooistra KL, Bibby MC, Boven E, Dreef-van der Meulen HC, Henrar REC, Fiebeg HH, Double JA, Hornstra HW, Pinedo HM, Workman P, Schwartsmann G. EO9 a novel bioreductive alkylating indoloquinone with preferential solid tumour activity and lack of bone marrow toxicity in preclinical models . Eur J Cancer. 29A:1993;897-906.
7. Walton MI, Bibby MC, Double JA, Plumb JA, 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.
8. Schellens JHM, Planting AST, van Acker BAC, Loos WJ, de Boer-Dennert M, van der Burg MEL, Koier I, Krediet RT, Stoter G, Verweij J. Phase I and pharmacology study of the novel indoloquinone bioreductive alkylating cytotoxic drug EO9. J Natl Cancer Inst. 86:1994;906-912.
9. Adams GE, Stratford IJ, Edwards HS, Bremner JCM, Cole S. Bioreductive drugs as post-irradiation sensitizers comparison of dual function agents with SR 4233 and the mitomycin C analogue EO9 . Int J Rad Oncol Biol Phys. 22:1992;717-720.
10. Robertson N, Haigh A, Adams GE, Stratford IJ. Factors affecting sensitivity to EO9 in rodent and tumor cells in vitro DT-diaphorase activity and hypoxia . Eur J Cancer. 30A:1994;1013-1019.
11. Pavlidis N, Hanauske AR, Gamucci T, Smyth J, te Velde A, Lan J, Verweij J. A randomized phase II study with two schedules of the novel indoloquinone EO9 in non-small-cell-lung cancer a study of the EORTC early clinical studies group (ECSG) . Anal Oncol. 7:1996;529-531.
12. Workman P, Binger M, Kooistra KL. Pharmacokinetics, distribution, and metabolism of the novel bioreductive alkylating indoloquinone EO9 in rodents. Int J Rad Oncol Biol Phys. 22:1992;713-716.
13. Binger M, Workman P. Gradient high-performance liquid chromatographic assay for the determination of the novel indoloquinone antitumour agent EO9 in biological specimens. J Chromatogr. 532:1990;321-336.
14. Spanswick VJ, Cummings J, Smyth JF. Enzymology of mitomycin C metabolic activation in tumour tissue characterization of a novel mitochondrial reductase . Biochem Pharmacol. 51:1996;1623-1630.
15. Layne E. Spectrophotometric and turbimetric methods for measuring proteins. Methods Enzymol. 3:1957;450-451.
16. Spanswick VJ, Molecular mechanisms of bioreductive drug activation in solid tumour tissue. PhD thesis, 1996.
17. Collard J, Matthew AM, Double JA, Bibby MC. EO9 relationship between DT-diaphorase levels and response in vitro and in vivo . Br J Cancer. 71:1995;1199-1203.
18. Robertson N, Stratford IJ, Houlbrook S, Carmichael J, Adams GE. The sensitivity of human cells to quinone bioreductive drugs what role for DT-diaphorase . Biochem Pharmacol. 44:1992;409-412.
19. Plumb JA, Workman P. Unusually marked hypoxic sensitization to indoloquinone EO9 and mitomycin C in a human colon-tumour cell line that lacks DT-diaphorase activity. Int J Cancer. 56:1994;134-139.
20. Traver RD, Horikoshi T, Danenberg KD, Stadlbauer THW, Danenberg PV, Ross D, Gibson NW. NAD(P)H quinone oxidoreductase gene expression in human colon carcinoma cells: characterization of a mutation which modulates DT-diaphorase activity and mitomycin C sensitivity . Cancer Res. 52:1992;797-802.
21. Ross D, Beall H, Traver RD, Siegel D, Phillips RM, Gibson NW. Bioactivation of quinones by DT-diaphorase molecular, biochemical and chemical studies . Oncol Res. 6:1994;493-500.
22. Siegel D, Gibson NW, Preusch PC, 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.
23. Smitskamp-Wilms E, Giaccone G, Pinedo HM, van der Laan BFAM, Peters GJ. DT-diaphorase activity in normal and neoplastic human tissues an indicator for sensitivity to bioreductive agents . Br J Cancer. 72:1995;917-921.
24. Plumb JA, Gerritsen M, Workman P. DT-diaphorase protects cells from the hypoxic cytotoxicity of indoloquinone EO9. Br J Cancer. 70:1994;1136-1143.
25. Bailey SM, Lewis AD, Workman P. Involvement of NADPH cytochrome P-450 in activation of EO9 to DNA damaging species. Br J Cancer. 69:(Suppl 21):1994;57.
26. Hodnick WF, Sartorelli AC. Reductive activation of mitomycin C by NADH cytochrome b5 reductase. Cancer Res. 53:1993;4907-4912.
27. Lewis AD, Clarke PE, Chen S, Workman P. Comparison of human and rodent recombinant DT-diaphorase proteins for their ability to metabolise the novel indoloquinone antitumour agent EO9. Proc Am Assoc Cancer Res. 35:1994;3844.
28. Phillips RM, Hulbert PB, Bibby MC, Sleigh NR, Double JA. In vitro activity of the novel indoloquinone EO9 and the influence of pH on cytotoxicity. Br J Cancer. 65:1992;359-364.
29. Maliepaard M, Wolf A, Groot SE, de Mol NJ, Janssen LHM. Indoloquinone EO9 DNA interstrand cross-linking upon reduction by DT-diaphorase or xanthine oxidase . Br J Cancer. 71:1995;836-839.
30. Bailey SM, Wyatt MD, Lewis AD, Hartley JA, Workman P. Involvement of DT-diaphorase in the DNA cross-linking and sequence selectivity of the novel indoloquinone antitumour agent EO9. Proc Am Assoc Cancer Res. 35:1994;384.
31. Pan S-S, Andrews PA, Glover CJ, Bachur NR. Reductive activation of mitomycin C and mitomycin C metabolites by NADPH-cytochrome P-450 reductase and xanthine oxidase. J Biol Chem. 259:1984;959-966.
32. Chirrey L, Cummings J, Halbert GW, Smyth JF. 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.
33. Bailey SM, Suggest N, Walton MI, Workman P. Structure-activity relationships for DT-diaphorase reduction of hypoxic cell directed agents indoloquinones and diaziridinyl benzoquinones . Int J Rad Oncol Biol Phys. 22:1992;649-653.
34. Smitskamp-Wilms E, Peters GJ, Pinedo HM, van Ark-Otte J, Giaccone G. Chemosensitivity to the indoloquinone EO9 is correlated with DT-diaphorase activity and its gene expression. Biochem Pharmacol. 47:1994;1325-1332.
35. Fitzsimmons SA, Workman P, Grever M, Paull K, Camalier R, Lewis AD. 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.
36. Walton MI, Smith PJ, Workman P. The role of NAD(P)H quinone reductase (EC 1.6.99.2, DT-diaphorase) in reductive bioactivation of the novel indoloquinone antitumour agent EO9 . Cancer Commun. 3:1991;199-206.
37. Gustafson DL, Beall HD, Bolton EM, Ross D, Waldren CA. Expression of human NAD(P)H quinone oxidoreductase (DT-diaphorase) in chinese hamster ovary cells: effect on the toxicity of antitumour quinones . Molec Pharmacol. 50:1996;728-735.
38. Saunders M, Jaffar M, Patterson AV, Naylor M, Adams GE, Harris A, Stratford IJ. Structural requirement for EO9 toxicity and dependence on P450 reductase for activation. Br J Cancer. 73:1996;27.
39. Robertson N, Lockyer SD, Barham HM and Stratford IJ, Reductive metabolism of EO9 by DT-diaphorase in human tumour cell lysates. Proc Int Conference Bioreductive Drugs Lake Taho, 16-19th Aug, 1994.
40. Beall HD, Mulcahy RM, Siegel D, Traver RD, Gibson NW, Ross D. Metabolism of bioreductive antitumour compounds by purified rat and human DT-diaphorase. Cancer Res. 54:1994;3196-3201.
41. Cummings J, Langdon SP, Ross D, Butler J. Antitumour activity of the novel bioreductive MeDZQ against human non-small cell lung cancer xenografts. Ann Oncol. 7:1996;39.