1,2,4-Benzotriazine 1,4-dioxides. An important class of hypoxic cytotoxins with antitumor activity

Anti-Cancer Drug Design

Volumn 13, Issue 6, 1998, Pages 575-592

  Kelson, Andrew B ^a   McNamara, James P ^a   Pandey, Anjali ^a   Ryan, Kenneth J ^a   Dorie, Mary Jo ^b   McAfee, Patricia A ^b   Menke, Douglas R ^b   Brown, J Martin ^b   Tracy, Michael ^a  

^a SRI INTERNATIONAL   (United States)

^b STANFORD UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Anticancer; Bioreductive activation; Hypoxic cytotoxins; Tirapazamine; Tumors

Indexed keywords

1,2,4 BENZOTRIAZINE 1,4 DIOXIDE; ANTINEOPLASTIC AGENT; CISPLATIN; TIRAPAZAMINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CLINICAL TRIAL; CYTOTOXICITY; DRUG SOLUBILITY; HUMAN; IRRADIATION; META ANALYSIS; PHASE 2 CLINICAL TRIAL; PHASE 3 CLINICAL TRIAL; PRIORITY JOURNAL; SOLID TUMOR;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL HYPOXIA; CHEMISTRY, PHYSICAL; DRUG DESIGN; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED C3H; MICE, SCID; MOLECULAR STRUCTURE; NEOPLASM TRANSPLANTATION; NEOPLASMS, EXPERIMENTAL; OXIDATION-REDUCTION; SOLUBILITY; TRIAZINES;

EID: 0031713612     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (50)

1. ADAMS, G.E., AHMED, I., SHELDON, P.W. & STRATFORD, I.J. (1984). RSU 1069, a 2-nitroimidazole containing an alkylating group: high efficiency as a radio- and chemosensitizer in vitro and in vivo. International Journal of Radiation Oncology Biology Physics, 10, 1653.
2. ATALLAH, R.H. & NAZER, M.Z. (1992) Oxides of 3-methyl-1,2,4-benzotriazine. Tetrahedron, 38, 1793.
3. BEDIKIAN, A.Y., LEGHA, S.S., ETON, O., BUZAID, A C., PAPADOPOULOS, N., COATES, S., SIMMONS, T., NEEFE, J. & VON ROEMELING, R. (1997). Phase II trial of tirapazamine combined with cisplatin in the chemotherapy of advanced malignant melanoma. Annals of Oncology, 8, 363.
4. BEIDERMAN, K.A , WANG, J , GRAHAM, R.P & BROWN, J.M (1991). SR 4233 cytotoxicity and metabolism in DNA repair-competent and repair-deficient cell cultures. British Journal of Cancer, 63, 358.
5. BROWN, J M. (1979). Evidence for acutely hypoxic cells in mouse tumours, and a possible mechanism of re-oxygenation. British Journal of Radiology, 52, 650.
6. BROWN, J.M. (1993). SR 4233 (tirapazamine): a new anticancer drug exploiting hypoxia in solid tumours. British Journal of Cancer, 67, 1163.
7. BROWN, J.M & LEMMON, M J. (1991). Tumor hypoxia can be exploited to preferentially sensitize tumors to fractionated irradiation. International Journal of Radiation Oncology Biology Physics, 20, 457.
8. BROWN, J.M. & SIIM, B G. (1996). Hypoxia-specific cytotoxins in cancer therapy. Seminars in Radiation Oncology, 6, 22.
9. BUNN, H.F. & POYTON R.O. (1996). Oxygen sensing and molecular adaptation to hypoxia. Physiology Reviews, 76, 839.
10. COLEMAN, C.N (1988). Hypoxia in tumours: a paradigm for the approach to biochemical and physiologic heterogeneity. Journal of the National Cancer Institute, 80, 310.
11. DORIE, M.J. & BROWN, J M (1993). Tumor-specific, schedule-dependent interaction between tirapazamine (SR 4233) and cisplatin. Cancer Research, 53, 4633.
12. DORIE, M.J. & BROWN, J.M. (1997). Modification of the antitumor activity of chemotherapeutic drugs by the hypoxic cytotoxic agent tirapazamine. Cancer Chemotherapy and Pharmacology, 39, 361.
13. FITZSIMMONS, S A , LEWIS, A.D., RILEY, R J. & WORKMAN. P. (1994). Reduction of 3-amino-1,2,4-benzotriazine-1,4-di-N-oxide (tirapazamine, WIN 59075, SR 4233) to a DNA-damaging species: a direct role for NADPH:cytochrome P450 oxidoreductase. Carcinogenesis, 15, 1503.
14. GIACCIA, A.J. (1996). Hypoxic stress proteins: survival of the fittest. Seminars in Radiation Oncology, 6, 46.
15. HALL, E.J. (1988). The oxygen effect and re-oxygenation. In Radiobiology for Radiologists. Hall, E.J. (ed.), p. 137. Lippincott: Philadelphia, PA.
16. JONES, G.D D & WEINFELD, M. (1996). Dual action of tirapazamine in the induction of DNA strand breaks. Cancer Research, 56, 1584.
17. KELSON, A.B., MCNAMARA, J.P., PANDEY, A., RYAN, K.J., DORIE, M.J., MCAFEE, P.A., MENKE, D.R., BROWN, J.M., & TRACY, M. (1995). Hypoxic cytotoxins. Synthesis and antitumour activity of SR 4941, a novel 3-alkyl substituted analogue of tirapazamine SR 4233 with improved in vivo efficacy Presented at the IXth International Conference on Chemical Modifiers of Cancer Treatment, Oxford, 22-26 August 1995.
18. KLEINBERG, M.L. & WANKE, L.A. (1995). New approaches and technologies in drug design and discovery. American Journal of Health-System Pharmacists, 52, 1323.
19. KOCH, C.J. (1993). Unusual oxygen concentration dependence of toxicity of SR 4233, a hypoxic cell toxin. Cancer Research, 53, 3992.
20. LADEROUTE, K, WARDMAN, P. & RAUTH, A M. (1988). Molecular mechanisms for the hypoxia-dependent activation of 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR 4233). Biochemical Pharmacology, 37, 1487.
21. LEE, W.W., BROWN, J.M., GRANGE, E.W., MARTINEZ, A.P., TRACY, M. & POLLART, D.J. (1997). 1,2,4-Benzotriazine oxides as radiosensitizers and selective cytotoxic agents. US Patent 5,624,925.
22. LLOYD, R.V., DULING, D.R., RUMYANTSEVA, V, MASON, R.P. & BRIDSON, P K. (1991). Microsomal reduction of 3-amino-1,2,4-benzotriazine 1,4-dioxide to a free radical. Molecular Pharmacology, 40, 440.
23. MCKEOWN, S.R., HEJMADI, M.V., MCINTYRE, I.A., MCALEER, J.J.A. & PATTERSON, L.H. (1995). AQ4N: an alkylaminoanthraquinone N-oxide showing bioreductive potential and positive interaction with radiation in vivo. British Journal of Cancer, 72, 76.
24. MCNAMARA, J.P., MARTINEZ, A.P., CHAN, Y.W., LEMMON, M.J., BROWN, J.M. & TRACY, M. (1991). Hyppxic cytotoxins. 2. Synthesis, physicochemical properties and biological activity of 3-(N,N-dialkylaminoalkylamino)-1,2,4-benzotriazine 1,4-dioxides. Presented at the VIIth International Conference on Chemical Modifiers of Cancer Treatment, Clearwater, Florida, 2-5 February 1991.
25. McNAMARA, J.P., KELSON, A.B., RYAN, K.J., TOSTO, L M., MENKE, D.R , BROWN, J.M. & TRACY, M. (1993). Hypoxic cytotoxins. 3-Alkyl-1,2,4-benzotriazine 1,4-dioxides: analogues of SR 4233 (WIN 59075) with comparable anti-tumor activity. Presented at the VIIIth International Conference on Chemical Modifiers of Cancer Treatment, Kyoto, Japan, 16-19 June 1993.
26. MINCHINTON, A I., COBS, L & BROWN, J M. (1993). Intermittent hypoxia: its presence in experimental tumours of different histological grade. Presented at the VIIIth International Meeting on Chemical Modifiers of Cancer Treatment, Kyoto, Japan, June 16-19, 1993.
27. OVERGAARD, J & HORSMAN, M.R. (1996). Modification of hypoxia-induced radioresistance in tumors by the use of oxygen and sensitizers. Seminars in Radiation Oncology, 6, 10.
28. PATTERSON, A V, BARHAM, H.M., CHINJE, E C., ADAMS, G.E., HARRIS, A.L. & STRATFORD, I.J. (1995). Importance of P450 reductase activity in determining sensitivity of breast tumour cells to the bioreductive drug, tirapazamine (SR 4233). British Journal of Cancer, 72, 1144.
29. PRIYADARSINI, K.I., TRACY, M. & WARDMAN, P. (1996). The one-electron reduction potential of 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine): a hypoxia-selective bioreductive drug. Free Radical Research, 25, 393.
30. RALEIGH, J.A., DEWHIRST, M.W. & THRALL, D.E. (1996). Measuring tumor hypoxia. Seminars in Radiation Oncology, 6, 37.
31. RICE, G.C., HOU, C A. & SCHIMKE, R.T. (1986). Transient hypoxia enhances the frequency of dihydrofolate reductase gene amplification in Chinese hamster ovary cells. Proceedings of the National Academy of Sciences, USA, 83, 5978.
32. RODRIGUEZ, G.I., VALDIVIESO, M., VON HOFF, D D, KRAUT, M. BURRIS, H.A., ECKARDT, J.R., LOCKWOOD, G., KENNEDY, H & VON ROEMELING, R (1996). A phase I/II trial of the combination of tirapazamine and cisplatin in patients with non-small cell lung cancer (NSCLC). Proceedings of the American Society of Clinical Oncology, 15, 1144 (abstract).
33. SAKATA, K., KWOK, T.T , MURPHY, B.J , LADEROUTE, K.R., GORDON, G.R. & SUTHERLAND, R.M (1991). Hypoxia-induced drug resistance: comparison to P-glycoprotein-associated drug resistance. British Journal of Cancer, 64, 809.
34. SARTORELLI, A.C. (1988). Therapeutic attack of hypoxic cells of solid tumors: presidential address. Cancer Research, 48, 775.
35. SEMENZA, G.L. & WANG, G.L. (1992). A nuclear factor induced by hypoxia via de novo protein synthesis binds to the human erythropoietin gene enhancer at a site required for transcription activation. Molecular and Cellular Biology, 12, 5447.
36. SHWEIKI, D , ITIN, A., SOFFER, D & KESHET, E. (1992). Vascular endothelial growth factor induced by hypoxia may mediate hypoxia-initiated angiogenesis. Nature, 359, 843.
37. SMITH, D.A., JONES, B.C. & WALKER. D.K. (1996). Design of drugs involving the concepts and theories of drug metabolism and pharmacokinetics. Medical Research Reviews, 16, 243.
38. SUTHERLAND, R.M., AUSSERER, W.A., MURPHY, B J. & LADEROUTE, K.R. (1996). Tumor hypoxia and heterogeneity: challenges and opportunities for the future. Seminars in Radiation Oncology, 6, 59.
39. TEICHER, B.A., LIU, S.D., LIU, J.T., HOLDEN, S.A. & HERMAN, T.S. (1993). A carbonic anhydrase inhibitor as a potential modulator of cancer therapies. Anticancer Research., 13, 1549.
40. THOMLINSON, R.H & GRAY, L.H. (1955). The histological structure of some human lung cancers and the possible implications for radiotherapy. British Journal of Cancer, 9, 539.
41. TOLLENAERE, J.P. (1996). The role of structure-based ligand design and molecular modeling in drug discovery. Pharmacy World and Science, 18, 56.
42. TREAT, J , HAYNES, B., JOHNSON, E , BELANI, C., GREENBERG, R., RODRIGUEZ, R., DROBBINS, P., MILLER, W., MEEHAN, L. & VON ROEMELING, R. (1997). Tirapazamme with cisplatin: a phase II trial in advanced stage non-small cell lung cancer (NSCLC). Proceedings of the American Society of Clinical Oncology, 16, 1633 (abstract).
43. VAUPEL, P., KALLINOWSKI, F. & OKUNIEFF, P (1989). Blood flow, oxygen and nutrient supply, and metabolic microenvironment of human tumours: a review. Cancer Research, 49, 6449.
44. WALTON M.I. & WORKMAN, P. (1990). Enzymology of the reductive bioactivation of SR 4233. Biochemical Pharmacology, 39, 1735.
45. WALTON, M.I. & WORKMAN, P. (1993). Pharmacokinetics and bioreductive metabolism of the novel benzotriazine di-N-oxide hypoxic cell cytotoxin tirapazamine (WIN 94075; SR 4233; NSC 130181). Journal of Pharmacology and Experimental Therapeutics, 265, 938.
46. WALTON, M.I., WOLF, C.R. & WORKMAN, P. (1992). The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR 4233, WIN 59075) by mouse liver. Biochemical Pharmacology, 44, 251.
47. WARDMAN, P., DENNIS, M.F , EVERETT, S.A , PATEL, K.B., STRATFORD, M.R L &. TRACY, M (1996). Radicals from one-electron reduction of nitro compounds, aromatic N-oxides, and quinones: the kinetic basis for hypoxia-selective, bioreductive drugs. Biochemical Society Symposia, 61, 171.
48. WORKMAN, P. (1983). New drugs against hypoxic cells. Cancer Topics, 4, 54.
49. WORKMAN, P., WALTON, M I , JOHNSON, J., BAKER, J F, GORDON, G.R., KELSON, A B. & TRACY, M. (1991). Identification of a new major metabolite of 3-amino-1,2,4-benzotriazine 1,4-dioxide (SR 4233, WIN 59075) in mouse urine. Presented at the VIIth International Meeting on Chemical Modifiers of Cancer Treatment, Clearwater, Florida, 2-5 February 1991.
50. ZEMAN, E.M., BROWN, J.M , LEMMON, M.J. HIRST, VK. & LEE, W.W (1986) SR 4233: a new bioreductive agent with high selective toxicity for hypoxic mammalian cells. International Journal of Radiation Oncology Biology Physics, 12, 1239.