The one-electron reduction potential of 3-amino-1,2,4-benzotriazine l,4-dioxide (tirapazamine): A hypoxia-selective bioreductive drug

Free Radical Research

Volumn 25, Issue 5, 1996, Pages 393-399

  Priyadarsini, K Indira ^a   Tracy, Michael ^b   Wardman, Peter ^a  

^a MOUNT VERNON HOSPITAL   (United Kingdom)

^b SRI INTERNATIONAL   (United States)

Author keywords

pK(a); Pulse radiolysis; Reduction potential; Tirapazamine

Indexed keywords

ANTHRAQUINONE; BENZYLVIOLOGEN; DUROQUINONE; QUINONE DERIVATIVE; TIRAPAZAMINE;

AQUEOUS SOLUTION; ARTICLE; ELECTRON TRANSPORT; HYPOXIA; PH; PKA; PULSE RADIOLYSIS; REDUCTION;

EID: 0029959194     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.3109/10715769609149061     Document Type: Article

References (21)

1. E. M. Zeman, J. M. Brown, M. J. Lemmon, V. K. Hirst and W. W. Lee (1986) SR-4233: a new bioreductive agent with high selective toxicity for hypoxic mammalian cells. International Journal of Radiation Oncology Biology and Physics, 12, 1239-1242.
2. K. Laderoute, P. Wardman and A. M. Rauth (1988) Molecular mechanisms for the hypoxia-dependent activation of 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR4233). Biochemical Pharmacology, 37, 1487-95.
3. J. M. Brown (1993) SR4233 (tirapazamine): a new anti-cancer drug exploiting hypoxia in solid tumours. British Journal of Cancer, 67, 1163-1170.
4. E. M. Zeman, M. A. Baker, M. J. Lemmon, C. I. Pearson, J. A. Adams, J. M. Brown, W. W. Lee and M. Tracy (1989) Structure activity relationships for benzotriazine di-N-oxides. International Journal of Radiation Oncology Biology and Physics, 16, 977-81.
5. G. E. Adams and I. J. Stratford (1994) Bioreductive drugs for cancer therapy: the search for tumor specificity. International Journal of Radiation Oncology Biology and Physics, 29, 231-238.
6. J. H. Tocher, N. S. Virk and D. I. Edwards (1990) Electrochemical studies and DNA damaging effects of the benzotriazine-N-oxides. Biochemical Pharmacology, 39, 781-786.
7. J. H. Tocher, N. S. Virk and D. I. Edwards (1990) Electrochemical properties as a function of pH of the benzotriazine di-N-oxides. Free Radical Research Communications, 10, 295-302.
8. J. H. Tocher and D. I. Edwards (1994) Electrochemical studies of tirapazamine: generation of the one-electron reduced product. Free Radical Research, 21, 277-283.
9. P. Wardman, M. F. Dennis, S. A. Everett, K. B. Patel, M. R. L. Stratford and M. Tracy (1995) Radicals from one-electron reduction of nitro compounds, aromatic N-oxides and quinones: the kinetic basis for hypoxia-selective, bioreductive drugs. In Free Radicals and Oxidative stress: Environment, Drugs and Food Additives (Biochemical Society Symposium 61). (eds. C. Rice-Evans, B. Halliwell, and G. G. Lunt), Portland Press, London, pp. 171-194.
10. P. Wardman, K. I. Priyadarsini, M. F. Dennis, S. A. Everett, M. A. Naylor, K. B. Patel, I. J. Stratford, M. R. L. Stratford and M. Tracy (1996) Chemical properties which control selectivity and efficacy of aromatic N-oxide bioreductive drugs. British Journal of Cancer, 73, (Suppl. XXVII), S000-S000.
11. D. Meisel and G. Czapski (1975) One-electron transfer equilibria and redox potentials of radicals studied by pulse radiolysis. Journal of Physical Chemistry, 79, 1503-1509.
12. D. Meisel and P. Neta (1975) One-electron reduction potentials of nitro compounds and radiosensitizers. Correlation with spin densities and their radical anions. Journal of the American Chemical Society, 97, 5198-5203.
13. P. Wardman (1989) Reduction potentials of one-electron couples involving free radicals in aqueous solution. Journal of Physical and Chemical Reference Data, 18, 1637-1755.
14. L. P. Candeias, S. A. Everett and P. Wardman (1993) Free radical intermediates in the oxidation of flavone-8-acetic acid: possible involvement in its anti-tumour activity. Free Radical Biology & Medicine, 15, 385-94.
15. G. V. Buxton, C. L. Greenstock, W. P. Helman and A. B. Ross (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals in aqueous solution. Journal of Physical and Chemical Reference Data, 17, 513-886.
16. P. Wardman and E. D. Clarke (1976) One-electron reduction potentials of substituted nitroimidazoles measured by pulse radiolysis. Journal of the Chemical Society, Faraday Transactions I, 72, 1377-90.
17. P. Wardman (1991) The reduction potential of benzyl viologen: an important reference compound for oxidant/radical redox couples. Free Radical Research Communications, 4, 57-67.
18. A. Ledwith (1977) Electron transfer reactions of paraquat. In Biochemical Mechanisms of Paraquat Toxicity (ed. A. P. Autor), Academic Press, New York, 21-36.
19. P. Wardman and E. D. Clarke (1987) Redox properties and rate constants in free-radical mediated damage. British Journal of Cancer, 55, 172-177.
20. P. Wardman (1990) Bioreductive activation of quinones: redox properties and thiol reactivity. Free Radical Research Communications, 8, 219-229.
21. P. Wardman (1985) Some reactions and properties of nitro radical-anions important in biology and medicine. Environmental Health Perspectives, 63, 101-112.