Effect of substituents on the metabolism of nitracrine in rat

Xenobiotica

Volumn 26, Issue 5, 1996, Pages 559-569

  Robertson, I G C ^a   Bland, T J ^a   Palmer, B D ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

BETA GLUCURONIDASE; DRUG METABOLITE; GLUCURONIDE; GLUTATHIONE TRANSFERASE; NITRACRINE; NITRACRINE DERIVATIVE; OXIDE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG BILE LEVEL; DRUG CONJUGATION; DRUG METABOLISM; DRUG OXIDATION; DRUG URINE LEVEL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTRAVENOUS DRUG ADMINISTRATION; LIVER CYTOSOL; MALE; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANIMALIA; RATTUS NORVEGICUS;

EID: 0029972988     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.3109/00498259609046732     Document Type: Article

References (21)

1. AL-KASSAB, S., BOYLAND, E., and WILLIAMS, K., 1963, An enzyme from rat liver catalysing conjugations with glutathione. 2. Replacement of nitro groups. Biochemical Journal, 87, 4-9.
2. 2-oxidized species of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rat liver. Carcinogenesis, 12, 2239-45.
3. DENNY, W. A., CHAMBERS, D., STEWART, G. M., and WILSON, W. R., 1985, Nitroacridines with selective toxicity towards hypoxic mammalian cells : synthesis and stability of tritiated derivatives. Journal of Labelled Compounds and Radiophamaceuticals 22, 995-1005.
4. GNIAZDOWSKI, M., FILIPSKI, J., and CHORAZY, M., 1979, Nitracrine. In Antibiotics V (Part 2), edited by F. E. Hahn (Berlin: Springer), pp. 275-297.
5. HODGKISS, R. J., BEGG, A. C., MIDDLETON, R. W., PARRICK, J., STRATFORD, M. R. L., WARDMAN, P., and WILSON, G. D., 1991, Fluorescent markers for hypoxic cells. A study of novel heterocyclic compounds that undergo bio-reductive binding. Biochemical Pharmacology, 41, 533-541.
6. JACKMAN, L. M., and STERNHELL, S., 1969, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry 2nd edn (Oxford; Pergamon), p. 202.
7. KASPERSEN, F. M., and VAN BOECKEL, C. A. A., 1987, A review of the methods of chemical synthesis of sulphate and glucuronide conjugates. Xenobiotica, 17, 1451-1471.
8. LEE, H. H., WILSON, W. R., FERRY, D. M., VAN ZIJL, P., PULLEN, S. M., and DENNY, W. A., 1996, Hypoxia-selective antitumour agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the bis-bioreductive agent nitracrine N-oxide. Journal of Medicinal Chemistry (in press).
9. 14C-(3′-dimethylamino-N-propylamino)acridine, a new antitumor and DNA cross-linking agent, to macromolecules of subcellular fractions isolated from rat liver and HeLa cells. Biochemical Pharmacology, 28, 3391-3402.
10. PAWLAK, J. W., PAWLAK, K., and KONOPA, J., 1983, The mode of action of cytotoxic and antitumor 1-nitroacridines. II. In vivo enzyme-mediated covalent binding of an 1-nitroacridine derivative, Ledakrin or nitracrine, with DNA and other macromolecules of mammalian or bacterial cells. Chemico-Biological Interactions, 43, 151-173.
11. ROBERTS, P. B., ANDERSON, R. F., and WILSON, W. R., 1987, Hypoxia-selective radiosensitization of mammalian cells by nitracrine, an electron-affinic DNA intercalator. International Journal of Radiation Biology, 51, 641-654.
12. ROBERTSON, I. G. C., PALMER, B. D., OFFICER, M., SIEGERS, D. J., PAXTON, J. W., and SHAW, G. J., 1991, Cytosol mediated metabolism of the experimental antitumour agent acridine carboxamide to the 9-acridone derivative. Biochemical Pharmacology, 42, 1879-1884.
13. STANLEY, J. S., JACKSON, O., MILLER, D. W., and DELUCA, D. C., 1989, Identification of the glutathione conjugate of 4-nitroquinoline-1-oxide formed in the reaction catalyzed by murine glutathione transferases. Carcinogenesis, 10, 587-591.
14. STEFANSKA, B. and LEDOCHOWSKI, A., 1968, Research on tumour-inhibiting compounds. Part XLVI. Derivatives of 1- and 3-nitro-9-aminoacridine. Roczniki Chemii, 42, 1973-1980.
15. TURESKY, R. J., BRACCO-HAMMER, I., MARKOVIC, J., RICHLI, U., KAPPELER, A. M., AND WELTI, D. H., 1990, The contribution of N-oxidation to the metabolism of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in rat hepatocytes Chemical Research in Toxicology, 3, 524-535.
16. WATTS, M. E., DENNIS, M. F., STRATFORD, M. R. L., and WARDMAN, P., 1986, Glutathione-reactive nitro compounds as radiosensitizers: mechanistic and therapeutic implications. International Journal of Radiation Oncology, Biology and Physics, 12, 1135-1138.
17. WILSON, W. R., ANDERSON, R. F., and DENNY, W. A., 1989a, Hypoxia selective antitumour agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine. Journal of Medicinal Chemistry, 32, 23-30.
18. WILSON, W. R., DENNY, W. A., STEWART, G. M., FENN, A., and PROBERT, J. C., 1986, Reductive metabolism and hypoxia-selective toxicity of nitracrine. International Journal of Radiation Oncology, Biology and Physics, 12, 1235-1238.
19. WILSON, W. R., DENNY, W. A., TWIGDEN, S. J., BAGULEY, B. C., and PROBERT, J. C., 1984, Selective toxicity of nitracrine to hypoxic mammalian cells. British Journal of Cancer, 49, 215-223.
20. WILSON, W. R., THOMPSON, L. H., ANDERSON, R. F., and DENNY, W. A., 1989b, Hypoxia-selective antitumour agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives. Journal of Medicinal Chemistry, 32, 31-38.
21. WILSON, W. R., VAN ZIJL, P., and DENNY, W. A., 1992, Bis-bioreductive agents as hypoxia-selective cytotoxins: nitracrine N-oxide. International Journal of Radiation Oncology, Biology and Physics, 22, 693-696.