9-[3-(2-nitro-1-imidazolyl)propylamino]-cyclopenteno[b]quinoline hydrochloride (NLCPQ-1). A novel DNA-affinic bioreductive agent as cytotoxin and radiosensitizer

Oncology Research

Volumn 8, Issue 10-11, 1996, Pages 425-434

  Papadopoulou, Maria V ^a   Ji, Ming ^a   Rao, Mira K ^a   Bloomer, William D ^a  

^a EVANSTON HOSPITAL   (United States)

Author keywords

bioreductive agent; DNA affinic agents; hypoxia; NLCPQ l; radiosensitizers

Indexed keywords

9 [3 (2 NITRO 1 IMIDAZOLYL)PROPYLAMINO] CYCLOPENTENO[B]QUINOLINE HYDROCHLORIDE; CYTOTOXIC AGENT; RADIOSENSITIZING AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CYTOTOXICITY TEST; DRUG ACTIVITY; DRUG CYTOTOXICITY; FEMALE; MALIGNANT NEOPLASTIC DISEASE; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PRIORITY JOURNAL; RADIOSENSITIZATION;

EID: 0030426530     PISSN: 09650407     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. 1. Adams, G. E. The clinical relevance of tumor hypoxia. Eur. J. Cancer 26:420-421; 1990.
2. 2 predicts survival in advanced cancer of the uterine cervix. Radiother. Oncol. 26:45-50; 1993.
3. 3. Stone, H. B.; Brown, J. M.; Phillips, T. L.; Sutherland, R. M. Oxygen in human tumors: correlations between methods of measurement and response to therapy. Radiat. Res. 136:422-434; 1993.
4. 4. Moulder, J. E.; Rockwell, S. Hypoxic fractions of solid tumors: experimental techniques, methods of analysis, and a survey of existing data. Int. J. Radiat. Oncol. Biol. Phys. 10:695-712; 1984.
5. 5. Okunieff, P.; Urano, M.; Kallinowski, F.; Vaupel, P.; Neuringer, L. J. Tumors growing in irradiated tissue: oxygenation, metabolic state, and pH. Int. J. Radiat. Oncol. Biol. Phys. 21:667-673; 1991.
6. 6. Rockwell, S.; Moulder, J. E. Hypoxic fractions of human tumors xenografted into mice: a review. Int. J. Radiat. Oncol. Biol. Phys. 19:197-202; 1990.
7. 7. Vaupel, P.; Kallinowski, F.; Okunieff, P. Blood flow, oxygen and nutrient supply, and metabolic microenvironment of human tumours: a review. Cancer Res. 49: 6449-6465; 1989.
8. 8. Adams, G. E. Redox, radiation and reductive bioactivation. Radiat. Res. 132:129-139; 1992.
9. 9. Adams, G. E.; Ahmed, I.; Sheldon, P. W.; Stratford, I. J. RSU-1069, a 2-nitroimidazole containing an alkylating group: high efficiency as a radio- and chemosensitizer in vitro and in vivo. Int. J. Radiat. Oncol. Biol. Phys. 10:1653-1656; 1984.
10. 10. Cole, S.; Stratford, I. J.; Fielden, E. M.; Adams, G. E.; Leopold, W.; Elliott, W.; Suto, M.; Sebolt-Leopold, J. Dual function nitroimidazoles less toxic than RSU 1069: selection of candidate drugs for clinical trial (RB 6145 and/or PD 130908). Int. J. Radiat. Oncol. Biol. Phys. 22:545-548; 1992.
11. 11. O'Neill, P.; McNeill, S. S.; Jenkins, T. C. Induction of DNA crosslinks in vitro upon reduction of the nitroimidazole-aziridines RSU-1069 and RSU-1131. Biochem. Pharmacol. 36:1787-1792; 1987.
12. 12. Wilson, W. R.; Denny, W. A.; Stewart, G. M.; Fenn, A.; Probert, J. C. Reductive metabolism and hypoxia-selective metabolism of nitracrine. Int. J. Radiat. Oncol. Biol. Phys. 12:1235-1238; 1986.
13. 13. Panicucci, R.; Heal, R.; Laderonte, K.; Cowan, D.; McClelland, R. A.; Rauth, A. M. NLP-1: a DNA intercalating hypoxic cell radiosensitizer and cytotoxin. Int. J. Radiat. Oncol. Biol. Phys. 16:1039-1043; 1989.
14. 14. Roberts, P. B.; Denny, W. A.; Wakelin, L. P. G.; Anderson, R. F.; Wilson, W. R. Radiosensitization of mammalian cells in vitro by nitroacridines. Radiat. Res. 123:153-164; 1990.
15. 15. Cowan, D. S. M.; Panicucci, R.; McClelland, R. A.; Rauth, A. M. Targeting radiosensitizers to DNA by attachment of an intercalating group: nitroimidazole-linked phenanthridines. Radiat. Res. 127:81-89; 1991.
16. 16. Papadopoulou, M. V.; Epperly, M. W.; Shields, D. S.; Bloomer, W.D. Radiosensitization and hypoxic cell toxicity of NLA-1 and NLA-2, two new bioreductive compounds. Jpn. J. Cancer Res. 83:410-414; 1992.
17. 17. Denny, W. A.; Roberts, P. B.; Anderson, R. F.; Brown, J. M.; Wilson, W. R. NLA-1. A 2-nitroimidazole radiosensitizer targeted to DNA by intercalation. Int. J. Radiat. Oncol. Biol. Phys. 22:553-556; 1992.
18. 18. Papadopoulou, M. V.; Bloomer, W. D. Nitroheterocyclic-linked acridines as DNA-targeting bioreductive agents. Drugs of the Future 18:231-238; 1993.
19. 19. Cowan, D. S. M.; Matejovic, J. F.; McClelland, R. A.; Rauth, A. M. DNA-targeted 2-nitroimidazoles: in vitro and in vivo studies. Br. J. Cancer 70:1064-1074; 1994.
20. 1H NMR studies of binding mode and kinetics. J. Med. Chem. 27:450-465; 1984.
21. 21. Denny, W. A.; Roos, I. A. G.; Wakelin, L. P. G. Interactions between antitumor activity, DNA breakage, and DNA binding kinetics for 9-aminoacridinecarboxamide antitumor agents. Anticancer Drug Des. 1: 141-147; 1986.
22. 22. Zwelling, L. DNA topoisomerase II as a target of antineoplastic drug therapy. Cancer Metastasis Rev. 4:263-276; 1985.
23. 23. Rosenzweig, H. S.; Papadopoulou, M. V.; Bloomer, W. D. A study of the interaction of NLA-compounds with topoisomerases I and II. Proc. Am. Assoc. Cancer Res. Annu. Meet. 35:362; 1994.
24. 24. Wilson, W. R.; Denny, W. A. DNA-binding nitroheterocycles as hypoxia-selective cytotoxins. In: Dewey, W. C.; Edington, M.; Fry, R. J. M.; Hall, E. J.; Whitmore, G. E. eds. Radiation research: a 20th-century perspective, Vol. 2. New York: Academic Press; 1992:pp. 796-801.
25. 25. Wilson, W. R.; Siim, B. G.; Denny, W. A.; VanZijl, P. L.; Taylor, M. L.; Chambers, D. M.; Roberts, P. B. 5-Nitro-4-(N,N-dimethylaminopropyl-amino)quinoline (5-nitraquine), a new DNA-affinic hypoxic cell radiosensitizer and bioreductive agent: comparison with nitracrine. Radiat. Res. 131:257-265; 1992.
26. 26. Denny, W. A.; Atwell, G. J.; Roberts, P. B.; Anderson, R. F.; Boyd, M.; Lock, C. J. K.; Wilson, W. R. Hypoxia-selective antitumor agents. 6. 4-( Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins. J. Med. Chem. 35:4832-4841; 1992.
27. 27. Papadopoulou, M. V.; Rosenzweig, H. S.; Doddi, M.; Bloomer, W. D. 9-[3-(2-Nitro-1-imidazolyl)propylamino]-1,2,3,4-tetrahydroacridine hydrochloride. A novel DNA-affinic hypoxic cell cytotoxin and radiosensitizer. Comparison with NLA-1. Oncol. Res. 6: 439-448; 1994.
28. 28. Papadopoulou, M. V.; Ji, M.; Bloomer, W. D. THNLA-1 as radio/chemosensitiser of EMT-6 tumours in mice. Br. J. Cancer 74(suppl. XXVII):S267-S270; 1996.
29. 29. Papadopoulou, M. V.; Ji, M.; Bloomer, W. D. THNLA-1: a DNA-targeted bioreductive agent as chemosensitizer in vitro and in vivo. In Vivo 10:49-58; 1996.
30. 30. Yamato, M.; Takeuchi, Y.; Hashigaki, K.; Ikeda, Y.; Chung, M. R.; Takeuchi, K.; Matsushima, M.; Tsuruo, T.; Tashire, T.; Tsukagoshi, S.; Yamashita, Y. Synthesis and antitumor activity of fused tetracyctic quinoline derivatives. 1. J. Med. Chem. 32:1295-1300; 1989.
31. 31. Robbie, M. A.; Baguley, B. C.; Denny, W. A.; Gavin, J. B.; Wilson, W. R. Mechanism of resistance of noncycling mammalian cells to 4′-(9-acridylamino)methanesulfon-m-anisidide: comparison of uptake, metabolism, and DNA breakage in log and plateau-phase Chinese hamster fibroblast cell cultures. Cancer Res. 48: 310-319; 1988.
32. 32. Fujita, T.; Iwasa, J.; Hansen, C. A new substituent constant, p, derived from partition coefficients. J. Am. Chem. Soc. 86:5175-5180; 1964.
33. 33. Morgan, A. P.; Lee, J. S.; Pulleyblank, D. E.; Murray, N. L.; Evans, D. H. Review: ethidium fluorescence assays. Part 1. Physicochemical studies. Nucl. Acids Res. 7:547-569; 1979.
34. 34. Rockwell, S. C.; Kallman, R. F.; Fajardo, L. F. Characteristics of a serially transplanted mouse mammary tumor and its tissue-culture-adapted derivative. J. Natl. Cancer Inst. 49:735-749; 1972.
35. 35. Brown, J. M.; Lemmon, M. J. Potentiation by the hypoxic cytotoxin SR 4233 of cell killing produced by fractionated irradiation of mouse tumors. Cancer Res. 50:7745-7749; 1990.
36. 36. Rowley, D. A.; Halliwell, B. DNA damage by superoxide-generating systems in relation to the mechanism of action of the antitumor antibiotic adriamycin. Biochim. Biophys. Acta 761:86-93; 1983.
37. 14C-labeled drug. Biochem. Pharmacol. 38:4253-4260; 1989.
38. 38. Hamilton, T. C.; Young, R. C.; McKoy, W. M.; Grotzinger, K. R.; Green, J. A.; Chu, E. W.; Whang-Peng, J.; Rogan, A. M.; Ozols, R. F. Characterization of a human ovarian carcinoma cell line (NIH:OVCAR-3) with androgen and estrogen receptors. Cancer Res. 43:5379-5389; 1983.
39. 39. Rogan, A. M.; Hamilton, T. C.; Young, R. C.; Klecker, R. W.; Ozols, R. F. Reversal of adriamycin resistance by verapamil in human ovarian cancer. Science 224: 994-996; 1984.
40. 40. Green, J. A.; Vistica, D. T.; Young, R. C.; Hamilton, T. C.; Rogan, A. M.; Ozols, R. F. Potentiation of metphalan cytotoxicity in human ovarian cancer cell lines by glutathione depletion. Cancer Res. 44:5427-5431; 1984.
41. 41.Papadopoulou, M. V.; Ji, M.; Doddi, M.; Khan, S. H.; Bloomer, W. D. Mechanistic studies regarding the potentiation of melphalan by the bioreductive compound THNLA-1 in vitro. Proc. Am. Assoc. Cancer Res. Annu. Meet. 37:355; 1996.
42. 42. Stratford, M. R. L.; Dennis, M. F.; Watts, M. E.; Watfa, R. R.; Woodcock, M. Radiosensitizer-DNA interactions in relation to intracellular uptake. Int. J. Radiat. Oncol. Biol. Phys. 16:1007-1010; 1989.
43. 43. Smith, P. J.; Anderson, C. O. Modification of the radiation sensitivity of human tumor cells by a bis-benzimidazole derivative. Int. J. Radiat. Biol. 46:331-344; 1984.