Reductive activation of nitroheterocyclic compounds

General Pharmacology

Volumn 28, Issue 4, 1997, Pages 485-487

  Tocher, Joanne H ^a  

^a UNIVERSITY OF EAST LONDON   (United Kingdom)

Author keywords

DNA damage; Mode of action; Nitroaromatic compounds; Reactive intermediates; Reductive activation

Indexed keywords

HETEROCYCLIC NITRO COMPOUND;

ANAEROBIC BACTERIUM; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; BACTERIAL INFECTION; CANCER THERAPY; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL; REVIEW;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; BACTERIA, ANAEROBIC; BACTERIAL INFECTIONS; BIOTRANSFORMATION; HUMANS; MUTAGENS; NEOPLASMS; NITROFURANS; NITROIMIDAZOLES; OXIDATION-REDUCTION;

EID: 0030990382     PISSN: 03063623     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0306-3623(96)00283-2     Document Type: Review

References (27)

1. Aboagye E. O., Lewis A. D., Johnson A., Workman P., Tracy M. and Huxham I. M. (1995) The novel fluorinated 2-nitroimidazole hypoxia probe SR-4554: reductive metabolism and semiquantitative localisation in human ovarian cancer multicellular spheroids as measured by electron energy loss spectroscopic analysis B. J. Cancer 72, 312-318.
2. Adams G. E. (1992) Redox, radiation and reductive bioactivation. Radiat. Res. 132, 129-139.
3. Adams G. E. and Stratford I. J. (1986) Hypoxia-mediated nitroheterocyclic drugs in the radio-and chemotherapy of cancer. Biochem. Pharmacol. 35, 71-76.
4. Adams G. E. and Stratford I. J. (1994) Bioreductive drugs for cancer therapy: the search for tumor specificity. Int. J. Radiat. Oncol. Biol. Phys. 29, 231-238.
5. Debnath A. K., Lopez de Compadre R. L., Debnath G., Shusterman A. J. and Hansch C. (1991) Structure-activity relationship of mutagenic aromatic and heteroaromatic nitrocompounds. Correlation with molecular orbital energies and hydrophobicity. J. Med. Chem. 34, 786-797.
6. Dische S. (1991) A review of hypoxic cell radiosensitization. Int. J. Radiat. Oncol. Biol. Phys. 20, 147-152.
7. Edwards D. I. (1986) Reduction of nitroimidazoles in vitro and DNA damage. Biochem. Pharmacol. 35, 53-58.
8. Edwards D.I. (1993a) Nitroimidazole drugs - action and resistance mechanisms I. Mechanisms of action. J. Antimicrob. Chemother. 31, 9-20.
9. Edwards D.I. (1993b) Nitroimidazole drugs - action and resistance mechanisms II. Mechanisms of resistance. J. Antimicrob. Chemother. 31, 201-210.
10. Edwards D.I., Knox R. J. and Knight R. C. (1982) Structure-cytotoxicity relationships of nitroimidazoles in an in vitro system. Int. J. Radiat. Oncol. Biol. Phys. 8, 791-793.
11. Greenwood D. (1995) Antimicrobial Chemotherapy, (3rd Edn.) Oxford University Press, Oxford.
12. Henry Y., Guissani A. and Hickel B (1987) Radicals of nitroimidazole derivatives: pH dependence of rates of formation and decay related to acidbase equilibria. Int. J. Radiat. Biol. 51, 797-809.
13. Jenkins T. C., Parrick J. and Porssa M. (1994) DNA-binding properties of nitroarene oligopeptides designed as hypoxia-selective agents. Anti-Cancer Drug Design 9, 477-493.
14. Jung H., Shaik A. U., Heflich R. H. and Fu P. P. (1991) Nitro group orientation, reduction potential and direct-acting mutagenicity of nitro-polycyclic aromatic hydrocarbons. Environment. Mol. Mutagenesis 17, 169-180.
15. Kedderis G. L. and Miwa G. T. (1988) The metabolic activation of nitroheterocyclic therapeutic agents. Drug. Met. Rev. 19, 33-62.
16. Knox R. J., Knight R. C. and Edwards D. I. (1981) Interaction of nitroimidazole drugs with DNA in vitro: structure-activity relationships. Br. J. Cancer. 44, 741-745.
17. Knox R. J., Edwards D. I. and Knight R. C. (1984) The mechanism of nitroimidazole damage to DNA: coulometric evidence. Int. J. Radiat. Oncol. Biol. Phys. 10, 1315-1318.
18. Logan L. P. H., Gummet P. A., Misiewicz J. J., Karim Q. N., Walker M. M. and Baron G. H. (1991) One week eradication regime for Helicobacter pylori. Lancet II, 1449-1452.
19. Palmer B. D., van Zijl P., Denny W. A. and Wilson W. R. (1995) Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[n,n-bis(2-chloroethyl)amino]-2,4-dinitro-benzamide. J. Med. Chem. 38, 1229-1241.
20. Rozenski J., De Ranter C. J. and Verplanken H. (1995) Quantitative structute-activity relationships for antimicrobial nitroheterocyclic drugs. Quant. Struct. Act. Relat. 14, 134-141.
21. Skolimowski I. M., Knight R. C. and Edwards D. I. (1983) Molecular basis of chloramphenicol and thiamphenicol toxicity to DNA in vitro. J. Antimicrob. Chemother. 12, 535-542.
22. Smith M. A. and Edwards D. I. (1995) The influence of microaerophilia and anaerobiosis on metronidazole uptake in Helicobacter pylori. J. Antimicrob. Chemother. 36, 453-461.
23. Tocher J. H. and Edwards D. I. (1990) Electrochemical characteristics of nitroheterocyclic compounds of biological interest V. Measurement and comparison of radical lifetimes. Int. J. Radiat. Biol. 57, 45-53.
24. Tocher J. H. and Edwards D. I. (1994) Evidence for the direct interaction of reduced metronidazole derivatives with DNA bases. Biochem. Pharmacol. 48, 1089-1094.
25. Tocher J. H., Knight R. C. and Edwards D.I. (1989) Electrochemical characteristics of nitroheterocyclic compounds of biological interest II. Nitrosochloramphenicol. Free Rad. Res. Commun. 5, 319-326.
26. Voogd C. E. (1981) On the mutagenicity of nitroimidazoles. Mutat. Res. 86, 243-277.
27. Watkinsbruner D., Scott C., Lawton C., Delrowe J., Rotman M., Buswell L., Beard C. and Cella D. (1995) RTOGs first quality of life study - RTOG 90-20: a phase II trial of external beam radiation with etanidazole for locally advanced prostate cancer. Int. J. Radiat. Oncol. Biol. Phys. 33, 901-906.