Cross-linking and sequence specific alkylation of DNA by aziridinylquinones. 1. Quinone methides

Journal of Medicinal Chemistry

Volumn 39, Issue 2, 1996, Pages 531-537

  Mayalarp, Stephen P ^a   Hargreaves, Rob H J ^a   Butler, John ^a   Caroline O'Hare, C ^b   Hartley, John A ^b  

^a CHRISTIE HOSPITAL   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; AZIRIDINYLBENZOQUINONE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CONTROLLED STUDY; CROSS LINKING; DNA SEQUENCE; DRUG DNA INTERACTION; DRUG MECHANISM; HUMAN; HUMAN CELL;

EID: 0030025890     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950629q     Document Type: Article

References (40)

1. Schold, S. C.; Friedman, H. S.; Bjornsson, T. D.; Falleta, J. M. Treatment of patients with recurrent primary brain tumours with AZQ. Neurology 1984, 34, 615-619.
2. Bender, J. F.; Grillo-Lopez, A. J.; Posada, J. G. Diaziquone. Invest. New Drugs 1983, 1, 71-84.
3. Obe, G.; Beek, B. Trenimon: Biochemical, physiological and genetic effects on cells and organisms. Mutat. Res. 1979, 65, 21-70.
4. Szmigiero, L.; Kohn, K. W. Mechanisms of DNA strand breakage and interstrand cross-linking by diaziridinylbenzoquinone (Diaziquone) in isolated nuclei from human cells. Cancer Res. 1984, 44, 4453-4457.
5. Siegel, D.; Gibson, N. W.; Preusch, P. C.; Ross, D. Metabolism of diaziquone by NAD(P)H:(quinone acceptor) oxireductase (DT-diaphorase); role in diaziquone-induced DNA damage and cytotoxicity in human colon carcinoma cells. Cancer Res. 1990, 50, 7293-7300.
6. Butler, J.; Dzielendziak, A.; Lea, J. S.; Ward, T. H.; Hoey, B. M. Contrasting cytotoxic mechanisms of similar antitumour diaziridinybenzoquinones. Free Radical Res. Commun. 1990, 8, 231-239.
7. Butler, J.; Hoey, B. M. Redox Cycling drugs and DNA damage. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: London, 1993; pp 243-265.
8. Dzielendziak, A.; Butler, J.; Hoey, B. M.; Lea, J. S.; Ward, T. H. A comparison of the structural and cytotoxic activity of novel AZQ analogues. Cancer Res. 1990, 5, 2003-2007.
9. Hartley, J. A.; Berardini, M.; Ponti, M.; Gibson, N. W.; Thompson, A. S.; Thurston, D. E.; Hoey, B. M.; Butler, J. DNA cross-linking and sequence selectivity of aziridinylbenzoquinones: A unique reaction at 5′-GC-3′ sequences with 2,5-diaziridinyl-1,4-benzoquinone upon reduction. Biochemistry 1991, 30, 11719-11724.
10. Alley, S. C.; Brameld, K. A.; Hopkins, P. B. DNA interstrand cross-linking by 2,5-bis(1-aziridinyl)-1,4-benzoquinone: Nucleotide sequence preferences and covalent structure of the dG-to-dG cross- links at 5′-d(GN(n)C) in synthetic oligonucleotide duplexes. J. Am. Chem. Soc. 1994, 116, 2734-2741.
11. Berardini, M. D.; Souhami, R. L.; Lee, C.-S.; Gibson, N. W.; Butler, J.; Hartley, J. A. Two structurally related diaziridinyl-benzoquinones preferentially cross-link DNA at different sites upon reduction with DT-Diaphorase. Biochemistry 1993, 32, 3306-3312.
12. Ward, T. H.; Haran, M. S.; Whittaker, D.; Watson, A. J.; Howard, T. D.; Butler, J. Cross resistance studies on two K562 sublines resistant to diaziridinyl- benzoquinones. Biochem. Pharmacol. 1995, 50, 459-464.
13. Thompson, D. C.; Thompson, J. A.; Sugamarin, M.; Moldeus, P. Biological and toxicological consequences of quinone methide formation. Chem. Biol. Int. 1992, 86, 129-162.
14. Clark, W. M. Oxidation-Reduction Potentials; Bailliere, Tindall.; Cox Publishers: London, 1960; pp 346-348.
15. Lemus, R. H.; Skibo, E. B. Design of pyrimido[4,5-g] quinazoline-based anthraquinone mimics. Structure-activity relationships for quinone methide formation and the influence of internal hydrogen bonds on quinone methide fate. J. Org. Chem. 1992, 57, 5649-5660.
16. Lin, A. J.; Sartorelli, A. C. 2,3-dimethyl-5,6-bis(methylene)-1,4-benzoquinone. The active intermediate of bioreductive alkyalting agents. J. Org. Chem. 1972, 38, 813-815.
17. Wagner, H.-U.; Gompper, R. Quinone Methides. In The Chemistry of the quinonoid compounds:Part II; Patai, S., Ed.; John Wiley: London, 1974; pp 1145-1178.
18. Moore, J. A. Triethyleneimines. In Heterocyclic compounds with three- and four-membered rings: Part 2. The Chemistry of Heterocyclic compounds; Weissberger, A., Ed.; Interscience Publishers: London, 1964; pp 885-977.
19. Powis, G. Free radical formation by antitumour quinones. Free Radicals Biol. Med. 1989, 6, 63-101.
20. Butler, J.; Hoey, B. M. The one electron reduction potential of several substrates can be related to their reduction rates by cytochrome P450 reductase. Biochim. Biophys. Acta 1993, 1161, 73-78.
21. Clark, E. D.; Goulding, K. H.; Wardman, P. Anaerobic reduction of nitroimidazoles by reduced flavin mononucleotide and by xanthine oxidase. Biochem. Pharmacol. 1980, 31, 2684-2687.
22. Butler, J.; Hoey, B. M. Reactions of glutathione and glutathione radicals with benzoquinones. Free Radicals Biol. Med. 1992, 12, 337.
23. Butler, J.; Hoey, B. M. Diaziridinylbenzoquinones. Trombay Symposium on Radiation and Photochemistry Vol. I; Atomic Energy of India: India, 1994; pp 149-154.
24. Gibson, N. W.; Hartley, J. A.; Butler, J.; Siegel, D.; Ross, D. The relationship between DT-diaphorase mediated metabolism of a series of diaziridinylbenzoquinones and DNA damage and cytotoxicity. Mol. Pharmacol. 1992, 42, 531-537.
25. Bean, F. R. Preparation of C-Alkyl Hydroquinones and C-Alkyl p-amino phenols. U.S. Patent 2,533,203, Dec. 12, 1950.
26. Reeves, W. A.; Drake, G. L.; Hoffpauir, C. L. Ethylenimine by flash distillation. J. Am. Chem. Soc. 1951, 73, 3522.
27. Petersen, S.; Gauss, W.; Ulschant, E. Synthesis of simple quinone derivatives with fungicidal, bacteriostatic and cytostatic properties. Angew. Chem. 1955, 67, 217-231.
28. Wallenfels, K.; Draber, W. Influence of substituents on electron and vibration spectra of amino quinones. Tetrahedron 1964, 20 (8), 1889-1912.
29. Wallenfels, K. Amino quinone derivatives, German Patent 1,137,744, Oct. 11, 1962.
30. Moore, H. W.; Shelden, H. R.; Shellhamer, D. F. Rearrangement of azidoquinones. III. Reaction of 1,4-benzoquinone with sodium azide. J. Org. Chem. 1969, 34, 1999-2001.
31. Moore, H. W.; Cajipe, G. Selective chlorination of aminoquinones. Synthesis of 2-amino-3-chloro-1,4-benzoquinones. Synthesis 1973, 1, 49-50.
32. Petersen, S.; Gauss, W.; Urbschat, E. Synthesis of simple quinone derivatives with fungicidal, bacteriostatic and cytostatic properties. Angew. Chem. 1955, 67, 217-231.
33. Baxter, I.; Cameron, D. W.; Giles, R. G. F. Ring opening of Aziridin-1-yl-quinones. J. Chem. Soc. 1969, 1325-1328.
34. Whalley, W. B. Organic fluoro-compounds. Part 1. Hydroxyderivatives of benzotrifluoride. J. Chem. Soc. 1949, 3016-3020.
35. Littell, R.; Allen, G. R. The behaviour of 2-halo- and 2-trifluoromethyl-1,4-benzoquinones in the Nenitzescu Indole Synthesis. J. Org. Chem. 1968, 33, 2064-2069.
36. Maniatis, T.; Fritsch, E. F.; Sambrook, J. Molecular Cloning. A Laboratory Manual; Cold Spring Harbor Laboratory: Cold Spring Harbor, NY, 1982.
37. Maxam, A. M.; Gilbert, W. Sequencing end-labeled DNA with base specific chemical cleavages. Methods Enzymol. 1980, 65, 499-560.
38. Hartley, J. A.; Berardini, M.; Souhami, R. L. An agarose gel method for the determination of DNA interstrand cross-linking applicable to the measurement of total and "second-arm" cross-link reactions. Anal. Biochem. 1991, 193, 131-134.
39. Mattes, W. B.; Hartley, J. A.; Kohn, K. W. Mechanism of DNA strand breakage by piperidine at sites of N7-alkyl guanine. Biochim. Biophys. Acta 1986, 868, 71-76.
40. Carmichael, J.; DeGraff, W. G.; Gazdar, A. F.; Minna, J. D.; Mitchell, J. B. Evaluation of tetrazolium-based semiautomatic colorimetric assay: assessment of chemosensetivity testing. Cancer Res. 1987, 47, 936-942.