DNA cross-linking agents as antitumor drugs

Chemical Reviews

Volumn 98, Issue 8, 1998, Pages 2723-2795

  Rajski, Scott R ^a   Williams, Robert M ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001676690     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9800199     Document Type: Article

References (50)

1. (a) Self-Splicing of Group I Introns, Cech, T. R. Annu. Rev. Biochem. 1990, 59, 543.
2. (b) Structure and Activities of Group 11 Introns. Michel, F.; Ferai, J. L. Annu. Rev. Biochem. 1995, 64, 435.
3. (c) Cech, T. R. In The RNA World: Gesteland, R. F., Atkins, J. F., Eds.; Cold Spring Harbour: New York, 1993; p 239.
4. Voet, D.; Voet J. G. Biochemistry; John Wiley & Sons: New York, 1990; pp 793-804.
5. (a) Sequence-Specific Cleavage of Double Helical DNA by Triple Helix Formation, Moser, H. D.; Dervan, P. B. Science 1987, 238, 645.
6. (b) Formation of a Three-Stranded Polynucleotide Molecule, Felsenfeld, G.; Davis, D. R.; Rich, A. J. Am. Chem. Soc. 1957, 79, 2023.
7. (c) Felsenfeld, G.; Miles, H. T. Annu. Rev. Biochem. 1967, 36, 407.
8. The Tumor Suppressor Genes, Levine, A. J. Annu. Rev. Biochem. 1993, 65, 623 and references therein.
9. (a) Mechanisms of Transcriptional Synergism Between Distinct Virus-Iducible Enhancer Elements, Maniatas, T.; Thanos, D.; Du, W. Cell 1993, 74, 887.
10. (b) Transcription Factors: Structural Families and Principles of Recognition, Pabo, C. O.; Sauer, R.T. Annu. Rev. Biochem. 1992, 61, 1053.
11. (a) DNA Excision Repair, Sancar, A. Annu. Rev. Biochem. 1996, 65, 43.
12. (b) O6-methylguanine Inhibits the Binding of Transcription Factors to DNA, Bonfanti, M.; Broggini, M.; Prontera, C.; D'Incalci, M. Nucleic Acids Res. 1991, 19, 5739.
13. (c) Metal Dependence of Transcriptional Switching in Escherichia coli Acta, Myers, L. C.; Jackow, F.; Verdine, G. L. J. Biol. Chem. 1995, 270, 6664.
14. (d) Methylation Dependent Functional Switch Mechanism Newly Found in Escherichia coli Acta Protein, Ohkubo, T.; Sakashita, H.; Sakuma, T.; Kainosho, M.; Sekiguchi, M.; Morikawa, K. J. Am. Chem. Soc. 1994, 116, 6035.
15. (a) Molecular structure of nucleic acids, Watson, J. D.; Crick, F. H. C. Nature 1953, 171, 737.
16. Genetic Implications of the Structure of Deoxyribonucleic Acid, Watson, J. D.; Crick, F. H. C. Nature 1953, 171, 964.
17. (a) Eukaryotic DNA Replication, Campbell, J. L. Annu. Rev. Biochem. 1986, 55, 733.
18. (b) Single-stranded DNA Binding Proteins Required for DNA Replication, Chase, J. W.; Williams, K. R. Annu. Rev. Biochem. 1986, 55, 103.
19. (c) DNA Replication, Kornberg, A. J. Biol. Chem. 1988, 263, 1.
20. (d) Prokaryotic DNA Replication Systems, Nossal, N. G. Annu. Rev. Biochem. 1983, 52, 581.
21. The Replication of DNA in Escherichia Coli, Meselson, M.; Stahl, F. W. Proc. Natl. Acad. Sci. 1958, 44, 671.
22. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking see: (a) Kohn, K. W. In Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-cancer Drug Action; Neidle, S., Waring, M., Eds.; Verlag Chemie: Weinheim, 1994; pp 315. (b) Alkylation of DNA and its Aftermath, Lawley, P. D. BioEssays 1995, 17, 561. (c) Biological Relevance and Consequences of Chemical- or Metal-Induced DNA Cross-Linking, Paustenbach, D. J.; Finley, B. L.; Kacew, S. Proc. Soc. Exp. Biol. Med. 1996, 211, 211. (d) The Effects of DNA Covalent Adducts on in Vitro Transcription, Gniazdowski, M.; Cera, C. Chem. Rev. 1996, 96, 619.
23. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking see: (a) Kohn, K. W. In Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-cancer Drug Action; Neidle, S., Waring, M., Eds.; Verlag Chemie: Weinheim, 1994; pp 315. (b) Alkylation of DNA and its Aftermath, Lawley, P. D. BioEssays 1995, 17, 561. (c) Biological Relevance and Consequences of Chemical- or Metal-Induced DNA Cross-Linking, Paustenbach, D. J.; Finley, B. L.; Kacew, S. Proc. Soc. Exp. Biol. Med. 1996, 211, 211. (d) The Effects of DNA Covalent Adducts on in Vitro Transcription, Gniazdowski, M.; Cera, C. Chem. Rev. 1996, 96, 619.
24. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking see: (a) Kohn, K. W. In Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-cancer Drug Action; Neidle, S., Waring, M., Eds.; Verlag Chemie: Weinheim, 1994; pp 315. (b) Alkylation of DNA and its Aftermath, Lawley, P. D. BioEssays 1995, 17, 561. (c) Biological Relevance and Consequences of Chemical- or Metal-Induced DNA Cross-Linking, Paustenbach, D. J.; Finley, B. L.; Kacew, S. Proc. Soc. Exp. Biol. Med. 1996, 211, 211. (d) The Effects of DNA Covalent Adducts on in Vitro Transcription, Gniazdowski, M.; Cera, C. Chem. Rev. 1996, 96, 619.
25. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking see: (a) Kohn, K. W. In Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-cancer Drug Action; Neidle, S., Waring, M., Eds.; Verlag Chemie: Weinheim, 1994; pp 315. (b) Alkylation of DNA and its Aftermath, Lawley, P. D. BioEssays 1995, 17, 561. (c) Biological Relevance and Consequences of Chemical- or Metal-Induced DNA Cross-Linking, Paustenbach, D. J.; Finley, B. L.; Kacew, S. Proc. Soc. Exp. Biol. Med. 1996, 211, 211. (d) The Effects of DNA Covalent Adducts on in Vitro Transcription, Gniazdowski, M.; Cera, C. Chem. Rev. 1996, 96, 619.
26. Sequence Preferences of DNA Interstrand Cross-Linking Agents: Importance of Minimal DNA Structural Reorganization in the Cross-Linking Reaction of Mechlorethamine, Cisplatin, and Mitomycin C, Hopkins, P. B.; Millard, J. T.; Woo, J.; Weidner, M. F.; Kirchner, J. J.; Sigurdsson, S. T.; Raucher, S. Tetrahedron 1991, 47, 2475.
27. Inactivation of Bacteriophage T7 by Mono- and Difunctional Sulphur Mustards in Relation to Cross-linking and Depurination of Bacteriophage DNA, Lawley, P. D.; Lethbridge, J. H.; Edwards, P. A.; Shooter, K. V. J. Mol. Biol. 1969, 39, 181.
28. Base-specific Arrest of in Vitro DNA Replication by Carcinogenic Chromium: Relationship to DNA Interstrand Cross-Linking, Bridgewater, L. C.; Manning, F. C. R.; Patierno, S. R. Carcinogenesis 1994, 15, 2421.
29. (a) Perone, V. B. Microb. Toxins 1972, 8, 71.
30. (b) Parrish, J. A.; Fitzpatrick, T. B.; Tanenbaum, L.; Pathak, M. A. N. Engl. J. Med. 1974, 291, 1207.
31. (c) Dall'Acqua, F.; Caffieri, S. Photochem. Photobiol. 1988, 10, 1.
32. (d) Psoralen Photobiology, Gasparro, F. P. Photochem. Photobiol. 1996, 63, 553.
33. (e) Parrish, J. A.; Stern, R. S.; Pathak, M. A.; Fitzpatrick, T. B. Photochemotherapy of Skin Diseases. In The Science of Photomedicine; Regan, J. D., Parrish, J. A., Eds.; Plenum Press: New York, 1982; p 595.
34. (a) Homodinuclear (Pt,Pt) and Heterodinuclear (Ru,Pt) Metal Compounds as DNA-Protein Cross-Linking Agents: Potential Suicide DNA Lesions, Van Houten, B.; Illenye, S.; Qu, Y.; Farrell, N. Biochemistry 1993, 32, 11794.
35. (b) Photoreactivity of Platinum-(II) in Cisplatin-Modified DNA Affords Specific Cross-Links to HMG Domain Proteins, Lippard, S. J.; Kane, S. A. Biochemistry 1996, 35, 2180.
36. (a) Reversible DNA, Geiduschek, E. P. Proc. Natl. Acad. Sci. U.S.A. 1961, 47, 950.
37. (b) A Molecular Mechanism of Mitomycin Action: Linking of Complementary DNA Strands, Iyer, V. N.; Szybalski, W. Proc. Natl. Acad. Sci. U.S.A. 1963, 50, 355.
38. (c) Inter-strand Cross-linking of DNA by Nitrogen Mustard, Kohn, K. W.; Spears, C. L.; Doty, P. J. Mol. Biol. 1966, 19, 266.
39. (a) The Biological Actions and Therapeutic Applications of the β-Chloroethyl amines and Sulfides, Gilman, A.; Phillips, F. S. Science 1946, 103, 409.
40. (b) Haskel, C. M. Cancer Treatment, 2nd ed.; Saunders: Philadelphia, 1990.
41. The Alkylation of Guanosine and Guanylic Acid, Brookes, P.; Lawley, P. D. J. Chem. Soc. 1961, 3923.
42. Brookes, P.; Lawley, P. D. Biochem. J. 1961, 80, 496.
43. Formation and Removal of DNA Cross-Links Induced by Melphalan and Nitrogen Mustard in Relation to Drug-induced Cytotoxity in Human Melanoma Cells, Hansson, J.; Lewensohn, R.; Ringborg, U.; Nilsson, B. Cancer Res. 1987, 47, 2631.
44. (a) Mechlorethamine Cross-Links Deoxyguanosine Residues at 5′ GNC Sequences in Duplex DNA Fragments, Hopkins, P. B.; Raucher, S.; Millard, J. T. J. Am. Chem. Soc. 1990, 112, 2459.
45. (b) Synthesis of a Duplex Oligonucleotide Containing a Nitrogen Mustard Interstrand DNA-DNA Cross-Link, Ojwang, J. O.; Grueneberg, D. A.; Loechler, E. L. Cancer Res. 1989, 49, 6529.
46. (a) Covalent Structure of a Nitrogen Mustard-Induced DNA Interstrand Cross-Link: An N7-to-N7 Linkage of Deoxyguanosine Residues at the Duplex Sequence 5′-d(GNC), Rink, S. M.; Solomon, M. S.; Taylor, M. J.; Sharanabasava, R. B.; McLaughlin, L. W.; Hopkins, P. B. J. Am. Chem. Soc. 1993, 115, 2551.
47. (b) A Mechlorethamine-Induced DNA Interstrand Cross-Link Bends Duplex DNA, Rink, S. M.; Hopkins, P. B. Biochemistry 1995, 34, 1439.
48. Efficient, Specific Interstrand Cross-Linking of Double-Stranded DNA by a Chlorambucil-Modified, Triplex-Forming Oligonucleotide, Kutyavin, I. V.; Gamper, H. B.; Gall A. A.; Meyer, R. B., Jr. J. Am. Chem. Soc. 1993, 115, 9303.
49. (a) Targeting of Cytotoxic Agents by Polyamine Synthesis of a Chlorambucil-Spermidine Conjugate, Cohen, G. M.; Cullis, P. M.; Harltey, J. A.; Mather, A.; Symons, M. C. R.; Wheelhouse, R. T. J. Chem. Soc., Chem. Commun. 1992, 298.
50. (b) Targeting of Tumor Cells and DNA by a Chlorambucil-Spermidine Conjugate, Holley, J. P.; Mather, A.; Wheelhouse, R. T.; Cullis, P. M.; Hartley, J. A.; Bingham, J. P.; Cohen, G. M. Cancer Res. 1992, 52, 4190.