Interstrand Cross-linking of DNA by 1,3-Bis(2-chloroethyl)-1-nitrosourea and Other 1-(2-haloethyl)-1-nitrosoureas

Cancer Research

Volumn 37, Issue 5, 1977, Pages 1450-1454

  Kohn, Kurt W ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARMUSTINE; CHLOROETHYLNITROSOUREA; DNA; LOMUSTINE; METHYLNITROSOUREA;

3 CYCLOHEXYL 1 (2 FLUOROETHYL) 1 NITROSOUREA; CROSS LINKING; IN VITRO STUDY; THEORETICAL STUDY;

CARMUSTINE; CHEMISTRY; DNA; KINETICS; LOMUSTINE; METHYLNITROSOUREA; NITROSOUREA COMPOUNDS;

EID: 0017641428     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. Brookes, P., and Lawley, P. D. The Reaction of Mono-and Di-functional Alkylating Agents with Nucleic Acids. Biochem. J., 80: 496-503, 1961.
2. Burnotte, J., and Verly, W. G. Crosslinking of Methylated DNA by Moderate Heating at Neutral pH. Biochim. Biophys. Acta, 262: 449-452, 1972.
3. Cheng, C. J., Fujimura, S., Grunberger, D., and Weinstein, I. B. Interaction of CCNU with Nucleic Acids and Proteins in Vivo and in Vitro. Cancer Res., 32: 22–27, 1972.
4. Colvin, M., Brundrett, R. B., Cowens, W., Jardine, I., and Ludlum, D. B. A Chemical Basis for the Antitumor Activity of Chloroethylnitrosoureas. Biochem. Pharmacol., 25: 695–699, 1976.
5. Colvin, M., Cowens, J. W., Brundrett, R. B., Kramer, B. S., and Ludlum, D. B. Decomposition of BCNU in Aqueous Solution. Biochem. Biophys. Res. Commun., 60: 515–520, 1974.
6. Freese, E., and Cashel, M. Crosslinking of DNA by Exposure to Low pH. Biochim. Biophys. Acta, 91: 67–77, 1964.
7. Geiduschek, E. P. “Reversible” DNA. Proc. Natl. Acad. Sci. U. S., 47: 950–955, 1961.
8. Iyer, V. N., and Szybalski, W. A Molecular Mechanism of Mitomycin Action: Linking of Complementary DNA Strands. Proc. Natl. Acad. Sci. U. S., 50: 355–362, 1963.
9. Johnston, T. P., McCaleb, G. S., Opliger, P. S., Laster, W. R., and Montgomery, J. A. Synthesis of Potential Anticancer Agents. 38. N-Nitrosoureas. 4. Further Synthesis and Evaluation of Haloethyl Derivatives. J. Med. Chem., 14: 600–614, 1971.
10. Johnston, T. P., McCaleb, G. S., Opliger, P. S., and Montgomery, J. A. Synthesis of Potential Anticancer Agents. 36. N-Nitrosoureas. II. Haloalkyl Derivatives. J. Med. Chem., 9: 892-911, 1966.
11. Kohn, K. W. Interstrand Cross-linking of DNA by Chloroethylnitrosoureas. Federation Proc., 35: 1708, 1976.
12. Kohn, K. W., Spears, C. L., and Doty, P. Interstrand Crosslinking of DNA by Nitrogen Mustard. J. Mol. Biol., 19: 266-288, 1966.
13. Kramer, B. S., Fenselau, C. C., and Ludlum, D. B. Reaction of BCNU with Polycytidylic Acid. Substitution of the Cytosine Ring. Biochem. Biophys. Res. Commun., 56: 783–788, 1974.
14. Lawley, P. D., and Brookes, P. D. Interstrand Cross-linking of DNA by Di-functional Alkylating Agents. J. Mol. Biol., 25: 143–160, 1967.
15. Lawley, P. D., Orr, D. J., and Jarman, M. Isolation and Identification of Products from Alkylation of Nucleic Acids: Ethyl-and Isopropyl-purines. Biochem. J., 145: 73–84, 1975.
16. Lipsett, M. N., and Weissbach, A. The Site of Alkylation of Nucleic Acids by Mitomycin. Biochemistry, 4: 206–211, 1965.
17. Montgomery, J. A., James, R., McCaleb, G. S., and Johnston, T. P. The Modes of Decomposition of BCNU and Related Compounds. J. Med. Chem., 10: 668–674, 1967.
18. Reed, D. J., May, H. E., Boose, R. B., Gregory, K. M., and Beilstein, M. A. 2-Chloroethanol Formation during Chemical Degradation of CCNU and Trans-Methyl CCNU; Evidence for a 2-Chloroethyl Alkylating Intermediate. Cancer Res., 35: 568–576, 1975.
19. Schabel, F. M., Jr., Johnston, T. P., McCaleb, G. S., Montgomery, J. A., Laster, W. R., and Skipper, H. E. Experimental Evaluation of Potential Anticancer Agents. VIII. Effects of Certain Nitrosoureas and Intracerebral L1210 Leukemia. Cancer Res., 23: 725–733, 1963.
20. Singer, B. The Chemical Effects of Nucleic Acid Alkylation and Their Relations to Mutagenesis and Carcinogenesis. Progr. Nucleic Acid Res. Mol. Biol., 15: 219–284, 1975.
21. Stacey, K. A., Cobb, M., Cousens, S. F., and Alexander, P. Reactions of the “Radiomimetic” Alkylating Agents with Macromolecules in Vitro. Ann. N. Y. Acad. Sci., 68: 682–701, 1958.
22. Sun, L., and Singer, B. The Specificity of Different Classes of Ethylating Agents toward Various Sites of HeLa Cell DNA and in Vivo. Biochemistry, 14: 1795–1802, 1975.
23. Thornton, E. R. Solvolysis Mechanisms, p. 165. New York: Ronald Press, 1964.
24. Vinograd, J., Morris, J., Davidson, N., and Dove, W. F., Jr. Buoyant Behavior of Viral and Bacterial DNA in Alkaline CsCl. Proc. Natl. Acad. Sci. U. S., 49: 12–17, 1963.
25. Wheeler, G. P. Mechanism of Action of Alkylating Agents: Nitrosoureas. In: A. C. Sartorelli, and D. G. Johns (eds.), Handbook of Experimental Pharmacology, Vol. 38, pp. 65–84. Berlin: Springer-Verlag, 1975.