Reductive activation of a hydroxylamine hemiacetal derivative of dehydromonocrotaline: The first reductively activated pyrrolizidine alkaloid capable of cross-linking DNA

Angewandte Chemie - International Edition

Volumn 38, Issue 23, 1999, Pages 3501-3503

  Tepe, Jetze J ^a   Williams, Robert M ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

Alkaloids; DNA structures; Drug research; Monocrotaline

Indexed keywords

CYTOCHROME P450; HYDROXYLAMINE; MONOCROTALINE PYRROLE; PYRROLIZIDINE ALKALOID;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DNA CROSS LINKING; DNA STRUCTURE; DRUG RESEARCH; LIVER TOXICITY; OXIDATION; PROTEIN DNA BINDING; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0033521204     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3501::AID-ANIE3501>3.0.CO;2-W     Document Type: Article

References (29)

1. A. R. Mattocks, Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, London, 1986.
2. L. W. Smith, C. C. J. Culvenor, J. Nat. Prod. 1981, 44, 129.
3. "Human Health Implications of Pyrrolizidine Alkaloids and Herbs Containing Them": R. J. Huxtable in Toxicants of Plant Origin, Vol I: Alkaloids (Ed.: P. R. Checke), CRC Press, Boca Raton, FL, 1989, pp. 41-86.
4. a) C. L. Miranda, W. Chung, R. E. Reed, X. Zhao, M. C. Henderson, J.-L. Wang, D. E. Williams, D. R. Buhler, Biochem. Biophys. Res. Commun. 1991, 178, 546;
5. b) D. E. Williams, R. E. Reed, B. Kedzierski, G. A. Dannan, F. P. Guengerich, D. R. Buhler, Drug Metab. Dispos. 1989, 17, 58.
6. C. L. Miranda, R. E. Reed, F. P. Guengerich, D. R. Buhler, Carcinogenesis 1991, 12, 515.
7. H. Niwa, T. Ogawa, O. Okamoto, K. Yamada, Tetrahedron Lett. 1991, 32, 927.
8. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking, see a) K. W. Kohn in Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-Cancer Drug Action (Eds.: S. Neidle, M. Waring), VCH, Weinheim, 1994, p. 315; b) P. D. Lawley, BioEssays 1995, 17, 561; c) D. J. Paustenbach, B. L. Finley, S. Kacew, Proc. Soc. Exp. Biol. Med. 1996, 211, 211; d) M. Gniazdowski, C. Cera, Chem. Rev. 1996, 96, 619; e) J. R. Hincks, H. Y. Kim, H. J. Segall, R. J. Molyneaux, F. R. Stermitz, R. A. Coulombe, Jr., Toxicol. Appl. Pharmacol. 1991, 111, 90.
9. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking, see a) K. W. Kohn in Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-Cancer Drug Action (Eds.: S. Neidle, M. Waring), VCH, Weinheim, 1994, p. 315; b) P. D. Lawley, BioEssays 1995, 17, 561; c) D. J. Paustenbach, B. L. Finley, S. Kacew, Proc. Soc. Exp. Biol. Med. 1996, 211, 211; d) M. Gniazdowski, C. Cera, Chem. Rev. 1996, 96, 619; e) J. R. Hincks, H. Y. Kim, H. J. Segall, R. J. Molyneaux, F. R. Stermitz, R. A. Coulombe, Jr., Toxicol. Appl. Pharmacol. 1991, 111, 90.
10. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking, see a) K. W. Kohn in Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-Cancer Drug Action (Eds.: S. Neidle, M. Waring), VCH, Weinheim, 1994, p. 315; b) P. D. Lawley, BioEssays 1995, 17, 561; c) D. J. Paustenbach, B. L. Finley, S. Kacew, Proc. Soc. Exp. Biol. Med. 1996, 211, 211; d) M. Gniazdowski, C. Cera, Chem. Rev. 1996, 96, 619; e) J. R. Hincks, H. Y. Kim, H. J. Segall, R. J. Molyneaux, F. R. Stermitz, R. A. Coulombe, Jr., Toxicol. Appl. Pharmacol. 1991, 111, 90.
11. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking, see a) K. W. Kohn in Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-Cancer Drug Action (Eds.: S. Neidle, M. Waring), VCH, Weinheim, 1994, p. 315; b) P. D. Lawley, BioEssays 1995, 17, 561; c) D. J. Paustenbach, B. L. Finley, S. Kacew, Proc. Soc. Exp. Biol. Med. 1996, 211, 211; d) M. Gniazdowski, C. Cera, Chem. Rev. 1996, 96, 619; e) J. R. Hincks, H. Y. Kim, H. J. Segall, R. J. Molyneaux, F. R. Stermitz, R. A. Coulombe, Jr., Toxicol. Appl. Pharmacol. 1991, 111, 90.
12. For excellent general reviews pertaining to the biological relevance of DNA interstrand cross-linking, see a) K. W. Kohn in Topics in Structural & Molecular Biology: 3) Molecular Aspects of Anti-Cancer Drug Action (Eds.: S. Neidle, M. Waring), VCH, Weinheim, 1994, p. 315; b) P. D. Lawley, BioEssays 1995, 17, 561; c) D. J. Paustenbach, B. L. Finley, S. Kacew, Proc. Soc. Exp. Biol. Med. 1996, 211, 211; d) M. Gniazdowski, C. Cera, Chem. Rev. 1996, 96, 619; e) J. R. Hincks, H. Y. Kim, H. J. Segall, R. J. Molyneaux, F. R. Stermitz, R. A. Coulombe, Jr., Toxicol. Appl. Pharmacol. 1991, 111, 90.
13. S. R. Rajski, R. M. Williams, Chem. Rev. 1998, 98, 2723.
14. a) M. F. Weidner, S. T. Sigurdsson, P. B. Hopkins, Biochemistry 1990, 29, 9225:
15. b) J. Woo, S. T. Sigurdsson, P. B. Hopkins, J. Am. Chem. Soc. 1993, 115, 3407.
16. a) H.-Y. Kim, F. R. Stermitz, R. A. Coulombe, Jr., Carcinogenesis 1995, 16, 2691;
17. b) R. A. Coulombe, G. L. Drew, F. R. Stermitz, Toxicol. Appl. Pharmacol. 1999, 154, 198.
18. J. M. Brown, A. Koonng, J. Natl. Cancer Inst. 1991, 83, 178.
19. "Hypoxia-Selective Cytotoxins": W. A. Denny in Cancer Chemotherapeutic Agents (Ed.: W. O. Foye), ACS Press, Washington, D.C., 1995, chap. 14, pp. 483-500.
20. a) J. J. Tepe, R. M. Williams, J. Am. Chem. Soc. 1999, 121, 2951;
21. b) S. B. Rollins, R. M. Williams, Tetrahedron Lett. 1997, 38, 4033.
22. Monocrotaline used in this study was purchased from Aldrich Chemical Co.
23. [13a]
24. M. M. Paz, P. B. Hopkins, Tetrahedron Lett. 1997, 38, 343.
25. T. R. Cech, Biochemistry 1981, 20, 1431.
26. P. N. Borer, Handbook of Biochemistry and Molecular Biology, CRC Press, Boca Raton, FL, 1975.
27. M. M. Paz, P. B. Hopkins, J. Am. Chem. Soc. 1997, 119, 5999.
28. a) R. M. Williams, S. R. Rajski, S. B. Rollins, Chem. Biol. 1997, 4, 127;
29. b) S. R. Rajski, Dissertation, Colorado State University, 1997.