A semiempirical computational study of electron transfer reactivity of one- vs. two-ring model systems for anthracycline pharmacophores. I. A rationale for mode of action

Journal of Computational Chemistry

Volumn 17, Issue 2, 1996, Pages 204-225

  Sawyer, Alesia ^a   Sullivan, Erica ^a   Mariam, Yitbarek H ^a  

^a CLARK ATLANTA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001470050     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1096-987x(19960130)17:2<204::aid-jcc8>3.0.co;2-%23     Document Type: Article

References (51)

1. (a) J. K. Lace and C. F. Curran, In Principles of Cardiac Toxicology, S. I. Baskin, Ed., CRC Press, Boca Raton, FL, 1991, Chap. 16, p. 541 and references therein;
2. (b) B. Halliwell and J. M. C. Gutteridge, Free Radicals in Biology and Medicine, 2nd ed., Clarendon Press, Oxford, UK, 1989, Chap. 6 p. 299;
3. (c) F. Arcamone, Doxorubicin: Anticancer Antibiotics, Academic Press, New York, 1981;
4. (d) S. R. Angle and W. Yang, J. Am. Chem. Soc., 112, 4524 (1990);
5. (e) G. C. Neri, B. Neri, M. Bandinelli, M. D. Tacca, R. Danesi, and R. Riccardi, Oncology, 48, 327 (1991);
6. (f) G. Gaudiano, M. Frigero, P. Bravo, and T. H. Koch, J. Am. Chem. Soc., 114, 3107 (1992); ibid., 112, 6704 (1990), other references therein.
7. (f) G. Gaudiano, M. Frigero, P. Bravo, and T. H. Koch, J. Am. Chem. Soc., 114, 3107 (1992); ibid., 112, 6704 (1990), other references therein.
8. V. Favaudon, Biochimie, 64, 457 (1982).
9. (a) K. Handa and S. Sato, Gann, 66, 43 (1975);
10. (b) ibid., 67, 523 (1976);
11. (c) S. Sato, M. Iwazumi, and K. Handa, Gann, 68, 803 (1977).
12. (a) G. L. Tong, D. W. Henry, and E. M. Acton, J. Med. Chem., 22, 36 (1979);
13. (b) E. M. Acton, R. A. Jensen, and J. H. Peters, In Anthracycline Antibiotics in Cancer Therapy, F. M. Muggia, C. W. Young, and S. K. Carter, Eds., Martinus Nijhoff, Boston, 1982, p. 205;
14. (c) R. I. Glaser, K. D. Hartman, and C. L. Richardson, Cancer Res., 42, 117 (1982).
15. (a) J. W. Lown, H. H. Chen, and J. A. Plambeck, Biochem. Pharm., 28, 2563 (1979);
16. (b) ibid., 31, 575 (1982);
17. (c) K. J. A. Davies, J. H. Doroshow, and H. P. Hochstein, FEBS Lett., 153, 227 (1983);
18. (d) E. G. Mimnaugh, M. A. Trush, E. G. Ciarrocchi, M. Lestingi, M. Fontana, S. Spadasi, and A. Montecucco, Biochem. J., 279, 141 (1991);
19. (e) J. Nafzinger, C. Auclair, J. C. Florent, J. J. Guillosson, and C. Monneret, Lechemie Res., 15, 709 (1991);
20. (f) E. G. Mimnaugh, M. A. Trush, E. Ginsburg and T. E. Gram, Cancer Res., 42, 3574 (1982).
21. B. R. J. Abdella and J. Fisher, J. Environ. Health Perspect., 64, 3 (1985).
22. D. M. Bird, M. Boldt, and T. H. Koch, J. Am. Chem. Soc., 109, 4046 (1987).
23. (a) J. W. Lown, Acc. Chem. Res., 15, 381 (1982);
24. (b) N. J. F. Dodd and T. Mukherjee, Biochem. Pharmac., 33, 379 (1984);
25. (c) H. Nohland, W. Jordan, Biochem. Biophys. Res. Comm., 114, 197 (1983).
26. M. E. Brewster, J. J. Kaminski, and N. Bodor, J. Am. Chem. Soc., 110, 6337 (1988).
27. W. J. Walsh, J. Comp. Chem., 11, 644 (1990).
28. D. F. V. Lewis, In Reviews in Computational Chemistry, K. B. Lipkowitz and D. B. Boyd, Eds., VCH Publishers, New York, 1992, p. 200.
29. M. E. Brewster, M. J. Huang, J. J. Kaminski, E. Pop, and N. Bodor, J. Comp. Chem., 12, 1278 (1991), and other references therein.
30. M. N. Ramos, and B. de B. Neto, J. Comp. Chem., 11, 569 (1990).
31. (a) R. G. Parr and R. G. Pearson, J. Am. Chem. Soc., 105, 7512 (1983);
32. (b) R. G. Parr, R. A. Donnelly, M. Levy, and W. E. Palke, J. Chem. Phys., 68, 3801 (1978);
33. (c) R. Pearson, J. Am. Chem. Soc., 107, 6801 (1988).
34. R. G. Pearson, Proc. Natl. Acad. Sci. USA, 83, 8440 (1986).
35. M. Giambiagi and J. Pires, Chem. Phys. Lett., 152, 222 (1988).
36. M. J. S. Dewar, E. G. Zoebich, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).
37. J. J. P. Stewart, Quantum Chemistry Program Exchange (QCPE) Program 455, Department of Chemistry, Indiana University, Bloomington, IN, 1989.
38. BIOSYM Technologies, Inc., San Diego, CA, 1991.
39. AMPAC (AMPAC 4.5, 1993), Semichem, 12715 W. 66th Terrace, Shawnee, KS, 1993.
40. Serena Software, BIoomington, IN, 1989.
41. T. Koopmans, Physica, 1, 104 (1934).
42. D. E. Shriver, P. W. Atkins, and C. H. Langford, Inorganic Chemistry, W. H. Freeman, New York, 1990, p. 28.
43. C. J. Cramer and D. G. Truhlar, Science, 256, 213 (1992).
44. A. Szabo and N. S. Ostlund, Modern Quantum Chemistry, McGraw-Hill, New York, 1989, p. 128.
45. A. Sawyer and Y. H. Mariam, J. Comp.-Aided Mol. Design, submitted.
46. B. Halliwell and J. M. C. Gutteridge, Free Radicals in Biology and Medicine, 2nd ed., Clarendon Press, Oxford, UK, 1989, p. 12.
47. R. G. Pearson, J. Chem. Educ., 64, 561 (1987).
48. M. Palumbo, G. Palu, and S. Marciani Mango, In H. Van der Goot, G. Domany, L. Pallos, and H. Timmerman, Eds., Pharmacochemistry Library, Vol. 12, Elsevier, New York, 1989, p. 757.
49. I. B. Afanas'ev, Ed., Superoxide Ion: Chemistry and Biological Implications CRC Press, Boca Raton, FL, 1989, Vol. I, p. 157.
50. I. B. Alfanas'ev, Ed., Superoxide Ion: Chemistry and Biological Implications, Vol. I, CRC Press, Boca Raton, FL, 1989, p. 20.
51. D. T. Sawyer, J. L. Roberts, T. S. Calderwood, T. Tsuchiya, and J. J. Stamp, In. Oxygen Radicals and Their Scavenger Systems, G. Cohen and R. A. Greenwald, Eds., Elsevier Biomedical, New York, Vol. I, 1983, p. 8.