A redox pathway leading to the alkylation of nucleic acids by doxorubicin and related anthracyclines: Application to the design of antitumor drugs for resistant cancer

Current Pharmaceutical Design

Volumn 4, Issue 3, 1998, Pages 203-218

  Taatjes, Dylan J ^a   Fenick, David J ^a   Gaudiano, Giorgio ^a,c   Koch, Tad H ^a,b  

^a UNIVERSITY OF COLORADO   (United States)

^b UNIVERSITY OF COLORADO CANCER CENTER   (United States)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE DERIVATIVE; DAUNOFORM; DAUNORUBICIN; DAUNORUBICIN DERIVATIVE; DOXOFORM; DOXORUBICIN; DOXORUBICIN DERIVATIVE; EPIRUBICIN; EPIRUBICIN DERIVATIVE; FORMALDEHYDE; TENIPOSIDE; UNCLASSIFIED DRUG; VM 16;

ANTINEOPLASTIC ACTIVITY; CANCER; CELL STRAIN MCF 7; DNA ADDUCT; DNA ALKYLATION; DNA CROSS LINKING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MULTIDRUG RESISTANCE; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PRIORITY JOURNAL; REVIEW;

ALKYLATING AGENTS; ANTHRACYCLINES; ANTINEOPLASTIC AGENTS; CHEMISTRY, PHARMACEUTICAL; DNA ADDUCTS; DOXORUBICIN; DRUG DESIGN; DRUG RESISTANCE, NEOPLASM; MOLECULAR STRUCTURE; NUCLEIC ACIDS; OXIDATION-REDUCTION;

EID: 0031809232     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (116)

1. DiMarco, A.; Gaetani, M.; Scarpinato, B. Cancer Chemother. Rep (Part I), 1969, 53, 33
2. Arcamone, F. Doxorubicin Anticancer Antibiotics; Academic Press: New York, 1981.
3. Vita, V. T. D., Hellman, S.; Rosenberg, S. A., eds. Cancer. Principles and Practice of Oncology; J B. Lippincott Co.: Philadelphia, 1993.
4. Weiss, R. B. Semin. Oncol., 1992, 19, 670
5. Frederick, C. A.; Williams, L. D.; Ughetto, G., Vander Marel, G. A.; Van Boom, J.; Rich, A.; Wang, A. H. J. Biochemistry, 1990, 29, 2538.
6. Chaires, J. B.; Satyanarayana, S.; Suh, D.; Fokt, I.; Przewloka, T.; Priebe, W. Biochemistry, 1996, 35, 2047
7. Pommier, Y. In Anthracycline Antibiotics: New Analogues, Methods of Delivery, and Mechanisms of Action; Priebe, W., Eds.; American Chemical Society: Washington, DC, 1995; p 183.
8. Sweatman, T. W.; Israel, M. In Cancer Therapeutics, Experimental and Clinical Agents; Teicher, B. A., Eds.; Humana Press: Totowa, NJ, 1997; p 113.
9. Cullinane, C., van Rosmalen, A.; Phillips, D. R. Biochemistry, 1994, 33, 4632.
10. Myers, C. E.; Gianni, L.; Simone, C. B.; Klecker, R.; Greene, R. Biochemistry, 1982, 21, 1707.
11. Cullinane, C.; Cutts, S. M.; van Rosmalen, A ; Phillips, D R. Nucleic Acids Res., 1994, 22, 2296.
12. Vile, G. F.; Winterbourn, C. C. J. Free Rad. Biol. Med., 1986, 2, 393.
13. van Rosmalen, A.; Cullinane, C ; Cutts, S. M.; Phillips, D. R Nucleic Acids Res , 1995, 23, 42.
14. Gaudiano, G., Koch, T H. Chem. Res. Toxicol, 1991, 4, 2.
15. Gaudiano, G.; Frigerio, M.; Sangsurasak, C.; Bravo, P.; Koch, T. H. J. Am. Chem. Soc. , 1992, 114, 5546.
16. Egholm, M ; Koch, T. H. J. Am. Chem. Soc., 1989, 111, 8291.
17. Borowy-Borowski, H.; Lipman, R.; Tomasz, M Biochemistry, 1990, 29, 2999.
18. Borowy-Borowski, H.; Lipman, R.; Chowdary, D.; Tomasz, M. Biochemistry, 1990, 29, 2992.
19. Bartoszek, A ; Wolf, C. R. Biochem. Pharmacol., 1992, 43, 1449
20. Pan, S.; Pedersen, L.; Bachur, N. R. Mol. Pharmacol., 1981, 19, 184
21. Skladanowski, A.; Konopa, J. Biochem. Pharmacol., 1994, 47, 2279.
22. Skladanowski, A.; Konopa, J. Biochem. Pharmacol., 1994, 47, 2269
23. Skladanowski, A ; Konopa, J. Biochem. Pharmacol., 1993, 46, 375
24. Sinha, B. K.; Trush, M. A.; Kennedy, K. A ; Mimnaugh, E. G. Cancer Res., 1984, 44, 2892.
25. Gaudiano, G.; Resing, K ; Koch, T. H. J. Am. Chem. Soc., 1994, 116, 6537.
26. Gaudiano, G.; Koch, T. H. J. Am. Chem. Soc , 1990, 112, 9423.
27. Gaudiano, G.; Frank, E.; Wysor, M. S ; Averbuch, S. D.; Koch, T. H. J. Org. Chem., 1993, 58, 7355.
28. Taatjes, D. J.; Gaudiano, G.; Resing, K.; Koch, T. H. J. Med. Chem., 1996, 39, 4135.
29. Taatjes, D. J ; Gaudiano, G.; Resing, K.; Koch, T. J. Med Chem., 1997, 40, 1276
30. Wang, A. H J ; Gao, Y. G.; Liaw, Y. C.; Li, Y. k. Biochemistry, 1991, 30, 3812.
31. Shiraishi, H ; Kataoka, M.; Morta, Y., Umemoto, J. Free Rad. Res. Commun., 1993, 19, 315.
32. Taatjes, D J.; Gaudiano, G.; Koch, T. H Chem. Res. Toxicol., 1997, 10, 953.
33. Bagchi, D.; Bagchi, M ; Hassoun, E. A.; Kelly, J.; Stohs, S. J. Toxicology, 1995, 95, 1.
34. Thorndike, J.; Beck, W S. Cancer Res., 1977, 37, 1125.
35. Yazdanpanah, M ; Luo, X.; Lau, R.; Greenberg, M.; Fisher, L. J.; Lehotay, D. C Free Rad. Biol. Med., 1997, 23, 870.
36. Doroshow, J. H. In Anthracycline Antibiotics: New Analogues, Methods of Delivery, and Mechanisms of Action; Priebe, W., Eds.; American Chemical Society: Washington, DC, 1995; p 259.
37. Voest, E. E.; van Acker, S. A.; van der Vijgh, W. J.; van Asbeck, B. S ; Bast, A. J. Mol. Cell Cardiol., 1994, 26, 1179.
38. Hershko, C.; Link, G.; Tzahor, M.; Kaltwasser, J. P.; Athias, P.; Grynberg, A.; Pinson, A. J Lab Clin Med, 1993, 122, 245.
39. Doroshow, J. H. Biochem. Biophys. Res. Commun., 1986, 135, 330.
40. Mimnaugh, E G.; Fairchild, C. R.; Fruehauf, J P.; Sinha, B. K. Biochem. Pharmacol., 1991, 42, 391.
41. Volm, M.; Mattem, J ; Samsel, B. Br. J. Cancer, 1991, 64, 700.
42. Fenick, D. J.; Taatjes, D. J.; Koch, T H J Med. Chem., 1997, 40, 2452.
43. Naylor, S.; Mason, R. P ; Sanders, J. K. M.; Williams, D H.; Moncti, G. Biochem J. 1988, 249, 573.
44. Russo, A , Mitchell, J B. Cancer Treat Rep., 1985, 69, 1293.
45. Cowan, K. H.; Batist, G.; Tulpule, A.; Sinha, B. K.; Myers, C. E. Proc. Natl Acad. Sci USA, 1986, 83, 9328.
46. Barkworth, P M R , Crabb, T. A J Chem. Soc. Perkin II, 1982, 91.
47. Barkworth, P. M. R.; Crabb, T. A. J. Chem. Soc. Perkin Trans. I, 1983, 2807.
48. Crabb, T. A ; Roch, O. G.; Robinson, P. Magn Reson Chem., 1986, 24, 1069.
49. Taatjes, D J.; Fenick, D J.; Koch, T H. J. Med. Chem., 1998, in press.
50. Weenen, H.; Maanen, J. M. v.; Planque, M. M. d ; McVie, J. G.; Pinedo, H. M. Eur. J. Cancer Clin. Oncol., 1984, 20, 919.
51. Leng, F.; Savkur, R ; Fokt, I.; Przewloka, T , Priebe, W ; Chaires, J. B. J. Am. Chem Soc., 1996, 118, 4731.
52. Acton, E. M.; Tong, G. L ; Mosher, C. W.; Wolgemuth, R. L J. Med. Chem., 1984, 27, 638.
53. Ikeda, D.; Ajito, K., Kondo, S.; Takeuchi, T. Chem. Lett., 1990, 1431.
54. Nagy, A.; Armatis, P.; Schally, A. V. Proc. Natl. Acad Sci USA, 1996, 93, 2464.
55. Zwelling, L. A.; Altschuler, E ; Cherif, A.; Farquhar, D. Cancer Res., 1991, 51, 6704.
56. Scudder, S. A.; Brown, J. M.; Sikic, B. I. J. Natl Cancer Inst., 1988, 80, 1294.
57. Cullinane, C.; Phillips, D R. FEBS Lett. 1991, 293, 195.
58. Cullinane, C.; Phillips, D. R. Biochemistry, 1994, 33, 6207.
59. Ross, W. E.; Bradley, M. O. Biochim. Biophys. Acta, 1981, 654, 129.
60. Zwelling, L. A.; Michaels, S.; Erickson, L. C.; Ungerleider, R. S.; Nichols, M.; Kohn, K. W. Biochemistry, 1981, 20, 6553.
61. Tewey, K. M.; Rowe, T. C.; Yang, L ; Halligan, B. D ; Liu, L F Science, 1984, 226, 466.
62. Liu, L. F.; Rowe, T. C.; Yang, L ; Tewey, K. M.; Chen, G. C. J Biol. Chem., 1983, 258, 15365.
63. Chen, A. Y.; Liu, L. F. Annual Rev. Pharmacol. Toxicol., 1994, 34, 191.
64. Beck, W. T.; Danks, M. K.; Wolverton, J. S.; Kim, R.; Chen, M. Adv. Enzyme Reg., 1993, 33, 113.
65. Wang, J. C. Annu. Rev Biochem., 1996, 65, 635
66. Rowe, T C.; Tewey, K. M.; Liu, L F. J. Biol. Chem., 1984, 259, 9177.
67. Pommier, Y.; Leteurtre, F ; Fesen, M. R.; Fujimori, A.; Bertrand, R.; Solary, E.; Kohlhagen, G.; Kohn, K. W. Cancer Invest., 1994, 12, 530.
68. Patel, S.; Sprung, A. V.; Keller, B. A.; Heaton, V. J ; Fisher, L M. Mol. Pharmacol., 1997, 52, 658
69. Potmesil, M. In Anthracycline and anthracenedione-based anticancer agents;Lown, J. W., Eds.; Elsevier Science: Amsterdam, 1988; p 447
70. Giaccone, G.; Gazadar, A. F.; Beck, H.; Zunino, F.; Capranico, G. Cancer Res , 1992, 52, 1666
71. Nip, J.; Strom, D. K.; Fee, B. E.; Zambetti, G., Cleveland, J. L.; Hiebert, S. W Mol. Cell Biol., 1997, 17, 1049.
72. Vichi, P.; Song, J.; Hess, J.; Tritton, T. R. In Anthracycline Antibiotics: New Analogues, Methods of Delivery and Mechanisms of Action, Priebe, W., Eds ; American Chemical Society: Washington DC, 1995; p 242
73. Binaschi, M , Capranico, G., De Isabella, P.; Mariani, M.; Supino, R., Tinelli, S ; Zunino, F. Int. J. Cancer, 1990, 45, 347
74. Binaschi, M.; Capranico, G.; Dal Bo, L.; Zunino, F. Mol. Pharmacol., 1997, 51, 1053.
75. Long, B H.; Musial, S. T.; Brattain, M. G. Cancer Res., 1985, 45, 3106.
76. Safa, A R Cancer Invest , 1993, 11, 46.
77. Kartner, N.; Ling, V Sci Am , 1989, 260, 44.
78. Zaman, G. J. R ; Fleus, M. J.; van Leusden, M. R.; de Haas, M.; Mulder, H S.; Lankelma, J.; Pinedo, H M.; Scheper, R. J.; Baas, F.; Broxterman, H. J., Borst, P. Proc. Nat. Acad. Sci., 1994, 91, 8822.
79. Leier, I.; Jedlitschky, G.; Buchholz, U.; Cole, S. P. C.; Deeley, R. G ; Keppler, D J. Biol. Chem., 1994, 269, 27807.
80. Heijn, M ; Hooijberg, J. H.; Scheffer, G. L.; Szabo, G.; Westerhoff, H. V.; Lankelma, J. Biochim. Biophys. Acta, 1997, 1326, 12.
81. Safa, A R.; Glover, C. J.; Meyers, M. B ; Biedler, J. L.; Felsted, R. L. J. Biol Chem , 1986, 261, 6137.
82. Grant, C. E.; Valdimarsson, G.; Hipfner, D. R ; Almquist, K. C.; Cole, S. P. C.; Deeley, R. G. Cancer Res., 1994, 54, 357.
83. Frezard, F.; Garnier-Suillerot, A. Eur. J. Biochem., 1991, 196, 483
84. Hayes, J. D.; Pulford, D. J. Crit. Rev. Biochem. Mol. Biol., 1995, 30, 445.
85. Marbeuf-Gueye, C., Broxterman, H. J.; Dubru, F.; Priebe, W.; Garnier-Suillerot, A. Mol. Pharmacol., 1998, 53, 141.
86. Lampidis, T. J.; Kolonias, D.; Podona, T.; Israel, M.; Safa, A. R.; Lothstein, L.; Savaraj, N.; Tapiero, H.; Priebe, W. Biochemistry, 1997, 36, 2679
87. Ishikawa, T. Trends Biochem. Sci, 1992, 17, 463
88. Zaman, G. J. R.; Lankelma, J.; van Tellingen, O.; Beijnen, J.; Dekker, H.; Paulusma, C.; Oude Elferink, R. P. J.; Baas, F.; Borst, P. Proc. Natl. Acad. Sci., 1995, 92, 7690.
89. Kasahara, K ; Fujiwara, Y.; Sugimoto, Y.; Nishio, K.; Tamura, T.; Matsuda, T.; Saijo, N J. Natl. Cancer Inst., 1992, 84, 113.
90. Cole, S. P. C.; Chanda, E. R.; Dicke, F. P.; Gerlach, J. H., Mirski, S. E L Cancer Res., 1991, 51, 3345.
91. Deffie, A. M.; Batra, J. K.; Goldenberg, G J. Cancer Res., 1989, 49, 58
92. Withoff, S.; Keith, W N.; Knol, A. J.; Coutts, J. C.; Hoare, S. F.; Mulder, N H.; de Vries, E G. E. Br. J. Cancer, 1996, 74, 502.
93. De Isabella, P ; Capranico, G.; Binaschi, M.; Tinelli, S.; Zunino, F. Mol. Pharmacol., 1990, 57, 11.
94. Feldhoff, P. W.; Mirski, S. E. L.; Cole, S P. C.; Sullivan, D. M. Cancer Res., 1994, 54, 756.
95. Goldenberg, G. J.; Wang, H.; Blair, G. W. Cancer Res., 1986, 46, 2978.
96. Capranico, G.; Riva, A.; Tinelli, S.; Dasdia, T.; Zunino, F. Cancer Res , 1987, 47, 3752.
97. Meijer, C.; Mulder, N H ; Timmer-Bosscha, H.; Zijlstra, J. G ; de Vries, E. G E. Cancer Res., 1987, 47, 4613
98. Zijlstra, J. G.; de Vries, E. G. E , Mulder, N. H. Cancer Res., 1987, 47, 1780
99. Zwelling, L A ; Slovak, M. L ; Doroshow, J. H ; Hinds, M.; Chan, D.; Parker, E.; Mayes, J.; Sie, K L ; Meltzer, P. S.; Trent, J. M. J. Natl Cancer Inst , 1990, 82, 1553.
100. Cole, S. P. C.; Dowries, H. F ; Mirski, S. E L ; Clements, D J Mol. Pharmacol., 1998, 37, 192.
101. Deffie, A. M.; Alam, T ; Seneviratne, C.; Beenken, S. W.; Batra, J. K.; Shea, T. C.; Henner, W. D.; Goldenberg, G. J. Cancer Res., 1988, 48, 3595.
102. Efferth, T.; Mattern, J.; Volm, M Oncol , 1992, 49, 368.
103. Dusre, L ; Mimnaugh, E. G.; Myers, C. E.; Sinha, B K. Cancer Res., 1989, 49, 511
104. Deffie, A. M.; Bosman, D. J.; Goldenberg, G. J. Cancer Res., 1989, 49, 6879.
105. Bugg, B. Y.; Danks, M. K ; Beck, W. T.; Suttle, D. P Proc. Natl. Acad. Sci., 1991, 88, 7654.
106. DeVore, R. F.; Corbett, A. H.; Osheroff, N. Cancer Res , 1992, 52, 2156.
107. Batist, G.; Tulpule, A.; Sinha, B. K.; Katki, A. G.; Myers, C. E , Cowan, K. H. J Biol. Chem., 1986, 261, 15.
108. Sinha, B. K.; Katki, A. G.; Batist, G.; Cowan, K. H.; Myers, C. E Biochem. Pharmacol., 1987, 36, 793
109. Kramer, R. A.; Zakher, J.; Kim, G. Science, 1988, 241, 694.
110. Kuo, M T.; Bao, J.; Furuichi, M., Yamane, Y.; Gomi, A.; Savaraj, N.; Masuzawa, T ; Ishikawa, T. Biochem Pharmacol., 1998, 55, 605.
111. Armstrong, R. N. Chem Res. Toxicol., 1997, 10, 2.
112. Meister, A. J. Biol. Chem., 1988, 263, 17205.
113. Kuo, M. T.; Bao, J ; Curley, S. A.; Ikeguchi, M ; Johnston, D. A.; Ishikawa, T. Cancer Res., 1996, 56, 3642.
114. Michiels, C.; Raes, M., Toussaint, O., Remacle, J Free Rad. Biol. Med , 1994, 17, 235.
115. Sinha, B K.; Kati, A. G.; Batist, G.; Cowan, K. H.; Myers, C. E Biochemistry, 1987, 26, 3776.
116. Kessel, D ; Wilberding, C. Cancer Res., 1985, 45, 1687