New developments in the use of nitrogen mustard alkylating agents as anticancer drugs

Advances in DNA Sequence-Specific Agents

Volumn 3, Issue C, 1998, Pages 157-178

  Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957073295     PISSN: 1067568X     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1067-568X(98)80008-X     Document Type: Article

References (120)

1. Hansson J., Lewensohn R., Ringborg U., and Nilsson B. Cancer Res. 47 (1987) 2631
2. Peiper R.O., Futscher B.W., and Erickson L.C. Carcinogenesis 10 (1989) 1307
3. Niculescu-Duvaz I., Baracu I., and Balaban A.T. In: Wilman D.E.V. (Ed). Chemistry of Antitumour Agents (1989), Blackie, London 63
4. Wilman D.E.V., and Connors T.A. In: Neidle S., and Waring M.J. (Eds). Molecular Aspects of Anticancer Drug Action (1983), Macmillan, London 233
5. Kohn K.W., Hartley J.A., and Mattes W.B. Nucleic Acids Res. 15 (1987) 10531
6. Pullman A., and Pullman B. Quart. Rev. Biophys. 14 (1981) 289
7. Prakash A.S., Denny W.A., Gourdie T.A., Valu K.K., Woodgate P.D., and Wakelin L.P.G. Biochemistry 29 (1990) 9799
8. Osborne M.R., Wilman D.E.V., and Lawley P.D. Chem. Res. Tox. 8 (1995) 316
9. Osborne M.R., and Lawley P.D. Chem.-Biol. Int. 89 (1993) 49
10. Wang P., Bauer G.B., Kellogg G.E., Abraham D.J., and Povirk L.F. Mutagenesis 9 (1994) 133
11. Brookes P., and Lawley P.D. J. Chem. Soc. (1961) 3923
12. Lawley P.D., and Brookes P. J. Mol. Biol. 25 (1967) 143
13. Millard J.T., Raucher S., and Hopkins P.B. J. Am. Chem. Soc. 112 (1990) 2459
14. Bardos T.J., Datta-Gupta N., Hebborn P., and Triggle D.J. J. Med. Chem. 8 (1965) 167
15. O'Connor C.J., Denny W.A., Fan J.-Y., Gravatt G.L., Grigor B.A., and McLennan D.J. J. Chem. Soc. Perkin Trans. 2 (1991) 1933
16. Panthananickal A., Hansch C., Leo A., and Quinn F.R. J. Med. Chem. 21 (1978) 16
17. Palmer B.D., Wilson W.R., Pullen S.M., and Denny W.A. J. Med. Chem. 33 (1990) 112
18. Wang A.L., and Tew K.D. Cancer Treatment Repts. 69 (1985) 677
19. Suzukake K., Vistica B.P., and Vistica D.T. Biochem. Pharmacol. 32 (1983) 165
20. Brendel M., and Ruhland A. Mutation Res. 133 (1984) 51
21. Denny W.A. Anti-Cancer Drug Des. 4 (1989) 241
22. Gourdie T.A., Valu K.K., Gravatt G.L., Boritzki T.J., Baguley B.C., Wilson W.R., Woodgate P.D., and Denny W.A. J. Med. Chem. 33 (1990) 1177
23. Mattes W.B., Hartley J.A., and Kohn K.W. Nucleic Acids Res. 14 (1986) 2971
24. Hurley L.H., Lee C.-S., McGovren J.P., Warpehoski M.A., Mitchell M.A., Kelly R.C., and Aristoff P.A. Biochemistry 27 (1988) 3886
25. Scudder S.A., Brown J.M., and Sikic I.B. J. Natl. Cancer Inst. 80 (1988) 1294
26. Creech H.J., Preston R.K., Peck R.M., O'Connell A.S., and Ames B.N. J. Med. Chem. 15 (1972) 739
27. Preston R.K., Peck R.M., Breuninger E., Miller A.J., and Creech H.J. J. Med. Chem. 7 (1964) 471
28. Denny W.A., Baguley B.C., Cain B.F., and Waring M.J. Antitumour acridines. In: Neidle S., and Waring M.J. (Eds). Molecular Aspects of Anticancer Drug Action (1983), Macmillan, London 1
29. Ferguson L.R., and Denny W.A. Mutat. Res. 258 (1991) 123
30. Valu K.K., Gourdie T.A., Gravatt G.L., Boritzki T.J., Woodgate P.D., Baguley B.C., and Denny W.A. J. Med. Chem. 33 (1990) 3014
31. Koyama M., Kelly T.R., and Wanatabe K.A. J. Med. Chem. 31 (1988) 284
32. Koyama M., Takahashi K., Chou T.-C., Darzynkiewicz Z., Kapuscinski J., Kelly T.R., and Wanatabe K.A. J. Med. Chem. 32 (1989) 1594
33. O'Connor C.J., Denny W.A., Gamage R.S.K., and Fan J.-Y. Chem.-Biol. Int. 85 (1992) 1
34. Ferguson L.R., Turner P.M., Gourdie T.A., Valu K.K., and Denny W.A. Mutat. Res. 215 (1989) 213
35. Kohn K.W., Orr A., O'Connor P.M., Guziec L.J., and Guziec F.S. J. Med. Chem. 37 (1994) 67
36. Fleming G.F., Ratain M.J., O'Brien S.M., Schilsky R.I., Hoffman P.C., Richards J.M., Vogelzang M.J., Kasunic D.A., and Earhart R.H. J. Natl. Cancer Inst. 86 (1994) 368
37. Li L.H., DeKoning T.F., Kelly R.C., Krueger W.C., McGovren J.P., Padbury G.E., Petzold G.L., Wallace T.L., Ouding R.J., Prairie M.D., and Gebhard I. Cancer Res. 52 (1992) 4904
38. Kopka M.L., Yoon C., Goodsell D., Pjura P., and Dickerson R.E. Proc. Natl. Acad. Sci. USA 82 (1985) 1376
39. Pelton J.G., and Wemmer D.E. J. Am. Chem. Soc. 112 (1990) 1393
40. Baker B.F., and Dervan P.B. J. Am. Chem. Soc. 107 (1985) 8266
41. Krowicki K., Balzarini J., De Clercq E., Newnan R.A., and Lown J.W. J. Med. Chem. 31 (1988) 341
42. Arcamone F.M., Animati F., Barbieri B., Configliacchi E., D'Alessio R., Geroni C., Giuliani F.C., Lazzari E., Menozzi M., Mongelli N., Penco S., and Verini M.A. J. Med. Chem. 32 (1989) 774
43. Broggini M., Coley H.M., Mongelli N., Pesenti E., Wyatt M.D., Hartley J.A., and D'Incalci M. Nucleic Acids Res. 23 (1995) 81
44. Broggini M., Erba E., Ponti M., Ballinari D., Geroni C., Spreafico F., and D'Incalci M. Cancer Res. 51 (1991) 199
45. Lee M., Rhodes A.L., Wyatt M.D., D'Incalci M., Forrow S., and Hartley J.A. J. Med. Chem. 36 (1993) 863
46. Lee M., Rhodes A.L., Wyatt M.D., Forrow S., and Hartley J.A. Anti-Cancer Drug Des. 8 (1992) 173
47. Hartley J.A., Wyatt M.D., Garbiras B.J., Richter C., and Lee M. Biorg. Med. Chem. Lett. 4 (1994) 2412
48. Pjura P.E., Grzeskowiak K., and Dickerson R.E. J. Mol. Biol. 197 (1987) 257
49. Teng M., Usman N., Frederick C.A., and Wang A.H.-J. Nucleic Acids Res. 16 (1988) 2671
50. Carrondo M., Coll M., Ayami J., Wang A.H.-J., van der Marel G.A., van Boom J.H., and Rich A. Biochemistry 28 (1989) 7849
51. Patel S.K., Kvols L.K., Rubin J., O'Connell M.J., Edmonson J.H., Ames M.M., and Kovach J.S. Invest. New Drugs 9 (1991) 53
52. Gravatt G.L., Baguley B.C., Wilson W.R., and Denny W.A. J. Med. Chem. 37 (1994) 4338
53. Denny W.A., Atwell G.J., Baguley B.C., and Cain B.F. J. Med. Chem. 22 (1979) 134
54. Leupin W., Chazin W.J., Hyberts S., Denny W.A., Stewart G.M., and Wuthrich K. Biochemistry 25 (1986) 5902
55. Chen S.M., Leupin W., Rance M., and Chazin W.J. Biochemistry 31 (1992) 4406
56. Gao Y.-G., Siriram M., Denny W.A., and Wang H.-J. Biochemistry 32 (1993) 9639
57. O'Connor C.J., Denny W.A., and Fan J.-Y. Chem-Biol. Int. 77 (1991) 223
58. Gravatt G.L., Baguley B.C., Wilson W.R., and Denny W.A. J. Med. Chem. 34 (1991) 1552
59. Oettgen H.F., Clifford P., and Burchenal J.H. Cancer Treatment Repts. 27 (1953) 45
60. Cain B.F., Atwell G.J., and Seelye R.N. J. Med. Chem. 12 (1969) 199
61. Braithwaite A.W., and Baguley B.C. Biochemistry 19 (1980) 1101
62. Prakash A.S., Valu K.K., Wakelin L.P.G., Woodgate P.D., and Denny W.A. Anti-Cancer Drug Des. 6 (1991) 195
63. Atwell G.J., Yaghi B.M., Turner P.R., Boyd M., O'Connor C.J., Ferguson L.R., Baguley B.C., and Denny W.A. Bioorg. Med. Chem. 6 (1995) 679
64. Denny W.A. Curr. Pharmaceut. Des. 2 (1996) 281
65. Vaupel P., Kallinowski F., and Okunieff P. Cancer Res. 49 (1989) 6449
66. Urtasun R.C., Chapman J.D., Raleigh J.A., Franko A.J., and Koch C.J. Int. J. Radiat. Oncol. Biol. Phys. 12 (1986) 1263
67. Coleman C.N. J. Natl. Cancer Inst. 80 (1988) 310
68. Chaplin D.J., Olive P.L., and Durand R.E. Cancer Res. 47 (1987) 597
69. Jain R.K. J. Natl. Cancer Inst. 81 (1989) 570
70. Durand R.E. J. Natl. Cancer Inst. 81 (1989) 146
71. Tannock I.F., and Rotin D. Cancer Res. 49 (1989) 4373
72. Tannock I.F. Br. J. Cancer 22 (1968) 258
73. Denny W.A., and Wilson W.R. J. Med. Chem. 29 (1986) 879
74. Wilson W.R. In: Waring M.J., and Ponder B.A.J. (Eds). Cancer Biology and Medicine (1992), Kluwer Academic, London 87
75. Denny W.A., Wilson W.R., and Hay M.P. Br. J. Cancer 74 Suppl. XXVII (1996) 32
76. Denny W.A., and Wilson W.R. Cancer. Met. Rev. 12 (1993) 135
77. Alston T.A., Porter D.J.T., and Bright H.J. Acc. Chem. Res. 16 (1983) 418
78. Palmer B.D., Wilson W.R., Cliffe S., and Denny W.A. J. Med. Chem. 35 (1992) 3214
79. Palmer B.D., Wilson W.R., Atwell G.J., Schultz D., Xu X.Z., and Denny W.A. J. Med. Chem. 217 (1994) 537
80. Stratford I.J., Williamson C., Hoe S., and Adams G.E. Radiation Res. 88 (1981) 502
81. Palmer B.D., Wilson W.R., Anderson R.F., Boyd M., and Denny W.A. J. Med. Chem. 39 (1996) 2518
82. Atwell G.J., Sykes B.M., O'Connor C.J., and Denny W.A. J. Med. Chem. 37 (1994) 371
83. Sykes B.M., Atwell G.J., Denny W.A., McLennan D.J., and O'Connor C.J. J. Chem. Soc. Perkin, Trans. 2 (1995) 337
84. Firestone A., Mulcahy R.T., and Borch R.F. J. Med. Chem. 34 (1991) 2933
85. Tercel M., Wilson W.R., and Denny W.A. J. Med. Chem. 36 (1993) 2578
86. Tercel M., Wilson W.R., Anderson R.F., and Denny W.A. J. Med. Chem. 39 (1996) 1084
87. Stock L.M., and Wasielewski M.R. J. Am. Chem. Soc. 97 (1975) 5620
88. Moreno S.N.J., Schreiber J., and Mason R.P. J. Biol. Chem. 261 (1986) 7811
89. Denny W.A., Wilson W.R., Tercel M., Van Zijl P., and Pullen S.M. Int. J. Radiat. Biol. Oncol. Phys. 29 (1994) 317
90. Norris R.K., Barker S.D., and Neta P. J. Am. Chem. Soc. 106 (1984) 3140
91. Ware D.C., Wilson W.R., Denny W.A., and Rickard C.E.F. J. Chem. Soc. Chem. Comm. (1991) 1171
92. Ware D.C., Palmer B.D., Wilson W.R., and Denny W.A. J. Med. Chem. 36 (1993) 1839
93. Anderson R.F., Denny W.A., Ware D.C., and Wilson W.R. Br. J. Cancer 74 Suppl. XXVII (1996) 48
94. Atwood J.D. Inorganic and Organometallic Reaction Mechanisms (1985), Brooks/Cole, Lancaster 87
95. (Supplement 1972). Perrin D.D. Dissociation Constants of Organic Bases in Aqueous Solution (1965), Butterworths, Monterey, CA
96. Wilson W.R., van Zijl P., and Denny W.A. Int. J. Radiat. Oncol. Biol. Phys. 22 (1992) 693
97. Patterson L.H. Cancer Met. Rev. 12 (1993) 119
98. White I.N.H., Suzanger M., Mattocks A.R., Bailey E., Farmer P.B., and Connors T.A. Carcinogenesis 10 (1991) 2113
99. Mann J., and Shervington L.A. J. Chem. Soc., Perkin Trans. 1 (1991) 2961
100. Kirkpatrick D.L., Schroeder H.L., and Chandler K.J. Anti-Cancer Drugs 5 (1994) 467
101. Tercel M., Wilson W.R., and Denny W.A. J. Med. Chem. 38 (1995) 1247
102. Bagshawe K.D. Anal. Proc. 27 (1990) 5
103. Pastan I., Chaudhary V., and FitzGerald D.J. Annu. Rev. Biochem. 61 (1992) 331
104. Pietersz G.A., and Krauer K. J. Drug Targeting 2 (1994) 183
105. Melton R.G., and Sherwood R.F. J. Natl. Cancer Inst. 88 (1996) 153
106. Hay M.P., and Denny W.A. Drugs of the Future 21 (1996) 917
107. Springer C.J., Bagshawe K.D., Searle F., Bisset G.M.F., and Jarman M. J. Med. Chem. 33 (1990) 677
108. Dowell R.I., Springer C.J., Davies D.H., Hadley E.M., Burke P.J., Boyle F.T., Melton R.G., Connors T.A., Blakey D.C., and Mauger A.B. J. Med. Chem. 39 (1996) 1100
109. Springer C.J., and Niculescu-Duvaz I. Anti-Cancer Drug Des. 10 (1995) 361
110. Bagshawe K.D., Sharma S.K., Springer C.J., and Rogers G.T. Annals Oncol. 5 (1994) 879
111. Vrudhula V.M., Svensson H.P., Kennedy K.A., Senter P.D., and Wallace P.M. Bioconj. Chem. 4 (1993) 334
112. Alexander R.P., Beeley N.R.A., Driscoll M., ONeill F.P., Millican T.A., Pratt A.J., and Willenbrock F.W. Tetrahedron Lett. 32 (1991) 3269
113. Vivekananda M.V., Senter P.D., Fischer K.J., and Wallace P.M. J. Med. Chem. 36 (1993) 919
114. Smyth M.J., Pietersz G.A., and McKenzie I.F.C. Cancer Res. 47 (1987) 62
115. Wang S.-M., Chern J.-W., Yeh M.-Y., Ng J.C., Tung E., and Roffler S.R. Cancer Res. 52 (1992) 4484
116. Michael N.P., Brehm J.K., Anlezark G.M., and Minton N.P. FEMS Microbiol. Lett. 124 (1994) 195
117. Mauger A.B., Burke P.J., Somani H.H., Friedlos F., and Knox R.J. J. Med. Chem. 37 (1994) 3452
118. Knox R.J., Friedlos F., Sherwood R.F., Melton R.G., and Anlezark G.M. Biochem. Pharmacol. 44 (1992) 2297
119. Anlezark G.M., Melton R.G., Sherwood R.F., Knox R.J., Friedlos F., Wilson W.R., Denny W.A., and Palmer B.D. Biochem. Pharmacol. 50 (1995) 609
120. Atwell G.J., Boyd M., Palmer B.D., Anderson R.F., Pullen S.M., Wilson W.R., and Denny W.A. Anti-Cancer Drug Des. 11 (1996) 553