A novel class of achiral seco-analogs of CC-1065 and the duocarmycins: Design, synthesis, DNA binding, and anticancer properties

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 23, 2004, Pages 6221-6236

  Kupchinsky, Stanley ^a   Centioni, Sara ^a   Howard, Tiffany ^a   Trzupek, John ^a   Roller, Shane ^a   Carnahan, Virginia ^a   Townes, Heather ^a   Purnell, Bethany ^a   Price, Carly ^a   Handl, Heather ^a   Summerville, Kaitlin ^a   Johnson, Kimberly ^a   Toth, James ^a   Hudson, Stephen ^a   Kiakos, Konstantinos ^b   Hartley, John A ^b   Lee, Moses ^a  

^a FURMAN UNIVERSITY   (United States)

^b ROYAL FREE HOSPITAL   (United Kingdom)

Author keywords

CC 1065; Cytotoxicity; DNA alkylation; Duocarmycins; Sequence specificity

Indexed keywords

4 (2 BROMOETHYL) 3 (5,6,7 TRIMETHOXYINDOLE 2 CARBOXAMINO)PHENOL; 4 (2 BROMOETHYL) 3 [5 (5 BENZOFURAN 2 CARBOXAMIDO)INDOLE 2 CARBOXAMIDO]PHENOL; 4 (2 CHLOROETHYL) 3 (2 METHOXYCINNAMOYLAMIDO)PHENOL; 4 (2 CHLOROETHYL) 3 (2,6 DIMETHOXY 5 PYRIDYL)ETHEN 1 YLCARBOXAMIDOPHENOL; 4 (2 CHLOROETHYL) 3 (3 METHOXYCINNAMOYLAMIDO)PHENOL; 4 (2 CHLOROETHYL) 3 (4 METHOXYCINNAMOYLAMIDO)PHENOL; 4 (2 CHLOROETHYL) 3 (5 METHOXYINDOLE 2 CARBOXAMINO)PHENOL; 4 (2 CHLOROETHYL) 3 (5,6,7 TRIMETHOXYINDOLE 2 CARBOXAMINO)PHENOL; 4 (2 CHLOROETHYL) 3 (6 METHOXY 5 PYRIDYL)ETHEN 1 YLCARBOXAMIDOPHENOL; 4 (2 CHLOROETHYL) 3 [2 [4 N,N (DIETHYL)AMINOPHENYL]BENZIMIDAZOLE 6 CARBOXAMIDO]PHENOL; 4 (2 CHLOROETHYL) 3 [5 (5 BENZOFURAN 2 CARBOXAMIDO)INDOLE 2 CARBOXAMIDO]PHENOL; 4 (2 CHLOROETHYL) 3 [[5 [4 BIS(2 CHLOROETHY)AMINO]BENZAMIDO]INDOLE 2 CARBOXAMIDO]PHENOL; 4 (2 IODOETHYL) 3 (5,6,7 TRIMETHOXYINDOLE 2 CARBOXAMINO)PHENOL; ADOZELESIN; ANTINEOPLASTIC AGENT; BENZIMIDAZOLE; DUOCARMYCIN DERIVATIVE; HALIDE; HYDROCHLORIC ACID; INDOLE; N [2 (2 BROMOETHYL) 4 HYDROXYPHENYL] 1 METHYL 4 (1 METHYL 4 BUTANAMIDOPYRROLE 2 CARBOXAMIDO)PYRROLE 2 CARBOXAMIDE; PLASMID DNA; PYRIDINE DERIVATIVE; PYRROLE; RACHELMYCIN; RACHELMYCIN DERIVATIVE; TAQ POLYMERASE; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BONE MARROW CELL; CANCER CELL CULTURE; CANCER CENTER; CELL GROWTH; CHIRALITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DNA CLEAVAGE; DRUG ACTIVITY; DRUG DESIGN; DRUG DNA BINDING; DRUG DOSE REDUCTION; DRUG POTENCY; DRUG SCREENING; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; FLOW CYTOMETRY; HUMAN; HUMAN CELL; HYPOTHESIS; IC 50; IN VITRO STUDY; IN VIVO STUDY; MELANOMA; MOUSE; NONHUMAN; PHARMACOPHORE; PLASMID; SCORING SYSTEM; SOLID TUMOR; STRUCTURE ACTIVITY RELATION; THERMAL ANALYSIS; TUMOR GROWTH; WEIGHT REDUCTION;

ANIMALS; ANTINEOPLASTIC AGENTS; BINDING SITES; CELL LINE, TUMOR; CELL PROLIFERATION; DNA; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; HUMANS; INDOLES; INHIBITORY CONCENTRATION 50; MELANOMA, EXPERIMENTAL; MICE; MICE, SCID; PYRROLIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSPLANTATION, HETEROLOGOUS;

ANIMALIA; MINK CELL FOCUS-FORMING VIRUS; MURINAE; PUFFINUS AURICULARIS;

EID: 7444267815     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.08.051     Document Type: Article

References (69)

1. G.B. Jones M. Palumbo Advances in DNA Sequence Specific Agents Vol. 3 1998 JAI Greenwich, CT
2. F.M. Arcamone, F. Animati, B. Barbieri, E. Confligliacchi, R. D'Alessio, C. Geroni, F.C. Giuliani, E. Lazzari, M. Menozzi, N. Mongelli, S. Penco, and M.A. Verini J. Med. Chem. 32 1989 774
3. L.H. Li, T.L. Wallace, T.F. DeKoning, M.A. Warpehoski, R.C. Kelly, M.D. Prairie, and W.C. Drueger Invest. New Drugs 5 1987 329
4. L.H. Li, R.C. Kelly, M.A. Warpehoski, J.P. McGovern, I. Gebhard, and T.F. DeKoning Invest. New Drugs 9 1991 137
5. M. Warpehoski L.H. Hurley Advances in DNA Sequence Specific Agents Vol. 1 1992 JAI Greenwich, CT 217 245
6. D.L. Boger, and D.S. Johnson Angew. Chem., Int. Ed. 35 1996 1438
7. D.L. Boger, and D.S. Johnson Proc. Natl. Acad. Sci. U.S.A. 92 1995 3642
8. D.L. Boger Acc. Chem. Res. 28 1995 20
9. D.L. Boger Chemtracts: Org. Chem. 4 1991 329
10. L.J. Hanka, A. Dietz, S.A. Gerpheide, S.L. Kuentzel, and D.G. Martin J. Antibiot. 31 1978 1211
11. J.P. McGovern, G.L. Clarke, E.A. Pratte, and T.F. DeKoning J. Antibiot. 37 1983 63
12. M.A. Warpehoski, J. Gebhard, R.C. Kelly, W.C. Krueger, L.H. Li, and J.P. McGovern J. Med. Chem. 31 1988 590
13. H. Ichimura, T. Ogawa, K. Takahashi, E. Kobayashi, I. Kawamoto, T. Yasuzawa, I. Takahashi, and H. Nakano J. Antibiot. 43 1990 1037
14. T. Yaszawa, Y. Saitoh, M. Ichimura, I. Takahashi, and H. Sano J. Antibiot. 44 1991 445
15. T. Yasuzawa, K. Muroi, M. Ichimura, I. Takahashi, T. Ogawa, K. Takahashi, H. Sano, and Y. Saitoh Chem. Pharm. Bull. 43 1995 378
16. M. Ichimura, T. Ogawa, K. Takahashi, A. Mihara, I. Takahashi, and H. Nakano Oncol. Res. 5 1993 165
17. K. Gomi, E. Kobayashi, K. Miyoshi, T. Ashizawa, A. Okamoto, T. Ogawa, S. Katsumata, A. Mihara, M. Okabe, and T. Hirata Jpn. J. Cancer Res. 83 1992 113
18. L.H. Hurley, V.S. Reynolds, D.H. Swenson, G.L. Petzold, and T.A. Scahill Science 226 1984 843
19. D.L. Boger, D.S. Johnson, and W. Yun J. Am. Chem. Soc. 116 1994 1635
20. V.L. Reynolds, I.J. Molineux, D.J. Kaplan, D.H. Swenson, and L.H. Hurley Biochemistry 24 1985 6228
21. D.L. Boger, J.A. McKie, N. Han, C.M. Tarbie, H.W. Riggs, and P.A. Kitos Bioorg. Med. Chem. Lett. 6 1996 659 and references cited therein
22. R.D. Hightower, B.U. Sevin, J.P. Pevras, M. Untch, R. Angioli, and H. Averette Gynecol. Oncol. 42 1992 186
23. S. Cote, and R.L. Momparler Anti-Cancer Drugs 4 1993 327
24. G.F. Fleming, S.M. Ratain, R.L. O'Brien, P.C. Schilsky, R. Ramos, J.M. Richards, N.J. Vogelzang, D.A. Kasunic, and R.H. Earhart J. Natl. Cancer Inst. 86 1994 368
25. B.J. Foster, P.M. Larusso, E. Poplin, M. Zalupski, M. Valdivieso, A. Wozniak, L. Flaherty, D.A. Kasunic, R.H. Earhart, and L.H. Baker Invest. New Drugs 13 1996 321
26. H. Burris, R. Earhart, J. Kuhn, D. Shaffer, L. Smith, G. Weiss, D. Kusanic, G. Radbury, L. Campbell, and D. Von Hoff Proc. Am. Assoc. Cancer Res. 33 1992 265
27. H.A. Burris, V.C. Dleras, M. Tunca, R.H. Earhart, J.R. Eckardt, G.I. Rodriguez, D.S. Shaffer, S.M. Fields, E. Campbell, L. Scaaf, D. Kasunic, and D.D. Von Hoff Anti-cancer Drugs 8 1997 588
28. B.J. Foster, P.M. LoRusso, E. Poplin, M. Zalupski, M. Valdivieso, A. Wozniak, L. Flaherty, D.A. Kasunic, R.H. Earhart, and L.H. Baker Invest. New Drugs 13 1996 321
29. L.H. Li, J.F. Dekoning, R.C. Kelly, W.C. Krueger, J.P. McGovern, G.E. Padbury, G.L. Petzold, T.L. Wallace, R.J. Ouding, M.D. Praire, and I. Gebhard Cancer Res. 52 1992 4904
30. O. van Telligen, C.J.A. Punt, A. Awada, D.J.T. Wagener, M.J. Piccart, Y. Groot, L.J. Scaaf, R.E.C. Henrar, W.J. Nooijen, and J.H. Beijnen Cancer Chemother. Pharmacol. 41 1998 377
31. D.L. Walker, F.M. Reid, and M.M. Ames Cancer Chemother. Pharmacol. 34 1994 317
32. D.A. Volpe, J.E. Tomaszewski, R.E. Parchment, A. Garg, K.P. Flora, M.J. Murphy, and C.K. Grieshaber Cancer. Chemother. Pharmacol. 39 1996 143
33. H.C. Pitot IV, C. Erlichman, J.M. Reid, J.A. Sloan, M.M. Ames, P.G. Bagniewski, P. Atherton-Skaff, A.A. Adjei, J. Rubin, D. Rayson, and R.M. Goldberg Proc. Am. Assoc. Cancer Res. 40 1999 91
34. S. Nagamura, E. Kobayashi, K. Gomi, and H. Saito Bioorg. Med. Chem. Lett. 6 1996 2147 and references cited therein
35. S.R. Alberts, C. Erlichman, J.M. Reid, M.M. Ames, J.A. Sloan, and R.L. Richardson Proc. Am. Assoc. Cancer Res. 37 1996 393
36. J.L. Abbruzzese, T. Madden, and R.A. Newman Proc. Am. Assoc. Cancer Res. 37 1996 165
37. H. Niitani, N. Horikoshi, K. Hasegawa, M. Fukuoka, S. Kudoh, and M. Hino Proc. Am. Assoc. Cancer Res. 36 1995 243
38. A. Asai, S. Nagamura, E. Kobayashi, K. Gomi, and H. Saito Bioorg. Med. Chem. Lett. 9 1999 2995
39. D.L. Boger, and J.A. McKie J. Org. Chem. 60 1995 1271
40. D.L. Boger, W. Yun, and N. Han Bioorg. Med. Chem. 3 1995 1429
41. P.A. Aristoff, and P.D. Johnson J. Org. Chem. 57 1992 6234
42. P.G. Baraldi, B. Cacciari, M.J. Pinedo de las Infantas, R. Romagnoli, G. Spatullo, P. Cozzi, and N. Mongelli Anti-Cancer Drug Design 12 1997 67
43. F. Mohamadi, M.M. Spees, G.S. Staten, P. Marder, J.K. Kipka, and D.A. Johnson J. Med. Chem. 37 1994 232
44. D.L. Boger, S.A. Munk, H. Zarrinmayeh, T. Ishizaki, J. Haught, and M. Bina Tetrahedron 47 1991 2661
45. D.L. Boger, T. Ishizaki, H. Zarrinmayeh, S.A. Munk, P.A. Kitos, and O. Suntorwart J. Am. Chem. Soc. 112 1990 8961
46. T.T. Howard, B.M. Lingerfelt, B.L. Purnell, A.E. Scott, C.A. Price, H.M. Townes, L. McNulty, H.L. Handl, K. Summerville, S.J. Hudson, P.J. Bowen, K. Kiakos, J.A. Hartley, and M. Lee Bioorg. Med. Chem. 10 2002 2941
47. D.L. Boger, and M.S.S. Palanki J. Am. Chem. Soc. 114 1992 9318
48. D.L. Boger, D.S. Johnson, M.S.S. Palanki, P.A. Kitos, J. Chang, and P. Dowell Bioorg. Med. Chem. 1 1993 27
49. T.A. Bryson, and G.A. Roth Tetrahedron Lett. 29 1988 2197
50. R.H. White, P.G. Parsons, A.S. Prakash, and D.J. Young Bioorg. Med. Chem. Lett. 5 1995 1869
51. R. Baird, and S. Winstein J. Am. Chem. Soc. 85 1963 567
52. N. Amishiro, S. Nagamura, C. Murakata, A. Okamoto, E. Kobayashi, M. Asada, K. Gomi, T. Tamaoki, M. Okabe, N. Yamaguchi, K. Yamaguchi, and H. Saito Bioorg. Med. Chem. 8 2000 381
53. S.Y. Breusegem, R.M. Clegg, and F.G. Loontiens J. Mol. Biol. 315 2002 1049
54. S. Neidle Nat. Prod. Rep. 18 2001 291
55. M. Ponti, S.M. Forrow, R.L. Souhami, M. D'Incalci, and J.A. Hartley Nucl. Acids Res. 19 1991 2929
56. L.H. Hurley, and P.H. Draves S. Neidle M. Waring Molecular Aspects of Anticancer Drug-DNA Interactions Vol. 1 1993 CRC Press Boca Raton, FL 89 133
57. C.H. Lin, C.G. Hill, and L.H. Hurley Chem. Res. Toxicol. 5 1992 167
58. J. Carmichael, W.G. DeGraff, A.F. Gadzar, J.D. Minna, and J.B. Mitchell Cancer Res. 47 1987 936
59. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Visitica, J.T. Warren, S.K. Bokesch, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1107
60. D.L. Boger, and W. Yun J. Am. Chem. Soc. 116 1994 7996
61. G.J. Atwell, W.R. Wilson, and W.A. Denny Bioorg. Med. Chem. Lett. 1997 1493
62. S.A. Jennings, T.T. Howard, S.G. Roller, N. Brooks, C. O'Hare, K. Kiakos, J.A. Hartley, P.J. Burke, and M. Lee Heterocycl. Commun. 7 2002 7
63. R.B. Boyd Principles Practices Oncol. 3 1989 1
64. W. Wrasidlo, D.S. Johnson, and D.L. Boger Bioorg. Med. Chem. Lett. 4 1994 631
65. Y. Wang, H. Yuan, W. Ye, S.C. Wright, H. Wang, and J.W. Larrick J. Med. Chem. 43 2000 1541
66. T. Pecere, M.V. Gazzola, C. Mucignat, C. Parolin, F.D. Vecchia, A. Cavaggioni, G. Basso, A. Diaspro, B. Salvato, M. Carli, and G. Palu Cancer Res. 60 2000 2800
67. M.G. Hollingshead, M.C. Alley, R.F. Camalier, B.J. Abbott, J.G. Mayo, L. Malspeis, and M.R. Grever Life Sci. 57 1995 131
68. R.B. Boyd B. Teicher Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials, and Approval 1997 Humana Totowa, NJ 23 42
69. S.C. Stinson Chem. Eng. News June 2 1997 28