Observations on the covalent cross-linking of the binding domain (BD) of the High Mobility Group I/Y (HMG I/Y) proteins to DNA by FR66979

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 6, 2000, Pages 1331-1342

  Rajski, Scott R ^a   Williams, Robert M ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA BINDING PROTEIN; FR 66979; MITOMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CROSS LINKING; DNA BINDING; PROTEIN CROSS LINKING;

AMINO ACID MOTIFS; AMINO ACID SEQUENCE; ANTIBIOTICS, ANTINEOPLASTIC; BASE SEQUENCE; BINDING SITES; CROSS-LINKING REAGENTS; DNA; HIGH MOBILITY GROUP PROTEINS; HMGA1A PROTEIN; MODELS, MOLECULAR; OXAZINES; PROTEIN BINDING; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRANSCRIPTION FACTORS;

EID: 0034053625     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00078-X     Document Type: Article

References (78)

1. Lawley P.D. Bioessays. 17:1995;561.
2. Paustenbach D.J., Finley B.L., Kacew S. Proc. Soc. Exp. Biol. Med. 211:1996;211.
3. Rajski S.R., Williams R.M. Chem. Rev. 98:1998;2723.
4. Bridgewater L.C., Manning F.C.R., Patierno S.R. Carcinogenesis. 15:1994;2421.
5. (a) Sancar, A. Annu. Rev. Biochem. 1996, 65, 43.
6. (b) Lawley, P. D.; Lethbridge, J. H.; Edwards, P. A.; Shooter, K. V. J. Mol. Biol. 1969, 39, 181.
7. (a) Iwami, M.; Kiyoto, S.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiotics 1987, 40, 589.
8. (b) Kiyoto, S.; Shibata, T.; Yamashita, M.; Komori, T.; Okuhara, M.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiotics, 1987, 40, 594.
9. (c) Uchida, I.; Takase, S.; Kayakiri, H.; Kiyoto, S.; Hashimoto, M.; Tada, T.; Koda, S.; Morimoto, Y. J. Am. Chem. Soc. 1987, 109, 4108.
10. (a) Shimomura, K.; Hirai, O.; Mizota, T.; Matsumoto, S.; Mori, J.; Shibayama, F.; Kikuchi, H. J. Antibiotics, 1987, 40, 600.
11. (b) Hirai, O.; Shimomura, K.; Mizota, T.; Matsumoto, S.; Mori, J.; Kikuchi, H. J. Antibiotics 1987, 40, 607.
12. (c) Masuda, K.; Makamura, T.; Shimomura, K.; Shibata, T.; Terano, H.; Kohsaka, M. J. Antibiotics 1988, 41, 1497.
13. (d) Masuda, K.; Nakamura, T.; Mizota, T.; Mori, J.; Shimomura, K. Cancer Res. l988, 48, 5l72.
14. Terano H., Takase S., Hosoda J., Kohsaka M. J. Antibiotics. 42:1989;145.
15. (a) Shimomura, K.; Manda, T.; Mukumoto, S.; Masuda, K.; Nakamura, T.; Mizota, T.; Matsumoto, S.; Nishigaki, F.; Oku, T.; Mori, J.; Shibayama, F. Cancer Res. 1988, 48, 1166.
16. (b) Nakamura, T.; Masuda, K.; Matsumoto, S.; Oku, T.; Manda, T.; Mori, J.; Shimomura, K. Japan. J. Pharmacol. 1989, 49, 317.
17. (a) Naoe, Y.; Inami, M.; Matsumoto, S.; Nishigaki, F.; Tsujimoto, S.; Kawamura, I.; Miyayasu, K.; Manda, T.; Shimomura, K. Cancer Chemother. Pharmacol. 1998, 42, 31.
18. (b) Naoe, Y.; Inami, M.; Kawamura, I.; Nishigaki, F.; Tsujimoto, S.; Matsumoto, S.; Manda, T.; Shimomura, K. Jpn. J. Cancer Res. 1998, 89, 666.
19. (c) Naoe, Y.; Inami, M.; Takagaki, S.; Matsumoto, S.; Kawamura, I.; Nishigaki, F.; Tsujimoto, S.; Manda, T.; Shimomura, K. Jpn. J. Cancer Res. 1998, 89, 1047.
20. (d) Naoe, Y.; Inami, M.; Matsumoto, S.; Takagaki, S.; Fujiwara, T.; Yamazaki, S.; Kawamura, I.; Nishigaki, F.; Tsujimoto, S.; Manda, T.; Shimomura, K. Jpn. J. Cancer Res. 1998, 89, 1306.
21. (e) Naoe, Y.; Kawamura, I.; Inami, M.; Matsumoto, S.; Nishigaki, F.; Tsujimoto, S.; Manda, T.; Shimomura, K. Jpn. J. Cancer Res. 1998, 89, 1318. For recent results of the Phase I clinical trials of FK317, see:
22. (f) Furuse, K.; Hasegawa, K.; Kudo, S.; Niitaru, H. Proc. Am. Soc. Clin. Oncol., 1999, 18, 179a. (abstract #689).
23. (g) Ravandi, F.; Wenske, C.; Royca, M.; Hoff, P.; Brito, R.; Zukowski, T.; Mekki, Q.; Pazdur, R. Proc. Am. Soc. Clin. Oncol. 1999, 18, 225a, (abstract #867).
24. (a) Tomasz, M; Lipman, R.; Chowdary, D.; Pawlak, J.; Verdine, G.; Nakanishi, K. Science, 1987, 235, 1204;
25. (b) Tomasz, M. Chem. Biol. 1995, 2, 575 and references cited therein.
26. (a) Iyengar, B. S.; Door, R. T.; Remers, W. A.; Kowal, C. D. J. Med. Chem. 1988, 31, 1579.
27. (b) Remers, W. A.,; Rao, S. N.; Wunz, T. P.; Kollman, P. A. J. Med. Chem. 1988, 31, 1612.
28. (c) Iyengar, B. S.; Remers, W. A.; Catino, J. J. J. Med. Chem. 1989, 32, 1866.
29. (d) E. O.; Verboom, W.; Scheltinga, M. W.; Reinhoudt, D. N.; Lelieveld, P.; Fiebig, H. H.; Winterhalter, B. R.; Double, J. A.; Bibby, M. C. J. Med. Chem. 1989, 32, 1612.
30. (e) Tomasz, M.; Lipman, R.; Snyder, J. K.; Nakanishi, K. J. Am. Chem. Soc. 1983, 105, 2059.
31. (f) Tomasz, M.; Lipman, R.; Verdine, G.; Nakanishi, K. Biochemistry, 1986, 25, 4337.
32. (g) Verdine, G. L.; McGuinness, B. F.; Nakanishi, K.; Tomasz, M. Heterocycles, 1987, 25, 577.
33. (h) McGuinness, B.; Nakanishi, K.; Lipman, R.; Tomasz, M. Tetrahedron Lett. 1988, 29, 4673.
34. (i) Hashimoto, Y.; Shudo, K.; Okamoto, T. Tetrahedron Lett. 1982, 23, 677.
35. (j) Zein, N.; Kohn, H. J. Am. Chem. Soc. 1987, 109, 1576;
36. (k) Zein, N.; Kohn, H. J. Am. Chem. Soc. 1986, 108, 296.
37. (l) Egbertson, M.; Danishefsky, S. J. J. Am. Chem. Soc. 1987, 109, 2204.
38. (m) Kohn, H.; Hong, Y. P. J. Am. Chem. Soc. 1990, 112, 4596.
39. (n) Millard, J. T.; Weidner, M. F.; Raucher, S.; Hopkins, P. B. J. Am. Chem. Soc. 1990, 112, 3637.
40. (o) Sartorelli, A. C.; Pristos, C. A. Cancer Research, 1986, 46, 3528.
41. (a) Williams, R. M.; Rajski, S. R. Tetrahedron Lett. 1992, 33, 2929.
42. (b) Williams, R. M.; Rajski, S. R. Tetrahedron Lett. 1993, 34, 7023.
43. (c) Huang, H.; Rajski, S. R.; Williams, R. M.; Hopkins, P. B. Tetrahedron Lett. 1994, 35, 9669.
44. (a). Huang, H.; Pratum, T. K.; Hopkins, P. B. J. Am. Chem. Soc. 1994, 116, 2703.
45. (b) Woo, J.; Sigurdsson, S. Th.; Hopkins, P. B. J. Am. Chem. Soc. 1993, 115, 1199.
46. (c) Paz, M. M.; Hopkins, P. B. Tetrahedron Lett. 1997, 38, 343;
47. (d) Paz, M. M.; Hopkins, P. B. J. Am. Chem. Soc. 1997, 119, 5999.
48. Williams R.M., Rajski S.R., Rollins S.B. Chem. Biol. 4:1997;127.
49. Kim H.Y., Stermitz F.R., Coulombe R.A. Carcinogenesis. 16:1995;2691.
50. For excellent reviews see: (a) Pabo, C. O.; Sauer, R. T. Ann. Rev. Biochem. 1992, 61, 1053.
51. (b) Takeda, Y.; Ohlendorf, D. H.; Anderson, W. F.; Matthews, B. W. Science, 1983, 221, 1020.
52. (c) Travers, A. Annu. Rev. Biochem. 1989, 58, 427.
53. (d) Seeman, N. C.; Rosemberg, J. M.; Rich, A. Proc. Natl. Acad. Sci. USA 1976, 73, 804.
54. (a) Neidle, S. O. FEBS 1992, 298, 97.
55. (b) Turnell, W. G.; Satchwell, S. C.; Travers, A. A. FEBS, 1988, 232, 263.
56. Eckner R., Birnstiel M.L. Nucleic Acids Research. 17:1989;5947.
57. (a) Reeves, R.; Nissen, M. S. J. Biol. Chem. 1990, 265, 8573.
58. (b) Reeves, R.; Langan, T. A.; Nissen, M. S. Proc. Nat. Acad. Sci. USA 1991, 88, 1671.
59. Grosschedl, R.; Giese, K.; Pagel, J. Trends Genetics, 1994, 10, 94.
60. (a) Du, W.; Thanos, D.; Maniatis, T. Cell, 1993, 74, 887.
61. (b) Thanos, D.; Maniatis, T. Cell, 1992, 71, 777.
62. Siino J.S., Nissen M.S., Reeves R. Biochem. Biophys. Res. Comm. 207:1995;497.
63. Evans J.N.S., Zajicek J., Nissen M.S., Munske G., Smith V., Reeves R. Int. J. Peptide Protein Res. 45:1995;554.
64. Reeves R., Wolffe A.P. Biochemistry. 35:1996;5063.
65. Geierstanger B.H., Volkman B.F., Kremer W., Wemmer D.E. Biochemistry. 33:1994;5347.
66. For additional citations petinent to Asx turns see: (a) Imperiali, B.; Spencer, J. R.; Struthers, M. D. J. Am. Chem. Soc. 1994, 116, 8424.
67. (b) Abbadi, A.; Mcharfi, M.; Premilat, S.; Boussard, G.; Marraud, M. J. Am. Chem. Soc. 1991, 113, 2729.
68. (c) Aubry, A.; Abbadi, A.; Boussard, G.; Marraud, M. New Journal of Chemistry 1987, 11, 739.
69. For a preliminary account of this work, see: Rajski, S. R.; Rollins, S. B.; Williams, R. M. J. Am. Chem. Soc. 1998, 120, 2192.
70. Of particular interest, is the recent report by Lippard on the cisplatin-HMG1-DNA cross-link: (a) Kane, S. A.; Lippard, S. J. Biochemistry 1996, 35, 2180.
71. (b) Sancar, A.; Hearst, J. H.; Sastry, S. S.; Spielmann, P. H.; Hoang, Q. S. Biochemistry 1993, 32, 5526.
72. (c) Farrell, N.; Appleton, T. G.; Qu, Y.; Roberts, J. D.; Soares-Fontes, A. P.; Skov, K. A.; Wu, P.; Zou, Y. Biochemistry 1995, 34, 15480.
73. Huth J.R., Bewley C.A., Nissen M.S., Evans J.N.S., Reeves R., Gronenborn A.M., Clore G.M. Nature Struct. Biol. 4:1997;657.
74. Coordinates for the PRGRP fragment of HMG I/Y bound to the recognition sequence 5'-AATT-3' were courtesy of Professor D. Wemmer (UC Berkeley).
75. It should be noted that addition of a 2% Triton X-100 aqueous solution to the reactions did not significantly improve the recovery of radiolabeled DNA-protein adducts.
76. The susceptibility towards β-elimination of the peptidic Schiff base formed with apurinic sites upon digestion with piperidine is supported by: (a) Singh, M. P.; Hill, C. G.; Peoc'h, D.; Rayner, B.; Imbach, J. L.; Lown, W. J. Biochemistry 1994, 33, 10271; and
77. (b) Bailly, V.; Verly, W. G. Biochem. J. 1988, 253, 553.
78. Borer, P. N. Handb. Biochem. Mol. Biology. CRC Press, 1975.