DNA complexing minor groove-binding ligands: Perspectives in antitumour and antimicrobial drug design

Current Medicinal Chemistry

Volumn 3, Issue 6, 1996, Pages 379-406

  Pindur, U ^a   Fischer, G ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL; ANTHRAMYCIN; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ANTITRYPANOSOMAL AGENT; BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; CALICHEAMICIN; CONGOCIDINE; DISTAMYCIN A; DISTAMYCIN A DERIVATIVE; DUOCARMYCIN A; HEDAMYCIN; HOE 33342; INTERCALATING AGENT; LEXITROPSIN; NEOTHRAMYCIN; NEOTHRAMYCIN A; PENTAMIDINE; PIBENZIMOL; PIPERAZINE; PLURAMYCIN; PROPAMIDINE; SIBIROMYCIN; TOMAYMYCIN;

BINDING SITE; CHEMICAL MODIFICATION; DNA SEQUENCE; DRUG DESIGN; DRUG DEVELOPMENT; DRUG DNA BINDING; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REVIEW; X RAY CRYSTALLOGRAPHY;

EID: 0030444841     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (146)

1. (a) Neidle, S.; Pearl, L.H.; Skelly, J.V. Biochem. J., 1987, 243, 1-13.
2. (b) Kopka, M.L.; Larsen, T.A. In Nucleic Acid Targeted Drug Design; C.L. Probst; T.J. Perun; M. Dekker, Eds., New York, 1992, pp. 303-374.
3. Neidle, S. In The Design of Drugs to Macromolecular Targets; C. R. Beddell, Ed.; John Wiley & Sons Ltd.: Chichester, 1992, pp. 173-210.
4. Lown, J.W., Ed., In Anthracycline and Anthracene-dione-based Anticancer Agents; Elsevier. Amsterdam, 1989.
5. Borowski, E.; Shugar, D. In Molecular Aspects of Chemotherapy; Pergamon Press. New York, 1991.
6. Bauch, H.-J. Medizin. Monatsschr. Pharm., 1989, 1, 8-45.
7. (a) Lerman, L S J. Mol. Biol., 1961, 3, 18-30.
8. (b) Lerman, L.S. Proc. Natl. Acad Sci. USA, 1963, 49, 94-102.
9. Hamilton, L. D.; Fuller, W.; Reich, E. Nature, 1963, 198, 538-540.
10. Dean, P.M. In Molecular Foundations of Drug-receptor Interaction; University Press: Cambridge, 1987, pp. 150-185.
11. Dervan, P.B. Science, 1986, 232, 464-471.
12. (a) Kennard, O.; Hunter, W.N. Angew. Chem., Int. Ed. Engl., 1991, 30, 1254-1279.
13. (b) Miller, K.J.; Pycior, J.F. Biopolymers, 1979, 18, 2683-2719.
14. (c) Miller, K.J.; Macrea, J.; Pycior, J.F. Biopolymers, 1980, 19, 2067-2089.
15. (a) Sobell, H.M. In Nucleic Acid Geometry and Dynamics; R.H. Sarma, Ed., Pergamon Press: New York, 1980; pp. 289-313.
16. (b) W. Saenger, In Principle of Nucleic Acid Structure, Springer Verlag: New York, 1984.
17. (a) Chandrasekaran, S.; Kusuma, S. Magn. Res. Chem., 1986, 24, 630-637.
18. (b) Feigon, J ; Denny, W.A ; Leupin, W.; Kearnes, D.R. J. Med. Chem., 1984, 27, 450-465.
19. (a) Tuite, E.; Kelly, J.M. Biopolymers, 1995, 35, 419-433.
20. (b) Suh, D.; Chaires, J.B. Biorg. & Med Chem., 1995, 3, 723-728.
21. Mauffret, O.; Rene, B.; Convert, O.; Monnot, M.; Lescot, E.; Fermandjian, S. Biopolymers, 1991, 31, 1325-1341.
22. Van Dyke, M.W., Hertzberg, R P.; Dervan, P.B. Proc. Natl. Acad. Sci. USA, 1982, 79, 5470-5474.
23. Drager, M.; Haber, M.; Erfanian-Abdoust, H.; Pindur, U.; Sattler, K. Monaten. Chem, 1993, 124, 559-576.
24. Pindur, U.; Rehn, C. Monatsh. Chem., 1996, 127, in press.
25. Pindur, U.; Rehn, C. Monatsh. Chem., 1996, 127, in press.
26. Pindur, U.; Haber, M.; Sattler, K. J. Chem. Educ., 1993, 70, 263-272.
27. (a) Pabo, C.O.; Sauer, R.T. Annu. Rev. Biochem., 1992, 61, 1953-1095.
28. (b) Suzuki, M. Structure, 1994, 2, 317-326.
29. Chen, Y.; Lown, J.W. J. Am. Chem. Soc., 1994, 116, 6995-7005.
30. Seeman, N.C.; Rosenberg, J.M.; Rich, A. Proc. Natl. Acad. Sci. USA, 1976, 73, 804-808.
31. Dickerson, R.E.; Kopka, M.L.; Pjura, P. Chemica Scripta, 1986, 26B, 139-145.
32. (a) Dickerson, R.E.; Kopka, M.L.; Pjura, P.E. In DNA Ligand Interactions; W. Guschlbauer; W. Saenger, Eds.; Plenum, 1987; pp. 45-62.
33. (b) Kopka, M.L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R.E. Natl. Acad. Sci., 1985, 82, 1376-1380.
34. (c) Kopka, M.L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R.E. In Technology Nucleic Acids; W. Saenger, Ed.; Springer Verlag: New York, 1989; Vol. VII/1b, pp. 277-348.
35. Chen, A.Y.; Yu, C.; Gatto, B.; Liu, L.F. Proc. Natl. Acad. Sci. USA, 1993, 90, 8131-8135.
36. Thrum, H. Naturwiss., 1959, 46, 87.
37. Arcamone, F.; Penco, S.; Orezzi, P.; Nicolella, V.; Pirelli, A. Nature, 1964, 203, 1064-1065.
38. Zimmer, C.; Wahnert, U. Progr. Biophys. Molec. Biol., 1986, 47, 31-112.
39. Kopka, M.L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R.E. J. Mol. Biol., 1985, 183, 553-556.
40. Kopka, M.L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R.E. Proc. Natl. Acad. Sci. USA, 1985, 82, 1376-1380.
41. Coll, M.; Frederick, C.A.; Wang, A.H.-J.; Rich, A. Proc. Natl. Acad. Sci. USA, 1987, 84, 8385-8389.
42. Coll, M.; Aymami, J.; van der Marel, G.A.; van Boom, J.H.; Rich, A.; Wang, A.H.-J. Biochemistry, 1989, 28, 310-320.
43. Patel, D.J. Proc. Natl. Acad. Sci. USA, 1982, 79, 6424-6428.
44. Patel, J.; Shapiro, L. J. Biol. Chem., 1986, 261, 1230-1240.
45. Gao, F.; Reynolds, CA.; Richards, W.G. Molec. Pharmacology, 1989, 35, 232-241. For a Molecular Modelling review of groovebinding drugs see also Neidle, S.; Pearl, L.M.; Skelly, J.V. Biochem. J., 1987b, 243, 1-13.
46. Gao, F.; Reynolds, CA.; Richards, W.G. Molec. Pharmacology, 1989, 35, 232-241. For a Molecular Modelling review of groovebinding drugs see also Neidle, S.; Pearl, L.M.; Skelly, J.V. Biochem. J., 1987b, 243, 1-13.
47. Gao, F.; Richards, W.G. Molec. Pharmacology, 1990, 37, 341-346.
48. Schultz, P.G.; Dervan, P.B. J. Biomol. Struct. Dyn , 1984, 1, 1133-1147.
49. Ward, B.; Rehfuss, R.; Goodisman, J.; Dabrowiak, J.C. Biochemistry, 1988, 27, 1198-1205.
50. Portugal, J.; Waring, M.J. Eur. J. Biochem., 1987, 167, 281-289.
51. Coll, M.; Frederick, C.A.; Wang, A.H.-J.; Rich, A. Proc. Natl. Acad. Sci. USA, 1987, 84, 8385-8389.
52. Klevit, R E.; Wemmer, D.E.; Reid, B.R. Biochemistry, 1986, 25, 3296-3303.
53. Pelton, J.G.; Wemmer, D.E. Biochemistry, 1988, 27, 8088-8096.
54. Pelton, J.G.; Wemmer, D.E. Proc. Natl. Acad. Sci. USA, 1989, 86, 5723-5727.
55. Pelton, J.G.; Wemmer, D.E. J. Am. Chem. Soc., 1930, 112, 1393-1399.
56. Sigurdsson, S.T ; Hopkins, P.B. Tetrahedron, 1994, 50, 12065-12084.
57. Bruice, T.C.; Mei, H.-Y., He, G.-X., Lopez, U. Proc. Natl. Acad. Sci USA, 1992, 89, 1700-.
58. He, G.-X.; Browne, K.A.; Groppe, J.C.; Blasko, A.; Mei, H.-Y ; Bruice, T.C. J. Am. Chem. Soc., 1993, 115, 7061-7071.
59. Browne, K.A.; He, G -X.; Bruice, T.C. J. Am. Chem. Soc., 1993, 115, 7072-7079.
60. Blasko, A.; Browne. K.A.; Bruice, T.C. J. Am. Chem. Soc., 1994, 116, 3726-3737.
61. Lee, M.; Shea, R.G.; Hartley, J.A., Kissinger, K ; Pon, R.T., Vesnaver, G.; Breslauer, K.J.; Dabrowniak, J.C.; Lown, J.W. J. Am. Chem. Soc., 1989, 111, 345-354.
62. Yamamoto, Y.; Cai, J.; Nakamura, H.; Sadayori, N.; Asao, N.; Nemoto, H. J. Org.Chem., 1995, 60, 3352-3357.
63. Chidester, C.G.; Krueger, W.C.; Mizsak, S.A.; Duchamp, D.J.; Martin, D.G. J. Am. Chem. Soc., 1981, 103, 7629-7635.
64. (a) Hurley, L H.; Draves, P.H. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S.; M. Waring, Eds.; CRC Press: Ann Arbor, MI, 1993; Vol. 1, pp. 89-.
65. (b) Warpehoski, M.A. In Advances in DNA Sequence Specific, Agents; L.H. Hurley, Ed.; JAI Press, Greenwich, CT, 1992; Vol. 1, pp.217-.
66. Boger, D.L. In Heterocycles in Bioorganic Chemistry; J. Bergman; H.C van der Plas; M. Simonyi, Eds.; Royal Society of Chemistry: Cambridge, 1991; pp. 103-129.
67. (a) Boger, D.L.; Johnson, D.S.; Yun, W.; Tarby, C.M. Bioorg. Med. Chem, 1994, 2, 115-.
68. (b) Boger, D.L.; Coleman, R.S.; Invergo, B.J.; Sakya, S.M.; Ishizaki, T.; Munk, S.A.; Zarrinmayeh, H ; Kitos, P.A.; Thompson, S.C. J. Am. Chem. Soc., 1990, 112, 4623-4632.
69. Ichimura,M ; Ogawa, T.; Takahashi, K.; Kobayashi, E.; Kawamoto, I.; Yasuzawa, T.; Takahashi, I ; Nakano, H. J. Antibiot, 1990, 43, 1037-.
70. Ichimura, M.; Ogawa, T.; Katsumata, S.; Takahashi, K.; Takahashi, I.; Nakano, H. J. Antibiot., 1991, 44, 1045-
71. Takahashi, I.; Takahashi, K.; Ichimura, M.; Morimoto, M.; Asano, K.; Kawamoto, I.; Tomita, F.; Nakano, H. J. Antibiot., 1988, 41, 1915-.
72. Yasuzawa, T.; Iida, T., Muroi, K.; Ichimura, M.; Takahashi, K ; Sano, H. Chem. Pharm. Bull., 1988, 36, 3728-.
73. (a) Nakano, H.; Takahashi, I.; Ichimura, M.; Kawamoto, I.; Asano, K.; Tomita, F.; Sano, H.; Yasuzawa, T.; Morimoto, M.; Fujimoto, K. PCT Int. Appl., 1987, WO87 06265.
74. (b) Nakano, H.; Takahashi, I.; Ichimura, M.; Kawamoto, I.; Asano, K.; Tomita, F.; Sano, H.; Yasuzawa, T.; Morimoto, M ; Fujimoto, K. Chem. Abstr., 1988, 108, 110858.
75. Ogawa, T.; Ichimura, M.; Katsumata, S.; Morimoto, M.; Takahashi, K. J. Antibiot., 1989, 42, 1299-.
76. (a) Ohba, K.; Watabe, H.; Sasaki, T.; Takeuchi, Y.; Kodama, Y.; Nakazawa, T.; Yamamoto, H.; Shomura, T.; Sezaki, M.; Kondo, S. J. Antibiot, 1988, 41, 1515-.
77. (b) Ishii, S.; Nagasawa, M.; Kariya, Y.; Yamamoto, H.; Inouye, S.; Kondo, S. J. Antibiot., 1989, 42, 1713-.
78. Boger, D.L. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press, Greenwich, CT, 1992, Vol. 2, pp. 1-.
79. (a) Boger, D.L. Acc. Chem Res., 1995, 28, 20-29.
80. (b) Boger, D.L ; Mesini, P. JACS, 1995, 117, 11647-11655.
81. (a) Boger, D.L.; Johnson, D.S.; Jun, W. J. Am. Chem. Soc , 1994, 116, 1635-1656.
82. (b) Boger, D.L.; Johnson, D.S. Proc. Natl. Acad Sci., 1995, 92, 3642-3649.
83. Kopka, M.L.; Yoon, C.; Goodsell, D ; Pjura, P.; Dickerson, R.E. J. Mol. Biol., 1985, 183, 553-556.
84. Kopka, M.L.; Yoon, C.; Goodsell, D.; Pjura, P ; Dickerson, R.E. Proc. Natl. Acad. Sci., 1981, 82, 7281-7284.
85. Lown, J.W.; Krowicki, K.; Bhat, U.G.; Skorobogaty, B.; Ward, B.; Dabrowiak, J.C. Biochemistry, 1986, 25, 7408-7416.
86. Lown, J.W.; Krowicki, K.; Balzarini, J.; De Clerq, E. J. Med. Chem., 1986, 29, 1210-1214.
87. Lown, J.W.; Krowicki, K. J. Org. Chem., 1985, 50, 3774-3779.
88. Krowicki, K ; Lee, M., Hartley, J.A.; Ward, B.; Kissinger, K.; Skorobogaty, A.; Dabrowiak, J.C.; Lown, J.W. Molecular recognition between oligopeptides and nucleic acids - Rational design of sequence specific DNA binding agents In Structure and Expression; R.H Sarma; M.H. Sarma, Eds.; Adenine Press: Schenectady, 1988; Vol. 2, pp. 251-271.
89. Lee, M ; Chang, D.-K ; Hartley, J.A.; Pon, R.T.; Krowicki, K.; Lown, J.W. Biochemistry, 1988, 27, 445-455.
90. Lee, M.; Krowicki, K.; Shea, R.G.; Lown, J.W.; Pon, R.T. J. Molec. Recog., 1989, 2, 84-95.
91. Bailly, C.; Houssin, R.; Bernier, J.-L.; Henichart, J.-P. Tetrahedron, 1988, 44, 5833-5843.
92. Loewe, H.; Urbanietz, J. Abstracts and Reviews of Eight International Congress on Tropical Medicine and Malaria, 139, Teheran, Iran, 1968.
93. Lammler, G.; Herzog, H.; Saupe, E.; Schutze, H.R. Bull. Wld. Hlth. Org., 1971, 44, 751-765.
94. Holmquist, G. Chomosoma, 1975, 49, 333-356.
95. Yamamoto, A.; Araki, T.; Fujimori, K.; Yamada, H.; Yamaguchi, H.; Izumi, K.; Matsumoto, K. Histochemisiry, 1989, 9265-9268.
96. Murray, V.; Martin, R.F. J. Mol. Biol, 1988, 203, 63-73.
97. Searle, M.S.; Embrey, K.J. Nucl. Acid. Res., 1990, 18, 3753-3762.
98. Pjura, P.E.; Grzeskowiak, K.; Dickerson, R.E. J. Mol. Biol., 1987, 197, 257-271.
99. Teng, M.-K.; Usman, N.; Frederick, C.A.; Wang, A.H.-J. Nucl. Acid. Res., 1988, 16, 2671-2690.
100. Quintana, J.R.; Lipanov, A.A; Dickerson, R.E. Biochemistry, 1991, 30, 10294-10306.
101. (a) de C.T. Carrondo, M.A.A F.; Coll, M.; Aymami, J.; Wang, A.H.-J.; van der Maral, G.A.; van Boom, J.H.; Rich, A. Biochemistry, 1989, 28, 7849-7659.
102. (b) Gravait, G.L.; Baguley, B.C.; Wilson, R.W.; Denny, W.A. J. Med. Chem., 1994, 37, 4338-4345.
103. Dann, O.; Bergen, G.; Demant, E.; Volz, G. Justus Liebigs Ann. Chem., 1971, 749, 68-89.
104. Chandra, P.; Mildner, B.; Dann, O.; Metz, A. Mol. Cel. Biochem., 1977, 18, 81-86.
105. Mildner, B.; Metz, A.; Chandra, P. Cancer Letters, 1978, 4, 89-98.
106. Kapuscinski, J.; Szer, W. Nucl. Acids Res., 1979, 6, 3519-3534.
107. Russel, W.; Newman, C.; Williamson, D.H. Nature, 1975, 253, 462-462.
108. Lin, M.S.; Comings, D.E.; Alli, O.S. Chromosoma, 1977, 60, 15-25.
109. Schweizer, D.; Ambros, P.; Andrle, M. Explt. Cell. Res., 1978, 111, 327-332.
110. Kapuscinski, J.; Yanagi, K. Nucl. Acids. Res., 1979, 6, 3535-3542.
111. Macera, M J.; Babu, A., Verma, R.S. Oncology, 1989, 46, 61-62.
112. Takahama, M.; Kagaya, A. J. Histochem. Cytochem., 1988, 36, 1061-1067.
113. Manzini, G ; Barcellona, M.L; Avitabile, M.; Quadrifoglio, F. Nucl. Acids Res., 1983, 11, 8861-8876.
114. Kubista, M.; Akerman, B.; Norden, B. Biochemistry, 1987, 26, 4545-4553.
115. Cavatorta, P.; Masotti, L.; Szabo, A.G. Biophys. Chem., 1985, 22, 11-16.
116. Larsen, T.; Goodsell, D.S.; Casclo, D.; Grzeskowiak, K.; Dickerson, R.E. J. Biomol. Struct Dyn., 1954, 7, 477-491.
117. Montgomery, A.B.; Luce, J.M.; Turner, J.; Lin, E.T; Debs, R.J.; Corkerey, K.J.; Brunette, E.N.; Hopewell, P.C. Lancet, 1987, ii, 480-481.
118. Nunn, C.M.; Neidle, S. J. Med. Chem., 1995, 38, 2317-2325.
119. (a) Edwards, K J., Brown, D.G , Spink, N.; Skelly, J.V.; Neidle, S. J. Mol. Biol., 1992, 226, 1161-1173.
120. (b) Nunn, C.M.; Jenkins, T.C.; Neidle, S. Biochemistry, 1993, 32, 13838-13943.
121. Fox, K.R.; Sanson, C.E.; Stevens, M.F.G. FEBS Letters, 1990, 266, 150-154.
122. Jensch, H. Arzneimittelforsch., 1955, 5, 634-635.
123. Newton, B.A.; Le Page, R.W.F. Proc. Biochem. Soc., 1967, 105, 50P.
124. (a) Newton, B.A. In Antibiotics; Springer: New York, 1975; Vol. 3, pp. 34-47.
125. (b) Festy, B.; Lallemant, A.M.; Riou, G.; Brack, C.; Delain, E. C. R., Acad Sci. Paris Ser., 1970, D271, 684-687.
126. Gresh, N.; Pullman, B. Molec. Pharmacol., 1984, 25, 452-458.
127. Brown, D.G ; Sanderson, M.R.; Skelly, J.V.; Jenkins, T.C.; Brown, T.; Garman, E.; Stewart, D.I.; Neidle, S. EMBO, 1990, 9, 1329-1334.
128. Yoshida, M.; Banville, D.C.; Shafer, R.H. Biochemistry, 1990, 29, 6589-6592.
129. Jenkins, T.C.; Hurley, L.H.; Neidle, S.; Thurston, D.E. J. Med. Chem., 1994, 37, 4529-4537
130. Dervan, P.B. Science, 1989, 232, 464-471.
131. Remers, W.A. In The Chemistry of Antitumour Antibiotics; Wiley: New York, 1988; Vol. 2, pp. 28-92.
132. (a) Hansen, M.; Hurley, L. J. Am. Chem. Soc., 1995, 117, 2421-2429.
133. (b) Hansen, M.; Hurley, L.H. Acc. Chem. Res. 1996, 29, 249-258.
134. Sun, D.; Hansen, M.; Clement, J.J.; Hurley, L.H. Biochemistry, 1993, 32, 8068-8074.
135. Sun, D.; Hansen, M.; Hurley, L.H. J. Am. Chem. Soc., 1995, 117, 2430-2440.
136. (a) Nicolaou, K.C.; Dai, W. Angew. Chem., Int. Ed. Engl., 1991, 30, 1387-1416.
137. (b) Borders, D.B.; Doyle, T.W. In Enediyne Antibiotics as Antitumour Agents; Dekker: New York, 1995.
138. Lee, M.D.; Ellestad, G.A.; Boders, D.B. Acc. Chem. Res., 1991, 24, 235-243.
139. Zein, N.; Sinha, A.M.; MacGabren, W.J.; Ellestad, G.A. Science, 1988, 240, 1198-1201.
140. De Voss, J.J.; Townsend, C.A.; Ding, W.D.; Morton, G.O.; Ellestad, G.A.; Zein, N.; Tabor, A.B.; Schreiber, S.L. J. Am. Chem. Soc., 1990, 112, 9669-9670.
141. Hangeland, J.J.; De Voss, J.J.; Health, J.A.; Townsend, C.A.; Ding, W.D.; Ashcroft, J.S.; Ellestad, G.A. J. Am. Chem. Soc., 1992, 114, 9200-9202.
142. Bergman ,R.G. Acc. Chem. Res., 1973, 6, 25-31.
143. Paloma, L.G.; Smith, J A ; Chazin, W.J.; Nicolaou, K.C. J. Am. Chem. Soc., 1994, 116, 3697-3708.
144. Ikemoto, N.; Kumar, R.A.; Dedon, P.C ; Danishefsky, S.J.; Patel, D.J. J. Am. Chem. Soc., 1994, 116, 9387-9388.
145. Toshima, K.; Ohta, K.; Takaaki, K.; Nakamura, T.; Nakata, M.; Kinoshita, M.; Matsumura, S.; Bioorg. & Med. Chemistry, 1996, 4, 105-113.
146. Moon, J.H.; Kim, S.K.; Sehlstedt, U.; Rodger, A ; Norden, B. Biopolymers, 1996, 38, 593-606.