Dications that target the DNA minor groove: Compound design and preparation, DNA interactions, cellular distribution and biological activity

Current Medicinal Chemistry - Anti-Cancer Agents

Volumn 5, Issue 4, 2005, Pages 389-408

  Wilson, W David ^a   Nguyen, Binh ^a   Tanious, Farial A ^a   Mathis, Amanda ^b   Hall, James Edwin ^b   Stephens, Chad E ^a   Boykin, David W ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

Antiparasitic drugs; Antiparasitic mechanism of action; DNA minor groove; DNA drug complexes; Drug uptake and distribution; Drug prodrug design and synthesis; Kinetoplast

Indexed keywords

2,5 BIS(4 AMIDINOPHENYL)FURAN; 6 [5 (4 AMIDINOPHENYL)FURAN 2 YL]NICOTINAMIDINE; ANTIPARASITIC AGENT; BENZIMIDAZOLE DERIVATIVE; BUTAMIDINE; CARBAMIC ACID DERIVATIVE; CGP 40215A; DB 1005; DB 1008; DB 1010; DB 289; DB 290; DB 293; DB 377; DB 512; DB 555; DB 596; DB 818; DB 820; DB 821; DB 844; DIAMIDINE DERIVATIVE; DIMINAZENE ACETURATE; DNA; FURAMIDINE; N METHOXY 6 [5 [4 (N METHOXYAMIDINO)PHENYL]FURAN 2 YL]NICOTINAMIDINE; PENTAMIDINE; PRODRUG; PROPAMIDINE; THIOPENE; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CELLULAR DISTRIBUTION; CLINICAL TRIAL; DNA BINDING; DNA SEQUENCE; DRUG DESIGN; DRUG EFFICACY; DRUG MECHANISM; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; IN VITRO STUDY; IN VIVO STUDY; KINETOPLAST; LEISHMANIA; LEISHMANIASIS; NONHUMAN; SIDE EFFECT; TRYPANOSOMA; TRYPANOSOMIASIS;

ANIMALS; ANTIPARASITIC AGENTS; DISEASE; DNA; DRUG DESIGN; HUMANS; PHARMACEUTICAL PREPARATIONS;

EID: 22144474782     PISSN: 15680118     EISSN: None     Source Type: Journal    
DOI: 10.2174/1568011054222319     Document Type: Article

References (91)

1. Ehrlich, P., "Partial Cell Functions" Nobel Lectures, Physiology or Medicine 1901-1921, Elsevier Publishing Company, Amsterdam, 1967.
2. Watkins, B.M. Trends Parasitology, 2003, 19, 477.
3. World Health Organization (WHO) Research Results: Nos. 1, 6. and 7; African trypanosomiasis; Fact Sheet Number 259; World Health Organization Publications: Geneva, 2001.
4. American Association of Blood Banks, Oct. 10, 2003.
5. Barrett, M.P.; Burchmore, R.J.S.; Stich, A.; Lazzari, J.O.; Frasch, A.C.; Cazzulo, J.J.; Krishna, S. The Lancet, 2003, 36, 469.
6. Bouteille, B.; Oukem, O.; Bisser, S.; Dumas, M. "Treatment perspectives for human African trypanosomiasis" Blackwell Publishing Fundamental & Clinical Pharmacology, 2003, 17, pp. 171-181.
7. Bakhsi, R.P.; Shapiro, T.A. Mini Reviews in Medicinal Chemistry, 2003, 3, 597.
8. Bray, P.G.; Barrett, M. P.; Ward, S.A.; de Koning, H.P. Trends Parasitology, 2003, 19, 232.
9. Tidwell, R.R., Boykin, W.D. In DNA and RNA Binders: from Small Molecules to Drugs; Demeunynck, M., Bailly, C., Wilson, W.D., Eds.; Wiley-VCH, 2003; Vol. 2, Chapter 16, pp. 414-460.
10. Matovu, E.; Stewart, M.L.; Geiser, F.; Brun, R.; Maser, P.; Wallace, L.J.M.; Burchmore, R.J.; Enyaru, J.C.K.; Barrett, M.P.; Kaminsky, R.; Seebeck, T., de Koning, H.P. Eukaryotic Cell, 2003, 2, 1003.
11. Carter, N.S.; Berger, B.J.; Fairlamb, A.H. J. Biol. Chem., 1995, 270, 28153.
12. Ismail, M.; Brun, R.; Tanious, F.; Wilson, W.D.; Boykin, D.W. J. Med. Chem., 2003, 46, 4761.
13. Fairlamb, A.H. Trends in Parasitology, 2003, 19, 488.
14. Wilson, W.D.; Tanious, F.A.; Buczak, H.; Venkatramanan, M.K.; Das, B.P.; Boykin, D.W. The Jerusalem Symposia on Quantum Chemistry and Biochemistry Pulman, B. and Jortner, J. eds; Kluwer Academic Publishers, 1990; 23, pp. 331-353.
15. Docampo and Moreno, Parasitology Today, 1999, 15, 11, 443.
16. Docampo and Moreno, Molecular and Biochemical Parasitology, 2001, 33, 151.
17. Ruiz, F.A.; Rodrigues, C.O.; Docampo, R.J. J. Biol. Chem., 2001, 276, 26114.
18. Allan, R.A.; Miller, J.J. Can. J. Microbiol, 1980, 26, 912.
19. Ruiz, F.A.; Marchesini, N.; Seufferheld, M.; Govindjee; Docampo, R. J. Biol. Chem., 2001, 276, 46196.
20. Shapiro, T.A.; Englund, P.T. Annu. Rev. Microbiol., 1995, 49, 117.
21. Klingbeil, M.M.; Drew, M.E.; Liu, Y.; Morris, J.C.; Motyka, S.A; Saxowsky, T.T.; Wang, Z.; Englund, P.T. The Protist, 2001, 152, 255.
22. Simpson, L. Int. Rev. Cytol., 1986, 99, 119.
23. Estévez, A.M.; Simpson, L. Gene, 1999, 240, 247.
24. Madison-Antenucci, S.; Grams, J.; Hajduk, S.L. Cell, 2002, 108, 435.
25. Marini, J.C.; Levene, S.D.; Crothers, D.M.; Englund, P. T. Cold Spring Harbor Symposium Quant. Biol. 1983, 47, 279.
26. Marini, J.C.; Effron, P.N.; Goodman, T.C.; Singleton, C.K.; Wells, R.D.; Wartell, R.M.; Englund, P.T. J Biol Chem., 1984, 259, 8974.
27. Mallena, S.; Lee, M. P.; Bailly, C.; Neidle, S.; Kumar, A.; Boykin, D. W.; Wilson, W. D. J. Am. Chem. Soc., 2004, 126, 13659.
28. Wang, Z.; Englund, P. T. EMBO J., 2001, 4674.
29. Bodley, A.L. and Shapiro, T.A. Proc. Natl. Acad. Sci. USA, 1995, 92, 3726.
30. Bodley, A.L.; Cumming, J.N.; Shapiro, T.A. Biochem. Pharmacol., 1998, 55, 709.
31. Agbe, A.; Yielding, K.L. J. Parasitol, 1995, 6, 968.
32. Schnaufer, A.; Domingo, G.J.; Stuart, K. International Journal for Parasitology; 2002, 32, 1071.
33. Basselin, M.; Denise, H.; Coombs, G.H.; Barrett, M.P. Antimicrobial Agents Chemo., 2002, 46, 3731.
34. Schnaufer, A.; Panigrahi, A.K.; Panicucci, B.; Igo, R.P. Jr.; Wirtz, E.; Salavati, R.; Stuart, K. Science, 2001, 291, 2159.
35. Wilson, W.D. In DNA and Aspects of Molecular Biology; First ed.; Kool, E.T., Ed.; Elsevier Science Ltd., 1999, Vol. 7, pp. 427-476.
36. Neidle, S. Nat. Prod. Rep., 2001, 18, 291.
37. Reddy, B.S.; Sondhi, S. M.; Lown, J. W. Pharmacol. Ther., 1999, 84, 1.
38. Geierstanger, B.H.; Wemmer, D.E. Annu. Rev. Biophys. Biomol. Struct., 1995, 4, 63.
39. Rezler, E. M.; Bearss, D. J.; Hurley, L. H. Annu. Rev. Pharmacol. Toxicol., 2002, 43, 359.
40. Turner, P.R.; Denny, W.A. Curr. Drug Targets, 2000, 1, 1.
41. Hamelberg, D.; Williams, L.D.; Wilson, W.D. J. Am. Chem. Soc., 2001, 123, 7745.
42. Bloomfield, V.A.; Crothers, D.M.; Ignacio Tinoco, J. Nucleic Acids: Structures, Properties, and Functions; University Science Books: Sausalito, CA, 2000.
43. Laughton, C.A.; Tanious, F.; Nunn, C.M.; Boykin, D.W.; Wilson, W. D.; Neidle, S. Biochemistry, 1996, 35, 5655.
44. Das, B.P.; Boykin, D.W. J. Med. Chem., 1976, 20, 531.
45. Boykin, D. W.; Kumar, A.; Bender, B. K.; Hall, J. E; Tidwell, R.R., Bioorganic Med. Chem. Letters, 1996, 6, 3017.
46. Bajic, M.; Kumar, A.; Boykin, D.W. Heterocyclic Comm., 1996, 2, 135.
47. Kumar, A.; Stephens, C.E.; Boykin, D.W. Heterocyclic Comm., 1999, 5, 301.
48. Nguyen, B.; Tardy, C.; Bailly, C.; Colson, P.; Houssier, C.; Kumar, A.; Boykin, D. W.; Wilson, W.D. Biopolymers, 2002, 63, 281.
49. Easterbrook, J. D.; Hall, J. E; Jones, S. K.; Tidwell, R.R.; Tanious, F. A.; Wilson, W. D.; Francesconi; I.; Kumar, A.; Boykin, D. W.; Brun, R. manuscript in preparation.
50. Chaires, J.B.; Ren, J.; Hamelberg, D.; Kumar, A.; Pandya, V.; Boykin, D.W.; Wilson, W.D. J. Med. Chem., 2004, 47, 5729.
51. Edwards, K.J.; Jenkins, T.C.; Neidle, S. Biochemistry, 1992, 31, 7104.
52. Nunn, C.M.; Neidle, S. J. Med. Chem., 1995, 33, 2317.
53. Cory, M.; Tidwell, R.R.; Fairley, T.A. J. Med Chem., 1992, 35, 431.
54. Donkor, I.; Huang, T.L.; Tao, B.; Rattendi, D.; Lane, S.; Vargas, M.; Goldberg, B.; Bacchi, C. J. Med. Chem., 2003, 46, 1041.
55. Brun, R.; Buhler, Y.; Sandmeier, U.; Kaminsky, R.; Bacchi, C.J.; Rattendi, D.; Lane, S.; Croft, S.L.; Snowdon, D.; Yardley, V.; Caravatti, G.; Frei, J.; Stanek, J.; Mett, H. Antimicrob. Agents Chemother., 1996, 40, 1442.
56. Nguyen, B.; Lee, M.P.; Hamelberg, D.; Joubert, A.; Bailly, C.; Brun, R.; Neidle, S.; Wilson, W.D. J. Am. Chem. Soc., 2002, 124, 13680.
57. Stanek, J.; Caravatti, G.; Capraro, H.-G.; Furet, P.; Mett, H.; Schneider, P.; Regenass, U. J. Med. Chem., 1993, 36, 46.
58. Nguyen, B.; Hamelberg, D.; Bailly, C.; Colson, P.; Stanek, J.; Brun, R.; Neidle, S.; Wilson, W.D. Biophys. J., 2004, 86, 1028.
59. Fairley, T.A.; Tidwell, R.R.; Donkor, I.; Naiman, N.A.; Ohemeng, K.A.; Lombardy, R.J.; Bentley, J.A.; Cory, M. J. Med. Chem., 1993, 36, 1746.
60. Czarny, A.; Boykin, D.W.; Wood, A.A.; Nunn, C.M.; Neidle, S.; Zhao, M.; Wilson, W.D. J. Am. Chem. Soc., 1995, 117, 4716.
61. Tanious F. A.; Hamelberg, D.; Bailly, C.; Czarny, A.; Boykin, D.W.; Wilson, D.W., J. Am. Chem. Soc., 2004, 126, 143.
62. Wang, L.; Bailly, C.; Kumar, A.; Ding, D.; Bajic, M.; Boykin, D.W.; Wilson, W.D. Proc. Natl. Acad. Sci. U.S.A., 2000, 97, 12.
63. Wang, L.; Carrasco, C.; Kumar, A.; Stephens, C.E.; Bailly, C.; Boykin, D.W.; Wilson, W.D. Biochemistry, 2001, 40, 2511.
64. Bundgaard, H. In Design of Prodrugs; Bundgaard, H.; Ed.; Elsevier: Amsterdam, The Netherlands, 1985, pp. 1-92.
65. Bundgaard, H. In A Textbook of Drug Design and Development, Krogsgaard-Larsen, P.; Bundgaard, H; Ed.; Harwood Academic Publ: Switzerland, 1991, pp. 113-191.
66. Oszczapowicz, J. In The Chemistry of Amidines and Imidates; S. Patai Ed.; John Wiley & Sons: Chichester, 1991, Vol. 2 pp. 623-688.
67. Friis, G.J.; Bundgaard, H. In A Textbook of Drug Design and Development, second ed., Krogsgaard-Larsen, P.; Liljefors, T.; Madsen, U.; Ed.; Overseas Pub: Amsterdam, The Netherlands, 1996, pp. 351-385.
68. Digenis, G.A.; J.V. Swintosky, J.V. Drug latentiation, Handbook of Experimental Pharmacology, 1975, 28, pp. 86-112.
69. Sinkula, A.A.; Yalkowsky, A. J. Pharm. Sci., 1975, 64, 181.
70. Pitman, I.H. Med. Res. Rev., 1981, 1, 189.
71. Bundgaard, H.; Nielsen, N.M. J. Med Chem., 1987, 30, 451.
72. Ettamayer, P.; Amidon, G.L.; Clement, B.; Testa, B. J. Med. Chem., 2004, 47, 2393.
73. Weller, T.; Alieg, L.; Beresini, M.; Blackburn, B.; Bunting, S.; Hadvary, P.; Muller, M.H.; Knopp, D.; Levet-Trafit, B.; Lipari, M.T.; Modi, N.B.; Muller.; Refino, C.J.; Schmitt, M.; Schonholzer, P.; Weiss, S.; Steiner, B. J. Med. Chem., 1996, 39, 3139.
74. Shahrokh, Z.; Lee, E.; Olivero, A.G.; Matamoros, R.A.; Roborage, K.D.; Lee, A.; Weise, K.J.; Blackburn, B.K.; Powell, M.F. Pharm. Res., 1998, 15, 434.
75. Clement, B; Immel, M.; Terlinden, R.; Wingen, F.J.; Arch. Pharm., 1992, 325, 61.
76. Hall, J.E.; Kerrigan, J.E.; Ramachandran, K.; Bender, B.C.; Stanko, J.P.; Jones, S.K.; Patrick, D.A.; Tidwell, R. R. Antimicro. Agents Chemother., 1998, 42, 666.
77. Ansede, J. H.; Anbazhagan, M.; Brun, R.; Easterbrook, J.; Hall, J E. J. Med Chem., 2004, 47, 4335.
78. Zhou, L.;Voyksner, R.D.; Thakker, D.R.;Stephens, C.E.; Anbazhagan, M.; Boykin, D.W.; Hall, J.E.; Tidwell, R.R. J. Mass Spec., 2004, 39, 351.
79. Saulter, J.; Boykin, D.W.; Kalvass, J.; Tidwell, R.R.; Hall, J.E. Drug Metab. Rev., 2003, 35, 185.
80. Ansede, J.H.; Voyksner, R.D.; Ismail, M.A.; Boykin, D.W.; Tidwell, R.R.; Hall, J. E. unpublished results.
81. Rahmathullah, S.M.; Hall, J. E.; Bender, B.C.; McCurdy, D.R.; Tidwell, R.R.; Boykin, D.W. J. Med Chem., 1999, 42, 3994.
82. Eloy, F.; Lenaers, R. Chem. Rev., 1962, 62, 155.
83. Anbazhagan, M.; Boykin, D. W. Heterocyclic Comm., 2003, 9, 117.
84. Beltrao, T. M.; Srivastava, R. M. An Acad. Brasi. Cinc., 1978, 50, 159.
85. Incles, C.M.; Schultes, C.M.; Neidle, S. Curr Opin Investig Drugs, 2003, 4, 675.
86. Rezler, E.M.; Bearss, D.J.; Hurley, L.H. Annu. Rev. Pharmacol. Toxicol., 2003, 43, 359.
87. Alberti, P.; Lacroix, L.; Guittat, L., Hélène, C.; Mergny, J.L. Mini. Rev. Med. Chem. 2003, 3, 23.
88. Gowan, S.M.; Heald, R.; Stevens, M.F.; Kelland, L.R. Mol. Pharmacol., 2001, 60, 981.
89. Seenisamy, J.; Rezler, E.M.; Powell, T.J.; Tye, D.; Gokhale, V.; Joshi, C.S.; Siddiqui-Jain, A.; Hurley, L.H. J. Am. Chem. Soc. 2004, 126, 8702.
90. Horn, D. Curr. Mol. Med. 2004, 4, 563.
91. Rudenko G. Biochem. Soc. Trans. 2000, 28, 536.