Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 24, 2005, Pages 6718-6726

  Ismail, Mohamed A ^a   Batista Parra, Adalgisa ^a   Miao, Yi ^a   Wilson, W David ^a   Wenzler, Tanja ^b   Brun, Reto ^b   Boykin, David W ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3' AMIDINOBIPHENYL 4 YL) 1H BENZIMIDAZOL 5 AMIDINE ACETATE; 2 (4' AMIDINO 2' HYDROXYBIPHENYL 4 YL) 1H BENZIMIDAZOL 5 AMIDINE ACETATE; 2 (4' AMIDINO 2' METHYLBIPHENYL 4 YL) 1H BENZIMIDAZOL 5 AMIDINE ACETATE; 2 (4' AMIDINO 3 FLUOROBIPHENYL 4 YL) 1H BENZIMIDAZOL 5 AMIDINE ACETATE; 2 (4' AMIDINO 3' FLUOROBIPHENYL 4 YL) 1H BENZIMIDAZOL 5 AMIDINE ACETATE; 2 (4' AMIDINOBIPHENYL 4 YL) 1H BENZIMIDAZOL 5 AMIDINE; 2 [4 (5 AMIDINOPYRIDIN 2 YL)PHENYL] 1H BENZIMIDAZOL 5 AMIDINE ACETATE; 2 [4 (6 AMIDINOPYRIDINE 3 YL)PHENYL] 1H BENZIMIDAZOL 5 AMIDINE ACETATE; 3,4 DIAMINOBENZONITRILE; 4 BROMO 2 FLUOROBENZALDEHYDE; 4 CYANOPHENYLBORONIC ACID; ACETIC ACID; ALCOHOL; ALDEHYDE DERIVATIVE; ANTIPROTOZOAL AGENT; BENZIMIDAZOLE DERIVATIVE; BIS O ACETOXYAMIDOXIME; BORONIC ACID DERIVATIVE; DIAMIDINE DERIVATIVE; DNA; NITRILE; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

AFRICAN TRYPANOSOMIASIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; DISEASE MODEL; DNA BINDING; DRUG ACTIVITY; DRUG SYNTHESIS; DRUG TARGETING; GENE TARGETING; HYDROGENATION; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PLASMODIUM FALCIPARUM; POLYMERIZATION; SUZUKI REACTION; TRYPANOSOMA RHODESIENSE;

ANIMALS; ANTIPROTOZOAL AGENTS; BENZIMIDAZOLES; BIPHENYL COMPOUNDS; CATIONS, DIVALENT; DNA, PROTOZOAN; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE;

ANIMALIA; PLASMODIUM FALCIPARUM; TRYPANOSOMA BRUCEI RHODESIENSE;

EID: 27644499431     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.07.024     Document Type: Article

References (28)

1. R.R. Tidwell, and D.W. Boykin Dicationic DNA Minor Groove Binders as Antimicrobial Agents M. Demeunynck C. Bailly W.D. Wilson Small Molecule DNA and RNA Binders; From Synthesis to Nucleic Acid Complexes Vol. 2 2003 Wiley-VCH New York 414
2. W.D. Wilson, B. Nguyen, F.A. Tanious, A. Mathis, J.E. Hall, C.E. Stephens, and D.W. Boykin Dications that target the DNA minor groove: Compound design and preparation, DNA interactions, cellular distribution and biological activity Curr. Med. Chem. 5 2005 389
3. J.N. Ashley, H.J. Barber, A.J. Ewins, G. Newbery, and A.D.H. Self J. Chem. Soc. 1942 103
4. A.H. Fairlamb Trends Parasitol. 19 2003 488
5. B. Bouteille, O. Oukem, S. Bisser, and M. Dumas Fundam. Clin. Pharmacol. 17 2003 171
6. Yeramian, P. D.; Castagnini, L. A.; Allen, J. A.; Umesh, L.; Gotuzzo, E. Efficacy and Safety of DB289, A new oral drug for treatment of Pneumocystis carinii pneumonia (PCP) in AIDS patients. Presented at the 43rd Annual Interscience Conference on Antimicrobial Agents and Chemotherapy Meeting, September 14-17, 2003, Chicago, IL.
7. Yeramian, P.; Krudsood, S.; Chalermrut, K.; Silachamroon, U.; Allen, J.; Brun, R.; Meshnick, S.; Tidwell, R.; Looareesuwan, S. Efficacy of DB289 in acute uncomplicated P. falciparum/P. vivax malaria. Presented at the 52nd Annual Meeting of the American Society of Tropical Medicine and Hygiene, December 3-7, 2003, Philadelphia, PA.
8. C.C. Dykstra, D.R. McClernon, L.P. Elwell, and R.R. Tidwell Antimicrob. Agents Chemother. 38 1994 1890
9. C. Bailly, L. Dassonneville, C. Carrascol, D. Lucasl, A. Kumar, D.W. Boykin, and W.D. Wilson Anti-Cancer Drug Des. 14 1999 47
10. D.J. Fitzgerald, and J.N. Anderson J. Biol. Chem. 274 1999 27128
11. D. Henderson, and L.H. Hurley Nat. Med. 1 1995 525
12. E. Matovu, M.L. Stewart, F. Geiser, R. Brun, P. Maser, L.J.M. Wallace, R.J. Burchmore, J.C.K. Enyaru, M.P. Barrett, R. Kaminsky, T. Seebeck, and H.P. de Koning Eukaryot. Cell 2 2003 1003
13. D. Goodsell, and R.E. Dickerson J. Med. Chem. 29 1986 245
14. M. Cory, R.R. Tidwell, and T.A. Fairley J. Med. Chem. 35 1992 431
15. A. Czarny, D.W. Boykin, A.A. Wood, C.M. Nunn, S. Neidle, M.R.J. Zhao, and W.D. Wilson J. Am. Chem. Soc. 117 1995 4716
16. S. Mazur, F.A. Tanious, D. Ding, A. Kumar, D.W. Boykin, S. Neidle, and W.D. Wilson J. Mol. Biol. 300 2000 321
17. W.D. Wilson, F.A. Tanious, D. Ding, A. Kumar, D.W. Boykin, P. Colson, C. Houssier, and C. Bailey J. Am. Chem. Soc. 120 1998 10310
18. S.A. Shaikh, S.R. Ahmed, and B.A. Jayaram Arch. Biochem. Biophys. 429 2004 81
19. D.W. Boykin, A. Kumar, G. Xiao, W.D. Wilson, B.K. Bender, D.R. McCurdy, J.E. Hall, and R.R. Tidwell J. Med. Chem. 41 1998 124
20. D.W. Boykin, A. Kumar, J. Spychala, M. Zhou, R.L. Lombardy, W.D. Wilson, C.C. Dykstra, S.K. Jones, J.E. Hall, R.R. Tidwell, C. Laughton, C.M. Nunn, and S. Neidle J. Med. Chem. 38 1995 912
21. M.A. Ismail, R. Brun, T. Wenzler, F.A. Tanious, W.D. Wilson, and D.W. Boykin Bioorg. Med. Chem. 12 2004 5405 and references cited therein
22. R. Brun, Y. Buhler, U. Sandmeier, R. Kaminsky, C.J. Bacchi, D. Rattendi, S. Lane, S.L. Croft, D. Snowdon, Caravatti, G. Yardley, J. Frei, J. Stanek, and H. Mett Antimicrob. Agents Chemother. 40 1996 1442
23. B. Nguyen, M.P.H. Lee, D. Hamelberg, A. Joubert, C. Bailly, R. Brun, S. Neidle, and D.W. Wilson J. Am. Chem. Soc. 124 2002 13680
24. B. Nguyen, D. Hamelberg, C. Bailly, P. Colson, J. Stanek, R. Brun, S. Neidle, and D.W. Wilson Biophys. J. 86 2004 1028
25. A. Kumar, R.A. Rhodes, J. Spychala, W.D. Wilson, D.W. Boykin, R.R. Tidwell, C.C. Dykstra, J.E., Jones, S.K. Hall, and R.F. Schinazi Eur. J. Med. Chem. 30 1995 99
26. M.A. Ismail, R. Brun, J.D. Easterbrook, F.A. Tanious, W.D. Wilson, and D.W. Boykin J. Med. Chem. 46 2003 4761
27. B.M. Raz, M. Iten, Y. Grether-Buhler, R. Kaminsky, and R. Brun Acta Trop. 68 1997 139
28. M.A. Ismail, M. Anbazhagan, C.E. Stephens, and D.W. Boykin Synth. Commun. 34 2004 751