Synthesis and activity of azaterphenyl diamidines against Trypanosoma brucei rhodesiense and Plasmodium falciparum

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 18, 2009, Pages 6651-6658

  Hu, Laixing ^a   Arafa, Reem K ^a   Ismail, Mohamed A ^a   Patel, Alpa ^a   Munde, Manoj ^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

Antiprotozoal agents; Azaterphenyl; Diamidines; DNA binding affinity

Indexed keywords

2,5 BIS(4' AMIDINOPHENYL)PYRIDAZINE; AMIDINE; ANTIPROTOZOAL AGENT; AZAFURAMIDINE; AZATERPHENYL DIAMIDINE DERIVATIVE; DIAMIDINE DERIVATIVE; FURAMIDINE; NITROGEN; PHENYL[1,2']PYRIDINYL[5',2']PYRIDINYL 4,5'' BISAMIDINE; PHENYL[1,2']PYRIDINYL[5',5'']PYRIDINYL 4,2'' BISAMIDINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIPROTOZOAL ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CORRELATION ANALYSIS; CYTOTOXICITY; DRUG ACTIVITY; DRUG DNA BINDING; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PLASMODIUM FALCIPARUM; RAT; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA RHODESIENSE;

ANIMALS; ANTIPROTOZOAL AGENTS; INHIBITORY CONCENTRATION 50; MALARIA, FALCIPARUM; MICE; PARASITIC SENSITIVITY TESTS; PENTAMIDINE; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA BRUCEI RHODESIENSE; TRYPANOSOMIASIS, AFRICAN;

PLASMODIUM FALCIPARUM; TRYPANOSOMA BRUCEI RHODESIENSE;

EID: 69249117854     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.07.080     Document Type: Article

References (35)

1. Fairlamb A.H. Trends Parasitol. 19 (2003) 488
2. Bouteille B., Oukem O., Bisser S., and Duma M. Fundam. Clin. Pharmacol. 17 (2003) 171
3. Tidwell R.R., and Boykin D.W. Dicationic DNA Minor Groove Binders as Antimicrobial agents. In: Demeunynck M., Bailly C., and Wilson W.D. (Eds). Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes Vol. 2 (2003), Wiley, New York 414-460
4. Wilson W.D., Nguyen B., Tanious F.A., Mathis A., hall J.E., Stephens C.E., and Boykin D.W. Curr. Med. Chem. Anti-Cancer agents 5 (2005) 389
5. Soeiro M.N.C., de Souza E.M., Stephens C.E., and Boykin D.W. Exp. Opin. Invest. Drugs 14 (2005) 957
6. Dardonville C. Exp. Ther. Pat. 15 (2005) 1241
7. Werbovetz K.A. Curr. Opin. Invest. Drugs 7 (2006) 147
8. Thuita J.K., Karanja S.M., Wenzler T., Mdachi R.E., Ngotho J.M., Kagira J.M., Tidwell R., and Brun R. Acta Tropica 108 (2008) 6
9. Ismail M.A., Brun R., Easterbrook J.D., Tanious F.A., Wilson W.D., and Boykin D.W. J. Med. Chem. 46 (2003) 4761
10. Ansede J.H., Voyksner R.D., Ismail M.A., Boykin D.W., Tidwell R.R., and Hall J.E. Xenobiotica 35 (2005) 211
11. Boykin D.W., Kumar A., Spychala J., Zhou M., Lombardy R., Wilson W.D., Dykstra C.C., Jones S.K., Hall J.E., Tidwell R.R., Laughton C., Nunn C.M., and Neidle S. J. Med. Chem. 38 (1995) 912
12. Boykin D.W., Kumar A., Xiao G., Wilson W.D., Bender B.C., McCurdy D.R., Hall J.E., and Tidwell R.R. J. Med. Chem. 41 (1998) 124
13. Francesconi I., Wilson W.D., Tanious F.A., Hall J.E., Bender B.C., Tidwell R.R., McCurdy D., and Boykin D.W. J. Med. Chem. 42 (1999) 2260
14. Laughton C.A., Tanious F.A., Nunn C.M., Boykin D.W., Wilson W.D., and Neidle S. Biochemistry 35 (1996) 5655
15. Trent J.O., Clark G.R., Kumar A., Wilson W.D., Boykin D.W., Hall J.E., Tidwell R.R., Blagburn B.L., and Neidle S.J. J. Med. Chem. 39 (1996) 4554
16. Wilson W.D., Tanious F.A., Ding D., Kumar A., Boykin D.W., Colson P., Houssier C., and Bailly C. J. Am. Chem. Soc. 120 (1998) 10310
17. Bailly C., Dassonneville L., Carrascol C., Lucasl D., Kumar A., Boykin D.W., and Wilson W.D. Anti-Cancer Drug Des. 14 (1999) 47
18. Fitzgerald D.J., and Anderson J.N. J. Biol. Chem. 274 (1999) 27128
19. Dykatra C.C., McClernon D.R., Elwell L.P., and Tidwell R.R. Antimicrob. Agents Chemother. 38 (1994) 1890
20. Henderson D., and Hurley L.H. Nat. Med. 1 (1995) 525
21. Lanteri C.A., Stewart M.L., Brock J.M., Alibu V.P., Meshnick S.R., and Tidwell R.R. Mol. Pharmacol. 70 (2006) 1585
22. Mathis A.M., Holman J.L., Sturk L.M., Ismail M.A., Boykin D.W., Tidwell R.D., and Hall J.E. Antimicrob. Agents Chemother. 50 (2006) 2185
23. Mathis A.M., Bridges A.S., Ismail M.A., Kumar A., Francesconi I., Anbazhagan M., Hu Q., Tanious F.A., Wanzler T., Saulter J., Wilson W.D., Brun R., Boykin D.W., Tidwell R.D., and Hall J.E. Antimicrob. Agents Chemother. 51 (2007) 2801
24. Goodsell D., and Dickerson R.E. J. Med. Chem. 29 (1986) 727
25. Nguyen B., Lee M.P., Hamelberg D., Bailly C., Brun R., Neidle S., and Wilson W.D. J. Am. Chem. Soc. 124 (2002) 13680
26. Nguyen B., Hamelberg D., Bailly C., Colson J., Stenek J., Brun R., Neidle S., and Wilson W.D. Biophys. J. 86 (2004) 1028
27. Miao Y., Lee M.P.H., Parkinson G.N., Batista-Parra A., Ismail M.A., Neidle S., Boykin D.W., and Wilson D.W. Biochemistry 44 (2005) 14701
28. Ismail M.A., Arafa R.K., Brun R., Wenzler T., Miao Y., Wilson D.W., Generaux C., Bridges A., Hall J.E., and Boykin D.W. J. Med. Chem. 49 (2006) 5324
29. Munde M., Ismail M.A., Arafa R., Peixoto P., Collar C.J., Liu Y., Hu L., David-Cordonnier M.-H., Lansiaux A., Bailly C., Boykin D.W., and Wilson W.D. J. Am. Chem. Soc. 129 (2007) 13732
30. Hu L., Arafa R.K., Ismail M.A., Wenzler T., Brun R., Munde M., Wilson W.D., Nzimiro S., Samyesudhas S., Werbovetz K.A., and Boykin D.W. Bioorg. Med. Chem. Lett. 18 (2008) 247
31. Jampilek J., Dolezal M., Kunes J., Satinsky D., and Raich I. Curr. Org. Chem. 9 (2005) 49
32. Purfield A.E., Tidwell R.R., and Meshnick S.R. Malar. J. 8 (2009) 104
33. Bakunova S.M., Bakunov S.A., Patrick D.A., Kumar E.V.K.S., Ohemeng K.A., Bridges A.S., Wenzler T., Barszcz T., Kilgore Jones S., Werbovetz K.A., Brun R., and Tidwell R.R. J. Med. Chem. 52 (2009) 2016
34. Nguyen C., Kasinathan G., Leal-Cortijo I., Musso-Buendia A., Kaiser M., Brun R., Ruiz-Perez L.M., Johansson N.G., Gonzalez-Pacanowska D., and Gilbert I.H. J. Med. Chem. 48 (2005) 5942
35. Ellingson R.C., and Henry R.L. J. Am. Chem. Soc. 71 (1949) 2798