Diphenyl furans and aza analogs: Effects of structural modification on in vitro activity, DNA binding, and accumulation and distribution in trypanosomes

Antimicrobial Agents and Chemotherapy

Volumn 51, Issue 8, 2007, Pages 2801-2810

  Mathis, Amanda M ^a   Bridges, Arlene S ^a   Ismail, Mohamed A ^c   Kumar, Arvind ^c   Francesconi, Iris ^c   Anbazhagan, Mariappan ^c   Hu, Qiyue ^c   Tanious, Farial A ^c   Wenzler, Tanja ^d   Saulter, Janelle ^a   Wilson, W David ^c   Brun, Reto ^d   Boykin, David W ^c   Tidwell, Richard R ^b   Hall, James Edwin ^a,b,e  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^c GEORGIA STATE UNIVERSITY   (United States)

^d SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^e University of North Carolina   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 BIS(4 AMIDINOPHENYL)FURAN; DB 1017; DB 103; DB 1057; DB 244; DB 249; DB 569; DB 60; DB 690; DB 820; DB 829; DB 867; DB 879; DB 935; DIAMIDINE DERIVATIVE; FURAN DERIVATIVE; PENTAMIDINE; UNCLASSIFIED DRUG;

AFRICAN TRYPANOSOMIASIS; ARTICLE; DNA BINDING; DRUG MECHANISM; DRUG STRUCTURE; KINETOPLAST; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TRYPANOSOMA;

ANIMALS; BENZAMIDINES; DNA, PROTOZOAN; DOSE-RESPONSE RELATIONSHIP, DRUG; FURANS; INHIBITORY CONCENTRATION 50; ORGANELLES; PARASITIC SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMA BRUCEI RHODESIENSE;

EID: 34547621809     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.00005-07     Document Type: Article

References (35)

1. Boykin, D. 2002. Antimicrobial activity of the DNA minor groove binders luramidine and analogs. J. Braz. Chem. Soc. 13:763-771.
2. Boykin, D. W., A. Kumar, J. Spychala, M. Zhou, R. J. Lombardy, W. D. Wilson, C. C. Dykstra, S. K. Jones, J. E. Hall, R. R. Tidwell, et al. 1995. Dicationic diarylfurans as anti-Pneumocystis carinii agents. J. Med. Chem. 38:912-916.
3. Boykin, D. W., A. Kumar, G. Xiao, W. D. Wilson, B. C. Bender, D. R. McCurdy, J. E. Hall, and R. R. Tidwell. 1998. 2,5-Bis[4-(N- alkylamidino)phenyl]furans as anti-Pneumocystis carinii agents. J. Med. Chem. 41:124-129.
4. Bray, P. G., M. P. Barrett, S. A. Ward, and H. P. de Koning. 2003. Pentamidine uptake and resistance in pathogenic protozoa: past, present and future. Trends Parasitol. 19:232-239.
5. Carter, N. S., B. J. Berger, and A. H. Fairlamb. 1995. Uptake of diamidine drugs by the P2 nucleoside transporter in melarsen-sensitive and -resistant Trypanosoma brucei brucei. J. Biol. Chem. 270:28153-28157.
6. Croft, S. L., M. P. Barrett, and J. A. Urbina. 2005. Chemotherapy of trypanosomiases and leishmaniasis. Trends Parasitol. 21:508-512.
7. Das, B. P., and D. W. Boykin. 1977. Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans. J. Med. Chem. 20:531-536.
8. de Koning, H. P. 2001. Transporters in African trypanosomes: role in drug action and resistance. Int. J. Parasitol. 31:512-522.
9. de Koning, H. P., L. F. Anderson, M. Stewart, R. J. Burchmore, L. J. Wallace, and M. P. Barrett. 2004. The trypanocide diminazene aceturate is accumulated predominantly through the TbAT1 purine transporter: additional insights on diamidine resistance in African trypanosomes. Antimicrob. Agents Chemother. 48:1515-1519.
10. De Souza, E. M., R. Menna-Barreto, T. C. Araujo-Jorge, A. Kumar, Q. Hu, D. W. Boykin, and M. N. Soeiro. 2006. Antiparasitic activity of aromatic diamidines is related to apoptosis-like death in Trypanosoma cruzi. Parasitology 133:75-79.
11. de Souza, E. M., G. M. Oliveira, D. W. Boykin, A. Kumar, Q. Hu, and N. Soeiro Mde. 2006. Trypanocidal activity of the phenyl-substituted analogue of furamidine DB569 against Trypanosoma cruzi infection in vivo. J. Antimicrob. Chemother. 58:610-614.
12. 2+ storage compartment in trypanosomatids and apicomplexan parasites. Parasitol. Today 15:443-448.
13. Geiser, F., A. Luscher, H. P. de Koning, T. Seebeck, and P. Maser. 2005. Molecular pharmacology of adenosine transport in Trypanosoma brucei: P1/P2 revisited. Mol. Pharmacol. 68:589-595.
14. Ismail, M. A., R. K. Arafa, R. Brun, T. Wenzler, Y. Miao, W. D. Wilson, C. Generaux, A. Bridges, J. E. Hall, and D. W. Boykin. 2006. Synthesis, DNA affinity, and antiprotozoal activity of linear dications: terphenyl diamidines and analogues. J. Med. Chem. 49:5324-5332.
15. Ismail, M. A., A. Batista-Parra, Y. Miao, W. D. Wilson, T. Wenzler, R. Brun, and D. W. Boykin. 2005. Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents. Bioorg. Med. Chem. 13:6718-6726.
16. Ismail, M. A., R. Brun, J. D. Easterbrook, F. A. Tanious, W. D. Wilson, and D. W. Boykin. 2003. Synthesis and antiprotozoal activity of aza-analogues of furamidine. J. Med. Chem. 46:4761-4769.
17. Ismail, M. A., R. Brun, T. Wenzler, F. A. Tanious, W. D. Wilson, and D. W. Boykin. 2004. Dicationic biphenyl benzimidazole derivatives as antiprotozoal agents. Bioorg. Med. Chem. 12:5405-5413.
18. Ismail, M. A., R. Brun, T. Wenzler, F. A. Tanious, W. D. Wilson, and D. W. Boykin. 2004. Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents. J. Med. Chem. 47:3658-3664.
19. Lansiaux, A., L. Dassonneville, M. Facompre, A. Kumar, C. E. Stephens, M. Bajic, F. Tanious, W. D. Wilson, D. W. Boykin, and C. Bailly. 2002. Distribution of furamidine analogues in tumor cells: influence of the number of positive charges. J. Med. Chem. 45:1994-2002.
20. Lansiaux, A., F. Tanious, Z. Mishal, L. Dassonneville, A. Kumar, C. E. Stephens, Q. Hu, W. D. Wilson, D. W. Boykin, and C. Bailly. 2002. Distribution of furamidine analogues in tumor cells: targeting of the nucleus or mitochondria depending on the amidine substitution. Cancer Res. 62:7219-7229.
21. Lanteri, C. 2005. Mechanisms of uptake and action of DB75 [2,5-bis(4-amidinophenyl)furan] in African trypanosomes. Ph.D. dissertation. University of North Carolina, Chapel Hill.
22. Lanteri, C. A., M. L. Stewart, J. M. Brock, V. P. Alibu, S. R. Meshnick, R. R. Tidwell, and M. P. Barrett. 2006. Roles for the Trypanosoma brucei P2 transporter in DB75 uptake and resistance. Mol. Pharmacol. 70:1585-1592.
23. Mallena, S., M. P. Lee, C. Bailly, S. Neidle, A. Kumar, D. W. Boykin, and W. D. Wilson. 2004. Thiophene-based diamidine forms a "super" at binding minor groove agent. J. Am. Chem. Soc. 126:13659-13669.
24. Mathis, A. M., J. L. Holman, L. M. Sturk, M. A. Ismail, D. W. Boykin, R. R. Tidwell, and J. E. Hall. 2006. Accumulation and intracellular distribution of antitrypanosomal diamidine compounds DB75 and DB820 in African trypanosomes. Antimicrob. Agents Chemother. 50:2185-2191.
25. Peregrine, A. S., and M. Mamman. 1993. Pharmacology of diminazene: a review. Acta Trop. 54:185-203.
26. Raz, B., M. Iten, Y. Grether-Buhler, R. Kaminsky, and R. Brun. 1997. The Alamar Blue assay to determine drug sensitivity of African trypanosomes (T.b. rhodesiense and T.b. gambiense) in vitro. Acta Trop. 68:139-147.
27. Shapiro, T. A., and P. T. Englund. 1990. Selective cleavage of kinetoplast DNA minicircles promoted by antitrypanosomal drugs. Proc. Natl. Acad. Sci. USA 87:950-954.
28. Shapiro, T. A., V. A. Klein, and P. T. Englund. 1989. Drug-promoted cleavage of kinetoplast DNA minicircles. Evidence for type II topoisomerase activity in trypanosome mitochondria. J. Biol. Chem. 264:4173-4178.
29. Stewart, M. L., S. Krishna, R. J. Burchmore, R. Brun, H. P. de Koning, D. W. Boykin, R. R. Tidwell, J. E. Hall, and M. P. Barrett. 2005. Detection of arsenical drug resistance in Trypanosoma brucei with a simple fluorescence test. Lancet 366:486-487.
30. Sturk, L. M., J. L. Brock, C. R. Bagnell, J. E. Hall, and R. R. Tidwell. 2004. Distribution and quantitation of the anti-trypanosomal diamidine 2,5-bis(4-amidinophenyl)furan (DB75) and its N-methoxy prodrug DB289 in murine brain tissue. Acta Trop. 91:131-143.
31. Tijssen, J. P., H. W. Beekes, and J. Van Steveninck. 1982. Localization of polyphosphates in Saccharomyces fragilis, as revealed by 4′,6-diamidino-2-phenylindole fluorescence. Biochim. Biophys. Acta 721:394-398.
32. Werbovetz, K. 2006. Diamidines as antitrypanosomal, antileishmanial and antimalarial agents. Curr. Opin. Investig. Drugs 7:147-157.
33. Williamson, J. 1979. Effects of trypanocides on the fine structure of target organisms. Pharmacol. Ther. 7:445-512.
34. Wilson, W. D., B. Nguyen, F. Tanious, A. Mathis, J. E. Hall, C. Stephens, and D. W. Boykin. 2005. Dications that target the DNA minor groove: compound design and preparation, DNA interactions, cellular distribution, and biological activity. Curr. Med. Chem. Anticancer Agents 5:389-408.
35. Wilson, W. D., F. A. Tanious, M. Fernandez-Saiz, and C. T. Rigl. 1997. Evaluation of drug-nucleic acid interactions by thermal melting curves. Methods Mol. Biol. 90:219-240.