In vitro antifungal activities of a series of dication-substituted carbazoles, furans, and benzimidazoles

Antimicrobial Agents and Chemotherapy

Volumn 42, Issue 10, 1998, Pages 2503-2510

  Del Poeta, Maurizio ^a,b   Schell, Wiley A ^a   Dykstra, Christine C ^c   Jones, Susan K ^d   Tidwell, Richard R ^d   Kumar, Arvind ^e   Boykin, David W ^e   Perfect, John R ^a  

^a DUKE UNIVERSITY MEDICAL CENTER   (United States)

^b UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^c AUBURN UNIVERSITY   (United States)

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

^e GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENT; BENZIMIDAZOLE DERIVATIVE; CARBAZOLE DERIVATIVE; FLUCONAZOLE; FURAN DERIVATIVE;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; IMMUNE DEFICIENCY; MINIMUM INHIBITORY CONCENTRATION; MYCOSIS; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0031662778     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.42.10.2503     Document Type: Article

References (32)

1. Bell, C. A., M. Cory, T. A. Fairley, J. E. Hall, and R. R. Tidwell. 1991. Structure-activity relationships of pentamidine analogs against Giardia lamblia and correlation of antigiardial activity with DNA-binding affinity. Antimicrob. Agents Chemother. 35:1099-1107.
2. Bell, C. A., C. C. Dykstra, N. N. Naiman, M. Cory, T. A. Fairley, and R. R. Tidwell. 1993. Structure-activity studies of dicationic substituted bis-benzimidazoles against Giardia lamblia: correlation of antigiardial activity with DNA binding affinity and giardial topoisomerase II inhibition. Antimicrob. Agents Chemother. 37:2668-2673.
3. Blagburn, B. L., K. L. Drain, T. M. Land, P. H. Moore, D. S. Lindsay, A. Kumar, J. Shi, D. W. Boykin, and R. R. Tidwell. Dicationic furans inhibit development of Cryptosporidium parvum in HSD/ICR suckling Swiss mice. Submitted for publication.
4. Boykin, D. W., A. Kumar, J. E. Hall, B. C. Bender, and R. R. Tidwell. 1996. Anti-pneumocystis activity of bis-amidoximes and bis-o-alkylamidoximes prodrugs. Biorg. Med. Chem. Lett. 6:3017-3020.
5. Boykin, D. W., A. Kumar, J. Spychala, M. Zhou, R. J. Lombardy, W. D. Wilson, C. C. Dykstra, J. E. Hall, S. K. Jones, R. R. Tidwell, C. Laughton, and S. Neidle. 1495. Dicationic diaryl furans as anti-Pneumocystis carinii agents. J. Med. Chem. 38:912-916.
6. Boykin, D. W., A. G. Kumar 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.
7. Cameron, M. L., W. A. Schell, S. Bruch, J. A. Bartlett, H. A. Waskin, and J. R. Perfect. 1993. Correlation of in vitro fluconazole resistance of Candida isolates in relation to therapy and symptoms of individuals seropositive for human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 37: 2449-2453.
8. Czarny, A., D. W. Boykin, A. A. Wood, C. M. Nunn, S. Neidle, M. Zhao, and W. D. Wilson. 1995. Analysis of van der Waals and electrostatic contributions in the interactions of minor groove binding benzimidazoles with DNA. J. Am. Chem. Soc. 117:4716-4717.
9. Czarny, A., W. D. Wilson, and D. W. Boykin. 1996. Synthesis of monocationic and dicationic analogs of Hoechst 33258. J. Heterocycl. Chem. 33:1393-1397.
10. 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.
11. Del Poeta, M., W. A. Schell, C. C. Dykstra, S. K. Jones, R. R. Tidwell, A. Czarny, M. Bajic, M. Bajic, A. Kumar, D. Boykin, and J. R. Perfect. 1998. Structure-in vitro activity relationships of pentamidine analogues and dicationic substituted bis-benzimidazoles as new antifungal agents. Antimicrob. Agents and Chemother. 42:2495-2502.
12. Del Poeta, M., W. A. Schell, and J. R. Perfect. 1998. Personal communication.
13. Fox, R., K. R. Neal, C. L. S. Leen, M. E. Ellis, and B. K. Mandal. 1991. Fluconazole resistant Candida in AIDS. J. Infect. 22:201-204.
14. Hall, J. E., J. E. Kerrigan, K. Ramachandran, B. C. Bender, J. P. Stanko, S. K. Jones, D. A. Patrick, and R. R. Tidwell. 1998. Anti-Pneumocystis activities of aromatic diamidoxime prodrugs. Antimicrob. Agents Chemother. 42:666-674.
15. Hildebrandt, E. F., D. W. Boykin, R. R. Tidwell, and C. C. Dykstra. 1998. Identification and characterization of an endo/exonuclease in Pneumocystis carinii that is inhibited by dicationic diaryl furans with efficacy against pneumocystis pneumonia. J. Eukaryot. Microbiol. 45:112-121.
16. Hopkins, K. T., A. Kumar, M. Bajic, B. C. Bender, J. E. Hall, R. R. Tidwell, D. W. Boykin, and W. D. Wilson. Anti-Pneumocystis carinii activity of extended aryl furan amidines. Submitted for publication.
17. Jones, S. K., J. E. Hall, M. A. Allen, S. D. Morrison, K. A. Ohemeng, V. V. Reddy, J. D. Geratz, and R. R. Tidwell. 1990. Novel pentamidine analogs in the treatment of experimental Pneumocystis carinii pneumonia. Antimicrob. Agents Chemother. 34:1026-1030.
18. Kumar, A., D. W. Boykin, W. D. Wilson, S. K. Jones, B. K. Bender, C. C. Dykstra, J. E. Hall, and R. R. Tidwell. 1996. Anti-Pneumocystis carinii pneumonia activity of dicationic 2,4-diarylpyrimidines. Eur. J. Med. Chem. 31: 767-773.
19. Ludewig, G., J. Marin, Y. Li, and C. Staben. 1994. Effects of pentamidine isethionate on Saccharomyces cerevisiae. Antimicrob. Agents Chemother. 38:1123-1128.
20. McGinnis, M. R. 1980. Susceptibility testing and bioassay procedure, p. 431. In Laboratory handbook of medical mycology. Academic Press, Inc., New York, N.Y.
21. National Committee for Clinical Laboratory Standards. 1995. Reference method for broth dilution susceptibility testing of yeasts. Document M27-T. Tenative standard. National Committee for Clinical Laboratory Standards, Wayne Pa.
22. Patrick, D. A., D. W. Boykin, W. D. Wilson, F. A. Tanious, J. Spychala, B. C. Bender, J. E. Hall, C. C. Dykstra, K. A. Ohemeng, and R. R. Tidwell. 1997. Anti-Pneumocystis carinii pneumonia activity of dicationic carbazoles. Eur. J. Med. Chem. 32:781-793.
23. Pfaller, M. A., A. J. Rhine-Chalberg, S. W. Redding, J. Smith, G. Farinacci, A. W. Fothergill, and M. G. Rinaldi. 1994. Variations in fluconazole susceptibility and electrophoretic karyotype among oral isolates of Candida albicans from AIDS and oral candidiasis. J. Clin. Microbiol. 32:59-64.
24. 23a. Tidwell, R. R. Unpublished data.
25. Tidwell, R. R., and C. A. Bell. 1993. Pentamidine and related compounds in the treatment of Pneumocystis carinii infection, p. 561-583. In P. D. Walzer (ed.), Pentamidine and related compounds in the treatment of Pneumocystis carinii Infection. Marcel Dekker, Inc., New York, N.Y.
26. Tidwell, R. R., J. D. Geratz, O. Dann, G. Volz, D. Zeh, and H. Loewe. 1978. Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases. J. Med. Chem. 21:613-623.
27. Tidwell, R. R., S. K. Jones, J. D. Geratz, K. A. Ohemeng, C. A. Bell, B. J. Berger, and J. E. Hall. 1990. Development of pentamidine analogues as new agents for the treatment of Pneumocystis carinii pneumonia. Ann. N.Y. Acad. Sci. 616:421-441.
28. Tidwell, R. R., S. K. Jones, J. D. Geratz, K. A. Ohemeng, M. Cory, and J. E. Hall. 1990. Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia. J. Med. Chem. 33:1252-1257.
29. Tidwell, R. R., S. K. Jones, N. A. Naiman, L. C. Berger, W. B. Brake, C. C. Dykstra, and J. E. Hall. 1993. Activity of cationically substituted bis-benzimidazoles against experimental Pneumocystis carinii pneumonia. Antimicrob. Agents Chemother. 37:1713-1716.
30. Trent, J. O., G. R. Clark, S. Neidle, A. Kumar, W. D. Wilson, D. W. Boykin, J. E. Hall, R. R. Tidwell, and B. L. Blagburn. 1996. Targeting the minor groove: crystal structures of two complexes between furan derivatives of berenil and the DNA dodecamer. J. Med. Chem. 39:4554-4562.
31. Willocks, L., C. L. S. Leen, R. P. Bretle, D. Urquhart, T. B. Russel, and L. J. R. Milne. 1991. Fluconazole resistance in AIDS patients. J. Antimicrob. Chemother. 28:937-939.
32. Xiao, G., K. Li, C. T. Tigl, A. Kumar, D. W. Boykin, and W. D. Wilson. 1998. Inhibition of HIV-1 Rev-RRE complex: structure-inhibition analysis with unfused aromatic cations. Unpublished data.