Fungicidal effects of some derivatives of 2-ferrocenyl-benzimidazoles: A possible template for antifungal drug design

Khaled H. Abu-Elteen, Raid J. Abdel-Jalil, Mawieh A. Hamad, M. Ghaleb, Khalid M. Khen, W. Voelter

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The minimum inhibitory concentration (MIC) and minimum, fungicidal concentration (MFC) for a group of newly synthesized derivatives of 2-ferrocenyl-5-fluoro-6-(4-substituted-1-pipera-zinyl) benzimidazoles were determined using a broth macrodilution method following clinical and laboratory standards institute (CLSI) recommendation for medically important Candida sp. The data demonstrate that compounds 4-fluoro-5-(4-methyl-1-piperazinyl)-2-nitroaniline(5a), 4-Fluoro-5-(4-phenyl-1-piperazinyl)-2-nitroaniline(5b), 2-ferrocenyl-5-fluoro-6-(4-methyl-1-piperazinyl) benzimidazole (7a), 2-ferrocenyl-5-fluoro-6-(4-phenyl-1-piperazinyl) benzimidazole (7b) and 2-ferrocenyl-5-fluoro-6-[4-(4-fluorophenyl)-1-piperazinyl] benzimidazole (7e) were found to have potent in vitro antiftingal activity with MICs at which 80% of the strains were inhibited (MIC80s) of 15-125 μg mL-1. The active compounds were further screened in order to establish their mode of action on the basis of inhibitory effects on growth, budding, germ-tube formation and leakage of cytoplasmic content release after treatment. In comparison to control drugs (e.g., nystatin, miconazole nitrate, and ketoconazole). Some derivatives of the 4-fluoro-5-(4-substituted-1-piperazinyl)-2-nitroanilines (series 5) and 2-ferrocenyl-5-fluoro-6-(4-substituted-1-piperazinyl)-[1H] benzi-midazoles (series 7) were found to be more potent in lower micro-molar concentrations (15-500 μg mL-1). It is clear from the data presented here that further studies on the structure-activity relationships, mechanisms of action and in vivo efficacies of these compounds are warranted to determine their clinical potential.

Original languageEnglish
Pages (from-to)673-681
Number of pages9
JournalJournal of Medical Sciences
Volume8
Issue number8
DOIs
Publication statusPublished - Dec 15 2008

Fingerprint

Benzimidazoles
Drug Design
Miconazole
Nystatin
Ketoconazole
Drug and Narcotic Control
Microbial Sensitivity Tests
Structure-Activity Relationship
Candida
Growth
benzimidazole
2-nitroaniline

Keywords

  • Antifungal susceptibility
  • Benzimidazoles derivatives
  • Candida sp
  • Drug design
  • Virulence factors

ASJC Scopus subject areas

  • Medicine(all)

Cite this

Fungicidal effects of some derivatives of 2-ferrocenyl-benzimidazoles : A possible template for antifungal drug design. / Abu-Elteen, Khaled H.; Abdel-Jalil, Raid J.; Hamad, Mawieh A.; Ghaleb, M.; Khen, Khalid M.; Voelter, W.

In: Journal of Medical Sciences, Vol. 8, No. 8, 15.12.2008, p. 673-681.

Research output: Contribution to journalArticle

Abu-Elteen, Khaled H. ; Abdel-Jalil, Raid J. ; Hamad, Mawieh A. ; Ghaleb, M. ; Khen, Khalid M. ; Voelter, W. / Fungicidal effects of some derivatives of 2-ferrocenyl-benzimidazoles : A possible template for antifungal drug design. In: Journal of Medical Sciences. 2008 ; Vol. 8, No. 8. pp. 673-681.
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