Jump to main content
Jump to site search

Issue 44, 2016
Previous Article Next Article

Assessment of the nematocidal activity of metallocenyl analogues of monepantel

Author affiliations


In this study, we present the design, synthesis, characterization and biological evaluation of structurally new ferrocenyl and ruthenocenyl derivatives of the organic anthelmintic monepantel (Zolvix®). All seven metallocenyl derivatives prepared (4a/b, 5a/b, 6a/b and 7) were isolated as racemates and characterized by 1H, 13C and 19F NMR spectroscopies, mass spectrometry, IR spectroscopy and elemental microanalysis. The molecular structures of four compounds (4a/b, 6a and 7) were further confirmed by X-ray crystallography. The biological activities of the organometallic intermediates (4a/b) and organometallic derivatives of monepantel (5a/b, 6a/b and 7) were evaluated in vitro using parasitic nematodes of major importance in livestock, namely Haemonchus contortus and Trichostrongylus colubriformis. Two ferrocenyl compounds (4a and 6a) showed nematocidal activity, while the analogous ruthenocenyl compounds (4b and 6b) were not active at the highest concentration tested (10 μg mL−1). In order to obtain insight into the difference in activity between ferrocenyl and ruthenocenyl derivatives, the potential of the compounds for reactive oxidative species (ROS) production in live cells was assessed. Interestingly, neither the ferrocenyl nor the ruthenocenyl compounds (4a/b and 6a/b) produced significant ROS in HeLa cells when checked after 22 h, potentially indicating a redox-independent activity of 4a and 6a on the parasites. The selectivity of the compounds on parasites was confirmed by investigating their cytotoxicity profiles. None of these compounds was toxic either to HeLa or MRC-5 cells. Thus, 4a and 6a could be considered as interesting leads for further development of new classes of anti-parasitic agents.

Graphical abstract: Assessment of the nematocidal activity of metallocenyl analogues of monepantel

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 29 Aug 2016, accepted on 03 Oct 2016 and first published on 04 Oct 2016

Article type: Paper
DOI: 10.1039/C6DT03376H
Citation: Dalton Trans., 2016,45, 17662-17671
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Assessment of the nematocidal activity of metallocenyl analogues of monepantel

    J. Hess, M. Patra, A. Jabbar, V. Pierroz, S. Konatschnig, B. Spingler, S. Ferrari, R. B. Gasser and G. Gasser, Dalton Trans., 2016, 45, 17662
    DOI: 10.1039/C6DT03376H

Search articles by author