Title: Novel fungicidal benzylsulfanyl-phenylguanidines
Authors: Thevissen, Karin ×
Pellens, K.
De Brucker, Katrijn
François, I.E.J.A.
Chow, K.K.
Meert, Els
Meert, Wim
Van Minnebruggen, G.
Borgers, M.
Vroome, V.
Levin, Jeremy
De Vos, Dirk
Maes, L.
Cos, P.
Cammue, Bruno #
Issue Date: 2011
Publisher: Pergamon Press
Series Title: Bioorganic & Medicinal Chemistry Letters vol:21 issue:12 pages:3686-3692
Abstract: A series of substituted benzylsulfanyl-phenylamines 21 was synthesized, of which four substituted benzylsulfanyl-phenylguanidines (665, 666, 667 and 684) showed potent fungicidal activity (minimal fungicidal concentration, MFC ≤ 10μM for Candida albicans and C. glabrata). A benzylsulfanyl-phenyl scaffold with an unsubstituted guanidine resulted in less active compounds (MFC = 50-100μM), whereas substitution with an unsubstituted amine group resulted in compounds without fungicidal activity. Compounds 665, 666, 667 and 684 also showed activity against single C. albicans biofilms and biofilms consisting of C. albicans and Staphylococcus epidermidis (minimal concentration resulting in 50% eradication of the biofilm, BEC50 121μM for both biofilm setups). Compounds 665 and 666 combined potent fungicidal (MFC = 5μM) and bactericidal activity (minimal bactericidal concentration, MBC for S. epidermidis 4μM). In an in vivo Caenorhabditis elegans model, compounds 665 and 667 exhibited less toxicity than 666 and 684. Moreover, addition of those compounds to Candida-infected C. elegans cultures resulted in increased survival of Candida-infected worms, demonstrating their in vivo efficacy in a mini-host model.
ISSN: 0960-894X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Centre of Microbial and Plant Genetics
Centre for Surface Chemistry and Catalysis
× corresponding author
# (joint) last author

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