Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

Article


Galante, E., Geraci, Corrada, Sciuto, Sebastiano, Campo, Vanessa L., Carvalho, Ivone, Sesti-Costa, Renata, Guedes, Paulo M.M., Silva, João S., Hill, Lionel, Nepogodiev, Sergey A. and Field, Robert A. 2011. Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity. Tetrahedron. 67 (33), pp. 5902-5912.
AuthorsGalante, E., Geraci, Corrada, Sciuto, Sebastiano, Campo, Vanessa L., Carvalho, Ivone, Sesti-Costa, Renata, Guedes, Paulo M.M., Silva, João S., Hill, Lionel, Nepogodiev, Sergey A. and Field, Robert A.
Abstract

A new series of water-soluble tetravalent glycoclusters incorporating β-lactosyl residues attached to a central calix[4]arene core was synthesised using azide–alkyne Cu(I)-catalysed cycloaddition (‘click chemistry’). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14–21 atom spacer arms. The glycoclusters with a C4-symmetrical arrangement of β-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays.

JournalTetrahedron
Journal citation67 (33), pp. 5902-5912
ISSN00404020
Year2011
PublisherElsevier
Digital Object Identifier (DOI)doi:10.1016/j.tet.2011.06.065
Web address (URL)https://doi.org/10.1016/j.tet.2011.06.065
Publication dates
Print19 Aug 2011
Publication process dates
Deposited18 Aug 2017
Accepted20 Jun 2011
Copyright information© Elsevier 2011
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