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

E. Galante; C. Geraci; S. Sciuto; V.L. Campo; I. Carvalho; R. Sesti-Costa; P.M.M. Guedes; L. Hill; S.A. Nepogodiev; R.A. Field

doi:10.1016/j.tet.2011.06.065

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

E. Galante, C. Geraci, S. Sciuto, V.L. Campo, I. Carvalho, R. Sesti-Costa, P.M.M. Guedes, L. Hill, S.A. Nepogodiev, R.A. Field

Manchester Institute of Biotechnology

Research output: Contribution to journal › Article › peer-review

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.

Original language	Undefined
Pages (from-to)	5902-5912
Number of pages	11
Journal	Tetrahedron
Volume	67
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2011.06.065
Publication status	Published - 2011

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Manchester Institute of Biotechnology

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10.1016/j.tet.2011.06.065

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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 ({\textquoteleft}click chemistry{\textquoteright}). 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.",

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T1 - Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

AU - Galante, E.

AU - Geraci, C.

AU - Sciuto, S.

AU - Campo, V.L.

AU - Carvalho, I.

AU - Sesti-Costa, R.

AU - Guedes, P.M.M.

AU - Hill, L.

AU - Nepogodiev, S.A.

AU - Field, R.A.

PY - 2011

Y1 - 2011

N2 - 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.

AB - 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.

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DO - 10.1016/j.tet.2011.06.065

M3 - Article

SN - 0040-4020

VL - 67

SP - 5902

EP - 5912

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

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

Abstract

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