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

Eva Galante; Corrada Geraci; Sebastiano Sciuto; Vanessa L. Campo; Ivone Carvalho; Renata Sesti-Costa; Paulo M. M. Guedes; João S. Silva; Lionel Hill; Sergey A. Nepogodiev; Robert A. Field

doi:10.1016/j.tet.2011.06.065

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

Eva Galante
, Corrada Geraci
, Sebastiano Sciuto
, Vanessa L. Campo
, Ivone Carvalho
, Renata Sesti-Costa
, Paulo M. M. Guedes
, João S. Silva
, Lionel Hill
, Sergey A. Nepogodiev
, Robert A. Field

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

36 Citations (Scopus)

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	English
Pages (from-to)	5902-5912
Number of pages	11
Journal	Tetrahedron
Volume	67
Issue number	33
Early online date	25 Jun 2011
DOIs	https://doi.org/10.1016/j.tet.2011.06.065
Publication status	Published - 19 Aug 2011

Keywords

Calix[4]arene
Calixsugar
Glycocluster
Multivalency
Trypanosoma cruzi

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10.1016/j.tet.2011.06.065

Cite this

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title = "Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity",

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.",

keywords = "Calix[4]arene, Calixsugar, Glycocluster, Multivalency, Trypanosoma cruzi",

author = "Eva Galante and Corrada Geraci and Sebastiano Sciuto and Campo, \{Vanessa L.\} and Ivone Carvalho and Renata Sesti-Costa and Guedes, \{Paulo M. M.\} and Silva, \{Jo{\~a}o S.\} and Lionel Hill and Nepogodiev, \{Sergey A.\} and Field, \{Robert A.\}",

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day = "19",

doi = "10.1016/j.tet.2011.06.065",

language = "English",

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journal = "Tetrahedron",

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TY - JOUR

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

AU - Galante, Eva

AU - Geraci, Corrada

AU - Sciuto, Sebastiano

AU - Campo, Vanessa L.

AU - Carvalho, Ivone

AU - Sesti-Costa, Renata

AU - Guedes, Paulo M. M.

AU - Silva, João S.

AU - Hill, Lionel

AU - Nepogodiev, Sergey A.

AU - Field, Robert A.

PY - 2011/8/19

Y1 - 2011/8/19

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.

KW - Calix[4]arene

KW - Calixsugar

KW - Glycocluster

KW - Multivalency

KW - Trypanosoma cruzi

UR - https://www.scopus.com/pages/publications/79960229934

U2 - 10.1016/j.tet.2011.06.065

DO - 10.1016/j.tet.2011.06.065

M3 - Article

AN - SCOPUS:79960229934

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

Keywords

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