title: Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibitTrypanosoma cruzimacrophage invasion.
abstract: Reaction of 2-(2-(2-azidoethoxy)ethoxy)ethyl 6-O-(prop-2-ynyl)-β-d-galactopyranoside (7) under CuAAC conditions gives rise to mixed cyclic and linear triazole-linked oligomers, with individual compounds up to d.p. 5 isolable, along with mixed larger oligomers. The linear compounds resolveen blocfrom the cyclic materials by RP HPLC, but are separable by gel permeation chromatography. The triazole-linked oligomers-pseudo-galactooligomers-were demonstrated to be acceptor substrates for the multi-copy cell surfacetrans-sialidase of the human parasiteTrypanosoma cruzi. In addition, these multivalent TcTS ligands were able to block macrophage invasion byT. cruzi.
authors.affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, USP, Av. Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil.
authors.forename: Vanessa L
authors.initials: VL
authors.lastname: Campo
authors.affiliation: Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich NR4 7UH, UK.
authors.forename: Irina M
authors.initials: IM
authors.lastname: Ivanova
authors.affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, USP, Av. Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil.
authors.forename: Ivone
authors.initials: I
authors.lastname: Carvalho
authors.affiliation: Faculdade de Medicina de Ribeirão Preto, Department of Parasitology Microbiology and Immunology, USP, Av. Bandeirantes 3900, CEP 14049-900, Ribeirão Preto, SP, Brazil.
authors.forename: Carla D
authors.initials: CD
authors.lastname: Lopes
authors.affiliation: Faculdade de Medicina de Ribeirão Preto, Department of Parasitology Microbiology and Immunology, USP, Av. Bandeirantes 3900, CEP 14049-900, Ribeirão Preto, SP, Brazil.
authors.forename: Zumira A
authors.initials: ZA
authors.lastname: Carneiro
authors.affiliation: Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich NR4 7UH, UK.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Saalbach
authors.affiliation: Department of Microbiology, Immunology and Parasitology, Universidade Federal de São Paulo, Rua Botucatu 862 8, Andar 04023-062, São Paulo, SP, Brazil.
authors.forename: Sergio
authors.initials: S
authors.lastname: Schenkman
authors.affiliation: Faculdade de Medicina de Ribeirão Preto, Department of Parasitology Microbiology and Immunology, USP, Av. Bandeirantes 3900, CEP 14049-900, Ribeirão Preto, SP, Brazil.
authors.forename: João Santana
authors.initials: JS
authors.lastname: da Silva
authors.affiliation: Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich NR4 7UH, UK.
authors.forename: Sergey A
authors.initials: SA
authors.lastname: Nepogodiev
authors.affiliation: Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich NR4 7UH, UK.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Field
keywords: Click chemistry; Macrophage invasion; Pseudo-glycomacrocycles; Triazole-linked oligomers; Trypanosoma cruzi