Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

Vanessa L. Campo; Irina M. Ivanova; Ivone Carvalho; Carla D. Lopes; Zumira A. Carneiro; Gerhard Saalbach; Sergio Schenkman; João Santana da Silva; Sergey A. Nepogodiev; Robert A. Field

doi:10.1016/j.tet.2015.04.085

Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

Vanessa L. Campo, Irina M. Ivanova, Ivone Carvalho, Carla D. Lopes, Zumira A. Carneiro, Gerhard Saalbach, Sergio Schenkman, João Santana da Silva, Sergey A. Nepogodiev, Robert A. Field

School of Chemistry, Pharmacy and Pharmacology

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

28 Citations (Scopus)

Abstract

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 resolve en bloc from 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 surface trans-sialidase of the human parasite Trypanosoma cruzi. In addition, these multivalent TcTS ligands were able to block macrophage invasion by T. cruzi.

Original language	English
Article number	26688
Pages (from-to)	7344-7353
Number of pages	10
Journal	Tetrahedron
Volume	71
Issue number	39
Early online date	6 May 2015
DOIs	https://doi.org/10.1016/j.tet.2015.04.085
Publication status	Published - 17 Aug 2015

Keywords

Click chemistry
Macrophage invasion
Pseudo-glycomacrocycles
Triazole-linked oligomers
Trypanosoma cruzi

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Campo, V. L., Ivanova, I. M., Carvalho, I., Lopes, C. D., Carneiro, Z. A., Saalbach, G., Schenkman, S., da Silva, J. S., Nepogodiev, S. A., & Field, R. A. (2015). Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion. Tetrahedron, 71(39), 7344-7353. [26688]. https://doi.org/10.1016/j.tet.2015.04.085

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title = "Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion",

abstract = "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 resolve en bloc from 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 surface trans-sialidase of the human parasite Trypanosoma cruzi. In addition, these multivalent TcTS ligands were able to block macrophage invasion by T. cruzi.",

keywords = "Click chemistry, Macrophage invasion, Pseudo-glycomacrocycles, Triazole-linked oligomers, Trypanosoma cruzi",

author = "Campo, {Vanessa L.} and Ivanova, {Irina M.} and Ivone Carvalho and Lopes, {Carla D.} and Carneiro, {Zumira A.} and Gerhard Saalbach and Sergio Schenkman and {da Silva}, {Jo{\~a}o Santana} and Nepogodiev, {Sergey A.} and Field, {Robert A.}",

year = "2015",

month = aug,

day = "17",

doi = "10.1016/j.tet.2015.04.085",

language = "English",

volume = "71",

pages = "7344--7353",

journal = "Tetrahedron",

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Campo, VL, Ivanova, IM, Carvalho, I, Lopes, CD, Carneiro, ZA, Saalbach, G, Schenkman, S, da Silva, JS, Nepogodiev, SA & Field, RA 2015, 'Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion', Tetrahedron, vol. 71, no. 39, 26688, pp. 7344-7353. https://doi.org/10.1016/j.tet.2015.04.085

Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion. / Campo, Vanessa L.; Ivanova, Irina M.; Carvalho, Ivone et al.

In: Tetrahedron, Vol. 71, No. 39, 26688, 17.08.2015, p. 7344-7353.

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

TY - JOUR

T1 - Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

AU - Campo, Vanessa L.

AU - Ivanova, Irina M.

AU - Carvalho, Ivone

AU - Lopes, Carla D.

AU - Carneiro, Zumira A.

AU - Saalbach, Gerhard

AU - Schenkman, Sergio

AU - da Silva, João Santana

AU - Nepogodiev, Sergey A.

AU - Field, Robert A.

PY - 2015/8/17

Y1 - 2015/8/17

N2 - 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 resolve en bloc from 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 surface trans-sialidase of the human parasite Trypanosoma cruzi. In addition, these multivalent TcTS ligands were able to block macrophage invasion by T. cruzi.

AB - 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 resolve en bloc from 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 surface trans-sialidase of the human parasite Trypanosoma cruzi. In addition, these multivalent TcTS ligands were able to block macrophage invasion by T. cruzi.

KW - Click chemistry

KW - Macrophage invasion

KW - Pseudo-glycomacrocycles

KW - Triazole-linked oligomers

KW - Trypanosoma cruzi

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SP - 7344

EP - 7353

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 39

M1 - 26688

ER -

Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

Abstract

Keywords

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