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

Campo VL, Ivanova IM, Carvalho I, Lopes CD, Carneiro ZA, Saalbach G, Schenkman S, da Silva JS, Nepogodiev SA, Field RA - Tetrahedron (2015)

Bottom Line: 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 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.

View Article: PubMed Central - PubMed

Affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, USP, Av. Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil.

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.

No MeSH data available.


Related in: MedlinePlus

Representative images illustrating amastigote-form parasite numbers present inside macrophages infected with T. cruzi in (A) the absence and (B) the presence of 250 μM mixed length 1,4/1,5 triazole-linked linear oligomers. Arrows indicate cells infected with T. cruzi.
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fig5: Representative images illustrating amastigote-form parasite numbers present inside macrophages infected with T. cruzi in (A) the absence and (B) the presence of 250 μM mixed length 1,4/1,5 triazole-linked linear oligomers. Arrows indicate cells infected with T. cruzi.

Mentions: To complement the above assays, we also assessed differentiated amastigote-form Trypanosoma cruzi numbers inside infected macrophages, and the impact of triazole-linked oligomers on these numbers. In keeping with the trypomastigote results (Fig. 4 A), triazole-linked oligomers resulted in a reduction in the number of parasites found inside macrophages (Fig. 4 B; Fig. 5), with a general trend towards larger structures giving greater effect.


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

Campo VL, Ivanova IM, Carvalho I, Lopes CD, Carneiro ZA, Saalbach G, Schenkman S, da Silva JS, Nepogodiev SA, Field RA - Tetrahedron (2015)

Representative images illustrating amastigote-form parasite numbers present inside macrophages infected with T. cruzi in (A) the absence and (B) the presence of 250 μM mixed length 1,4/1,5 triazole-linked linear oligomers. Arrows indicate cells infected with T. cruzi.
© Copyright Policy - CC BY
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4542550&req=5

fig5: Representative images illustrating amastigote-form parasite numbers present inside macrophages infected with T. cruzi in (A) the absence and (B) the presence of 250 μM mixed length 1,4/1,5 triazole-linked linear oligomers. Arrows indicate cells infected with T. cruzi.
Mentions: To complement the above assays, we also assessed differentiated amastigote-form Trypanosoma cruzi numbers inside infected macrophages, and the impact of triazole-linked oligomers on these numbers. In keeping with the trypomastigote results (Fig. 4 A), triazole-linked oligomers resulted in a reduction in the number of parasites found inside macrophages (Fig. 4 B; Fig. 5), with a general trend towards larger structures giving greater effect.

Bottom Line: 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 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.

View Article: PubMed Central - PubMed

Affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, USP, Av. Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil.

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.

No MeSH data available.


Related in: MedlinePlus