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Molecules 2018, 23(8), 1890; https://doi.org/10.3390/molecules23081890

Effect of Dendrimer Generation and Aglyconic Linkers on the Binding Properties of Mannosylated Dendrimers Prepared by a Combined Convergent and Onion Peel Approach

1
Department of Chemistry, University of Québec a Montréal, P.O. Box 8888, Succ. Centre-Ville, Montréal, QC H3C 3P8, Canada
2
Glycovax Pharma Inc., 424 Guy, Suite 202, Montreal, QC H3J 1S6, Canada
*
Author to whom correspondence should be addressed.
Academic Editor: Ashok Kakkar
Received: 5 July 2018 / Revised: 24 July 2018 / Accepted: 25 July 2018 / Published: 28 July 2018
Full-Text   |   PDF [4384 KB, uploaded 28 July 2018]   |  

Abstract

An efficient study of carbohydrate-protein interactions was achieved using multivalent glycodendrimer library. Different dendrimers with varied peripheral sugar densities and linkers provided an arsenal of potential novel therapeutic agents that could be useful for better specific action and greater binding affinities against their cognate protein receptors. Highly effective click chemistry represents the basic method used for the synthesis of mannosylated dendrimers. To this end, we used propargylated scaffolds of varying sugar densities ranging from 2 to 18 for the attachment of azido mannopyranoside derivatives using copper catalyzed click cycloaddition. Mannopyranosides with short and pegylated aglycones were used to evaluate their effects on the kinetics of binding. The mannosylated dendrons were built using varied scaffolds toward the accelerated and combined “onion peel” strategy These carbohydrates have been designed to fight E. coli urinary infections, by inhibiting the formation of bacterial biofilms, thus neutralizing the adhesion of FimH type 1 lectin present at the tip of their fimbriae against the natural multiantennary oligomannosides of uroplakin 1a receptors expressed on uroepithelial tissues. Preliminary DLS studies of the mannosylated dendrimers to cross- link the leguminous lectin Con A used as a model showed their high potency as candidates to fight the E. coli adhesion and biofilm formation. View Full-Text
Keywords: dendrimers; mannose; click chemistry; E. coli; UTIs; FimH; DLS dendrimers; mannose; click chemistry; E. coli; UTIs; FimH; DLS
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Sehad, C.; Shiao, T.C.; Sallam, L.M.; Azzouz, A.; Roy, R. Effect of Dendrimer Generation and Aglyconic Linkers on the Binding Properties of Mannosylated Dendrimers Prepared by a Combined Convergent and Onion Peel Approach. Molecules 2018, 23, 1890.

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