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Synthesis of bivalent lactosides and their activity as sensors for differences between lectins in inter- and intrafamily comparisons.

Abstract：

:The synthesis of nine bivalent lactosides (based on ditriazoles, diamides, a glycocyclophane and an acyclic analogue of the glycocyclophane) and one monovalent lactosyl triazole facilitated the assessment of the sensitivity of plant/animal lectins to this type of ligand display. The inhibitory potency of the compounds was determined in two assays of increasing biorelevance. These were solid-phase and cell binding set-ups. Hereby, the ability of the compounds to inhibit the binding of two plant agglutinins and the entire set of adhesion/growth-regulatory galectins from one organism (chicken) to a glycoprotein or to cell surfaces was systematically evaluated. Differential sensitivities were detected between plant and animal lectins and also between distinct galectin forms within the chicken series. Two of the bivalent probes can be considered as sensors for interlectin differences. Most pronounced were the selectivities of N-glycosyl 1,2,3-triazole derivatives for the chimera-type galectin and its proteolytically truncated version.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

André S,Jarikote DV,Yan D,Vincenz L,Wang GN,Kaltner H,Murphy PV,Gabius HJ

doi

10.1016/j.bmcl.2011.11.010

subject

Has Abstract

pub_date

2012-01-01 00:00:00

pages

313-8

issue

1

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(11)01542-3

journal_volume

22

pub_type

杂志文章

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