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

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:22

Article

Andre, Sabine²  Jarikote, Dilip V.¹  Yan, Dandan^1,3  Vincenz, Lisa¹  Wang, Guan-Nan¹  Kaltner, Herbert²  Murphy, Paul V.¹  Gabius, Hans-Joachim² 

[1] Natl Univ Ireland, Sch Chem, Galway, Ireland

[2] Univ Munich, Fac Vet Med, Inst Physiol Chem, D-80539 Munich, Germany

[3] Univ Coll Dublin, Sch Chem & Chem Biol, Dublin 4, Ireland

关键词: Agglutinin;    Glycocluster;    Glycocyclophane;    Lectin;    N-Glycosyl 1,2,3-triazoles;   

DOI  :  10.1016/j.bmcl.2011.11.010

来源: Elsevier

【 摘 要 】

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. (C) 2011 Elsevier Ltd. All rights reserved.

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