Synthesis of bivalent lactosides and their activity as sensors for differences between lectins in inter- and intrafamily comparisons
Synthesis of bivalent lactosides and their activity as sensors for differences between lectins in inter- and intrafamily comparisons
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DOI：
10.1016/j.bmcl.2011.11.010
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发表时间：
2012-01-01
影响因子：
2.7
通讯作者：
Gabius, Hans-Joachim
中科院分区：
文献类型：
--
作者：
Andre, Sabine;Jarikote, Dilip V.;Gabius, Hans-Joachim
九种二价乳糖苷（基于双三唑、二酰胺、糖环芬和糖环芬的无环类似物）和一种单价乳糖基三唑的合成有助于评估植物/动物凝集素对此类配体展示的敏感性。化合物的抑制效力通过两项增加生物相关性的测定来确定。这些是固相和细胞结合装置。由此，系统地评估了化合物抑制来自一种生物体（鸡）的两种植物凝集素和整套粘附/生长调节半乳糖凝集素与糖蛋白或细胞表面结合的能力。在植物和动物凝集素之间以及在鸡系列中不同的半乳糖凝集素形式之间检测到不同的敏感性。两个二价探针可以被认为是间凝集素差异的传感器。最显着的是 N-糖基 1,2,3-三唑衍生物对嵌合型半乳糖凝集素及其蛋白水解截短形式的选择性。 (C) 2011 Elsevier Ltd. 保留所有权利。
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.