Immobilisation on polystyrene of diazirine derivatives of mono- and disaccharides:: Biological activities of modified surfaces
Immobilisation on polystyrene of diazirine derivatives of mono- and disaccharides:: Biological activities of modified surfaces
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DOI：
10.1016/s0968-0896(01)00172-9
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发表时间：
2001-11-01
影响因子：
3.5
通讯作者：
Sigrist, H
中科院分区：
文献类型：
--
作者：
Chevolot, Y;Martins, J;Sigrist, H
表面糖工程在生物材料和生物传感器中的潜力源于碳水化合物-蛋白质相互作用在生物系统中的重要性。这里采用的策略利用通过照射二氮丙啶产生的卡宾来实现碳水化合物的共价键合。在这里，我们描述了一个芳基二氮杂环丙烯含有二糖（乳糖）的合成。表面分析技术[X射线光电子能谱（XPS）和飞行时间二次离子质谱（ToF-SIMS）]证明其成功的表面固定在聚苯乙烯（PS）上。结果进行了比较，以前获得的芳基含有单糖（半乳糖）的diazirine。使用大鼠肝细胞、Allo A凝集素和α-2，6-唾液酸转移酶的固相半合成研究了半乳糖或乳糖修饰的PS样品的生物活性。Allo A与半乳糖修饰的PS有一定的结合，但与乳糖修饰的表面没有结合。用大鼠肝细胞获得了类似的结果。相比之下，乳糖修饰的PS的唾液酸化被实现，但不与半乳糖修饰的表面。不同的响应表明，生物活性不仅取决于碳水化合物本身，而且还取决于间隔区的结构和长度。(C)2001爱思唯尔科技有限公司版权所有。
The potential of surface glycoengineering for biomaterials and biosensors originates from the importance of carbohydrate-protein interactions in biological systems. The strategy employed here utilises carbene generated by illumination of diazirine to achieve covalent bonding of carbohydrates. Here, we describe the synthesis of an aryl diazirine containing a disaccharide (lactose). Surface analysis techniques [X-ray photoelectron spectroscopy (XPS) and time of flight secondary ion mass spectroscopy (ToF-SIMS)] demonstrate its successful surface immobilisation on polystyrene (PS). Results are compared to those previously obtained with an aryl diazirine containing a monosaccharide (galactose). The biological activity of galactose- or lactose-modified PS samples is studied using rat hepatocytes, Allo A lectin and solid-phase semi-synthesis with alpha -2,6-sialyltransferase. Allo A shows some binding to galactose-modified PS but none to lactose-modified surfaces. Similar results are obtained with rat hepatocytes. In contrast, sialylation of lactose-modified PS is achieved but not with galactose-modified surfaces. The different responses indicate that the biological activity depends not only on the carbohydrate per se but also on the structure and length of the spacer. (C) 2001 Elsevier Science Ltd. All rights reserved.