Synthesis and characterisation of novel glycoclusters based on cell penetrating heptakis(6-aminoethylamino-6-deoxy)-β-cyclodextrin
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- Lampropoulou, M. & Yannakopoulou, K. J Incl Phenom Macrocycl Chem (2011) 70: 345. doi:10.1007/s10847-010-9840-2
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The modification of a polyamino βCD, heptakis(6-aminoethylamino-6-deoxy)-βCD (bpen) with several monosaccharides (Man, GlcNAc, Gal, Glc), specific for bacterial lectin targeting is described. The first synthetic approach, based on disuccinimidyl carbonate-substituted monosaccharides had moderate success, whereas the second approach, based on thiopropanoic acid-linked monosaccharides, was more efficient. Each method gave the best result with a different monosaccharide. Given that bpen is known to penetrate cells, the new products are expected to possess both lectin recognition ability and membrane crossing properties.