Synthesis and characterisation of novel glycoclusters based on cell penetrating heptakis(6-aminoethylamino-6-deoxy)-β-cyclodextrin
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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.
KeywordsMonosaccharides Amino cyclodextrin Glycoclusters Cell penetrating
Funding by the program PENED 2003 (25% Greek GSRT, 75% EU) and Pharmaten S.A., as well as partial funding by the Marie Curie ITN CYCLON (project #237962) is kindly acknowledged.
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