Synthesis and biological evaluation of mannose-6-phosphate-coated multivalent dendritic cluster glycosides

The synthesis of multivalent dendritic cluster glycosides of mannopyranosyl-6-phosphate is presented. Poly(amido amine)-based dendrimers of 0.5-3.5 generations, containing carboxylic acid peripheral functionalities, were utilized so as to install 4, 8, 16 and 32 mannopyranosyl-6-phosphate residues a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2005-12, Vol.3 (23), p.4252-4257
Main Authors: Srinivas, Oruganti, Radhika, S, Bandaru, Narasimha Murthy, Nadimpalli, Siva Kumar, Jayaraman, Narayanaswamy
Format: Article
Language:English
Subjects:
Animals
Dendrimers - chemical synthesis
Dendrimers - chemistry
Glycosides - chemistry
Goats
Liver - chemistry
Mannosephosphates - chemistry
Polyamines - chemistry
Protein Binding
Receptor, IGF Type 2 - metabolism
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Summary:The synthesis of multivalent dendritic cluster glycosides of mannopyranosyl-6-phosphate is presented. Poly(amido amine)-based dendrimers of 0.5-3.5 generations, containing carboxylic acid peripheral functionalities, were utilized so as to install 4, 8, 16 and 32 mannopyranosyl-6-phosphate residues at the peripheries of the dendrimers. Amide bond formation between an amine-tethered mannopyranosyl-6-phosphate monomer unit and carboxylic acid-functionalized dendrimers was conducted to synthesize the dendritic cluster glycosides. The constitutions of the Man-6-P-containing dendrimers were assessed by 1H, 13C and 31P NMR spectroscopies and the sugar content analysis by a resorcinol assay. Preliminary biological studies with few newly synthesized Man-6-P-containing dendrimers showed that these compounds could bind the purified goat liver mannose 6-phosphate receptor (MPR 300) protein.
ISSN:1477-0520
1477-0539
DOI:10.1039/b506348e