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

Org Biomol Chem. 2005 Dec 7;3(23):4252-7. doi: 10.1039/b506348e. Epub 2005 Oct 31.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dendrimers / chemical synthesis*
  • Dendrimers / chemistry
  • Glycosides / chemistry*
  • Goats
  • Liver / chemistry
  • Mannosephosphates / chemistry*
  • Polyamines / chemistry
  • Protein Binding
  • Receptor, IGF Type 2 / metabolism*

Substances

  • Dendrimers
  • Glycosides
  • Mannosephosphates
  • PAMAM Starburst
  • Polyamines
  • Receptor, IGF Type 2
  • mannose-6-phosphate