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 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.
Srinivas
Oruganti
O
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
Radhika
S
S
Bandaru
Narasimha Murthy
NM
Nadimpalli
Siva Kumar
SK
Jayaraman
Narayanaswamy
N
D000818:Animals; D050091:Dendrimers / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006041:Goats; D008099:Liver / Q000737:chemistry; D008360:Mannosephosphates / Q000737:chemistry*; D011073:Polyamines / Q000737:chemistry; D011485:Protein Binding; D017527:Receptor, IGF Type 2 / Q000378:metabolism*
D050091:Dendrimers; D006027:Glycosides; D008360:Mannosephosphates; C104700:PAMAM Starburst; D011073:Polyamines; D017527:Receptor, IGF Type 2; C027693:mannose-6-phosphate