title: Synthesis of a new amphiphilic glycodendrimer with antiviral functionality.
abstract: A new third generation amphiphilic glycodendrimer was synthesized from a stearylamide lysine dendrimer by condensation of the oligosaccharide moiety. By stepwise condensation and deprotection of di-boc lysine from a core of stearyl amide lysine, a third-generation stearylamide lysine dendrimer was constructed. Acetyl cellobiose and glucose units with the carboxylic acid at the end of alkyl chain attached to the reducing end of the sugar moiety was condensed with surface amino groups of the third generation lysine dendrimer, respectively, to give a new stearylamide acetylcellobiose and acetylglucose lysine dendrimers. The structural analysis was carried out using NMR, IR, and matrix-associated laser desorption/ionization time-of-flight (MALDI TOF) mass spectroscopies. After deacetylation to recover hydroxyl groups and subsequent sulfation, the third-generation sulfated cellobiose stearylamide lysine dendrimer was preliminarily found to have high anti-HIV activity at a 50% effective concentration (EC(50)) as low as 6.4 μg/ml and low cytotoxicity at a 50% cytotoxic concentration (CC(50)) as high as 1000 μg/ml, indicating that the dendrimer gave the enhancement of the functionality of oligosaccharides with low molecular weights. The glycodendrimer with a hydrophobic stearyl chain is immobilized on hydrophobic surfaces by hydrophobic interaction and is expected to provide a new biomedical material with the surface functionality of hydrophilic sulfated oligosaccharides.
authors: College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, PR China.
authors: Shuqin
authors: S
authors: Han
authors: Taisei
authors: T
authors: Kanamoto
authors: Hideki
authors: H
authors: Nakashima
authors: Takashi
authors: T
authors: Yoshida
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002240:Carbohydrate Sequence; D002475:Cellobiose / Q000737:chemistry; D050091:Dendrimers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D008954:Models, Biological; D011107:Polylysine / Q000138:chemical synthesis / Q000737:chemistry; D013228:Stearates / Q000138:chemical synthesis / Q000737:chemistry; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D019380:Anti-HIV Agents; D000998:Antiviral Agents; D050091:Dendrimers; D006027:Glycosides; D013228:Stearates; D013501:Surface-Active Agents; C115579:stearyl-poly(lysine); D002475:Cellobiose; C040741:epsilon-tert-butyloxycarbonyl-lysine; D011107:Polylysine; D008239:Lysine