Synthesis and Cytotoxic Mechanism of Sulfated Alkyl Oligosaccharides Having Potent Anti-HIV Activity

Three sulfated 1-alkyl-triazole-maltoheptaosides bearing long-chain alkyl groups (C6, C12, and C18) at the reducing ends were synthesized subjected to surface plasmon resonance with liposomes elucidate cytotoxic mechanism of oligosaccharides having potent anti-HIV activity. With increasing length groups, cytotoxicity nonsulfated against MT-4 cells increased CC50 values 102 72 μg/mL from a low CC50>1000 μg/mL. Nonsulfated C18 chain showed highest apparent association-rate constant (ka=1.20×105 1.00×107 1/M, respectively) lowest dissociation-rate (kd=7.30×10‒7 1.39×10‒4 1/s, constants liposomes, indicating that longer-chains interact tightly liposomes. The results suggest longer-chain penetrate into lipid bilayer induce cytotoxicity. Considering proposed mechanism, antibacterial activity Gram-negative Escherichia coli Gram-positive Bacillus subtilis was preliminarily investigated, finding certain