Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers
Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers
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DOI：
10.1155/2015/317420
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发表时间：
2015-01-01
影响因子：
3.3
通讯作者：
Yoshida, Takashi
中科院分区：
文献类型：
--
作者：
Bai, Shiming;Budragchaa, Davaanyam;Yoshida, Takashi
具有长烷基的硫酸化吡喃葡萄糖是通过苄基化1,6-脱水吡喃葡萄糖与3-O-十八烷基1,6-脱水-β-D-吡喃葡萄糖单体的开环共聚，然后脱保护和硫酸化制备的。含有 2.8 和 4.7 mol% 3-O-十八烷基和较低分子量 (M-n) 超过 bar = 2.5 x 10(3) -5.1 x 10(3) 的水溶性硫酸化吡喃葡聚糖在 0.05-1.25 mu g/mL 时具有有效的抗 HIV 活性，即使分子量低于 (M-n) 超过 bar = 6 x 的硫酸化多糖10(3)的抗HIV活性较低。通过SPR、DSL和zeta电位分析与聚-L-赖氨酸作为蛋白质模型化合物的相互作用，表明硫酸化3-O-十八烷基吡喃葡聚糖具有高缔合和低解离速率常数，并且添加聚-L-赖氨酸后粒径增加。抗HIV活性是通过聚-L-赖氨酸的硫酸基团和氨基之间的静电相互作用以及疏水性长烷基链和亲水性硫酸化基团的协同作用诱导的。
Sulfated glucopyranans having long alkyl groups were prepared by the ring-opening copolymerization of benzylated 1,6-anhydroglucopyranose with 3-O-octadecyl 1,6-anhydro-beta-D-glucopyranose monomers, and subsequent deprotection and sulfation. Water-soluble sulfated glucopyranans with 2.8 and 4.7 mol% of 3-O-octadecyl group and lower molecular weight of (M-n) over bar = 2.5 x 10(3) -5.1 x 10(3) have potent anti-HIV activity at 0.05-1.25 mu g/mL, even though sulfated polysaccharides with molecular weights below (M-n) over bar = 6 x 10(3) had low anti-HIV activity. The interaction with poly-l-lysine as a model compound of proteins was analyzed by SPR, DSL, and zeta potential, indicating that the sulfated 3-O-octadecyl glucopyranans had high association and low dissociation rate constants, and the particle size increased after addition of poly-l-lysine. The anti-HIV activity was induced by electrostatic interaction between sulfate groups and amino groups of poly-l-lysine and by the synergistic effect of the hydrophobic long alkyl chain and hydrophilic sulfated group.