School of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya, Japan.
Carbohydr Res. 2013 Jun 7;374:49-58. doi: 10.1016/j.carres.2013.03.022. Epub 2013 Apr 3.
From a mixture of 4-nitrophenyl α-L-fucopyranoside and D-mannopyranose, 3-O-α-L-fucopyranosyl-D-mannopyranose was synthesised through the transferring action of α-fucosidase (Sumizyme PHY). 6(I),6(IV)-Di-O-(3-O-α-L-fucopyranosyl-α-D-mannopyranosyl)-cyclomaltoheptaose {8, 6(I),6(IV)-di-O-[α-L-Fuc-(1→3)-α-D-Man]-βCD} was chemically synthesised using the trichloroacetimidate method. The structures were confirmed by MS and NMR spectroscopy. A cell-based assay using the fucosyl βCD derivatives, including the newly synthesised 8, showed that derivatives with two branches of the α-L-Fuc or α-L-Fuc-(1→3)-α-D-Man residues possessed slight growth-promoting effects and lower toxicity in HCT116 cells compared to those with one branch. These compounds may be useful as drug carriers in targeted drug delivery systems.
从 4-硝基苯基α-L-岩藻吡喃糖苷和 D-甘露吡喃糖的混合物中，通过α-岩藻糖苷酶（Sumizyme PHY）的转移作用合成了 3-O-α-L-岩藻吡喃糖基-D-甘露吡喃糖。使用三氯乙酰亚胺酯法化学合成了 6（I），6（IV）-二-O-（3-O-α-L-岩藻吡喃基-α-D-甘露吡喃基）-环麦芽七糖{8,6（I），6（IV）-二-O-[α-L-Fuc-（1→3）-α-D-Man]-βCD}。通过 MS 和 NMR 光谱确认了结构。使用包括新合成的 8 的岩藻糖基βCD 衍生物的基于细胞的测定表明，与具有一个分支的衍生物相比，具有两个α-L-Fuc 或α-L-Fuc-（1→3）-α-D-Man 残基分支的衍生物在 HCT116 细胞中具有轻微的促生长作用和较低的毒性。这些化合物可用作靶向药物传递系统中的药物载体。
