β-葡萄糖脑苷脂酶抑制剂N-辛基-β-缬氨胺的化学修饰：4-差向异构体和4-O-(β-D-吡喃半乳糖基)衍生物的合成及生物学评价
Chemical modification of the beta-glucocerebrosidase inhibitor N-octyl-beta-valienamine: synthesis and biological evaluation of 4-epimeric and 4-O-(beta-D-galactopyranosyl) derivatives.
作者信息
Ogawa Seiichiro, Matsunaga Yuko Kobayashi, Suzuki Yoshiyuki
机构信息
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, 223-8522, Yokohama, Japan.
出版信息
Bioorg Med Chem. 2002 Jun;10(6):1967-72. doi: 10.1016/s0968-0896(02)00005-6.
N-Octyl-beta-valienemine (1), a potent beta-glucocerebrosidase inhibitor, was chemically transformed into two biologically interesting compounds: the 4-epimer, beta-galacto-type N-octyl-valienamine, and the 4-O-(beta-D-galactopyranosyl) derivative, a carba-lactosylceramide analogue. The former, interestingly, could be demonstrated to act as a very effective inhibitor (IC(50)=0.3 microM) of human beta-galactosidase. The latter exhibited moderate inhibitory activity (IC(50)=20 microM) against beta-glucocerebrosidase (mouse liver).
N-辛基-β-缬氨烯胺（1）是一种有效的β-葡萄糖脑苷脂酶抑制剂，经化学转化得到两种具有生物学意义的化合物：4-差向异构体，β-半乳糖型N-辛基缬氨胺，以及4-O-（β-D-吡喃半乳糖基）衍生物，一种碳环乳糖基神经酰胺类似物。有趣的是，前者可被证明是一种非常有效的人β-半乳糖苷酶抑制剂（IC50 = 0.3 μM）。后者对β-葡萄糖脑苷脂酶（小鼠肝脏）表现出中等抑制活性（IC50 = 20 μM）。
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