Kawada J, Toide K, Nishida M, Yoshimura Y, Tsujihara K
Diabetes. 1986 Jan;35(1):74-7. doi: 10.2337/diab.35.1.74.
The nonmetabolizable glucose analogue 3-O-methyl-glucose is known to protect pancreatic B-cells against streptozocin (STZ) when injected with or just before STZ. If 3-O-methyl-glucose and the sugar moiety of STZ compete for a glucose recognition site on B-cells, it seemed likely that 3-O-methyl-2-deoxy-2-( [(methylnitrosoamino)carbonyl]amino)-D-glucopyranose, an analogue of STZ with a 3-O-methyl-glucosyl residue, would cause experimental diabetes. This possibility was tested by synthesis of this analogue (alpha-anomer) and comparison of its diabetogenic activity in Wistar rats with that of STZ. Results showed that the compound was diabetogenic and as potent as STZ. This new analogue is the first of the various STZ derivatives reported to show diabetogenic activity. Its activity supports the idea that 3-O-methyl-glucose and STZ bind competitively with a glucose recognition site on pancreatic B-cells.
已知不可代谢的葡萄糖类似物3 - O - 甲基葡萄糖在与链脲佐菌素（STZ）同时注射或在STZ注射前注射时，可保护胰腺β细胞免受STZ损伤。如果3 - O - 甲基葡萄糖和STZ的糖部分竞争β细胞上的葡萄糖识别位点，那么带有3 - O - 甲基葡糖基残基的STZ类似物3 - O - 甲基 - 2 - 脱氧 - 2 - ([(甲基亚硝基氨基)羰基]氨基)-D - 吡喃葡萄糖似乎有可能导致实验性糖尿病。通过合成该类似物（α - 异头物）并比较其在Wistar大鼠中的致糖尿病活性与STZ的致糖尿病活性，对这种可能性进行了测试。结果表明该化合物具有致糖尿病作用，且与STZ的效力相当。这种新的类似物是所报道的各种STZ衍生物中首个显示出致糖尿病活性的。其活性支持了3 - O - 甲基葡萄糖和STZ与胰腺β细胞上的葡萄糖识别位点竞争性结合的观点。
