Dipartimento di Scienze Cliniche Luigi Sacco, Via G. B. Grassi 74, Università degli Studi di Milano, 20157 Milano, Italy.
Bioorg Med Chem. 2010 Jun 15;18(12):4249-54. doi: 10.1016/j.bmc.2010.04.093. Epub 2010 May 20.
The present study describes the synthesis, the characterization and the evaluation of some derivatives of N(6)-isopentenyladenosine on T24 human bladder carcinoma cells. In particular we have modified the hydroxyl groups in the ribose moiety, the position of the isopentenyl chain in the purine ring and the base moiety. The structures of the compounds were confirmed by standard studies of NMR, MS and elemental analysis. We here show that only two derivatives, 1-(3-methyl-2-butenylamino)-9-(3'-deoxy-beta-d-ribofuranosyl)-purine hydrobromide and 2-amino-6-(3-methyl-2- butenylamino)-9-(beta-d-ribofuranosyl)-purine, inhibit the growth of T24 cells, although to a lower extent than N(6)-isopentenyladenosine. We conclude that the integrity of ribosidic and purine moiety and the N(6) position of the chain are essential for maintaining the antiproliferative activity.
本研究描述了 N(6)-异戊烯基腺苷的一些衍生物在 T24 人膀胱癌细胞中的合成、表征和评价。特别是，我们修饰了核糖部分的羟基、嘌呤环中异戊烯链的位置和碱基部分。通过标准的 NMR、MS 和元素分析研究证实了化合物的结构。我们在这里表明，只有两种衍生物，1-(3-甲基-2-丁烯基氨基)-9-(3'-去氧-β-D-核糖呋喃基)-嘌呤氢溴酸盐和 2-氨基-6-(3-甲基-2-丁烯基氨基)-9-(β-D-核糖呋喃基)-嘌呤，抑制 T24 细胞的生长，尽管其抑制作用比 N(6)-异戊烯基腺苷低。我们得出结论，核糖部分和嘌呤部分的完整性以及链的 N(6)位置对于保持抗增殖活性是必不可少的。
