Graduate School of Pharmaceutical Sciences, Kyushu University.
Graduate School of Pharmaceutical Sciences, Nagasaki International University.
Chem Pharm Bull (Tokyo). 2020;68(12):1210-1219. doi: 10.1248/cpb.c20-00594.
N-Acetyl-7-nitroindoline has a characteristic reaction in that its acetyl group is photo-activated to acetylate amines to form amides. In this study, the N-acetyl-7-nitroindoline part was connected to the 2'-deoxyribose part at the 3- or 5-position or to a glycerol unit at the 3-position through an ethylene linker (1, 2, and 3, respectively). They were incorporated into the oligodeoxynucleotides, and their photo-reactivities toward the complementary RNA were evaluated. The acetyl group of 1 was photo-activated to form the deacelylated nitroso derivative without affecting the RNA strand. The photoreaction with 2 suggested acetylation of the RNA strand. In contrast, compound 3 formed the photo-cross-linked adduct with the RNA. These results have shown the potential application of N-acetyl-7-nitroindoline unit in aqueous solutions.
N-乙酰-7-硝基吲哚啉具有一个特征反应，其乙酰基在光照下被激活，从而酰化胺形成酰胺。在本研究中，N-乙酰-7-硝基吲哚啉部分通过乙烯连接体分别连接到 2'-脱氧核糖部分的 3-或 5-位，或者连接到甘油单元的 3-位（分别为 1、2 和 3）。它们被掺入寡脱氧核苷酸中，并评估了它们对互补 RNA 的光反应性。1 的乙酰基在光照下被激活，形成去乙酰化的亚硝酮衍生物，而不影响 RNA 链。与 2 的光反应表明 RNA 链的乙酰化。相比之下，化合物 3 与 RNA 形成光交联加合物。这些结果表明 N-乙酰-7-硝基吲哚啉单元在水溶液中的潜在应用。
