Abstract A set of poly(amide triazoles) (PT) was synthesized by azide-alkyne cycloaddition reactions from N,N-Bis[2-(propargylamido)ethyl]-N-[2-(tert-butoxycarbonylamino)ethyl] amine and 1,6-diazido-1,6-dideoxy- d -mannitol derivatives, having the secondary hydroxyl groups protected by removable acetal and/or acetyl groups. Either copper-catalyzed (CuAAC) as well as the classical thermal cycloaddition reactions were used to afford in good yields and medium molecular weight-linear PT featuring either 1,4- or 1,4/1,5-disubstituted triazole rings along the polymer chains, respectively. Full structural characterization of all PT was accomplished and comparatively studied. Protecting group removal allowed for modulating the flexibility and polarity of cationic polytriazoles (CP), entitling for structure-activity relationship insight of their self-assembling capabilities in the presence of nucleic acids. Hence, CP and DNA were formulated at different nitrogen-to-phosphate (N/P) ratios and the resulting polyplexes were characterized by Dynamic Light Scattering (DLS) and Transmission Electron Microscopy (TEM). All CP were able to condense DNA into positively-charged nanometric-sized and narrow-polydispersed particles that could mediated transfection into human embryonic stem cells (hESC) with negligible toxicity.

中文翻译：

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D-甘露醇基阳离子聚（酰胺三唑）及其与DNA自组装复合物的结构-性能关系

摘要 以 N,N-双[2-(炔丙基酰胺)乙基]-N-[2-(叔丁氧基羰基氨基)乙基]胺和1 ,6-二叠氮基-1,6-二脱氧-d-甘露醇衍生物，具有被可去除的缩醛和/或乙酰基保护的仲羟基。铜催化 (CuAAC) 以及经典的热环加成反应都用于提供高产率和中等分子量的线性 PT，其特征是沿聚合物具有 1,4- 或 1,4/1,5- 二取代的三唑环链，分别。完成并比较研究了所有 PT 的完整结构表征。保护基团的去除允许调节阳离子聚三唑 (CP) 的灵活性和极性，有权对其在核酸存在下的自组装能力的构效关系进行洞察。因此，CP 和 DNA 以不同的氮磷 (N/P) 比率配制，所得复合物通过动态光散射 (DLS) 和透射电子显微镜 (TEM) 进行表征。所有 CP 都能够将 DNA 浓缩成带正电荷的纳米尺寸和窄多分散颗粒，这些颗粒可以介导转染到人类胚胎干细胞 (hESC) 中，其毒性可忽略不计。