Guanidinoneomycin-maleimide molecular transporter: synthesis, chemistry and cellular uptake.
Guanidinoneomycin-maleimide molecular transporter: synthesis, chemistry and cellular uptake.
复制标题
DOI：
10.1039/d1ob01101d
复制
发表时间：
2021-07
影响因子：
3.2
通讯作者：
K. Hadidi;M. Bellucci;S. Dall’Angelo;A. Leeson-Payne;J. Rochford;J. D. Esko;Y. Tor;A. Volonterio
中科院分区：
文献类型：
--
作者：
K. Hadidi;M. Bellucci;S. Dall’Angelo;A. Leeson-Payne;J. Rochford;J. D. Esko;Y. Tor;A. Volonterio
胍基糖苷类化合物是一类非细胞毒性的分子转运体，能够以低纳摩尔浓度将高分子量的生物活性物质递送到细胞中。与胍基糖苷类的有效生物缀合先前已经通过利用用反应性但也不稳定的含N-羟基琥珀酰亚胺酯的接头修饰的胍基新霉素来证明。在此，我们报告了一种新的，稳定的胍基新霉素衍生物的合成，化学和应用，该衍生物具有高度特异性的马来酰亚胺部分，允许巯基马来酰亚胺点击化学，一种非常流行的生物缀合策略，拓宽了这些有趣和有用的递送载体的应用领域。
Guanidinoglycosides are a class of non-cytotoxic molecular transporters capable of delivering high molecular weight bioactive cargos into cells at low nanomolar concentrations. Efficient bioconjugation with guanidinoglycosides has been previously demonstrated by utilizing a guanidinoneomycin decorated with a reactive but also unstable N-hydroxysuccinimmide ester-containing linker. Herein we report the synthesis, chemistry, and application of a new, stable guanidinoneomycin derivative armed with a highly specific maleimide moiety which allows for thiol-maleimide click chemistry, a highly popular bioconjugation strategy, widening the field of application of these intriguing and useful delivery vehicles.