Synthesis and evaluation of a novel Rhodamine B pyrene [2]rotaxane as an intracellular delivery agent for doxorubicin
Synthesis and evaluation of a novel Rhodamine B pyrene [2]rotaxane as an intracellular delivery agent for doxorubicin
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新型罗丹明 B 芘 [2] 轮烷作为阿霉素细胞内递送剂的合成和评价
DOI：
10.1039/c5ob00934k
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发表时间：
2015
影响因子：
3.2
通讯作者：
Xiaofeng Bao
中科院分区：
文献类型：
--
作者：
Jiaxin Shi;Yuan Xu;Xinglong Wang;Luyong Zhang;Jing Zhu;Tao Pang;Xiaofeng Bao
设计、合成了一种新型罗丹明B衍生的主体[2]轮烷，其含有二苄基-24-冠-8（DB24C8）环作为轮，芘作为另一个荧光团封闭基团，并进行了结构表征。 RhBPy [2]轮烷的 1 H NMR 谱与 2 和 DB24C8 的 1 H NMR 谱、核欧沃豪瑟效应光谱 (NOESY)、质谱和荧光光谱的比较证实了 RhBPy [2]轮烷的互锁性质。通过1H NMR光谱研究的轮烷的温度依赖性进一步证明RhBPy [2]轮烷可以用作分子开关。 RhBPy [2]轮烷也被证明是一种有效的转运剂，可将癌症药物阿霉素 (DOX) 输送到肿瘤细胞中。事实上，RhBPy [2]轮烷传递的 DOX 可以有效抑制肿瘤细胞的生长。
A novel Rhodamine B-derivatized host [2]rotaxane, containing a dibenzyl-24-crown-8 (DB24C8) ring as the wheel and a pyrene as another fluorophore blocking group, was designed, synthesized and structurally characterized. A comparison of the 1H NMR spectra of RhBPy [2]rotaxane with those of 2 and DB24C8, nuclear Overhauser effect spectroscopy (NOESY), mass spectrometry and fluorescence spectroscopy confirmed the interlocked nature of RhBPy [2]rotaxane. The temperature dependence of the rotaxane studied by 1H NMR spectroscopy further demonstrated that RhBPy [2]rotaxane can be applied as a molecular switch. RhBPy [2]rotaxane has also been demonstrated to be an efficient transport agent for delivering the cancer drug doxorubicin (DOX) into tumor cells. Indeed, DOX delivered by RhBPy [2]rotaxane could effectively inhibit tumor cell growth.