Abstract：
A unique V-shaped \"chiral\" supramolecular scaffold, N-(4-pyridyl)-4-amino-1,8-naphthalimide Tröger\'s base (TBNap), was synthesized in good yield from a precursor N-(4-pyridyl)-4-amino-1,8-naphthalimide (Nap). TBNap was characterized using different spectroscopic methods and the molecular structure was elucidated by diffraction analysis. A new p-cymene-Ru(II)-curcumin conjugate (TB-Ru-Cur) was designed by reacting TBNap dipyridyl donor and ruthenium-curcuminato acceptor [RuCur = (p-cymene)Ru-(curcuminato)Cl] in the presence of silver triflate. TB-Ru-Cur was isolated in quantitative yield and characterized using Fourier transform infrared (FT-IR), NMR (1H, 13C, and 19F), and electrospray ionization mass spectrometry (ESI-MS), and the molecular structure has been predicted using a computational study. Both TBNap and TB-Ru-Cur exhibited intramolecular charge transfer (ICT)-based fluorescence emission. Furthermore, the anticancer properties of TBNap, Ru-Cur, and TB-Ru-Cur were assessed in different cancer cell lines. Gratifyingly, the conjugate TB-Ru-Cur displayed fast-cellular internalization and good cytotoxicity against HeLa, HCT-116, and HepG2 cancer cells and the estimated IC50 value was much lower than that of the precursors (TBNap and Ru-Cur) and the well-known chemotherapeutic drug cisplatin.
摘要：
独特的V形“手性”超分子支架，N-(4-吡啶基)-4-氨基-1,8-萘酰亚胺Tröger碱(TBNap),由前体N-(4-吡啶基)-4-氨基-1,8-萘酰亚胺(Nap)以良好的产率合成。使用不同的光谱方法表征TBNap，并通过衍射分析阐明分子结构。通过在三氟甲磺酸银的存在下使TBNap二吡啶基供体和钌-姜黄素受体[RuCur=（对氰甲酚）Ru-（姜黄素）Cl]反应，设计了一种新的对氰甲酚-Ru（II）-姜黄素缀合物（TB-Ru-Cur）。以定量收率分离出TB-Ru-Cur，并使用傅立叶变换红外（FT-IR）进行表征，NMR(1H,13C,和19F），和电喷雾电离质谱(ESI-MS)，分子结构已经通过计算研究预测。TBNap和TB-Ru-Cur均表现出基于分子内电荷转移(ICT)的荧光发射。此外，TBNap的抗癌特性，Ru-Cur,在不同的癌细胞系中评估TB-Ru-Cur。令人欣喜的是，偶联物TB-Ru-Cur对HeLa表现出快速的细胞内化和良好的细胞毒性，HCT-116和HepG2癌细胞的估计IC50值远低于前体细胞(TBNap和Ru-Cur)和众所周知的化疗药物顺铂。
