Abstract The synthesis of new conjugates of calix[4]resorcinarenes and methoxy-PEG via acylhydrazone bonds and their study in the formation of pH-sensitive low-toxic supramolecular drug delivery systems have described. The syntheses have been performed on the base of two calix[4]resorcinarenes in chair and boat conformations to obtain the dendrimer-like and amphiphilic conjugates, respectively. The structures of the conjugates have been confirmed by 1H, 13C NMR, and FT-IR spectroscopy, Maldi-TOF mass spectroscopy, and SLS method. The self-association of both amphiphilic and dendrimer-like conjugates has been found (NMR FT-PGSE, fluorimetry, DLS and TEM methods). The hydrolysis of the conjugates at pH 5.5 (proved by 1H NMR and FT-IR spectroscopy, DLS method) lead to the improved release of the conjugate-encapsulated Dox. The low hemolytic activity and low cytotoxicity against Chang liver cells of the conjugates and products of their hydrolysis have been demonstrated. Meanwhile, the improved cytotoxicity and photodynamic activity of conjugates-encapsulated drugs (Dox and Methylene Blue, respectively) has been found in vitro. The results have indicated the potential using of the calix[4]resorcinarene-mPEG conjugates bearing acylhydrazone bonds as supramolecular drug delivery systems.

中文翻译：

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带有酰基腙键的 pH 响应杯 [4] 间苯二酚-mPEG 缀合物：合成和研究作为超分子药物递送系统的潜力

摘要 描述了通过酰基腙键合成杯[4]间苯二酚和甲氧基-PEG 的新偶联物及其在形成 pH 敏感低毒超分子药物递送系统中的研究。已经在椅子和船构象的两个杯[4]间苯二酚的基础上进行了合成，分别获得了树枝状聚合物和两亲性共轭物。共轭物的结构已通过 1H、13C NMR、FT-IR 光谱、Maldi-TOF 质谱和 SLS 方法确认。已发现两亲性和树枝状聚合物样缀合物的自缔合（NMR FT-PGSE、荧光法、DLS 和 TEM 方法）。偶联物在 pH 5.5 时的水解（由 1H NMR 和 FT-IR 光谱、DLS 方法证明）导致偶联物封装的 Dox 的释放得到改善。已证明缀合物及其水解产物对 Chang 肝细胞的低溶血活性和低细胞毒性。同时，已在体外发现缀合物包封药物（分别为 Dox 和亚甲蓝）的细胞毒性和光动力学活性得到改善。结果表明带有酰基腙键的杯[4]间苯二酚-mPEG缀合物作为超分子药物递送系统的潜在用途。