Preparation Of Polyamine-β-Cyclodextrins-Genistein Complexes And Research Of Transmembrane Channels Based On Acyclic Cucurbit[n]Uril-Pillar[5]Arene

Supramolecular chemistry is an emerging edge discipline that studies the intermolecular aggregates formed by the combination of two or more molecules through intermolecular interactions,it is also called host-guest chemistry.Macrocyclic supramolecular such as cucurbit[n]uril,cyclodextrin,and pillar[n]arene are widely used in drug delivery,functional materials,bioimaging,chemical catalysis,and artificial transmembrane and other fields due to their special cavity,highly water-solubility and structure that easy-to-modify.In order to further explore the application of macrocyclic supramolecular host in drug delivery and artificial transmembrane channels.In this paper,inclusions of four polyamine-modifiedβ-cyclodextrin and genistein were prepared and characterized,the anti-tumor activity studies were performed by MTT assay.In addition,a series of linear supramolecular hosts of acyclic cucurbit[n]uril-pillar[5]arene-acyclic cucurbit[n]uril were synthesized as transmembrane channels,and the protons and alkali cations transmembrane transport ability of these linear supramolecules was verified.The specific research contents are as follows:1.The preparation,characterization and anti-tumor activity in vitro of polyamine-modifiedβ-cyclodextrin and genistein inclusion complexes were studied.First of all,the standard plot of genistein and the phase solubility plot analysis of four amino cyclodextrins and genistein proved that stoichiometric ratio of inclusion complexes between polyamine-modifiedβ-cyclodextrin and genistein was 1:1.Afterwards,~1H NMR and 2D ROESY were used to infer its possible inclusion mode.In addition,the inclusion complexes of polyamine-modifiedβ-cyclodextrin and genistein were characterized by SEM,XRD and FT-IR spectroscopy.Moreover,the solubility experiment proved that the water solubility of inclusion complexes of polyamine-modifiedβ-cyclodextrin and genistein were increased among 1000 folds.Finally,the MTT assay proved the cytotoxicity of inclusion complexes between polyamine-modifiedβ-cyclodextrin and genistein on the three human cancer cell lines Hep G2,H460 and HCT116 was significantly improved.This cyclodextrin-based drug delivery system is expected to improve the low water solubility and bioavailability of genistein in cancer treatment.2.A class of acyclic cucurbit[n]uril-pillar[5]arene-acyclic cucurbit[n]uril linear supramolecules was prepared as transmembrane channels.At first,through the chemical structure modification of the acyclic cucurbit[n]uril and the pillar[5]arene,a series of linear supramolecular hosts of acyclic cucurbit[n]uril-pillar[5]arene-acyclic cucurbit[n]uril were successfully synthesized.Then,~1H NMR and FT-IR spectroscopy proves that linear supramolecular have been successfully synthesized.In addition,the transmembrane ability of these linear supramolecular for protons and alkali metal cations was verified through vesicle experiments.The results showed these linear supramolecular can be inserted into the lipid bilayer and transport protons and alkali metal cations,and linear supramolecular with different chain lengths have different transmembrane abilities.Which provides a simple single-molecule transmembrane channel model for studying the transmembrane mechanism of substances.