Research And Application Of Supramolecular Self-Assembly Based On Water-soluble Pillar[5] Arene

With the rapid development of the field of supramolecular chemistry,the construction of functional nanostructures through the supramolecular self-assembly through non-covalent interactions between host and guest has gradually been studied.Some major macrocyclic compounds include crown ethers,cyclodextrin,cucurbituril,calixarene,and pillar arene.Among them,the water-soluble pillar[5]arene(WP5)modified with sodium carboxylate group,with the advantages of easy to synthesize and has high yield,good water solubility,high biocompatibility,stimulus response etc.,has been widely used.In this paper,WP5 was used as the macrocyclic host compound,and functional nanoparticles were constructed by self-assembly with various small molecular compounds as guests,and their properties and applications were studied.The specific contents are as follows:1.We used a kind of water-insoluble anti-cancer drug regorafenib as a small molecule,to form a complex with WP5 by the host-guest interaction.And a kind of nanoparticles was obtained by the self-assemble of complex.The change of morphology and the release of the anti-cancer drug were observed,which showed that it was pH-responsive.It was also characterized by DLS,Zeta potential,NMR,and fluorescence,and the binding constant,stoichiometric ratio were calculated.Finally,the vitro cytocompatibility experiments results showed that the nanoparticles had stronger anticancer activity to cancer cell than the blank anticancer drug regorafenib in aqueous solution at the same concentration.2.We chose aniline tetramer(TANI)with photothermal conversion performance as another guest small molecule,to form a complex with WP5(WP5(?)TANI)by the way of host-guest interaction,making the dispersibility of water-insoluble TANI in water significantly improved.We characterized its interaction by NMR,UV-vis,IR,and CV potentials.We found that WP5 has a significant stabilizing effect to the cations on TANI.3.With the help of TEM and DLS,We have observed that the above WP5(?)TANI complex self-assembled in water system to obtain a nanoparticle with vesicular morphology,and the morphology was pH responsive.We also calculated its CAC.Secondly,we characterized the UV-NIR absorption of the vesicles at pH=7.4 and pH=5.3,and the photothermal heating properties in vitro.In addition,we examine the influencing factors(concentration,laser power density)and stability of photothermal heating.Finally,in order to reveal the principle of photothermal heating,we calculated the photothermal conversion efficiency under NIR-? and NIR-? lasers.4.Based on the supramolecular vesicles formed by WP5(?)TANI complex,we selected a water-soluble anticancer drug DOX·HCl(doxorubicin hydrochloride)as a model and loaded it,and found that the drug-carrying property is good,and the release of the drug was also responsive of pH and NIR laser irradiation.Through cell biocompatibility experiments,the results show that the vesicles are highly water-soluble to normal cells,but have selective toxicity to cancer cells.Through in vivo experiments in mice,the effects of chemotherapeutic and photothermal treatment of the supramolecular drug-loaded vesicles were characterized.