Construction Of Amino Acid-Derived Pillar[5]Arene Nanoparticles And Their Selective Capture And Release Of Chiral Drugs

Chiral drugs are often characterized by one enantiomer being effective in treating disease and another being ineffective or even having an adverse effect.At present,about half of the active ingredients contain chiral center,there are still some chiral drugs on the market in the form of racemic.The preparation of single enantiomers is complex and costly,and racemization may occur during subsequent transportation or use.Even if a single-configuration chiral drug is isolated,it still has many defects,which need to be solved by drug delivery system.Based on the above problems and research prospect,we used Pillar[5]arene as molecular platform to prepare L-alanine/L-Phenylalanine derived Pillar[5]arene,four kinds of chiral supramolecular nanoparticles were constructed by self-assembly of Pillar[5]arene with sodium alginate(SA),sodium hyaluronate(HA),carboxymethyl chitosan(CMCS)and sodium dodecyl benzene sulfonate(SDBS),respectively.The selective capture and release of chiral compounds by chiral nanoparticles were investigated.This paper consists of five chapters.In the first chapter,the research progress in the field of chiral supramolecular nanomaterials is introduced,in chapter 2,chiral nanoparticles(L-Ala-P5/SA NPs)were prepared based on L-alanine Pillar[5]arene(L-Ala-P5)and sodium alginate(SA),and the selective capture and release of three pairs of ammonia alcohols by L-Ala-P5/SA NPs were investigated,the results showed that the prepared nanoparticles were stable in acidic environment and have good selectivity for enantiomeric capture and release the loaded drug in alkaline environment.In chapter 3,p H/enzyme dual-responsive chiral nanoparticles(L-Phe-P5NPs)were prepared by using L-Phe-P5 and sodium hyaluronate,the selective capture and release ability of the nanoparticles to three pairs of ammonia alcohols was investigated.The results showed that L-Phe-P5/HA NPs was stable in acidic environment and release drug in alkaline environment,the release rate is about 90%in the presence of hyaluronidase.In addition,the NPs have good selective capture and release ability.In chapter 4,p H-responsive chiral nanoparticles formed by selfassembly of L-Phe-P5 and carboxymethyl chitosan(CMCS)were prepared,the results showed that the NPs could release about 80% of the loaded ibuprofen.At the same time,L-Phe-P5/CMCS nanoparticles have good enantioselective capture and release ability.In chapter 5,the supramolecular drug delivery system based on L-Ala-P5 and sodium dodecylbenzene sulfonate(SDBS)was prepared to realize the effective delivery and controlled release of anticancer drugs.