title: Cyclodextrin-functionalized silica nanoparticles with dendrimer-like spacers for enantioselective capillary electrochromatography.
abstract: In this report, β-cyclodextrin (β-CD)-functionalized silica nanoparticles (SNPs) with dendrimer-like spacers were synthesized by first grafting the SNPs with different generations of polyamidoamines (PAMAMs), followed by modifying the grafted SNPs with mono-6-deoxy-(p-tolylsulfonyl)-β-CD. The β-cyclodextrin-modified silica nanoparticle-cored PAMAMs (SNP-PAMAM-β-CDs) were studied as chiral pseudostationary phases for separating three racemic drugs, namely, chlorpheniramine, nefopam, and verapamil. The β-CD-functionalized SNPs with dendrimer-like spacers were more enantioselective than native β-CD, and the structures of the dendritic spacers were highly influential on the separation. In 20 mM NaH2 PO4 , addition of 4.00 mg/mL SNP-G1.0-β-CD (corresponding to 1.12 mM β-CD) could baseline separate the enantiomers of chlorpheniramine and nefopam, and introduction of 7.00 mg/mL SNP-G0-β-CD (corresponding to 1.68 mM β-CD) resulted in enantioseparation of the verapamil racemates. On the contrary, the enantiomers of nefopam and verapamil could not be resolved in the presence of 15 mM native β-CD. Our results suggest that SNP-PAMAM-β-CDs hold great promise for enantioselective separations.
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, College of Chemistry, Ministry of Education, Beijing Normal University, Beijing, China.
authors.forename: Yujun
authors.initials: Y
authors.lastname: Guo
authors.forename: Weidong
authors.initials: W
authors.lastname: Qin
mesh_terms: D053801:Capillary Electrochromatography / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D050091:Dendrimers / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D053758:Nanoparticles / Q000737:chemistry*; D004364:Pharmaceutical Preparations / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D012822:Silicon Dioxide / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003505:Cyclodextrins; D050091:Dendrimers; C104700:PAMAM Starburst; D004364:Pharmaceutical Preparations; D012822:Silicon Dioxide
keywords: Capillary electrochromatography; Cyclodextrin; Enantioseparation; Polyamidoamine dendrimer; Pseudostationary phase