SYNTHESIS AND CHARACTERIZATION OF NOVEL MULTIFUNCTIONAL HOST COMPOUNDS.1.β-CYCLODEXTRIN DERIVATIVE BEARING DIETHANOLAMINE MOIETY

A novel β-cyclodextrin(β-CD)derivative bearing diethanolamine moiety was synthesized by a convenient method with 63% yield,and the new host compound was characterized by (13)~C-NMR,FT-IR spectra etc,

Determination Enantiomer Excess(e.e.%)of Chiral Sharpless Epoxides with β-Cyclodextrin Derivatives as Chiral Stationary Phases of Capillary Gas Chromatography

Using four β-cyclodextrin derivatives, 2,6-di-O-benzyl-3-O-heptanonyl-β-CD, 2,6-di- O-benzyl-3-O-octanonyl-β-CD, 2,3-di-O-benzyl-6-O-heptanonyl-β-CD, and 2,3-di-O-benzyl -6-O- octanonyl-β-CD, as chiral stationary phases of capillary gas chromatography （CGC）, the enantiomers of Sharpless epoxides were well separated. The enantiomer excess values （e.e.%） of some chiral Sharpless epoxides were also determined successfully using these CDs.

Selectivity of New β-Cyclodextrin Derivatives as CGC Stationary Phases and Application for the Analysis of Volatile Compounds in Traditional Chinese Medicines

New cyclodextrin derivatives （CDs）, heptakis（2, 6-di- O-methyl-3- O-methoxymethyl）-β-CD （ Ⅰ ） and heptakis（2, 3, 6-tri-O-methoxymethyl）-β-CD （ Ⅱ ）, were investigated for their chromatographic performance as stationary phases for capillary gas chromatography （CGC）. Both of the CDs exhibited good selectivity and satisfactory separation for test mixtures and aromatic positional isomers, and volatile compounds from Ligusticurn chuanxiong Hort. Additionally, the selectivity and elution orders of major compounds were compared with a well-recognized commercial column on the basis of the results by gas chromatography-mass spectrometry （GC-MS）. The present work demonstrates the good selectivity of the two new CDs and can be used as GC stationary phases for the separation of positional isomers and analytes in complex samples.

Selective binding of bile salts by β-cyclodextrin derivatives with appended quinolyl arms

Two β-cyclodextrin derivatives bearing appended quinolyl and isoquinolyl arms,i.e.mono-（6-quinolyl- 6-deoxy）-β-cyclodextrin（1） and mono-（6-isoquinolyl-6-deoxy）-β-cyclodextrin（2） were synthesized in satisfactory yields and fully characterized.Their original conformations and binding behaviors toward four bile salt guests,that is,sodium cholate（CA）,sodium deoxycholate（DCA）,sodium glycocholate （GCA）,and sodium taurocholate（TCA）,were investigated by means of fluorescence,circular dichroism and 2D NMR spectroscopy.The study of solution structures revealed that both quinolyl and isoquinolyl arms were located outside the cyclodextrin cavity.The results obtained from the fluorescence titrations showed that the binding abilities of hosts 1 and 2 with selected bile salts varied in an order of DCA 〉 CA 〉 GCA.The selective binding of hosts toward bile salt guests was discussed from the viewpoints of induced-fit and multiple binding.

Novel nanoparticles composed of chitosan and β-cyclodextrin derivatives as potential insoluble drug carrier

This research was aim to develop novel cyclodextrin/chitosan （CD/CS） nanocarriers for insoluble drug delivery through the mild ionic gelation method previously developed by our lab. A series of different β- cyclodextrin （β-CD） derivatives were incorporated into CS nanoparticles including hydroxypropyl-β- cyclodextrin （HP-β-CD）, sulphobutylether-β-cyclodextrin （SB-β-CD）, and 2,6-di-O-methy-βcyclodex- trin （DM-β-CD）. Various process parameters for nanoparticle preparation and their effects on physicochemical properties of CD/CS nanoparticles were investigated, such as the type of CD derivatives, CD and CS concentrations, the mass ratio of CS to TPP （CS/TRP）, and pH values. In the optimal condition, CDICS nanoparticles were obtained in the size range of 215-276 nm and with the zeta potential from 30.22 mV to 35.79 mY. Moreover, the stability study showed that the incorporation of CD rendered the CD/CS nanocarriers more stable than CS nanoparticles in PBS buffer at pH 6.8. For their easy preparation and adjustable parameters in nanoparticle formation as well as the diversified hydrophobic core of CD derivatives, the novel CD/CS nanoparticles developed herein might represent an interesting and versatile drug delivery platform for a variety of poorly water-soluble drugs with different physicochemical properties.

Gas Chromatographic Enantiomer Separation of Cyclopropane Derivatives on Three 2, 6-Di-O-allyl-3-O-acylated-β- cyclodextrins Chiral Stationary Phases

Eight pairs of enantiomers of cyclopropane derivatives were resolved on capillary gas chromatographic columns using three new 2, 6-di-O-allyl-3-O-acylated-β-cyclodextrins as chiral stationary phases. It was found that the three β-CDs can separate some of the racemic cyclopropane derivatives well.

Synthesis of Amino Acid Derived β-Cyclodextrins Used in Chiral Separation by Capillary Electrophoresis

Six new kinds of amino acid derived β-cyclodextrins were synthesized to improve their water solubility and chiral separation properties. They are heptakis{2,6-di-O-[3-L-(1-isopropyl carboxyl methyl amino)-2-(hydroxy) propyl]}-β-cyclodextrin (i.e. L-Val-β-CD), heptakis{2,6-di-O-[3-L-(1-benzyl carboxyl methyl amino)-2-hydroxy propyl]}-β-cyclodextrin (i.e. L-Phe-β-CD), heptakis{2,6-di-O-[3-(D, L-1-benzyl carboxyl methyl amino)-2-hydroxy propyl]}-β-cyclodextrin (i.e. D,L-Phe-β-CD), heptakis{2,6-di-O-[3-(L-1-hydroxymethyl carboxyl methyl amino)-2-hydroxy propyl]}-β-cyclodextrin (i.e. L-Ser-β-CD), heptakis{2,6-di-O-[3-(L-1-carboxylmethyl carboxyl methyl amino)- 2-hydroxy propyl]}-β-cyclodextrin (i.e. L-Asp-β-CD), heptakis{2,6-di-O-[3-(L-2-carboxyl tetramethylene amino)-2-hydroxy propyl]}-β-cyclodextrin (i.e. L-Pro-β-CD). Their chemical structures were certified using FTIR and ()~1H NMR. Except for L-Phe-β-CD and D,L-Phe-β-CD, that are in soluble in water, the other amino acid derived β-CDs all have good water solubility. D,L-tyrosine and promethazine were baselinely separated by L-Val-β-CD in capillary electrophoresis.

Synthesis of Crown Ether-tethered b-Cyclodextrin and Fabrication of Its Self-assembled Monolayer on Gold Surface

A novel b-cyclodextrin derivative 6 bearing a crown ether moiety has been synthesized by a convenient method in 9.4% yield. Its self-assembled monolayer (SAM) was fabricated on the gold surface, which was characterized by using surface-enhanced Raman spectra.

Synthesis of Methylated β-Cyclodextrins Derived Optically Active Poly(N-diphenylmethyl maleimide)

The methylated β-cyclodextrins derived optically active polymers are firs synthesized through asymmetric polymerization of N-diphenylmethyl maleimide with lithium salt of heptakis(2,6-O-dimethyl) β-cyclodextrin (DM-β-CD) as an initiator. The resulting polymers show negative specific rotation which is opposite in sign to that of DM-β-CD. The asymmetric induction is further confirmed by circular dichroism. The structure is characterized by IR and NMR spectroscopies

Extraction of artemisinin with hydroxypropyl-β-cyclodextrin aqueous solution for fabrication of drinkable extract

A process for extraction of artemisinin(Ars)from Artemisia annua L.based on aqueous solution of cyclodextrin derivative under ultrasonic irradiation was proposed.Among the test additives,the system containing edible hydroxypropyl-β-cyclodextrin(HPBCD)was shown to be efficient for this extraction.The optimal extraction conditions were predicted by artificial neural network,under which the extraction amount of Ars could reach 8.66 mg per gram of the leaves,much higher than the value in water(1.70 mg g-1).Kinetics study indicated that HPBCD enhanced the equilibrium amount of Ars in water,and ultrasonic irradiation accelerated extraction rate and reduced the activation energy.Mechanism study showed that the formation of Ars-HPBCD complex during extraction enhanced the water solubility of Ars and facilitated the extraction,and the configuration of Ars-HPBCD complex was modeled by molecular docking,which was further verified by characterizations.This work provides a convenient way to fabricate the traditional tea-based medicament of natural drugs to make production of this famous antimalarial medicine cheaper.