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...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.展开更多
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...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.展开更多
A three-dimensional diagram shows that the association constants (Ka) for the inclusionof a- and 6-CD with substitUted benzene are mainly correIated with the molar refraction (R.) andhydrophobic constant (%) of the su...A three-dimensional diagram shows that the association constants (Ka) for the inclusionof a- and 6-CD with substitUted benzene are mainly correIated with the molar refraction (R.) andhydrophobic constant (%) of the substitUents of guest compounds. It reveals that the inclusion ofcyclodextrin with the substitUted benzene is dondnantly driYen by van der Waals forces andhydrophobic interactions.展开更多
Using two b-cyclodextrin derivatives (CDs) with long chain of acyl groups as chiral stationary phases (CSPs) of capillary gas chromatography (CGC), the enantiomers of racemic allethrone and propargyllone were well res...Using two b-cyclodextrin derivatives (CDs) with long chain of acyl groups as chiral stationary phases (CSPs) of capillary gas chromatography (CGC), the enantiomers of racemic allethrone and propargyllone were well resolved after derived with acetyl chloride. The enantiomer excess values (e.e.%) of 1S-allethrone and 1S-propargyllone were also determined successfully using these CDs.展开更多
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,
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)...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.展开更多
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 th...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.展开更多
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-...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展开更多
A novel β-cyclodextrin derivative, 2, 6-di-O-butyl-3-O-acetyl-β-cyclodex- trin, was prepared and used as chiral stationary phase for capillary gas chromato- graphic resolution of enantiomers, lhe glass capillary col...A novel β-cyclodextrin derivative, 2, 6-di-O-butyl-3-O-acetyl-β-cyclodex- trin, was prepared and used as chiral stationary phase for capillary gas chromato- graphic resolution of enantiomers, lhe glass capillary columns with the derivative having low melting point and high thermal stability could produce more than 3000 plates per column meter and have proven to be good chlral columns to separate the enantiomers of some amino acids, derivatives of epoxy ethane and alkyl halide, etc.展开更多
A novel chiral stationary phase (CSP) was prepared by immobilizing mono(6A-N-1-(2-hydroxyl)-phenylethylimino-6A- deoxy)-β-cyclodextrin onto the surface of silica gel via a longer spacer. This chiral stationary ...A novel chiral stationary phase (CSP) was prepared by immobilizing mono(6A-N-1-(2-hydroxyl)-phenylethylimino-6A- deoxy)-β-cyclodextrin onto the surface of silica gel via a longer spacer. This chiral stationary phase exhibited good enantioselectivity for a variety of chiral compounds under reversed-phase conditions.展开更多
Inclusion of Acyclodextrin (ACD) with phenothiazine 1 and Nalkylpheno-thiazine derivatives (alkyl = ethyl 2, isobutyl 3 and isopentyl 4) in aqueous solution was studied by means of UV-vis spectroscopy. The association...Inclusion of Acyclodextrin (ACD) with phenothiazine 1 and Nalkylpheno-thiazine derivatives (alkyl = ethyl 2, isobutyl 3 and isopentyl 4) in aqueous solution was studied by means of UV-vis spectroscopy. The association constant Ka values for the inclusion of β-CD with 1, 2, 3 and 4 were determined to be 188, 214, 129 and 80 L/mol, respectively. It indicates that the stability of the inclusion complexes is dependent on the structure and the volume of the substituents in the guest compounds.展开更多
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 characteriz...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.展开更多
Inclusion behavior of oxybutynin (OBN) with hydroxypropyl-β-cyclodextrin (HP-β-CD) was investigated by ultraviolet absorption spectrum and fluorescence spectrum. A reliable determination of the complex stoichiometry...Inclusion behavior of oxybutynin (OBN) with hydroxypropyl-β-cyclodextrin (HP-β-CD) was investigated by ultraviolet absorption spectrum and fluorescence spectrum. A reliable determination of the complex stoichiometry was provided by the continuous variation technique. Alcohol was added to further investigate the mechanism of the inclusion behavior. Thermodynamic constants ΔG, ΔH and ΔS for inclusion interaction of OBN and HP-β-CD were determined. The results show that host-guest complex with molar ratio of 1-1 is formed, and inclusion stability constant between OBN and HP-β-CD is 54.9 L/mol determined by ultraviolet spectrum and 11.1 L/mol determined by fluorescence spectrum. OBN has weak binding ability with HP-β-CD in aqueous solution (stability constant <102 L/mol) and addition of alcohol leads to a decrease of stability constant, which indicates that the hydrophobic force contributes to the inclusion process. ΔG, ΔH and ΔS are all less than zero, which indicates that the inclusion process is a spontaneous and exothermic process.展开更多
Three new chiral stationary phases, 2,6 di O heptyl 3 O trimethylsilyl β cyclodextrin(DHTBCD), 2,6 di O pentyl 3 O trimethylsilyl β cyclodextrin (DPTBCD) and 2,6 di O butyl 3 O trimethylsilyl β cyclodextrin (DBTBCD...Three new chiral stationary phases, 2,6 di O heptyl 3 O trimethylsilyl β cyclodextrin(DHTBCD), 2,6 di O pentyl 3 O trimethylsilyl β cyclodextrin (DPTBCD) and 2,6 di O butyl 3 O trimethylsilyl β cyclodextrin (DBTBCD), were synthesized. Chromatographic properties such as column efficiency, thermal stability and column life span, were studied. The separations of enantiomers, such as ketone, esters, alcohols and olefines, were investigated on the alkylated and silylated β cyclodextrin stationary phases. The influence of diluent on chiral separation was studied. The experimental results indicate that the stationary phases show good chromatographic properties in separating enantiomers. It is observed that inclusion complexation and hydrogen bonding interaction hardly play a role in separating enantiomers.展开更多
Study of molecular recognition has been playing an important role in biomimeticchemistry. β-cyclodextrin (β-CD), the cyclic heptamer of glucopyranose, can form inclusioncomplexes with various types of organic compou...Study of molecular recognition has been playing an important role in biomimeticchemistry. β-cyclodextrin (β-CD), the cyclic heptamer of glucopyranose, can form inclusioncomplexes with various types of organic compounds (substrates) through its展开更多
β-Cyclodextrin (β-CD) and its derivatives functionalized magnetic nanoparticles (MNPs) with high saturated magnetism were fabricated successfully by an effective grafting method. The resultant carboxymethyl/hydr...β-Cyclodextrin (β-CD) and its derivatives functionalized magnetic nanoparticles (MNPs) with high saturated magnetism were fabricated successfully by an effective grafting method. The resultant carboxymethyl/hydroxy- propyl/sulfobutyl ether-β-CD-MNPs (CM/HP/SBE-β-CD-MNPs) nanocomposites were characterized by the TEM, FTIR, DLS, Zeta potential, XRD and VSM. In addition, the loading and release performance of the as-prepared nanocarriers for the hydrophobic anti-cancer drug curcumin was also investigated. The results revealed that the SBE-fl-CD-MNPs possessed the highest loading and release capacity in comparison with other two nanosystems. Cellular uptake and imaging suggested that the SBE-β-CD-MNPs entered into the cell, and curcumin could be suc-cessfully delivered into the cell by SBE-β-CD-MNPs nanocarrier. Moreover, cell toxicity experiments demonstrated the SBE-β-CD-MNPs were non-toxic, while curcumin loaded SBE-β-CD-MNPs showed high potential to kill the HepG2 cells. The as-prepared magnetic composites were expected to expand their potential applications in bio- medical field.展开更多
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 satisfac...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.展开更多
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- cyclode...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.展开更多
We report a simple "one pot" single step method to synthesize sulfoalkyl ether β-cyclodextrin (β-CD) derivatives in aqueous solution, which avoids the limitations associated with commonly used organic synt...We report a simple "one pot" single step method to synthesize sulfoalkyl ether β-cyclodextrin (β-CD) derivatives in aqueous solution, which avoids the limitations associated with commonly used organic synthesis of such derivatives including multi-step reactions, use of expensive, toxic, and often environmentally hazardous organic solvents and/or reagents. Using this method, we obtained sulfopropyl and sulfobutyl ethyl β-CDs. We characterized these two derivatives and evaluated their ability to enhance solubility of fluconazole, a commonly used antifungal drug with poor water solubility. Experimental results indicate that these derivatives are structurally analogous to some of the commercially available β-CD derivatives. More importantly, when they formed supramolecular inclusion complexes with fluconazole, they demonstrated similar, if not better, capacity to enhance fluconazole solubility compared with commercially available β-CD derivatives, suggesting that the simple "one pot" single step synthesis may provide an effective alternative approach to produce large quantity of β-CD derivatives as pharmaceutical biomaterials for medicinal applications.展开更多
文摘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.
基金This work was kindly supported by the National Natural Science Foundation of China(No.30471153,30170621and 21023478).
文摘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.
文摘A three-dimensional diagram shows that the association constants (Ka) for the inclusionof a- and 6-CD with substitUted benzene are mainly correIated with the molar refraction (R.) andhydrophobic constant (%) of the substitUents of guest compounds. It reveals that the inclusion ofcyclodextrin with the substitUted benzene is dondnantly driYen by van der Waals forces andhydrophobic interactions.
文摘Using two b-cyclodextrin derivatives (CDs) with long chain of acyl groups as chiral stationary phases (CSPs) of capillary gas chromatography (CGC), the enantiomers of racemic allethrone and propargyllone were well resolved after derived with acetyl chloride. The enantiomer excess values (e.e.%) of 1S-allethrone and 1S-propargyllone were also determined successfully using these CDs.
文摘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,
文摘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.
文摘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.
文摘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
文摘A novel β-cyclodextrin derivative, 2, 6-di-O-butyl-3-O-acetyl-β-cyclodex- trin, was prepared and used as chiral stationary phase for capillary gas chromato- graphic resolution of enantiomers, lhe glass capillary columns with the derivative having low melting point and high thermal stability could produce more than 3000 plates per column meter and have proven to be good chlral columns to separate the enantiomers of some amino acids, derivatives of epoxy ethane and alkyl halide, etc.
基金Financial support from the National Natural Science Foundation of China (No.20572009)
文摘A novel chiral stationary phase (CSP) was prepared by immobilizing mono(6A-N-1-(2-hydroxyl)-phenylethylimino-6A- deoxy)-β-cyclodextrin onto the surface of silica gel via a longer spacer. This chiral stationary phase exhibited good enantioselectivity for a variety of chiral compounds under reversed-phase conditions.
文摘Inclusion of Acyclodextrin (ACD) with phenothiazine 1 and Nalkylpheno-thiazine derivatives (alkyl = ethyl 2, isobutyl 3 and isopentyl 4) in aqueous solution was studied by means of UV-vis spectroscopy. The association constant Ka values for the inclusion of β-CD with 1, 2, 3 and 4 were determined to be 188, 214, 129 and 80 L/mol, respectively. It indicates that the stability of the inclusion complexes is dependent on the structure and the volume of the substituents in the guest compounds.
基金This work was supported by the National Natural Science Foundation of China.
文摘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.
基金Project(20976041) supported by the National Natural Science Foundation of China
文摘Inclusion behavior of oxybutynin (OBN) with hydroxypropyl-β-cyclodextrin (HP-β-CD) was investigated by ultraviolet absorption spectrum and fluorescence spectrum. A reliable determination of the complex stoichiometry was provided by the continuous variation technique. Alcohol was added to further investigate the mechanism of the inclusion behavior. Thermodynamic constants ΔG, ΔH and ΔS for inclusion interaction of OBN and HP-β-CD were determined. The results show that host-guest complex with molar ratio of 1-1 is formed, and inclusion stability constant between OBN and HP-β-CD is 54.9 L/mol determined by ultraviolet spectrum and 11.1 L/mol determined by fluorescence spectrum. OBN has weak binding ability with HP-β-CD in aqueous solution (stability constant <102 L/mol) and addition of alcohol leads to a decrease of stability constant, which indicates that the hydrophobic force contributes to the inclusion process. ΔG, ΔH and ΔS are all less than zero, which indicates that the inclusion process is a spontaneous and exothermic process.
文摘Three new chiral stationary phases, 2,6 di O heptyl 3 O trimethylsilyl β cyclodextrin(DHTBCD), 2,6 di O pentyl 3 O trimethylsilyl β cyclodextrin (DPTBCD) and 2,6 di O butyl 3 O trimethylsilyl β cyclodextrin (DBTBCD), were synthesized. Chromatographic properties such as column efficiency, thermal stability and column life span, were studied. The separations of enantiomers, such as ketone, esters, alcohols and olefines, were investigated on the alkylated and silylated β cyclodextrin stationary phases. The influence of diluent on chiral separation was studied. The experimental results indicate that the stationary phases show good chromatographic properties in separating enantiomers. It is observed that inclusion complexation and hydrogen bonding interaction hardly play a role in separating enantiomers.
文摘Study of molecular recognition has been playing an important role in biomimeticchemistry. β-cyclodextrin (β-CD), the cyclic heptamer of glucopyranose, can form inclusioncomplexes with various types of organic compounds (substrates) through its
文摘β-Cyclodextrin (β-CD) and its derivatives functionalized magnetic nanoparticles (MNPs) with high saturated magnetism were fabricated successfully by an effective grafting method. The resultant carboxymethyl/hydroxy- propyl/sulfobutyl ether-β-CD-MNPs (CM/HP/SBE-β-CD-MNPs) nanocomposites were characterized by the TEM, FTIR, DLS, Zeta potential, XRD and VSM. In addition, the loading and release performance of the as-prepared nanocarriers for the hydrophobic anti-cancer drug curcumin was also investigated. The results revealed that the SBE-fl-CD-MNPs possessed the highest loading and release capacity in comparison with other two nanosystems. Cellular uptake and imaging suggested that the SBE-β-CD-MNPs entered into the cell, and curcumin could be suc-cessfully delivered into the cell by SBE-β-CD-MNPs nanocarrier. Moreover, cell toxicity experiments demonstrated the SBE-β-CD-MNPs were non-toxic, while curcumin loaded SBE-β-CD-MNPs showed high potential to kill the HepG2 cells. The as-prepared magnetic composites were expected to expand their potential applications in bio- medical field.
基金973 Program(No.2011CB932502)NNSFC(Nos. 20932004,91027007 and 21272125)Program for New Century Excellent Talents in University(No.NCET-10-0500) for financial support
文摘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.
基金financially supported by Postdoctoral Science Foundation of China (No. 2014M550222)Shanghai Postdoctoral Sustentation Fund (No. 14R21410500)+2 种基金the support from School of Pharmacy, Fudan University & the Open Project Program of Key Lab of Smart Drug Delivery (Fudan University), Ministry of Education (No. SDD2014-2)State Key Laboratory of Molecular Engineering of Polymers (Fudan University, No. K2015-15)the Fundamental Research Funds for the Central Universities (Nos. 22A201514055 and WY1213013 ECUST)
文摘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.
文摘We report a simple "one pot" single step method to synthesize sulfoalkyl ether β-cyclodextrin (β-CD) derivatives in aqueous solution, which avoids the limitations associated with commonly used organic synthesis of such derivatives including multi-step reactions, use of expensive, toxic, and often environmentally hazardous organic solvents and/or reagents. Using this method, we obtained sulfopropyl and sulfobutyl ethyl β-CDs. We characterized these two derivatives and evaluated their ability to enhance solubility of fluconazole, a commonly used antifungal drug with poor water solubility. Experimental results indicate that these derivatives are structurally analogous to some of the commercially available β-CD derivatives. More importantly, when they formed supramolecular inclusion complexes with fluconazole, they demonstrated similar, if not better, capacity to enhance fluconazole solubility compared with commercially available β-CD derivatives, suggesting that the simple "one pot" single step synthesis may provide an effective alternative approach to produce large quantity of β-CD derivatives as pharmaceutical biomaterials for medicinal applications.