The problems of tailings storage and high-stress conditions in deep mining have emerged as critical factors that limit the security,efficiency,and sustainability of such mines.This study explores the potential to util...The problems of tailings storage and high-stress conditions in deep mining have emerged as critical factors that limit the security,efficiency,and sustainability of such mines.This study explores the potential to utilize tungsten tailings to create cementitious backfill(CTB)materials and investigates the macroscopic strength features and microscopic damage evolution mechanisms of different-sized CTBs with varying dosages of hydroxypropyl methyl cellulose(HPMC).Specimens with bottom diameters of 50,75,and 100 mm are combined with HPMC dosages of 0,0.15wt%,0.25wt%,and 0.35wt%.A diameter/height ratio of 1:2 is maintained for all CTB specimens.The experimental results show that as the HPMC dosage is increased from 0 to 0.35wt%,the uniaxial compressive strength(UCS)of the CTBs decreases significantly in a linear manner.The 75 mm×150 mm CTB specimen exhibits relatively high plasticity and toughness,with good plastic deformation and energy absorption capabilities,indicating significant size effects.HPMC introduces connected bubbles during the CTB pouring process,but it exhibits anti-segregation and anti-bleeding characteristics,thus reducing tailing settling.The hydration reaction of the CTB doped with HPMC is more uniform,and the Ca/Si atomic ratio dispersion at different sites is smaller.The three CTB sizes all exhibit combined tensile and shear failure,with the 75 mm×150 mm specimen exhibiting macroscopic tensile cracks and relatively few shear cracks.At the micro-scale,excessive ettringite and hydrated calcium silicate are interwoven and fuse,and the tungsten tailings are tightly wrapped.These results provide valuable data and notional insights for optimizing the fluidity of the backfill,and elucidate the strength and damage evolution of solidified materials during filling and extraction.This study contributes to the advancement of green,economical,safe,and sustainable mining practices.展开更多
Fluvoxamine(FXM)is a well-known selective serotonin reuptake inhibitor(SSRI)for treating depression and has recently been repurposed for efficacious treatment of coronavirus disease 2019.Although cyclodextrin(CD)encap...Fluvoxamine(FXM)is a well-known selective serotonin reuptake inhibitor(SSRI)for treating depression and has recently been repurposed for efficacious treatment of coronavirus disease 2019.Although cyclodextrin(CD)encapsulation effectively improves the physicochemical properties of structurally diverse SSRIs,the molecular understanding of their associations is deficient.This comprehensive study used single-crystal X-ray diffraction integrated with density functional theory(DFT)calculation to provide deep insights into the conformationally flexible FXM and its inclusion complexation withβ-CD.Xray analysis revealed the first crystallographic evidence of the uncomplexed 3FXM-H^(+)·3maleate-(1).Three FXM-H^(+)ions are counter-balanced by three planar maleate-ions to form a thin layer stabilized by infinite fused H-bond rings R_(4)^(4)(12)and R_(6)^(4)(16)and the interplay ofπ…π,CF…πand F…F interactions.For 2β-CD·2FXM-H^(+)·maleate^(2-)·23·2H_(2)O(2),the tail-to-tailβ-CD dimer encapsulates two FXM-H^(+)4-(trifluoromethyl)phenyl moieties,which are charge-balanced by the rare non-planar maleate2and stabilized by N…OH…O H-bonds and F…F interactions.This is a hostevip recognition pattern uniquely observed for allβ-CD complexes with halogen(X)-bearing SSRIs,indicating the essence of X…X interactions and the shielding of X-containing moieties in the wall of theβ-CD dimer.DFT calculations unveiled that the monomeric and dimericβ-CD-FXM complexes and FXM isomers are energetically stable,which alleviates the numbness and bitterness of the orally administered drug as previously patented.Additionally,an insightful conformational analysis of FXM emphasizes the importance of drug structural adaptation in pharmacological functions.展开更多
The effect of various concentrations of 2-hydroxypropyl-β-cyclodextrin （HP-β-CD） on the solubility of dihydroartemisinin （DHA） in aqueous solution at different pHs was investigated. The influence of different co...The effect of various concentrations of 2-hydroxypropyl-β-cyclodextrin （HP-β-CD） on the solubility of dihydroartemisinin （DHA） in aqueous solution at different pHs was investigated. The influence of different concentrations of 2-hydroxypropyl-β- eyclodextrin on the stability of dihydroartemisinin at 50, 60, 70 and 80 ℃ was also studied. Inclusion complex of dihydroartemisinin with 2-hydroxypropyl-β-cyclodextrin was prepared and characterized by X-ray diffraction and differential scanning calorimetry. The 2-hydroxypropyl-β-cyclodextrin effectively inhibited the hydrolysis of dihydroartemisinin and greatly increased its solubility. Furthermore, we showed that the higher concentrations of 2-hydroxypropyl-β-cyclodextrin, the better stability and solubility of dihydroartemisinin. When the temperature was increased, the stability of dihydroartemisinin decreased. Our results indicated that 2-hydroxypropyl-β-cyclodextrin can be used as a stabilizer and solubilizer of dihydroartemisinin.展开更多
In our previous study,a novel organic selenium compound Eb was synthesized and found to have significant antitumor activity with much less toxicity compared with the leading compound Ebselen.Unfortunately,Eb was pract...In our previous study,a novel organic selenium compound Eb was synthesized and found to have significant antitumor activity with much less toxicity compared with the leading compound Ebselen.Unfortunately,Eb was practically insoluble in water （2.57 μg/mL） and had very low oral bioavailability,thus its clinical application was greatly limited.In the present study,the inclusion complex of Eb with 2-hydroxypropyl-β-cyclodextrin （HP-βCD） was prepared and pharmacokinetics of Eb and the inclusion complex were investigated.The water solubility of Eb was dramatically enhanced by inclusion with HP-βCD,which reached 8.4 mg/mL.The pharmacokinetic study showed that the elimination half-life （t 1/2β） of Eb was between 22 h and 30 h and the distribution half-life （t 1/2α） of Eb was 1 h.The results indicated that Eb was rapidly distributed to tissues but slowly eliminated in rats.The absolute bioavailability of Eb/HP-βCD inclusion complex solution through the oral route was 28.3%,and it was 1552% that of Eb in its pure form.In summary,the absorption of Eb in the Eb/HP-βCD inclusion complex was better and faster than that of Eb in its pure form.展开更多
The goal of this study was to improve the solubility and oral bioavailability of tamibarotene by complexing it with hydroxypropyl-β-cyclodextrin(HP-β-CD).The inclusion complex of tamibarotene with hydroxypropyl-β-c...The goal of this study was to improve the solubility and oral bioavailability of tamibarotene by complexing it with hydroxypropyl-β-cyclodextrin(HP-β-CD).The inclusion complex of tamibarotene with hydroxypropyl-β-cyclodextrin(Am80-HP-β-CD)was prepared through a freeze-drying method at the mole ratio of 1:1(Am80:HP-β-CD).Fourier transform infrared spectroscopy(FT-IR)and differential scanning calorimetry(DSC)indicated the formation of Am80-HP-β-CD.In vitro dissolution studies showed that the solubility and dissolution percentage of Am80-HP-β-CD was improved substantially compared to Am80.An improved dissolution with approximately 97%drug release in 3 min was observed,in comparison with Am80 with approximately 60% release in 45 min.In vivo studies indicated that the AUC0-∞ has increased 2.79 times and the Cmax 4.37 times after the formation of inclusion complex.The decrease of tmaxindicated the Am80-HP-β-CD inclusion complex can be absorbed into blood faster.In short,the solubility and bio-availability of Am80 has notably increased with the complexation of HP-β-CD.Therefore,using the inclusion technique is a promising method to improve the solubility of insoluble drugs.展开更多
In order to set up a simple and effective method for resolution of optical isomers, hydroxypropyl-β-cyclodextrin was bonded to silica-gel, which can be used for preparation of thin-layer chromatography plates. Resolu...In order to set up a simple and effective method for resolution of optical isomers, hydroxypropyl-β-cyclodextrin was bonded to silica-gel, which can be used for preparation of thin-layer chromatography plates. Resolution of clenbuterol and propranolol were investigated on these thin-layer chromatography plates using different combinations of solvent systems at ambient temperature. The best simultaneous resolution was achieved in solvent system of acetonitrilen-butanol （50：50, v/v）. Rst values of resolution of clenbuterol hydrochloride and propranolol hydrochloride are 3.6 and 4.3, respectively. The spots of different enantiomers are separated clearly. The results showed that hydroxypropyl-β-cyclodextrin bonded silica-gel could be successful in resolution of chiral adrenergic drugs. The study offers a direct, rapid and reliable method for separation of this kind of optically active compounds.展开更多
Novel insulin-loaded nanoparticles based on hydroxypropyl-β-cyclodextrin modified carboxymethyl chitosan（CMC-HP-β-CD） were prepared to improve the oral bioavailability of insulin. The CMC-HP-β-CD was characterize...Novel insulin-loaded nanoparticles based on hydroxypropyl-β-cyclodextrin modified carboxymethyl chitosan（CMC-HP-β-CD） were prepared to improve the oral bioavailability of insulin. The CMC-HP-β-CD was characterized by FT-IR spectroscopy and 1H-NMR spectra. The insulin-loaded nanoparticles were prepared through crosslinking with calcium ions, and the morphology and size of the prepared nanoparticles were characterized by transmission electron microscopy（TEM） and dynamic light scattering（DLS）. Cumulative release in vitro study was performed respectively in simulated gastric medium fluid（SGF, p H=1.2）, simulated intestinal fluid（SIF, p H=6.8） and simulated colonic fluid（SCF, p H=7.4）. The encapsulation efficiency of insulin was up to 87.14 ± 4.32% through high-performance liquid chromatography（HPLC）. Statistics indicated that only 15% of the encapsulated insulin was released from the CMC-HP-β-CD nanoparticles in 36 h in SGF, and about 50% of the insulin could be released from the nanoparticles in SIF, whereas more than 80% was released in SCF. In addition, the solution containing insulin nanoparticles could effectively reduce the blood glucose level of diabetic mice. The cytotoxicity test showed that the samples had no cytotoxicity. CMC-HP-β-CD nanoparticles are promising candidates as potential carriers in oral insulin delivery systems.展开更多
Bakuchiol isolated from Psoralea corylifolia is a naturally occurring prenylated phenolic monoterpene with a variety of bioactivities.The aim of this study was to improve the water solubility and thermal stability of ...Bakuchiol isolated from Psoralea corylifolia is a naturally occurring prenylated phenolic monoterpene with a variety of bioactivities.The aim of this study was to improve the water solubility and thermal stability of bakuchiol through complexing it with hydroxypropyl-β-cyclodextrin(HP-β-CD).The bakuchiol/HP-β-CD inclusion complex's behavior and characterization were investigated by ultraviolet-visible(UV-vis)spectroscopy,Fourier transform infrared spectroscopy(FT-IR),thermogravimetric analysis(TGA),X-ray diffraction(XRD),1H nuclear magnetic resonance(NMR),and two-dimensional(2D)NMR.The obtained results indicated the formation of 1∶1 inclusion complex for bakuchiol with HP-β-CD.Water solubility of bakuchiol was significantly improved by complexation with HP-β-CD as demonstrated by phase solubility studies.The encapsulation of bakuchiol was confirmed by UV-vis,FT-IR,and XRD.The thermal stability was effectively enhanced by TGA and derivative thermogravimetry(DTG)analysis.In vitro antioxidant activity showed that bakuchiol/HP-β-CD inclusion complex had a little higher antioxidant ability than free bakuchiol.Moreover,we got the possible inclusion mode for the bakuchiol/HP-β-CD inclusion complex through NMR analysis.These results suggest that the inclusion complex can be a potentially useful approach in the design of novel formulations of bakuchiol for medical applications.展开更多
A cationic cyclodextrin derivative 6-O-（hydroxypropyltrimethylammonia）-β-cyclodextrin （GTA-β-CD） with low degree of substitution was prepared through a convenient method in solid phase. The product could be used...A cationic cyclodextrin derivative 6-O-（hydroxypropyltrimethylammonia）-β-cyclodextrin （GTA-β-CD） with low degree of substitution was prepared through a convenient method in solid phase. The product could be used as a valuable chiral selector in the capillary electrophoresis （CE） separation of some acidic drug enantiomers such as naproxen, ofloxacin, ibuprofen and warfarin.展开更多
To overcome the chemical instability of forsythiaside,the forsythiaside-hydroxypropyl-β-cyclodextrin inclusion complex was prepared by triturating. The inclusion complex was found having a varied UV spectrum and melt...To overcome the chemical instability of forsythiaside,the forsythiaside-hydroxypropyl-β-cyclodextrin inclusion complex was prepared by triturating. The inclusion complex was found having a varied UV spectrum and melt temperature point. Inclusion complex has a higher stability to UV light and temperature over forythiaside itself. Pharmacological evidence showed that inclusion complex has little effect on pharmacokinetics by chicken intravenous injection. This study is favorable for developing preparations for forsythiaside and its clinical application.展开更多
Domperidone Maleate (DOM), an antiemetic drug, has been used in treatment of adults and children. It has low aqueous solubility and hence low bioavailability. In present study, an attempt has been made to enhance the ...Domperidone Maleate (DOM), an antiemetic drug, has been used in treatment of adults and children. It has low aqueous solubility and hence low bioavailability. In present study, an attempt has been made to enhance the solubility of DOM by inclusion complexation with Hydroxypropyl-β-Cyclodextrin (HP-β-CD) using kneading technique and formulation of fast disintegrating tablets by using Sodium Starch Glycolate as superdisintegrant. Solubility analysis of DOM in different concentrations of HP-β-CD was carried out. Design of experiment (DOE) is done by using MINITAB 15.1 software to find out the variable for dissolution and disintegration time. HP-β-CD and SSG were identified as the variable for disintegration time and dissolution. For optimization of the concentration of HP-β-CD and SSG, two factors at two levels design through central composite design (CCD) were used which gave 13 formulations. All formulations are evaluated for characteristics such as weight variation, hardness, friability, disintegration time and dissolution of drug. Solubility of DOM increases linearly with increase in concentration of HP-β-CD. The optimum concentration of HP-β-CD is found to be in 1:2 molar ratios and SSG of 7%. The In-Vitro dissolution studies of optimized formulation and market sample were carried out in USP type II apparatus at different time intervals of 5, 10, 15 and 30 minutes at 50 rpm in 0.1 N HCl. The dissolution and disintegration time of optimized formulation is found better than market sample.展开更多
Inclusion complexes of nitro-compounds using β-cyclodextrin and hydroxypropyl-β-cyclodextrin as host molecule have been studied by cyclic voltammetric method. The inclusion constants of the corresponding complexes h...Inclusion complexes of nitro-compounds using β-cyclodextrin and hydroxypropyl-β-cyclodextrin as host molecule have been studied by cyclic voltammetric method. The inclusion constants of the corresponding complexes have been determined. Strong inclusion complexation by hydroxypropyl-β-cyclodextrin has been verified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 stoichiom...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 AG, AH and AS for inclusion interaction of OBN and HP-β-CD were determined. The results show that host-vip 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. AG, AH and AS are all less than zero, which indicates that the inclusion process is a spontaneous and exothermic process.展开更多
Cometabolic degradation is currently an effective and extensively way to remove high molecular weight polycyclic aromatic hydrocarbons(HMW-PAHs).Unfortunately,due to low bio-accessibility and high biotoxicity,the come...Cometabolic degradation is currently an effective and extensively way to remove high molecular weight polycyclic aromatic hydrocarbons(HMW-PAHs).Unfortunately,due to low bio-accessibility and high biotoxicity,the cometabolic degradation rate of HMW-PAHs is limited.Glycine-β-cyclodextrin(GCD)was obtained through amino modification ofβ-cyclodextrin(BCD)and added to cometabolic system of phenanthrene(PHE)and pyrene(PYR)to assist PYR biodegradation.Results show that the addition of GCD(100 mg/L)effectively improved the removal rate of PYR(20 mg/L)by 42.3%.GCD appeared to increase the bio-accessibility and reduce the biotoxicity of PHE and PYR,and then promoted the growth of Pseudomonas stutzeri DJP1 and stimulated the elevation of dehydrogenase(DHA)and catechol 12 dioxygenase(C12O)activities.The phthalate metabolic pathway was accelerated,which improved the cometabolic degradation.This study provided a new reference for the cometabolic degradation of HMW-PAHs.展开更多
Bio-based cyclodextrins(CDs)are a common research object in supramolecular chemistry.The special cavity structure of CDs can form supramolecular self-assemblies such as vesicles and microcrystals through weak interact...Bio-based cyclodextrins(CDs)are a common research object in supramolecular chemistry.The special cavity structure of CDs can form supramolecular self-assemblies such as vesicles and microcrystals through weak interaction with vip molecules.The different forms of supramolecular self-assemblies can be transformed into each other under certain conditions.The regulation of supramolecular self-assembly is not only helpful to understand the self-assembly principle,but also beneficial to its application.In the present study,the self-assembly behavior of epoxy-β-cyclodextrin(EP-β-CD)and mixed anionic and cationic surfactant system(sodium dodecyl sulfate/dodecyltrimethylammonium bromide,SDS/DTAB)in aqueous solution was studied.Morphological and particle size characterization found that the SDS/DTAB@EP-β-CD complex,as the basic building unit,self-assembled into worm-like micelles at lower temperatures and vesicles at higher temperatures.Nuclear magnetic resonance(NMR)and Fourier transform infrared spectroscopy(FT-IR)analysis revealed that the driving force for the formation of vesicles and worm-like micelles was the hydrogen bonds between EP-β-CD molecules,while water molecules played an important role in promoting vesicle formation between SDS/DTAB@EP-β-CD units.Herein,the mechanism of the morphologic transformation of SDS/DTAB@EP-β-CD supramolecular aggregates induced by temperature was elucidated by exploring the self-assembly process,which may provide an excellent basis for the development of delivery carriers.展开更多
[Objectives]To enhance the skin permeability of hydroxypropyl tetrahydropyrantriol and provide a reference for the subsequent prevention or treatment of skin aging.[Methods]The lyophilization process of hydroxypropyl ...[Objectives]To enhance the skin permeability of hydroxypropyl tetrahydropyrantriol and provide a reference for the subsequent prevention or treatment of skin aging.[Methods]The lyophilization process of hydroxypropyl tetrahydropyrantriol liposomes was investigated using a single factor method,and a quality evaluation system was established based on the appearance,particle size,PDI,and re-dispersibility of the lyophilized samples.[Results]The lyophilization process of hydroxypropyl tetrahydropyrantriol liposomes was determined by single factor experiments.The pre-freezing period was 16 h at-80℃,the total drying time was 36 h,and the addition of 10%mannitol-sucrose was used as the lyoprotectant.[Conclusions]The product prepared by the lyophilization method exhibits a fluffy and full appearance,with minimal shrinkage and collapse.The volume remains consistent before and after lyophilization,and the re-dispersibility is satisfactory.The re-dissolution process is rapid,and the particle size and polydispersity index(PDI)remain largely unchanged before and after lyophilization.展开更多
In this study, the adsorption effect of β-cyclodextrin modified biochar (BC) on phenanthrene (PHE) in contaminated soil was investigated, aiming to provide an efficient and environmentally friendly remediation strate...In this study, the adsorption effect of β-cyclodextrin modified biochar (BC) on phenanthrene (PHE) in contaminated soil was investigated, aiming to provide an efficient and environmentally friendly remediation strategy for Polycyclic Aromatic Hydrocarbons (PAHs) contaminated soil. Through kinetic and isotherm analysis, β-CDBC-CA showed excellent phenanthrene adsorption performance, and the adsorption effect increased with the increase of time and was affected by temperature. The results show that β-CDBC-CA can not only effectively adsorb phenanthrene in soil, but also serve as a surfactant to help desorption phenanthrene adsorbed by soil organic matter and improve the efficiency of microbial degradation. The experimental data showed that the Elovich model could describe the adsorption behavior of β-CDBC-CA on phenanthrene well, while Langmuir and Freundlich models performed better in fitting parameters, revealing the adsorption mechanism of phenanthrene in contaminated soil by β-cyclodextrin-modified biochar. In addition, temperature has a significant effect on the adsorption capacity of β-CDBC-CA, and its application in soil remediation can be optimized by adjusting temperature. This study not only provides new materials and technical means for soil remediation but also provides important data support for an in-depth understanding of the environmental behavior of PAHs. By citing relevant research results, this study further improves the control and understanding of environmental risks of PAHs, which is of great significance for the protection of ecological environment and human health.展开更多
In this paper, biochar (BC) was used as raw material, activated by deionizing aqueous solution, NaCl solution, CA solution and HCl solution respectively. Epichlorohydrin (EPI) was used as crosslinking agent, and β-cy...In this paper, biochar (BC) was used as raw material, activated by deionizing aqueous solution, NaCl solution, CA solution and HCl solution respectively. Epichlorohydrin (EPI) was used as crosslinking agent, and β-cyclodextrin (β-CD) was used to modify biochar (BC). The prepared modified biochar materials were labeled with β-CDBC, β-CDBC-Na, β-CDBC-CA and β-CDBC-H, respectively. The infrared spectrum, X-ray diffractometer, scanning electron microscope and specific surface area of the four modified materials were tested. The results showed that the C-O stretching vibration peak at 1020 cm<sup>−</sup><sup>1</sup> of the modified materials was slightly offset compared with that of biochar. The characteristic absorption peaks of XRD pattern decrease obviously at 2θ = 26.7˚ and 29.5˚. It can be obviously observed on the electron microscope image that the surface is loaded or formed clathrates, and BET data and graphs also show that the specific surface area of the modified biochar is larger. Therefore, β-cyclodextrin successfully modified biochar and formed clathrates on the surface of biochar or was loaded in the pore structure of biochar, especially β-CDBC-CA achieved better modification effect. Because biochar and β-cyclodextrin raw materials are cheap, easy to prepare and green, and less prone to secondary pollution, it has a good advantage in environmental governance.展开更多
基金National Key Research and Development Program of China(No.2022YFC2905004).
文摘The problems of tailings storage and high-stress conditions in deep mining have emerged as critical factors that limit the security,efficiency,and sustainability of such mines.This study explores the potential to utilize tungsten tailings to create cementitious backfill(CTB)materials and investigates the macroscopic strength features and microscopic damage evolution mechanisms of different-sized CTBs with varying dosages of hydroxypropyl methyl cellulose(HPMC).Specimens with bottom diameters of 50,75,and 100 mm are combined with HPMC dosages of 0,0.15wt%,0.25wt%,and 0.35wt%.A diameter/height ratio of 1:2 is maintained for all CTB specimens.The experimental results show that as the HPMC dosage is increased from 0 to 0.35wt%,the uniaxial compressive strength(UCS)of the CTBs decreases significantly in a linear manner.The 75 mm×150 mm CTB specimen exhibits relatively high plasticity and toughness,with good plastic deformation and energy absorption capabilities,indicating significant size effects.HPMC introduces connected bubbles during the CTB pouring process,but it exhibits anti-segregation and anti-bleeding characteristics,thus reducing tailing settling.The hydration reaction of the CTB doped with HPMC is more uniform,and the Ca/Si atomic ratio dispersion at different sites is smaller.The three CTB sizes all exhibit combined tensile and shear failure,with the 75 mm×150 mm specimen exhibiting macroscopic tensile cracks and relatively few shear cracks.At the micro-scale,excessive ettringite and hydrated calcium silicate are interwoven and fuse,and the tungsten tailings are tightly wrapped.These results provide valuable data and notional insights for optimizing the fluidity of the backfill,and elucidate the strength and damage evolution of solidified materials during filling and extraction.This study contributes to the advancement of green,economical,safe,and sustainable mining practices.
基金supported by the Ratchadapisek Sompoch Endowment Fund,Chulalongkorn University,Thailand(Grant No.:RCU_67_023_010).
文摘Fluvoxamine(FXM)is a well-known selective serotonin reuptake inhibitor(SSRI)for treating depression and has recently been repurposed for efficacious treatment of coronavirus disease 2019.Although cyclodextrin(CD)encapsulation effectively improves the physicochemical properties of structurally diverse SSRIs,the molecular understanding of their associations is deficient.This comprehensive study used single-crystal X-ray diffraction integrated with density functional theory(DFT)calculation to provide deep insights into the conformationally flexible FXM and its inclusion complexation withβ-CD.Xray analysis revealed the first crystallographic evidence of the uncomplexed 3FXM-H^(+)·3maleate-(1).Three FXM-H^(+)ions are counter-balanced by three planar maleate-ions to form a thin layer stabilized by infinite fused H-bond rings R_(4)^(4)(12)and R_(6)^(4)(16)and the interplay ofπ…π,CF…πand F…F interactions.For 2β-CD·2FXM-H^(+)·maleate^(2-)·23·2H_(2)O(2),the tail-to-tailβ-CD dimer encapsulates two FXM-H^(+)4-(trifluoromethyl)phenyl moieties,which are charge-balanced by the rare non-planar maleate2and stabilized by N…OH…O H-bonds and F…F interactions.This is a hostevip recognition pattern uniquely observed for allβ-CD complexes with halogen(X)-bearing SSRIs,indicating the essence of X…X interactions and the shielding of X-containing moieties in the wall of theβ-CD dimer.DFT calculations unveiled that the monomeric and dimericβ-CD-FXM complexes and FXM isomers are energetically stable,which alleviates the numbness and bitterness of the orally administered drug as previously patented.Additionally,an insightful conformational analysis of FXM emphasizes the importance of drug structural adaptation in pharmacological functions.
文摘The effect of various concentrations of 2-hydroxypropyl-β-cyclodextrin （HP-β-CD） on the solubility of dihydroartemisinin （DHA） in aqueous solution at different pHs was investigated. The influence of different concentrations of 2-hydroxypropyl-β- eyclodextrin on the stability of dihydroartemisinin at 50, 60, 70 and 80 ℃ was also studied. Inclusion complex of dihydroartemisinin with 2-hydroxypropyl-β-cyclodextrin was prepared and characterized by X-ray diffraction and differential scanning calorimetry. The 2-hydroxypropyl-β-cyclodextrin effectively inhibited the hydrolysis of dihydroartemisinin and greatly increased its solubility. Furthermore, we showed that the higher concentrations of 2-hydroxypropyl-β-cyclodextrin, the better stability and solubility of dihydroartemisinin. When the temperature was increased, the stability of dihydroartemisinin decreased. Our results indicated that 2-hydroxypropyl-β-cyclodextrin can be used as a stabilizer and solubilizer of dihydroartemisinin.
基金Natural Science Foundation of Beijing (Grant No. 7021001)the Foundation for the Special Program of the Following Novel Candidate Drug by Beijing S&T Committee (Grant No. H20220060190)National Natural Science Foundation (Grant No.30472036)
文摘In our previous study,a novel organic selenium compound Eb was synthesized and found to have significant antitumor activity with much less toxicity compared with the leading compound Ebselen.Unfortunately,Eb was practically insoluble in water （2.57 μg/mL） and had very low oral bioavailability,thus its clinical application was greatly limited.In the present study,the inclusion complex of Eb with 2-hydroxypropyl-β-cyclodextrin （HP-βCD） was prepared and pharmacokinetics of Eb and the inclusion complex were investigated.The water solubility of Eb was dramatically enhanced by inclusion with HP-βCD,which reached 8.4 mg/mL.The pharmacokinetic study showed that the elimination half-life （t 1/2β） of Eb was between 22 h and 30 h and the distribution half-life （t 1/2α） of Eb was 1 h.The results indicated that Eb was rapidly distributed to tissues but slowly eliminated in rats.The absolute bioavailability of Eb/HP-βCD inclusion complex solution through the oral route was 28.3%,and it was 1552% that of Eb in its pure form.In summary,the absorption of Eb in the Eb/HP-βCD inclusion complex was better and faster than that of Eb in its pure form.
文摘The goal of this study was to improve the solubility and oral bioavailability of tamibarotene by complexing it with hydroxypropyl-β-cyclodextrin(HP-β-CD).The inclusion complex of tamibarotene with hydroxypropyl-β-cyclodextrin(Am80-HP-β-CD)was prepared through a freeze-drying method at the mole ratio of 1:1(Am80:HP-β-CD).Fourier transform infrared spectroscopy(FT-IR)and differential scanning calorimetry(DSC)indicated the formation of Am80-HP-β-CD.In vitro dissolution studies showed that the solubility and dissolution percentage of Am80-HP-β-CD was improved substantially compared to Am80.An improved dissolution with approximately 97%drug release in 3 min was observed,in comparison with Am80 with approximately 60% release in 45 min.In vivo studies indicated that the AUC0-∞ has increased 2.79 times and the Cmax 4.37 times after the formation of inclusion complex.The decrease of tmaxindicated the Am80-HP-β-CD inclusion complex can be absorbed into blood faster.In short,the solubility and bio-availability of Am80 has notably increased with the complexation of HP-β-CD.Therefore,using the inclusion technique is a promising method to improve the solubility of insoluble drugs.
基金the National Natural Science Foundation of China(No.20376085,No.20576142)for its financial support.
文摘In order to set up a simple and effective method for resolution of optical isomers, hydroxypropyl-β-cyclodextrin was bonded to silica-gel, which can be used for preparation of thin-layer chromatography plates. Resolution of clenbuterol and propranolol were investigated on these thin-layer chromatography plates using different combinations of solvent systems at ambient temperature. The best simultaneous resolution was achieved in solvent system of acetonitrilen-butanol （50：50, v/v）. Rst values of resolution of clenbuterol hydrochloride and propranolol hydrochloride are 3.6 and 4.3, respectively. The spots of different enantiomers are separated clearly. The results showed that hydroxypropyl-β-cyclodextrin bonded silica-gel could be successful in resolution of chiral adrenergic drugs. The study offers a direct, rapid and reliable method for separation of this kind of optically active compounds.
基金Funded by the National Nature Science Foundation of China(No.51273156)the Open Foundation of Hubei key laboratory of Purification and Application of Plant Anti-cancer Active Ingredients(No.HLPAI2014005)
文摘Novel insulin-loaded nanoparticles based on hydroxypropyl-β-cyclodextrin modified carboxymethyl chitosan（CMC-HP-β-CD） were prepared to improve the oral bioavailability of insulin. The CMC-HP-β-CD was characterized by FT-IR spectroscopy and 1H-NMR spectra. The insulin-loaded nanoparticles were prepared through crosslinking with calcium ions, and the morphology and size of the prepared nanoparticles were characterized by transmission electron microscopy（TEM） and dynamic light scattering（DLS）. Cumulative release in vitro study was performed respectively in simulated gastric medium fluid（SGF, p H=1.2）, simulated intestinal fluid（SIF, p H=6.8） and simulated colonic fluid（SCF, p H=7.4）. The encapsulation efficiency of insulin was up to 87.14 ± 4.32% through high-performance liquid chromatography（HPLC）. Statistics indicated that only 15% of the encapsulated insulin was released from the CMC-HP-β-CD nanoparticles in 36 h in SGF, and about 50% of the insulin could be released from the nanoparticles in SIF, whereas more than 80% was released in SCF. In addition, the solution containing insulin nanoparticles could effectively reduce the blood glucose level of diabetic mice. The cytotoxicity test showed that the samples had no cytotoxicity. CMC-HP-β-CD nanoparticles are promising candidates as potential carriers in oral insulin delivery systems.
基金Fundamental Research Funds for the Central Universities(No.2232018D3-40)National Natural Science Foundation of China(No.81671508)。
文摘Bakuchiol isolated from Psoralea corylifolia is a naturally occurring prenylated phenolic monoterpene with a variety of bioactivities.The aim of this study was to improve the water solubility and thermal stability of bakuchiol through complexing it with hydroxypropyl-β-cyclodextrin(HP-β-CD).The bakuchiol/HP-β-CD inclusion complex's behavior and characterization were investigated by ultraviolet-visible(UV-vis)spectroscopy,Fourier transform infrared spectroscopy(FT-IR),thermogravimetric analysis(TGA),X-ray diffraction(XRD),1H nuclear magnetic resonance(NMR),and two-dimensional(2D)NMR.The obtained results indicated the formation of 1∶1 inclusion complex for bakuchiol with HP-β-CD.Water solubility of bakuchiol was significantly improved by complexation with HP-β-CD as demonstrated by phase solubility studies.The encapsulation of bakuchiol was confirmed by UV-vis,FT-IR,and XRD.The thermal stability was effectively enhanced by TGA and derivative thermogravimetry(DTG)analysis.In vitro antioxidant activity showed that bakuchiol/HP-β-CD inclusion complex had a little higher antioxidant ability than free bakuchiol.Moreover,we got the possible inclusion mode for the bakuchiol/HP-β-CD inclusion complex through NMR analysis.These results suggest that the inclusion complex can be a potentially useful approach in the design of novel formulations of bakuchiol for medical applications.
文摘A cationic cyclodextrin derivative 6-O-（hydroxypropyltrimethylammonia）-β-cyclodextrin （GTA-β-CD） with low degree of substitution was prepared through a convenient method in solid phase. The product could be used as a valuable chiral selector in the capillary electrophoresis （CE） separation of some acidic drug enantiomers such as naproxen, ofloxacin, ibuprofen and warfarin.
基金Supported by National Science&Technology Pillar Program during the TwelfthFive-year Plan Period(2011BAD34B01)National Natural Science Foundation of China(31372485,31172362)the opening fund from Beijing Key Laboratory of TCVM(BUA-TCVM-200904)
文摘To overcome the chemical instability of forsythiaside,the forsythiaside-hydroxypropyl-β-cyclodextrin inclusion complex was prepared by triturating. The inclusion complex was found having a varied UV spectrum and melt temperature point. Inclusion complex has a higher stability to UV light and temperature over forythiaside itself. Pharmacological evidence showed that inclusion complex has little effect on pharmacokinetics by chicken intravenous injection. This study is favorable for developing preparations for forsythiaside and its clinical application.
文摘Domperidone Maleate (DOM), an antiemetic drug, has been used in treatment of adults and children. It has low aqueous solubility and hence low bioavailability. In present study, an attempt has been made to enhance the solubility of DOM by inclusion complexation with Hydroxypropyl-β-Cyclodextrin (HP-β-CD) using kneading technique and formulation of fast disintegrating tablets by using Sodium Starch Glycolate as superdisintegrant. Solubility analysis of DOM in different concentrations of HP-β-CD was carried out. Design of experiment (DOE) is done by using MINITAB 15.1 software to find out the variable for dissolution and disintegration time. HP-β-CD and SSG were identified as the variable for disintegration time and dissolution. For optimization of the concentration of HP-β-CD and SSG, two factors at two levels design through central composite design (CCD) were used which gave 13 formulations. All formulations are evaluated for characteristics such as weight variation, hardness, friability, disintegration time and dissolution of drug. Solubility of DOM increases linearly with increase in concentration of HP-β-CD. The optimum concentration of HP-β-CD is found to be in 1:2 molar ratios and SSG of 7%. The In-Vitro dissolution studies of optimized formulation and market sample were carried out in USP type II apparatus at different time intervals of 5, 10, 15 and 30 minutes at 50 rpm in 0.1 N HCl. The dissolution and disintegration time of optimized formulation is found better than market sample.
文摘Inclusion complexes of nitro-compounds using β-cyclodextrin and hydroxypropyl-β-cyclodextrin as host molecule have been studied by cyclic voltammetric method. The inclusion constants of the corresponding complexes have been determined. Strong inclusion complexation by hydroxypropyl-β-cyclodextrin has been verified
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 AG, AH and AS for inclusion interaction of OBN and HP-β-CD were determined. The results show that host-vip 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. AG, AH and AS are all less than zero, which indicates that the inclusion process is a spontaneous and exothermic process.
基金Supported by the National Natural Science Foundation of China(No.51979255)。
文摘Cometabolic degradation is currently an effective and extensively way to remove high molecular weight polycyclic aromatic hydrocarbons(HMW-PAHs).Unfortunately,due to low bio-accessibility and high biotoxicity,the cometabolic degradation rate of HMW-PAHs is limited.Glycine-β-cyclodextrin(GCD)was obtained through amino modification ofβ-cyclodextrin(BCD)and added to cometabolic system of phenanthrene(PHE)and pyrene(PYR)to assist PYR biodegradation.Results show that the addition of GCD(100 mg/L)effectively improved the removal rate of PYR(20 mg/L)by 42.3%.GCD appeared to increase the bio-accessibility and reduce the biotoxicity of PHE and PYR,and then promoted the growth of Pseudomonas stutzeri DJP1 and stimulated the elevation of dehydrogenase(DHA)and catechol 12 dioxygenase(C12O)activities.The phthalate metabolic pathway was accelerated,which improved the cometabolic degradation.This study provided a new reference for the cometabolic degradation of HMW-PAHs.
基金China Postdoctoral Science Foundation(2020M681125)National Natural Science Foundation of China(32272254,31901618)Collaborative Innovation Center of Fragrance Flavour and Cosmetics.
文摘Bio-based cyclodextrins(CDs)are a common research object in supramolecular chemistry.The special cavity structure of CDs can form supramolecular self-assemblies such as vesicles and microcrystals through weak interaction with vip molecules.The different forms of supramolecular self-assemblies can be transformed into each other under certain conditions.The regulation of supramolecular self-assembly is not only helpful to understand the self-assembly principle,but also beneficial to its application.In the present study,the self-assembly behavior of epoxy-β-cyclodextrin(EP-β-CD)and mixed anionic and cationic surfactant system(sodium dodecyl sulfate/dodecyltrimethylammonium bromide,SDS/DTAB)in aqueous solution was studied.Morphological and particle size characterization found that the SDS/DTAB@EP-β-CD complex,as the basic building unit,self-assembled into worm-like micelles at lower temperatures and vesicles at higher temperatures.Nuclear magnetic resonance(NMR)and Fourier transform infrared spectroscopy(FT-IR)analysis revealed that the driving force for the formation of vesicles and worm-like micelles was the hydrogen bonds between EP-β-CD molecules,while water molecules played an important role in promoting vesicle formation between SDS/DTAB@EP-β-CD units.Herein,the mechanism of the morphologic transformation of SDS/DTAB@EP-β-CD supramolecular aggregates induced by temperature was elucidated by exploring the self-assembly process,which may provide an excellent basis for the development of delivery carriers.
基金Youth Science Foundation Project of Sichuan Provincial Department of Science and Technology(2022NSFSC1437)Special Project of Scientific and Technological Research of Sichuan Provincial Administration of Traditional Chinese Medicine(2021MS121)Fundamental Research Funds for the Central Universities of Southwest Minzu University(ZYN2022040).
文摘[Objectives]To enhance the skin permeability of hydroxypropyl tetrahydropyrantriol and provide a reference for the subsequent prevention or treatment of skin aging.[Methods]The lyophilization process of hydroxypropyl tetrahydropyrantriol liposomes was investigated using a single factor method,and a quality evaluation system was established based on the appearance,particle size,PDI,and re-dispersibility of the lyophilized samples.[Results]The lyophilization process of hydroxypropyl tetrahydropyrantriol liposomes was determined by single factor experiments.The pre-freezing period was 16 h at-80℃,the total drying time was 36 h,and the addition of 10%mannitol-sucrose was used as the lyoprotectant.[Conclusions]The product prepared by the lyophilization method exhibits a fluffy and full appearance,with minimal shrinkage and collapse.The volume remains consistent before and after lyophilization,and the re-dispersibility is satisfactory.The re-dissolution process is rapid,and the particle size and polydispersity index(PDI)remain largely unchanged before and after lyophilization.
文摘In this study, the adsorption effect of β-cyclodextrin modified biochar (BC) on phenanthrene (PHE) in contaminated soil was investigated, aiming to provide an efficient and environmentally friendly remediation strategy for Polycyclic Aromatic Hydrocarbons (PAHs) contaminated soil. Through kinetic and isotherm analysis, β-CDBC-CA showed excellent phenanthrene adsorption performance, and the adsorption effect increased with the increase of time and was affected by temperature. The results show that β-CDBC-CA can not only effectively adsorb phenanthrene in soil, but also serve as a surfactant to help desorption phenanthrene adsorbed by soil organic matter and improve the efficiency of microbial degradation. The experimental data showed that the Elovich model could describe the adsorption behavior of β-CDBC-CA on phenanthrene well, while Langmuir and Freundlich models performed better in fitting parameters, revealing the adsorption mechanism of phenanthrene in contaminated soil by β-cyclodextrin-modified biochar. In addition, temperature has a significant effect on the adsorption capacity of β-CDBC-CA, and its application in soil remediation can be optimized by adjusting temperature. This study not only provides new materials and technical means for soil remediation but also provides important data support for an in-depth understanding of the environmental behavior of PAHs. By citing relevant research results, this study further improves the control and understanding of environmental risks of PAHs, which is of great significance for the protection of ecological environment and human health.
文摘In this paper, biochar (BC) was used as raw material, activated by deionizing aqueous solution, NaCl solution, CA solution and HCl solution respectively. Epichlorohydrin (EPI) was used as crosslinking agent, and β-cyclodextrin (β-CD) was used to modify biochar (BC). The prepared modified biochar materials were labeled with β-CDBC, β-CDBC-Na, β-CDBC-CA and β-CDBC-H, respectively. The infrared spectrum, X-ray diffractometer, scanning electron microscope and specific surface area of the four modified materials were tested. The results showed that the C-O stretching vibration peak at 1020 cm<sup>−</sup><sup>1</sup> of the modified materials was slightly offset compared with that of biochar. The characteristic absorption peaks of XRD pattern decrease obviously at 2θ = 26.7˚ and 29.5˚. It can be obviously observed on the electron microscope image that the surface is loaded or formed clathrates, and BET data and graphs also show that the specific surface area of the modified biochar is larger. Therefore, β-cyclodextrin successfully modified biochar and formed clathrates on the surface of biochar or was loaded in the pore structure of biochar, especially β-CDBC-CA achieved better modification effect. Because biochar and β-cyclodextrin raw materials are cheap, easy to prepare and green, and less prone to secondary pollution, it has a good advantage in environmental governance.
