Aim To prepare and characterize the QURC-HP-β-CD inclusion complexes and investigate the thermodynamic parameters of the process. Methods QURC-HP-β-CD inclusion complexes were prepared by the grinding method. The eq...Aim To prepare and characterize the QURC-HP-β-CD inclusion complexes and investigate the thermodynamic parameters of the process. Methods QURC-HP-β-CD inclusion complexes were prepared by the grinding method. The equilibrium inclusion constants and thermodynamic parameters were determinated by phase solubility analysis. Dissolution tests were performed to study the dissolution rate of inclusion complexes. The formation of inclusion complexes was confirmed by differential scanning calorimetry （ DSC）, infrared spectroscopy （IR） , powder X-ray diffractometry （PXRD） and scanning electron microscopy （SEM）. Results The aqueous solubility of quercetin was greatly increased （ about 37 folds） by inclusion technique, and the initial dissolution rate was markedly improved （10 folds） in the first 5 min. The results of DSC and SEM photographs showed that quercetin crystal disappeared in inclusion complexes, which indicated the formation of new phase. FT-IR spectra showed that the carbonyl quercetin crystal grinding method. absorption band of quercetin was shifted. PXRD showed that the diffraction peak of disappeared. Conclusion QURC-HP-β-CD inclusion complexes are produced by the The solubility of quercetin is improved by the inclusion technique.展开更多
Both four-ann star-shaped poly（ε-caprolactone） （4sPCL） and two-ann linear PCL （2LPCL） were synthesized and their inclusion complexation with α-cyclodextrin （α-CD） were studied. The inclusion complexes （ICs...Both four-ann star-shaped poly（ε-caprolactone） （4sPCL） and two-ann linear PCL （2LPCL） were synthesized and their inclusion complexation with α-cyclodextrin （α-CD） were studied. The inclusion complexes （ICs） formed between the PCL polymers and α-CD were characterized by ^1H-NMR, DSC, TGA, WAXD, and FT-1R, respectively. Both branch ann number and molecular weight of the PCL polymers have apparent effect on the stoichiometry （CL：CD, mol：mol） of these ICs. All these analytical results indicate that the branch arms of the PCL polymers are incorporated into the hydrophobic α-CD cavities and their original crystalline properties are completely suppressed. Moreover, the inclusion complexation between two-ann linear or four-ann star-shaped PCL polymers and α-CD not only enhances the thermal stability of the vip PCL polymers but also improves that of α-CD.展开更多
The solid form of drugs plays a central role in optimizing the physicochemical properties of drugs,and new solid forms will provide more options to achieve the desirable pharmaceutical profiles of drugs.Recently,certa...The solid form of drugs plays a central role in optimizing the physicochemical properties of drugs,and new solid forms will provide more options to achieve the desirable pharmaceutical profiles of drugs.Recently,certain drugs have been found to form crystalline inclusion complexes（ICs） with multiple types of linear polymers,representing a new subcategory of pharmaceutical solids.In this study,we used diflunisal（DIF） as the model drug host and extended the vip of drug/polymer ICs from homopolymers to block copolymers of poly（ethylene glycol）（PEG） and poly（s-caprolactone）（PCL）.The block length in the vip copolymers showed a significant influence on the formation,thermal stability and dissolution behavior of the DIF ICs.Though the PEG block could hardly be included alone,it could indeed be included in the DIF ICs when the PCL block was long enough.The increase of the PCL block length produced IC crystals with improved thermal stability.The dissolution profiles of DIF/block copolymer ICs exhibited gradually decreased aqueous solubility and dissolution rate with the increasing PCL block length.These results demonstrate the possibility of using drug/polymer ICs to modulate the desired pharmaceutical profiles of drugs in a predictable and controllable manner.展开更多
The solid Supramolecular complexes of β-cyclodextrin （β-CD） with ethylenediamine 1, diethylenetriamine 2 and triethylamine 3 were obtained and characterized using elemental analysis, powder X-ray diffraction, infr...The solid Supramolecular complexes of β-cyclodextrin （β-CD） with ethylenediamine 1, diethylenetriamine 2 and triethylamine 3 were obtained and characterized using elemental analysis, powder X-ray diffraction, infrared spectroscopy, thermogravimetric analysis, and ^1H nuclear magnetic resonance spectroscopy. Based on the results of elemental analysis and ^1H NMR, the vip-host stoichiometries of the three solid complexes were determined to be 5：2 for 1-β-CD, hl for 2-β-CD, and 1：3 for 3-β-CD. The yields were relative to the molar volume ratio of vip to β-CD cavity, and increased in the order： 1-β-CD〈2-3-CD〈3-β-CD. X-ray diffraction patterns of the inclusion complexes gave very good exhibitions not only in location of diffraction peaks but also in shape and diffraction intensity of the peaks due to the intermolecular complexations between β-CD and the vips. The formation of host-vip inclusion complexes exhibited obviously enhanced phase change temperatures of the complexed vips such as 1 and 3. The H-5 protons located at the narrower rim inside the CD cavity experienced a higher shift upon inclusion while all other protons experienced lower shifts.展开更多
Ternary inclusion complexes β-cyclodextrin （β-CD）, rare earth metal ions （YbC13, YC13）, and 1,8-naphthalene- diamine/ 1,5-naphthalenediamine are synthesized in basic aqueous media, which are characterized via IH...Ternary inclusion complexes β-cyclodextrin （β-CD）, rare earth metal ions （YbC13, YC13）, and 1,8-naphthalene- diamine/ 1,5-naphthalenediamine are synthesized in basic aqueous media, which are characterized via IH NMR and IR spectroscopy. The stoichiometric proportion of β-CD ： YbC13 ： 1, 5-naphthalenedia- mine is 2：1：2, that of β-CD：YCI3 ： 1,8-naphthalenediamine is 2：1：1, and that of β-CD：YbC13 ： 1,8-naphthalenediamine is 2 ： 1 ： 1. The IR spectroscopy of the ternary inclusion complexes in the range of 935-1 000 cm 1 reveals the existence of the coordinate bond M---O or M---N. The possible conformations of the ternary inclusion complexes are depicted.展开更多
Parkinson's disease(PD)is a debilitating and progressive neurodegenerative disorder with complex pathology and multiple membrane barriers that hinder drug delivery,resulting in the absence of ideal therapeutic dru...Parkinson's disease(PD)is a debilitating and progressive neurodegenerative disorder with complex pathology and multiple membrane barriers that hinder drug delivery,resulting in the absence of ideal therapeutic drugs with minimal side effects[1].Recently,natural medicine has garnered significant attention due to its remarkable efficacy and limited side effects.Icariin,a naturally occurring flavonoid,exhibits excellent potential as a therapeutic agent for neurodegenerative disease[2].However,its clinical application is limited by poor water solubility,low bioavailability,and high clearance rates.Here,an aqueous formulation of icariin/hydroxypropyl-β-cyclodextrin(HP-β-CD)supramolecular inclusion complex was obtained to optimize icariin properties.Furthermore,icariin cyclodextrin supramolecular inclusion complex based thermosensitive(icariin gels)was innovated.At lower temperatures,it remained in a liquid phase with high fluidity.Upon reaching the gelation temperature,it underwent a transition to a gel phase with significantly reduced fluidity,which may be suitable for the design of an intranasal delivery system for PD treatment.The innovative approach capitalizes on the exceptional characteristics of HP-β-CD,which was utilized to synergize with nasal delivery for targeted brain delivery and with icariin for PD treatment[3,4].展开更多
At present, using cyclodextrins or cyclodextrin derivatives with suitable internal annular dimension to embed C60 so as to form inclusion complexes has been one of the main ways to improve C60＇s water-solubility. In ...At present, using cyclodextrins or cyclodextrin derivatives with suitable internal annular dimension to embed C60 so as to form inclusion complexes has been one of the main ways to improve C60＇s water-solubility. In three kinds of cyclodextrins (α-, β-, γ-CD), only γ-CD has cavity large enough to include C60 whereas α-, and β-CD have not. In the case of DMβCD, the "out-stretching" methyl groups enlarge the cavity so that it can include C60. Starting from the same thought, we use epichlorohydrin crosslinked展开更多
The linear component of starch,amylose,has the ability to interact with hydrophobic molecules forming inclusion complexes(ICs).These structures have gained a particular interest for potential food applications,either ...The linear component of starch,amylose,has the ability to interact with hydrophobic molecules forming inclusion complexes(ICs).These structures have gained a particular interest for potential food applications,either as dietary fiber or as delivery systems of bioactive compounds.In the second case,the complexation of sensitive molecules is directed to protect them from processing,storage and stomach conditions and to guarantee a sustained release in the gastrointestinal tract.The present review covers the analytical and technological aspects of inclusion complexes,with focus on their potential application in the development of functional foods.It was addressed by first explaining the methodologies used for the analytical assessment of their structural,thermal,and functional properties,followed by the study of the functionality of ICs as carrier agents of different bioactive compounds and food ingredients,including alpha-lipoic acid,α-linolenic and linoleic fatty acids,conjugated linoleic acid,ascorbyl palmitate,phenolic compounds,and flavors.It also covers the application of ICs in food products and the analysis of the potential industrial scalability of the formation process.The analytical methodologies allowed a complete characterization of the ICs.These structures have shown suitable functional properties as delivery systems of the bioactive compounds and flavors covered in this review.The incorporation of ICs in food has led to the development of products with improved nutritional and/or functional value.The successful formation of complexes using methods suitable for an industrial scale represents promising preliminary results to achieve the scalability of the ICs production in the near future.展开更多
Two inclusion complexes of β-cyclodextrin-7-hydroxycoumarin （1） and ,β-cyclodextrin-4-hydroxycoumarin （2） were prepared and their crystal structures were investigated by single crystal X-ray crystallography unde...Two inclusion complexes of β-cyclodextrin-7-hydroxycoumarin （1） and ,β-cyclodextrin-4-hydroxycoumarin （2） were prepared and their crystal structures were investigated by single crystal X-ray crystallography under cryogenic condition. Both structures consist of stacks of face-to-face cyclodextrin dimers arranged in brickwork-like pattern along the crystallographic a-axis. For complex 1, each of the two dimeric β-cyclodextrins includes one 7-hydroxycoumarin molecule that penetrates deeply into the cyclodextrin dimer and locates its lactonering at the center of the dimer cavity. For complex 2, each cyelodextrin dimer accommodates three 4-hydroxycoumarin molecules. One of them is sandwiched between two units of the cyclodextrin dimer, the other two are shallowly included in the cavities of the dimeric cyclodextrins respectively and protrude their lactone rings from the primary end of the cyclodextrin. The substituent effects of vip molecules on inclusion geometry of various coumarin molecules in fl-cyclodextrin were examined.展开更多
Two functionalized calixarenes in cone conformation L 2-3 have been synthesized and their intramolecular inclusion complexes (1∶1) with organic neutral molecules CH 3CN and CH 3NO 2 have been prepared and c...Two functionalized calixarenes in cone conformation L 2-3 have been synthesized and their intramolecular inclusion complexes (1∶1) with organic neutral molecules CH 3CN and CH 3NO 2 have been prepared and characterized, respectively. The X-ray crystallographic analysis shows that L 2 in L 2·CH 3CN·C 2H 5OH has C 4 symmestry and L 3 in L 3·CH 3NO 2 exhibits C 2 symmestry. The CH-π aromatic interactions between the CH group of the vip and the phenyl rings of the calix backbond have been proved to be able to stabilize the intramolecular inclusion complexes formed. The interaction is directional, but it is independent of the acidity of the vip. To gain information on CH-π interactions, suitable geometrical parameters have been calculated from the crystal data of intramolecular inclusion complexes. The results show that L 3·CH 3NO 2 with L 3 in C 2 symmestry can also be bound stably in the intramolecular inclusion complex, being consistent with the thermal analysis. The geometrical parameters and the results of the thermal analysis of L 1·CH 3CN and L 1·CH 3NO 2 were also given and discussed.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 effect of temperature-responsive solution behavior of PNIPAM-b-PPEOMA-b-PNIPAM on its inclusion complexation with α-cyclodextrin was studied. The triblock polymer was prepared by reversible addition-fragmentation...The effect of temperature-responsive solution behavior of PNIPAM-b-PPEOMA-b-PNIPAM on its inclusion complexation with α-cyclodextrin was studied. The triblock polymer was prepared by reversible addition-fragmentation chain transfer （RAFT） polymerization and formed inclusion complexes （ICs） after selective threading of the PEO segment of the triblock polymer through the cavities of α-CD units. For comparison, PPEOMA homopolymer was prepared and the inclusion complexation with α-CD was also studied. The ICs were prepared with a-CD when the polymer was in different conformations by changing the temperature, and the formed ICs were characterized by XRD, ^1H-NMR, TGA and DSC. The solutions of the ICs show temperature-responsive clear/turbid transition or fluidic emulsion/gel transition depending on the concentration of the α-CD added, and the stoichiometry determined by ^1H-NMR and TGA indicates that the stoichiometry of EO to α-CD of the resulted ICs increases with increasing of temperature.展开更多
Inclusion complexes(ICs) composed ofα-cyclodextrins(α-CD) and biodegradable comblike copolymers with poly(α,β-malic acid)(PMA) backbones and methylated poly(ethylene glycol)(mPEG) side chains were prepared by the ...Inclusion complexes(ICs) composed ofα-cyclodextrins(α-CD) and biodegradable comblike copolymers with poly(α,β-malic acid)(PMA) backbones and methylated poly(ethylene glycol)(mPEG) side chains were prepared by the host-vip reaction.Two series of ICs with mPEG750 and mPEG2000 were prepared.The stoichiometry(EG/CD) of all the ICs in mPEG2000 series was 3.1,no matter what the graft degree was.While in mPEG750 series,the stoichiometry(EG/CD) was very different:it increased with the amount of mPEG decreasing.Th...展开更多
The equilibrium melting point(T_(m)^(0))is a crucial thermodynamic parameter for characterizing the crystallization and melting behavior of semi-crystalline polymers.However,the direct measurement of T_(m)^(0) poses a...The equilibrium melting point(T_(m)^(0))is a crucial thermodynamic parameter for characterizing the crystallization and melting behavior of semi-crystalline polymers.However,the direct measurement of T_(m)^(0) poses a significant challenge because of the difficulty in physically fabricating fully-extended chain crystals of high-molecular-weight polymers.Therefore,various extrapolation equations for T_(m)^(0) have been proposed that utilize the thermal properties of ordinary folded-chain lamellae.Among these,the Gibbs-Thomson equation is one of the most commonly employed for modeling.Despite its widespread use,there are notable variations in the T_(m)^(0) values obtained by different research groups,even when based on similar samples.This raises questions about the validity and accuracy of using the Gibbs-Thomson equation to linearly extrapolate T_(m)^(0).In this study,we prepared a series of oligomer extended-chain crystals(ECCs)of poly(butylene succinate)(PBS)and used their properties for Gibbs-Thomson fitting.The results reveal a perfect linear relationship,with an extrapolated T_(m)^(0) value of 136.08℃.The basal surface free energy of the oligomer ECCs was calculated as 0.084 J/m^(2),which is approximately twice that of folded-chain lamellae.This difference is attributed to the aggregation of highly mobile free tails on the crystal surface.The two structural features of oligomer ECCs—large thickness and fixed surface—better fulfill the conditions for applying the Gibbs-Thomson equation,ensuring its validity and accuracy.Therefore,we believe that the Gibbs-Thomson fit can produce reliable results when sufficient high-quality data are used.展开更多
The formation of oxide inclusions in one of the carbon steel productions of Mobarakeh Steel Complex of Isfahan has been evaluated. Several samples from different steps of steel production were taken, from arc furnace,...The formation of oxide inclusions in one of the carbon steel productions of Mobarakeh Steel Complex of Isfahan has been evaluated. Several samples from different steps of steel production were taken, from arc furnace, ladle furnace, tundish, and continuous casting mold. Moreover, samples of slab and hot rolling products were prepared. The samples were investigated by optical and scanning electron microscopes equipped with the EDS system. According to the results, the number, composition, and kind of inclusions were directly influenced by the production variables. It was found that when the amount of dissolved oxygen was high （say more than 0. 002 5%）, the dissolved aluminum was able to reduce silicon oxide and react with the dissolved oxygen simultaneously, whilst, the dissolved aluminum could reduce the magnesium oxide only when the oxygen content was below 0. 000 5%. Based on this research, a mechanism for forming the complex inclusions was suggested. It was also found that if the aluminum is added to the melt as late as possible, a cleaner melt with fewer inclusions is prepared; this method will be more effective, especially in the case of complex inclusions.展开更多
Inclusion characteristic and microstructure steel were evaluated with scanning electron of rare earth （RE） elements containing microscopy with energy dispersive spec- troscopy （SEM-EDS）, element-mapping, optical m...Inclusion characteristic and microstructure steel were evaluated with scanning electron of rare earth （RE） elements containing microscopy with energy dispersive spec- troscopy （SEM-EDS）, element-mapping, optical microscopy （OM）, and automated feature analysis （AFA） option equipped with ASPEX PSEM. Factsage was used to calculate the equilibrium inclusion composition. Based on the calculation, an inclu- sion evolution mechanism was proposed. Furthermore, line scanning analysis was used to elucidate the intra-granular acicular ferrite （IAF） nucleation mechanism. The re- sult showed that two different inclusions exist in sample steel： （Mn-A1-Si-Ti-La-Ce-O） ＋MnS complex inclusion and isolated MnS inclusion. Almost all nucleation sites for IAF are complex inclusions, while single MnS inclusion cannot induce IAF. A possible formation mechanism of complex inclusion is proposed based on calculated results using Factsage, which agrees well with experimental results. A Mn-depletion zone （MDZ） which exists adjacent to the （Mn-A1-Si-Ti-La-Ce-O） ＋MnS complex inclusion can account for the IAF formation. However, the low volume fraction （1.49× 10-7） of effective inclusion may result in only 10% （volume fraction） IAF.展开更多
The inclusion-complex of CD-MCP （β-cyclodextrin （β-CD） including 1-methylcyclopropene （1-MCP）） was prepared and characterized. Basing on programmed-heating procedure and weight-temperature analysis, as well as...The inclusion-complex of CD-MCP （β-cyclodextrin （β-CD） including 1-methylcyclopropene （1-MCP）） was prepared and characterized. Basing on programmed-heating procedure and weight-temperature analysis, as well as the application of Satava-Sestak＇s, Ozawa＇s and Kissinger＇s methods, the mechanism and kinetics of thermal dissociation of this inclusion complex were studied. An additional mass loss is found at 170-180℃. The mechanism of thermal dissociation of CD-MCP is dominated by a one-dimensional random nucleation and subsequent growth process （A2/3）. The activation energy Es and the pre-exponential factor AS for the process are 102.14 kJ/mol and 3.63×10^10s^-1, respectively. This ES value shows that there is no strong chemical intere, ctions between β-CD and 1-MC;P,展开更多
Inclusion compound of retinoic acid with (-cyclodextrin was prepared by coprecipitating method, the structure of resulting product was studied by elemental analysis, differential scanning caloriemetry(DSC) analysis, F...Inclusion compound of retinoic acid with (-cyclodextrin was prepared by coprecipitating method, the structure of resulting product was studied by elemental analysis, differential scanning caloriemetry(DSC) analysis, FT-IR spectroscopy and X-ray diffractometry, and the formed supramolecule self-assembles in aqueous solution according to molar ratio 2:1 of host-vip.展开更多
An inclusion complex of b-cyclodextrin with andrographolide (Andro) was prepared by using a convenient method of microwave irradiation. The structure of the inclusion complex was determined by the 1H NMR, 2D NMR spect...An inclusion complex of b-cyclodextrin with andrographolide (Andro) was prepared by using a convenient method of microwave irradiation. The structure of the inclusion complex was determined by the 1H NMR, 2D NMR spectroscopy as well as the elemental analysis.展开更多
文摘Aim To prepare and characterize the QURC-HP-β-CD inclusion complexes and investigate the thermodynamic parameters of the process. Methods QURC-HP-β-CD inclusion complexes were prepared by the grinding method. The equilibrium inclusion constants and thermodynamic parameters were determinated by phase solubility analysis. Dissolution tests were performed to study the dissolution rate of inclusion complexes. The formation of inclusion complexes was confirmed by differential scanning calorimetry （ DSC）, infrared spectroscopy （IR） , powder X-ray diffractometry （PXRD） and scanning electron microscopy （SEM）. Results The aqueous solubility of quercetin was greatly increased （ about 37 folds） by inclusion technique, and the initial dissolution rate was markedly improved （10 folds） in the first 5 min. The results of DSC and SEM photographs showed that quercetin crystal disappeared in inclusion complexes, which indicated the formation of new phase. FT-IR spectra showed that the carbonyl quercetin crystal grinding method. absorption band of quercetin was shifted. PXRD showed that the diffraction peak of disappeared. Conclusion QURC-HP-β-CD inclusion complexes are produced by the The solubility of quercetin is improved by the inclusion technique.
基金This work was supported by the National Natural Science Foundation of China (No. 20404007).
文摘Both four-ann star-shaped poly（ε-caprolactone） （4sPCL） and two-ann linear PCL （2LPCL） were synthesized and their inclusion complexation with α-cyclodextrin （α-CD） were studied. The inclusion complexes （ICs） formed between the PCL polymers and α-CD were characterized by ^1H-NMR, DSC, TGA, WAXD, and FT-1R, respectively. Both branch ann number and molecular weight of the PCL polymers have apparent effect on the stoichiometry （CL：CD, mol：mol） of these ICs. All these analytical results indicate that the branch arms of the PCL polymers are incorporated into the hydrophobic α-CD cavities and their original crystalline properties are completely suppressed. Moreover, the inclusion complexation between two-ann linear or four-ann star-shaped PCL polymers and α-CD not only enhances the thermal stability of the vip PCL polymers but also improves that of α-CD.
基金financially supported by the National Natural Science Foundation of China(Nos.21434008,21374054)National Basic Research Program of China(973 Program,No.2014CB932202)
文摘The solid form of drugs plays a central role in optimizing the physicochemical properties of drugs,and new solid forms will provide more options to achieve the desirable pharmaceutical profiles of drugs.Recently,certain drugs have been found to form crystalline inclusion complexes（ICs） with multiple types of linear polymers,representing a new subcategory of pharmaceutical solids.In this study,we used diflunisal（DIF） as the model drug host and extended the vip of drug/polymer ICs from homopolymers to block copolymers of poly（ethylene glycol）（PEG） and poly（s-caprolactone）（PCL）.The block length in the vip copolymers showed a significant influence on the formation,thermal stability and dissolution behavior of the DIF ICs.Though the PEG block could hardly be included alone,it could indeed be included in the DIF ICs when the PCL block was long enough.The increase of the PCL block length produced IC crystals with improved thermal stability.The dissolution profiles of DIF/block copolymer ICs exhibited gradually decreased aqueous solubility and dissolution rate with the increasing PCL block length.These results demonstrate the possibility of using drug/polymer ICs to modulate the desired pharmaceutical profiles of drugs in a predictable and controllable manner.
文摘The solid Supramolecular complexes of β-cyclodextrin （β-CD） with ethylenediamine 1, diethylenetriamine 2 and triethylamine 3 were obtained and characterized using elemental analysis, powder X-ray diffraction, infrared spectroscopy, thermogravimetric analysis, and ^1H nuclear magnetic resonance spectroscopy. Based on the results of elemental analysis and ^1H NMR, the vip-host stoichiometries of the three solid complexes were determined to be 5：2 for 1-β-CD, hl for 2-β-CD, and 1：3 for 3-β-CD. The yields were relative to the molar volume ratio of vip to β-CD cavity, and increased in the order： 1-β-CD〈2-3-CD〈3-β-CD. X-ray diffraction patterns of the inclusion complexes gave very good exhibitions not only in location of diffraction peaks but also in shape and diffraction intensity of the peaks due to the intermolecular complexations between β-CD and the vips. The formation of host-vip inclusion complexes exhibited obviously enhanced phase change temperatures of the complexed vips such as 1 and 3. The H-5 protons located at the narrower rim inside the CD cavity experienced a higher shift upon inclusion while all other protons experienced lower shifts.
基金Supported by the Project of Education Department of Liaoning Province (20040084)
文摘Ternary inclusion complexes β-cyclodextrin （β-CD）, rare earth metal ions （YbC13, YC13）, and 1,8-naphthalene- diamine/ 1,5-naphthalenediamine are synthesized in basic aqueous media, which are characterized via IH NMR and IR spectroscopy. The stoichiometric proportion of β-CD ： YbC13 ： 1, 5-naphthalenedia- mine is 2：1：2, that of β-CD：YCI3 ： 1,8-naphthalenediamine is 2：1：1, and that of β-CD：YbC13 ： 1,8-naphthalenediamine is 2 ： 1 ： 1. The IR spectroscopy of the ternary inclusion complexes in the range of 935-1 000 cm 1 reveals the existence of the coordinate bond M---O or M---N. The possible conformations of the ternary inclusion complexes are depicted.
基金supported by the National Natural Science Foundation of China(Grant No.:82104399)the Science and Technology Project of Haihe Laboratory of Modern Chinese Medicine,China(Grant No.:22HHZYSS00001).
文摘Parkinson's disease(PD)is a debilitating and progressive neurodegenerative disorder with complex pathology and multiple membrane barriers that hinder drug delivery,resulting in the absence of ideal therapeutic drugs with minimal side effects[1].Recently,natural medicine has garnered significant attention due to its remarkable efficacy and limited side effects.Icariin,a naturally occurring flavonoid,exhibits excellent potential as a therapeutic agent for neurodegenerative disease[2].However,its clinical application is limited by poor water solubility,low bioavailability,and high clearance rates.Here,an aqueous formulation of icariin/hydroxypropyl-β-cyclodextrin(HP-β-CD)supramolecular inclusion complex was obtained to optimize icariin properties.Furthermore,icariin cyclodextrin supramolecular inclusion complex based thermosensitive(icariin gels)was innovated.At lower temperatures,it remained in a liquid phase with high fluidity.Upon reaching the gelation temperature,it underwent a transition to a gel phase with significantly reduced fluidity,which may be suitable for the design of an intranasal delivery system for PD treatment.The innovative approach capitalizes on the exceptional characteristics of HP-β-CD,which was utilized to synergize with nasal delivery for targeted brain delivery and with icariin for PD treatment[3,4].
基金Project supported by the Doctoral Fund of China and the Science Fund of the Chinese Academy of Sciences.
文摘At present, using cyclodextrins or cyclodextrin derivatives with suitable internal annular dimension to embed C60 so as to form inclusion complexes has been one of the main ways to improve C60＇s water-solubility. In three kinds of cyclodextrins (α-, β-, γ-CD), only γ-CD has cavity large enough to include C60 whereas α-, and β-CD have not. In the case of DMβCD, the "out-stretching" methyl groups enlarge the cavity so that it can include C60. Starting from the same thought, we use epichlorohydrin crosslinked
基金supported by the Universidad Nacional de La Plata(UNLP)(11/X756,X907)the Agencia Nacional de Promoci´on Científicay Tecnol´ogica(PICT 2016-0323,2020-01274)(Argentina)the la ValSe-Food Project CYTED 119RT0567(Spain).
文摘The linear component of starch,amylose,has the ability to interact with hydrophobic molecules forming inclusion complexes(ICs).These structures have gained a particular interest for potential food applications,either as dietary fiber or as delivery systems of bioactive compounds.In the second case,the complexation of sensitive molecules is directed to protect them from processing,storage and stomach conditions and to guarantee a sustained release in the gastrointestinal tract.The present review covers the analytical and technological aspects of inclusion complexes,with focus on their potential application in the development of functional foods.It was addressed by first explaining the methodologies used for the analytical assessment of their structural,thermal,and functional properties,followed by the study of the functionality of ICs as carrier agents of different bioactive compounds and food ingredients,including alpha-lipoic acid,α-linolenic and linoleic fatty acids,conjugated linoleic acid,ascorbyl palmitate,phenolic compounds,and flavors.It also covers the application of ICs in food products and the analysis of the potential industrial scalability of the formation process.The analytical methodologies allowed a complete characterization of the ICs.These structures have shown suitable functional properties as delivery systems of the bioactive compounds and flavors covered in this review.The incorporation of ICs in food has led to the development of products with improved nutritional and/or functional value.The successful formation of complexes using methods suitable for an industrial scale represents promising preliminary results to achieve the scalability of the ICs production in the near future.
基金Project supported by the Natural Science Foundation of Hainan Province （No. 808145）.
文摘Two inclusion complexes of β-cyclodextrin-7-hydroxycoumarin （1） and ,β-cyclodextrin-4-hydroxycoumarin （2） were prepared and their crystal structures were investigated by single crystal X-ray crystallography under cryogenic condition. Both structures consist of stacks of face-to-face cyclodextrin dimers arranged in brickwork-like pattern along the crystallographic a-axis. For complex 1, each of the two dimeric β-cyclodextrins includes one 7-hydroxycoumarin molecule that penetrates deeply into the cyclodextrin dimer and locates its lactonering at the center of the dimer cavity. For complex 2, each cyelodextrin dimer accommodates three 4-hydroxycoumarin molecules. One of them is sandwiched between two units of the cyclodextrin dimer, the other two are shallowly included in the cavities of the dimeric cyclodextrins respectively and protrude their lactone rings from the primary end of the cyclodextrin. The substituent effects of vip molecules on inclusion geometry of various coumarin molecules in fl-cyclodextrin were examined.
基金theNationalNaturalScienceFoundationofChina (No .2 9872 0 34 )andtheNaturalScienceFoundationofHenan ,China
文摘Two functionalized calixarenes in cone conformation L 2-3 have been synthesized and their intramolecular inclusion complexes (1∶1) with organic neutral molecules CH 3CN and CH 3NO 2 have been prepared and characterized, respectively. The X-ray crystallographic analysis shows that L 2 in L 2·CH 3CN·C 2H 5OH has C 4 symmestry and L 3 in L 3·CH 3NO 2 exhibits C 2 symmestry. The CH-π aromatic interactions between the CH group of the vip and the phenyl rings of the calix backbond have been proved to be able to stabilize the intramolecular inclusion complexes formed. The interaction is directional, but it is independent of the acidity of the vip. To gain information on CH-π interactions, suitable geometrical parameters have been calculated from the crystal data of intramolecular inclusion complexes. The results show that L 3·CH 3NO 2 with L 3 in C 2 symmestry can also be bound stably in the intramolecular inclusion complex, being consistent with the thermal analysis. The geometrical parameters and the results of the thermal analysis of L 1·CH 3CN and L 1·CH 3NO 2 were also given and discussed.
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.
基金financially supported by the Hunan Normal University for providing start-up
文摘The effect of temperature-responsive solution behavior of PNIPAM-b-PPEOMA-b-PNIPAM on its inclusion complexation with α-cyclodextrin was studied. The triblock polymer was prepared by reversible addition-fragmentation chain transfer （RAFT） polymerization and formed inclusion complexes （ICs） after selective threading of the PEO segment of the triblock polymer through the cavities of α-CD units. For comparison, PPEOMA homopolymer was prepared and the inclusion complexation with α-CD was also studied. The ICs were prepared with a-CD when the polymer was in different conformations by changing the temperature, and the formed ICs were characterized by XRD, ^1H-NMR, TGA and DSC. The solutions of the ICs show temperature-responsive clear/turbid transition or fluidic emulsion/gel transition depending on the concentration of the α-CD added, and the stoichiometry determined by ^1H-NMR and TGA indicates that the stoichiometry of EO to α-CD of the resulted ICs increases with increasing of temperature.
基金supported by the National Basic Research Program of China(National 973 program,No2005CB623903)National Natural Science Foundation of China(No20604016)Sichuan Youth Science & Technology Foundation(No07ZQ026-013)
文摘Inclusion complexes(ICs) composed ofα-cyclodextrins(α-CD) and biodegradable comblike copolymers with poly(α,β-malic acid)(PMA) backbones and methylated poly(ethylene glycol)(mPEG) side chains were prepared by the host-vip reaction.Two series of ICs with mPEG750 and mPEG2000 were prepared.The stoichiometry(EG/CD) of all the ICs in mPEG2000 series was 3.1,no matter what the graft degree was.While in mPEG750 series,the stoichiometry(EG/CD) was very different:it increased with the amount of mPEG decreasing.Th...
基金financially supported by the National Natural Science Foundation of China(Nos.22473113 and 22173116).
文摘The equilibrium melting point(T_(m)^(0))is a crucial thermodynamic parameter for characterizing the crystallization and melting behavior of semi-crystalline polymers.However,the direct measurement of T_(m)^(0) poses a significant challenge because of the difficulty in physically fabricating fully-extended chain crystals of high-molecular-weight polymers.Therefore,various extrapolation equations for T_(m)^(0) have been proposed that utilize the thermal properties of ordinary folded-chain lamellae.Among these,the Gibbs-Thomson equation is one of the most commonly employed for modeling.Despite its widespread use,there are notable variations in the T_(m)^(0) values obtained by different research groups,even when based on similar samples.This raises questions about the validity and accuracy of using the Gibbs-Thomson equation to linearly extrapolate T_(m)^(0).In this study,we prepared a series of oligomer extended-chain crystals(ECCs)of poly(butylene succinate)(PBS)and used their properties for Gibbs-Thomson fitting.The results reveal a perfect linear relationship,with an extrapolated T_(m)^(0) value of 136.08℃.The basal surface free energy of the oligomer ECCs was calculated as 0.084 J/m^(2),which is approximately twice that of folded-chain lamellae.This difference is attributed to the aggregation of highly mobile free tails on the crystal surface.The two structural features of oligomer ECCs—large thickness and fixed surface—better fulfill the conditions for applying the Gibbs-Thomson equation,ensuring its validity and accuracy.Therefore,we believe that the Gibbs-Thomson fit can produce reliable results when sufficient high-quality data are used.
文摘The formation of oxide inclusions in one of the carbon steel productions of Mobarakeh Steel Complex of Isfahan has been evaluated. Several samples from different steps of steel production were taken, from arc furnace, ladle furnace, tundish, and continuous casting mold. Moreover, samples of slab and hot rolling products were prepared. The samples were investigated by optical and scanning electron microscopes equipped with the EDS system. According to the results, the number, composition, and kind of inclusions were directly influenced by the production variables. It was found that when the amount of dissolved oxygen was high （say more than 0. 002 5%）, the dissolved aluminum was able to reduce silicon oxide and react with the dissolved oxygen simultaneously, whilst, the dissolved aluminum could reduce the magnesium oxide only when the oxygen content was below 0. 000 5%. Based on this research, a mechanism for forming the complex inclusions was suggested. It was also found that if the aluminum is added to the melt as late as possible, a cleaner melt with fewer inclusions is prepared; this method will be more effective, especially in the case of complex inclusions.
基金supported by the National Natural Science Foundation of China(No.2010CB30806)
文摘Inclusion characteristic and microstructure steel were evaluated with scanning electron of rare earth （RE） elements containing microscopy with energy dispersive spec- troscopy （SEM-EDS）, element-mapping, optical microscopy （OM）, and automated feature analysis （AFA） option equipped with ASPEX PSEM. Factsage was used to calculate the equilibrium inclusion composition. Based on the calculation, an inclu- sion evolution mechanism was proposed. Furthermore, line scanning analysis was used to elucidate the intra-granular acicular ferrite （IAF） nucleation mechanism. The re- sult showed that two different inclusions exist in sample steel： （Mn-A1-Si-Ti-La-Ce-O） ＋MnS complex inclusion and isolated MnS inclusion. Almost all nucleation sites for IAF are complex inclusions, while single MnS inclusion cannot induce IAF. A possible formation mechanism of complex inclusion is proposed based on calculated results using Factsage, which agrees well with experimental results. A Mn-depletion zone （MDZ） which exists adjacent to the （Mn-A1-Si-Ti-La-Ce-O） ＋MnS complex inclusion can account for the IAF formation. However, the low volume fraction （1.49× 10-7） of effective inclusion may result in only 10% （volume fraction） IAF.
文摘The inclusion-complex of CD-MCP （β-cyclodextrin （β-CD） including 1-methylcyclopropene （1-MCP）） was prepared and characterized. Basing on programmed-heating procedure and weight-temperature analysis, as well as the application of Satava-Sestak＇s, Ozawa＇s and Kissinger＇s methods, the mechanism and kinetics of thermal dissociation of this inclusion complex were studied. An additional mass loss is found at 170-180℃. The mechanism of thermal dissociation of CD-MCP is dominated by a one-dimensional random nucleation and subsequent growth process （A2/3）. The activation energy Es and the pre-exponential factor AS for the process are 102.14 kJ/mol and 3.63×10^10s^-1, respectively. This ES value shows that there is no strong chemical intere, ctions between β-CD and 1-MC;P,
文摘Inclusion compound of retinoic acid with (-cyclodextrin was prepared by coprecipitating method, the structure of resulting product was studied by elemental analysis, differential scanning caloriemetry(DSC) analysis, FT-IR spectroscopy and X-ray diffractometry, and the formed supramolecule self-assembles in aqueous solution according to molar ratio 2:1 of host-vip.
文摘An inclusion complex of b-cyclodextrin with andrographolide (Andro) was prepared by using a convenient method of microwave irradiation. The structure of the inclusion complex was determined by the 1H NMR, 2D NMR spectroscopy as well as the elemental analysis.
