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 guest PCL polymers but also improves that of α-CD.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 guest-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 guest 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 guests. The formation of host-guest inclusion complexes exhibited obviously enhanced phase change temperatures of the complexed guests 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
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 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 guest of drug/polymer ICs from homopolymers to block copolymers of poly（ethylene glycol）（PEG） and poly（s-caprolactone）（PCL）.The block length in the guest 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
Gallic acid(GA)is a kind of natural polyphenolic compound,but its low aqueous solubility restricts its application in the fields of food and medicine.Cyclodextrin can form inclusion complexes with guest molecules(e.g....Gallic acid(GA)is a kind of natural polyphenolic compound,but its low aqueous solubility restricts its application in the fields of food and medicine.Cyclodextrin can form inclusion complexes with guest molecules(e.g.,essential oils,food supplements)through cavities with special properties to improve aqueous solubility,thermal stability,and bioavailability of guest molecules.In this research,gallic acid/2-hydroxypropyl-β-cyclodextrin inclusion complexes(GA/2-HP-β-CD/ICs)were formed in a highly concentrated solution of 2-HP-β-CD.Bead-free and uniform nanofibrous webs(GA/2-HP-β-CD/IC-NWs)were produced successfully by electrospun GA/HP-β-CD/IC aqueous solution.The initial molar ratio(GA:2-HP-β-CD=1:1)of GA/2-HP-β-CD/IC in the solutions was largely maintained in GA/2-HP-β-CD/IC-NW.The aqueous solubility of GA was enhanced and GA/2-HP-β-CD/IC-NW has displayed fast dissolution property.Furthermore,in comparison with GA powder,GA/2-HP-β-CD/IC-NW demonstrated improved antioxidant capacity.The results suggested that GA/2-HP-β-CD/IC-NW have broad application prospects as orally fast dissolution systems for food supplements.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 guest molecules on inclusion geometry of various coumarin molecules in fl-cyclodextrin were examined.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
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 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 guest 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 guest. 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
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-guest 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 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
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-guest.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
The objective of this paper is to prepare vinpocetine(VIN)inclusion complex and evaluate its brain targeting effect after intranasal administration.In the present study,VIN inclusion complex was prepared in order to i...The objective of this paper is to prepare vinpocetine(VIN)inclusion complex and evaluate its brain targeting effect after intranasal administration.In the present study,VIN inclusion complex was prepared in order to increase its solubility.Stability constant(Kc)was used for host selection.Factors influencing properties of the inclusion complex was investigated.Formation of the inclusion complex was identified by solubility study and DSC analysis.The brain targeting effect of the complex after intranasal administration was studied in rats.It was demonstrated that properties of the inclusion complex was mainly influenced by cyclodextrin type,organic acids type,system pH and host/guest molar ratio.Multiple component complexes can be formed by the addition of citric acid,with solubility improved for more than 23 times.Furthermore,In vivo study revealed that after intranasal administration,the absolute bioavailability of vinpocetine inclusion complex was 88%.Compared with intravenous injection,significant brain targeting effect was achieved after intranasal delivery,with brain targeting index 1.67.In conclusion,by intranasal administration of VIN inclusion complex,a fast onset of action and good brain targeting effect can be achieved.Intranasal route is a promising approach for the treatment of CNS diseases.展开更多
Inclusion complex of Orange II with β-Cyclodextrin (β-CD) and the anti-photolysis effect under UV-light were investigated. The molar ratio of inclusion complex of β-Cyclodextrin and Orange Ⅱ is 1∶1. The formation...Inclusion complex of Orange II with β-Cyclodextrin (β-CD) and the anti-photolysis effect under UV-light were investigated. The molar ratio of inclusion complex of β-Cyclodextrin and Orange Ⅱ is 1∶1. The formation constant K=1.236×10 3 L/mol was determined by the UV and Fluorescence spectra respectively, which was quite in accordance with the calculation with a modified Benesi-Hildbrand equation. The inclusion complex was characterized by the IR spectra and the molar ratio of inclusion complex is 1∶1 too. The formation constant K=1.266×10 3 L/mol was determined by 1 H NMR analysis and was nearly the same by UV and fluorescence spectra. The photocatalytic decolorization rate of Orange Ⅱ solutions containing β-CD and TiO_ 2 was smaller by 51.9% than that of the Orange Ⅱ solutions only containing TiO_ 2 , while in the case of direct photolysis of Orange Ⅱ solutions, β-CD can lower the photolysis rate by 48.1% under UV-light. This result indicates β-CD can inhibit the photolysis and photocatalytic decolorization of Orange Ⅱ under UV-light. The β-CD inclusion complex was found to be persistent to UV-light photolysis.展开更多
PP can be included in the cavities of cyclodextrin (CD). The crystalline inclusion complex between β-CD and lowmolecular weight polypropylene (PP) was obtained and investigated. α-CD and γ-CD did not form crystalli...PP can be included in the cavities of cyclodextrin (CD). The crystalline inclusion complex between β-CD and lowmolecular weight polypropylene (PP) was obtained and investigated. α-CD and γ-CD did not form crystalline inclusioncomplexes with PP. The FTIR spectra, TGA, X-ray diffraction spectra were studied, ~1H-NMR spectra and ^(13)C CP/MAS NMR spectra were used to characterize the crystalline inclusion complexes.展开更多
Introduction Paclitaxel （as Taxol） is a kind of diterpenoid natural product extracted from Chinese yew. It has been reported to have high anti-tumor effects, such as the activity against oophorama, mammary cancer, ...Introduction Paclitaxel （as Taxol） is a kind of diterpenoid natural product extracted from Chinese yew. It has been reported to have high anti-tumor effects, such as the activity against oophorama, mammary cancer, encephaloma, cervical carcinoma, and non- small-cell lung carcinoma. One of the major problems of paclitaxel applied to therapy is its extremely low solubility in water. In addition, paclitaxel is administered as a slow infusion in a vehicle consisting of Cremophor EL （ polyoxyethylated castor oil ）. However, Cremophor has been observed to cause severe, occasionally fatal hypersensitivity reactions in animals and humans. Therefore, paclitaxel therapy includes a prophylactic regimen of antihistamines and corticosteroids , along with a prolonged infusion time to reduce the severity and incidence of hypersensitivity reactions. Because of the reasons mentioned above, currently its preparation needs to be improved further.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 guest PCL polymers but also improves that of α-CD.
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 guest-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 guest 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 guests. The formation of host-guest inclusion complexes exhibited obviously enhanced phase change temperatures of the complexed guests 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 guest of drug/polymer ICs from homopolymers to block copolymers of poly（ethylene glycol）（PEG） and poly（s-caprolactone）（PCL）.The block length in the guest 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.
基金This work was supported by the Project of the Jilin Province Development and Reform Commission,China(No.2020C023-5)the National Natural Science Foundation of China(No.31772058).
文摘Gallic acid(GA)is a kind of natural polyphenolic compound,but its low aqueous solubility restricts its application in the fields of food and medicine.Cyclodextrin can form inclusion complexes with guest molecules(e.g.,essential oils,food supplements)through cavities with special properties to improve aqueous solubility,thermal stability,and bioavailability of guest molecules.In this research,gallic acid/2-hydroxypropyl-β-cyclodextrin inclusion complexes(GA/2-HP-β-CD/ICs)were formed in a highly concentrated solution of 2-HP-β-CD.Bead-free and uniform nanofibrous webs(GA/2-HP-β-CD/IC-NWs)were produced successfully by electrospun GA/HP-β-CD/IC aqueous solution.The initial molar ratio(GA:2-HP-β-CD=1:1)of GA/2-HP-β-CD/IC in the solutions was largely maintained in GA/2-HP-β-CD/IC-NW.The aqueous solubility of GA was enhanced and GA/2-HP-β-CD/IC-NW has displayed fast dissolution property.Furthermore,in comparison with GA powder,GA/2-HP-β-CD/IC-NW demonstrated improved antioxidant capacity.The results suggested that GA/2-HP-β-CD/IC-NW have broad application prospects as orally fast dissolution systems for food supplements.
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 guest molecules on inclusion geometry of various coumarin molecules in fl-cyclodextrin were examined.
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 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 guest 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 guest. 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-guest 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...
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.
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-guest.
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.
文摘The objective of this paper is to prepare vinpocetine(VIN)inclusion complex and evaluate its brain targeting effect after intranasal administration.In the present study,VIN inclusion complex was prepared in order to increase its solubility.Stability constant(Kc)was used for host selection.Factors influencing properties of the inclusion complex was investigated.Formation of the inclusion complex was identified by solubility study and DSC analysis.The brain targeting effect of the complex after intranasal administration was studied in rats.It was demonstrated that properties of the inclusion complex was mainly influenced by cyclodextrin type,organic acids type,system pH and host/guest molar ratio.Multiple component complexes can be formed by the addition of citric acid,with solubility improved for more than 23 times.Furthermore,In vivo study revealed that after intranasal administration,the absolute bioavailability of vinpocetine inclusion complex was 88%.Compared with intravenous injection,significant brain targeting effect was achieved after intranasal delivery,with brain targeting index 1.67.In conclusion,by intranasal administration of VIN inclusion complex,a fast onset of action and good brain targeting effect can be achieved.Intranasal route is a promising approach for the treatment of CNS diseases.
文摘Inclusion complex of Orange II with β-Cyclodextrin (β-CD) and the anti-photolysis effect under UV-light were investigated. The molar ratio of inclusion complex of β-Cyclodextrin and Orange Ⅱ is 1∶1. The formation constant K=1.236×10 3 L/mol was determined by the UV and Fluorescence spectra respectively, which was quite in accordance with the calculation with a modified Benesi-Hildbrand equation. The inclusion complex was characterized by the IR spectra and the molar ratio of inclusion complex is 1∶1 too. The formation constant K=1.266×10 3 L/mol was determined by 1 H NMR analysis and was nearly the same by UV and fluorescence spectra. The photocatalytic decolorization rate of Orange Ⅱ solutions containing β-CD and TiO_ 2 was smaller by 51.9% than that of the Orange Ⅱ solutions only containing TiO_ 2 , while in the case of direct photolysis of Orange Ⅱ solutions, β-CD can lower the photolysis rate by 48.1% under UV-light. This result indicates β-CD can inhibit the photolysis and photocatalytic decolorization of Orange Ⅱ under UV-light. The β-CD inclusion complex was found to be persistent to UV-light photolysis.
基金This work was financially supported by the National Natural Science Foundation of China (Grant No. 29974017) and the fund of the Analytical Center and the Key Laboratory of Education Ministry for Optical and Magnetic Resonance Spectroscopy also sponsored
文摘PP can be included in the cavities of cyclodextrin (CD). The crystalline inclusion complex between β-CD and lowmolecular weight polypropylene (PP) was obtained and investigated. α-CD and γ-CD did not form crystalline inclusioncomplexes with PP. The FTIR spectra, TGA, X-ray diffraction spectra were studied, ~1H-NMR spectra and ^(13)C CP/MAS NMR spectra were used to characterize the crystalline inclusion complexes.
文摘Introduction Paclitaxel （as Taxol） is a kind of diterpenoid natural product extracted from Chinese yew. It has been reported to have high anti-tumor effects, such as the activity against oophorama, mammary cancer, encephaloma, cervical carcinoma, and non- small-cell lung carcinoma. One of the major problems of paclitaxel applied to therapy is its extremely low solubility in water. In addition, paclitaxel is administered as a slow infusion in a vehicle consisting of Cremophor EL （ polyoxyethylated castor oil ）. However, Cremophor has been observed to cause severe, occasionally fatal hypersensitivity reactions in animals and humans. Therefore, paclitaxel therapy includes a prophylactic regimen of antihistamines and corticosteroids , along with a prolonged infusion time to reduce the severity and incidence of hypersensitivity reactions. Because of the reasons mentioned above, currently its preparation needs to be improved further.
