共查询到20条相似文献,搜索用时 15 毫秒
1.
Vij Mohit Garse Harshal Dand Neha Kadam Vilasrao Hirlekar Rajashree 《Journal of inclusion phenomena and macrocyclic chemistry》2011,71(1-2):57-66
The aim of this study was to investigate the effect of hydroxypropyl-??-cyclodextrin (HP??CD) on the solubility and dissolution rate of Cefdinir (CEF). The methods that were employed to prepare CEF?CHP??CD complexes were Kneading (KN), Co-evaporation (CE), Spray drying (SD) and a novel approach of Microwave irradiation (MWI). The formation of inclusion complexes with HP??CD in the solid state, were characterized by Differential Scanning Calorimetry (DSC), Fourier Transformation Infrared spectroscopy (FTIR), Proton Nuclear Magnetic Resonance Spectroscopy (NMR), X Ray Diffraction (XRD) and Scanning Electron Microscopy (SEM) studies, and comparative studies on the in vitro dissolution of CEF were carried out. Phase solubility profile with HP??CD was classified as AL type, indicating the formation of 1:1 stoichiometric inclusion complexes. Characterization of binary systems by DSC, FTIR, NMR, XRD and SEM indicated that SD and MWI method resulted in formation of true complexes. Binary systems showed significant increase in dissolution rate as compared to plain drug. Amongst the various binary systems, MWI products were prepared in least time with better yield and highest dissolution rate. 相似文献
2.
Dipali Doiphode Shubhangee Gaikwad Yogesh Pore Bhanudas Kuchekar Sameer Late 《Journal of inclusion phenomena and macrocyclic chemistry》2008,62(1-2):43-50
The physicochemical properties and dissolution profile of zaleplon (ZPN) β-cyclodextrin (βCD) inclusion complex were investigated. The phase solubility profile of ZPN with β-cyclodextrin was classified as AL-type. Stability constant with 1:1 molar ratio was calculated from the phase solubility diagram and the aqueous solubility of ZPN was found to be enhanced by 714% (p < 0.001) for β-cyclodextrin. Binary systems of ZPN with βCD were prepared by kneading method. The solid-state properties of complex were characterized by differential scanning calorimetry, Fourier transformation-infrared spectroscopy and powder X-ray diffractometry. It could be concluded that ZPN could form inclusion complex with β-cyclodextrin. The dissolution profile of inclusion complex was determined and compared with those of ZPN alone and its physical mixture. The dissolution rate of ZPN was significantly increased by complexation with βCD, as compared with pure drug and physical mixture. 相似文献
3.
K. Majewska A. Skwierawska B. Kamińska M. Prześniak-Welenc 《Supramolecular chemistry》2018,30(1):20-31
Opipramol (OPI), a tricyclic antidepressant and anxiolytic compound, is administered orally in the form of a dihydrochloride. Salt form of the drug has a higher solubility in water and hence bioavailability and stability. A similar effect can be achieved by closing the hydrophobic part of the drug molecule in the cyclodextrin cavity. The paper presents opipramol inclusion complexes with beta-cyclodextrin (β-CD) in 1:1 molar ratio. Studies on the formation of inclusion complexes were carried out both in solution and in the solid state. The formation and physicochemical characterisation of the complexes were determined by UV spectroscopic measurement (UV–vis), Fourier Transform Infrared (FTIR) Spectroscopy, 1H Nuclear Magnetic Resonance (1H NMR, 2D NOESY NMR), thermoanalytical methods (TGA – Termogravimetric analysis, DSC – differential scanning calorimetry), X-ray diffractometry (XRD) and scanning electron microscopy (SEM). The phase solubility profile with β-CD was classified as the AN- type, indicating the formation of the inclusion complex with a drug. 相似文献
4.
Vij Mohit Garse Harshal Dand Neha Kadam Vilasrao Hirlekar Rajashree 《Journal of inclusion phenomena and macrocyclic chemistry》2010,67(1-2):39-47
The inclusion behaviour of β-cyclodextrin (βCD) was studied toward Cefdinir (CEF) in order to enhance the solubility and dissolution rate, following cyclodextrin complexation. Drug cyclodextrin solid systems were prepared by conventional methods of kneading (KN), co-evaporation (CE), spray drying (SD) and with a novel approach of microwave irradiation (MWI). The formation of inclusion complexes with βCD in the solid state, were confirmed by Differential scanning calorimetry (DSC), Fourier Transform Infrared spectroscopy (FTIR) and Scanning Electron Microscopy (SEM) studies, and comparative studies on the in vitro dissolution of CEF were carried out. Characterization of binary system by DSC, FTIR and SEM indicated that SD and MWI method resulted in formation of true complexes. Binary systems showed significant increase in dissolution rate as compared to plain drug. Amongst the binary systems MWI products were prepared in least time with better yield and highest dissolution rate. 相似文献
5.
A. Ruebner J. G. Moser D. Kirsch B. Spengler S. Andrees S. Roehrs 《Journal of inclusion phenomena and macrocyclic chemistry》1996,25(1-3):35-38
The aim of our investigation was the development of carrier systems for an application of inert drugs in polyphasic photodynamic tumor therapy. As carrier systems, -cyclodextrin dimers linked at their primary and secondary faces by spacers of varying lengths were synthesized. Cyclodextrins are known to form stable inclusion complexes with porphyrinoïd photosensitizers. The influence of spacer length on the -cyclodextrin dimer inclusion complexes with porphyrinoïd photosensitizers was studied. 相似文献
6.
J.R. Moyano J.M. Lines M.J. Arias J.I. Perez-Martinez G. Bettinetti F. Giordano 《Journal of inclusion phenomena and macrocyclic chemistry》1996,25(1-3):137-140
The study of complexation between GL and -CD in liquid medium has been carried out by phase-solubility,1H and13C NMR studies. A formation complex is observed from the phase solubility diagram, being the average association constant of 1094 M–1, The NMR studies revealed the preferent complexation of the aliphatic moiety of GL. The aromatic moiety is also entrapped, but in minor extent, by the CD molecules. 相似文献
7.
Takako Ishiguro Yukichi Sakata Hidetoshi Arima Daisuke Iohara Makoto Anraku Kaneto Uekama Fumitoshi Hirayama 《Journal of inclusion phenomena and macrocyclic chemistry》2018,92(1-2):147-155
The release control of fragrances, benzyl acetate (BA), citral (CR), linalool (LL), citronellol (CL) and linalyl acetate (LA), was conducted using β-cyclodextrin (β-CyD), 2-hydroxypropyl-β-CyD (HP-β-CyD) and 2,6-di-O-methyl β-CyD (DM-β-CyD). The release rate of the fragrances from 30% ethanol/water solution was significantly suppressed by the complexation with these CyDs, and the suppressing effect increased in the order of β-CyD?<?HP-β-CyD?<?DM-β-CyD. The concentration-dependent change of the release rate was quantitatively analyzed to obtain the stability constant (Kc) of the fragrance-CyD complexes. These Kc values were in good agreement with those determined by the solubility method. The results suggest that the release of fragrances can be prolonged by the complexation with β-CyDs and their effects can be controlled by choosing appropriate CyD derivatives with higher Kc values and by setting proper concentrations of the host molecules. 相似文献
8.
Kevin Hing-Nin Poon Yu-Ling Cheng 《Journal of inclusion phenomena and macrocyclic chemistry》2008,60(3-4):211-222
Quartz crystal microbalance (QCM) was used to study the self-assembly of per-6-thio-β-cyclodextrin (t7-βCD) on gold surfaces, and the subsequent inclusion interactions of immobilized βCD with adamantane-poly(ethylene glycol)
(5,000 MW, AD-PEG), 1-adamantanecarboxylic acid (AD-C) and 1-adamantylamine (AD-A). From a 50 μM solution of t7-βCD in 60:40 DMSO:H2O, a t7-βCD layer was formed on gold with surface density of 71.7 ± 2.7 pmol/cm2, corresponding to 80 ± 3% of close-packed monolayer coverage. Gold sensors with immobilized t7-βCD were then exposed alternately to six different concentrations of AD-PEG, 500 μM AD-C or 500 μM AD-A aqueous solutions
for association, and water for dissociation. Association of AD-PEG conformed to a Langmuir isotherm, with a best fit equilibrium
constant K = 125,000 ± 18,000 M−1. For AD-C and AD-A, association (k
a
) and dissociation (k
d
) rate constants were extracted from kinetic profiles by fitting to the Langmuir model, and equilibrium constants were calculated.
The parameters for AD-C were found to be: k
a
= 100 ± 5 M−1 s−1, k
d
= 110 (±18) × 10−4 s−1, and K = 9,400 ± 1,700 M−1. For AD-A, k
a
= 58 ± 6 M−1 s−1, k
d
= 154 (±7) × 10−4 s−1, and K = 3,800 ± 400 M−1. The results demonstrate the utility of QCM as a tool for studying small molecule surface adsorption and guest–host interactions
on surfaces. More specifically, the kinetic and thermodynamic data of AD-C, AD-A, and AD-PEG inclusion with immobilized t7-βCD form a basis for further surface association studies of AD-X conjugates to advance surface sensory and coupling applications. 相似文献
9.
R. Peila G. Migliavacca F. Aimone A. Ferri S. Sicardi 《Cellulose (London, England)》2012,19(4):1097-1105
Cotton yarns bobbins were treated in a water bath with different concentrations of a reactive β-cyclodextrin derivative. To quantify the amount of cyclodextrin fixed on the fiber different analytical methods were tested but none of them was reliable enough in the concentration range under investigation. Therefore, a new analytical method, fast and effective, was developed. From the measurement of cyclodextrin bath exhaustion, the amount of cyclodextrin chemically fixed and that physically adsorbed on the textile substrate was estimated. Two washing cycles were carried out to investigate the cyclodextrin washing fastness. 相似文献
10.
This paper describes a simple method for the synthesis of water-soluble, silver nanoparticle-encapsulated β-cyclodextrin by phase transfer of silver nanoparticles from organic to aqueous phase using β-cyclodextrin as a capping agent. β-Cyclodextrin–silver nanoparticle inclusion complex was purified, characterised by spectroscopic and microscopic analyses and tested in vitro against Pseudomonas aeruginosa, Staphylococcus aureus, Serratia marcescens, Escherichia coli and Klebsiella pneumoniae. The silver nanoparticle-encapsulated β-cyclodextrin inclusion complex displayed considerable antimicrobial activity and stability. 相似文献
11.
Chao Dong Ying Ye Liying Qian Guanglei Zhao Beihai He Huining Xiao 《Cellulose (London, England)》2014,21(3):1921-1932
Antibacterial-modified cellulose fiber was prepared by covalently bonding β-cyclodextrin (β-CD) with cellulose fiber via citric acid (CA) as crosslinking agent, followed by the inclusion of ciprofloxacin hydrochloride (CipHCl) as antibiotic. Effects of reaction time, temperature, concentration of β-cyclodextrin citrate (CA-β-CD) and pH on the grafting reaction were investigated, and the grafting ratio of β-CD onto cellulose fibers was 9.7 % at optimal conditions; the loading and releasing behaviors of CipHCl into/from β-CD grafted cellulose fibers were also revealed, the load amount of CipHCl into grafted cellulose fibers increased remarkably, and the release of CipHCl from the grafted cellulose fibers was prolonged. The microstructure, phase and thermal stability of modified cellulose fibers were characterized by FT-IR, 13C CPMAS NMR, X-ray diffraction and TGA. Considerably longer bacterial activity against E. coli and S. aureus was observed for grafted fibers loading CipHCl compared to virgin ones. Optical and mechanical properties of the paper sheets decreased generally with more antibacterial-modified fibers added. 相似文献
12.
FAN Zhi GUO MinJie DONG Bin DIAO ChunHua JING ZuoLiang & CHEN Xin College of Sciences Tianjin University of Science Technology Tianjin China 《中国科学:化学》2010,(5)
The mono-modified β-cyclodextrin derivative,6-O-(4-aminobenzoyl)-β-cyclodextrin(1) ,was synthesized and characterized. We compared its self-assembling behavior with structurally related β-cyclodextrin derivative,6-O-(4-hydroxybenzoyl)-βcyclodextrin(2) ,in aqueous solution and in the solid state using NMR spectroscopy and single crystal X-ray structure analysis. The two complexes displayed different self-assembling behaviors.Complex 1 formed a head-to-tail helical columnar superstructure in which the substit... 相似文献
13.
A mesoporous silica nanoparticle (MSN) based fluorescent sensor for dopamine was constructed with probes inside particle pores and β-cyclodextrin (β-CD) molecules on the particle surface as the selective barricade. The synergistic action of both the hydrophilic rim and hydrophobic cavity of β-CD ensures that the sensor can distinguish dopamine from other biological competitors. 相似文献
14.
Yunlong Wang Wenchao Li Yong Jiao Chuan Dong Yoshihisa Inoue 《Analytica chimica acta》2009,650(1):124-316
The inclusion complexes of isoquercitrin (IQ) with cyclodextrins (CDs) including β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD) and dimethyl-β-cyclodextrin (DM-β-CD) have been investigated using the methods of steady-state fluorescence, UV-vis absorption and induced circular dichroism. The stoichiometric ratio of the three complexes was found to be 1:1 and the stability constants (K) were estimated from spectrofluorometric titrations, as well as the thermodynamic parameters. Maximum inclusion ability was measured in the case of DM-β-CD due to the increased hydrophobicity of the host cavity, followed by HP-β-CD and β-CD. The effect of pH on the complexation process was also quantitatively assessed. IQ exists in different molecular forms depending on pH and β-CDs were most suitable for inclusion of the neutral form of IQ. The phase-solubility diagrams obtained with β-CD, HP-β-CD and DM-β-CD were all classical AL type. And DM-β-CD provided the best solubility enhancement, 12.3-fold increase compared to 2.8- and 7.5-fold increase for β-CD and HP-β-CD. The apparent stability constants obtained from the solubility data at 25 °C were comparable with those obtained from the fluorescence assays. Moreover, 1H NMR was carried out, which revealed that the IQ favorably inserted into the inner cavity from the chromone part instead of the phenyl part, which was in agreement with molecular modeling studies. 相似文献
15.
Inclusion complexation of chloropropham with β-cyclodextrin: preparation, characterization and molecular modeling 总被引:1,自引:0,他引:1
Ge X He J Qi F Yang Y Huang Z Lu R Huang L 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2011,81(1):397-403
An inclusion complex between the agrochemical chloropropham (CIPC) and β-cyclodextrin (β-CD) was prepared. A 2:1 host-guest stoichiometry was conformed by elemental analysis. From the phase solubility studies, the calculated stepwise stability constants were K(1)=224.6L/mol and K(2)=939.2L/mol, respectively. FT-IR, thermoanalysis and (1)H NMR spectra were applied to characterize the complex. It was speculated that the inclusion mode was two β-CD cavities included the chlorophenyl and the isopropyl moiety of one CIPC molecule, which was in agreement with the most predominant configuration optimized by molecular modeling. By complexation with β-CD, the water solubility and the thermal stability of CIPC were prominently improved. 相似文献
16.
Duc-Truc Pham Philip Clements Christopher J. Easton John Papageorgiou Bruce L. May 《Supramolecular chemistry》2013,25(6):510-519
This study shows that stereochemical factors largely determine the extent to which 6-(4′-t-butylphenylamino)-naphthalene-2-sulphonate, BNS? and its dimer, (BNS? )2, are complexed by β-cyclodextrin, βCD, and a range of linked βCD dimers. Fluorescence and 1H NMR studies, respectively, show that BNS? and (BNS? )2 form host–guest complexes with βCD of the stoichiometry βCD.BNS? (10? 4 K 1 = 4.67 dm3 mol? 1) and βCD.BNS2 2 ? (10? 2 K 2′ = 2.31 dm3 mol? 1), where the complexation constant K 1 = [βCD.BNS? ]/([βCD][BNS? ]) and K 2′ = [βCD. (BNS? )2]/([βCD.BNS? ][BNS? ]) in aqueous phosphate buffer at pH 7.0, I = 0.10 mol dm3 at 298.2 K. (The dimerisation of BNS? is characterised by 10? 2 K d = 2.65 dm3 mol? 1.) For N,N-bis((2AS,3AS)-3A-deoxy-3A-β-cyclodextrin)succinamide, 33βCD2su, N-((2AS,3AS)-3A-deoxy-3A-β-cyclodextrin)-N′-(6A-deoxy-6A-β-cyclodextrin)urea, 36βCD2su, N,N-bis(6A-deoxy-6A-β-cyclodextrin)succinamide, 66βCD2su, N-((2AS,3AS)-3A-deoxy-3A-β-cyclodextrin)-N′-(6A-deoxy-6A-β-cyclodextrin)urea, 36βCD2ur, and N,N-bis(6A-deoxy-6A-β-cyclodextrin)urea, 66βCD2ur, the analogous 10? 4 K 1 = 11.0, 101, 330, 29.6 and 435 dm3 mol? 1 and 10? 2 K 2′ = 2.56, 2.31, 2.59, 1.82 and 1.72 dm3 mol? 1, respectively. A similar variation occurs in K 1 derived by UV–vis methods. The factors causing the variations in K 1 and K 2 are discussed in conjunction with 1H ROESY NMR and molecular modelling studies. 相似文献
17.
18.
Stéphanie Marchand Aldona Guzek Pierre Leroy 《Journal of inclusion phenomena and macrocyclic chemistry》2010,66(3-4):409-416
RP-HPLC and the van’t Hoff law were used to study the association in which β-cyclodextrin forms inclusion complexes with aminothiol–phthaldialdehyde derivatives prepared from either glutathione (GSH) or γ-glutamylcysteine (γ-glucys) and either naphthalene-2,3-dicarboxaldehyde (NDA) or o-phthaldialdehyde (OPA). Elution was carried out at pH 8.5, the derivatization pH which gave the highest fluorescence signal during batch experiments. The variation of the retention factor (k) was monitored as a function of column temperature (10–35 °C) and β-cyclodextrin concentration (0–5 mM) in the mobile phase. Apparent binding constants, enthalpy and entropy were calculated from van’t Hoff plots for the complexation reaction. These data lay the groundwork for the improvement of high throughput GSH quantification methods using fluorimetry in biological and vegetal samples. 相似文献
19.
Su Long Xiao De Min Zhou Ming Yang Fei Yu Li He Zhang Pierre Sinay Yong Min Zhang 《中国化学快报》2012,23(12):1315-1318
Diisobutylaluminium hydride(DIBAL-H) promotes secondary rim regioselective bis-de-O-methylation of permethylatedβ-cyclodextrin (β-CD) to give diol 2.To gain an insight into the mechanism of this remarkable regioselective behavior,two corresponding permethylatedβ-CDs with an alcohol function at either 2- or 3-position were synthesized in our previous study.As a step further to this work,the two compounds were subjected to deoxygenation reaction with tributyltin hydride in the present of 2,2’- azobisisobutyronitrile affording the corresponding 2- and 3-deoxy permethylatedβ-CD derivatives(19 and 16).The structures of these two compounds were characterized by ID and 2D NMR and HRMS.Compounds 16 and 19 were unable to react with DIBALH which suggests that O-2~A and O-3~B are necessary for DIBAL-H promoted bis-de-O-methylation reaction of permethylatedβ-CD. 相似文献
20.
R. K. Sankaranarayanan S. Siva A. Antony Muthu Prabhu N. Rajendiran 《Journal of inclusion phenomena and macrocyclic chemistry》2010,67(3-4):461-470
Effect of β-cyclodextrin (β-CD) on the absorption and fluorescence spectra of 3,4,5-trihydroxybenzoic acid (THB) have been studied buffer solutions of different pHs (pH ~1, pH ~7 and pH ~10). The study reveals that in all the above pHs THB forms 1:1 inclusion complex. The hydroxyl groups are present in the interior part of the β-CD cavity and carboxyl group is present in the hydrophilic part of the β-CD cavity. Dual luminescence is observed at pH ~1 and pH ~7 solutions which shows that intramolecular charge transfer present at these pH. The broad spectral maximum at pH ~10 indicates that intramolecular proton transfer is present in THB. 相似文献