共查询到20条相似文献,搜索用时 15 毫秒
1.
Jef Speeters Peter Neeskens Jef Adriaensen Marcus Brewster 《Journal of inclusion phenomena and macrocyclic chemistry》2002,44(1-4):75-77
Phase solubility analysis is used to investigate the complex formation of alfaxalone with various cyclodextrins(2-hydroxypropyl--cyclodextrine [HPBCD],-cyclodextrin [BCD] and2-hydroxypropyl--cyclodextrin [HPGCD]).The complexationwith HPBCD was studied in more detail by looking at the effect of temperature on the stability constants using phase solubility analysis. HPLC-analysis was used to measure the dissolved amount of alfaxalone.The solubility of alfaxalone increases linearly with increasing concentration of cyclodextrin, suggesting the formation of a 1 : 1 complex. For the parent BCD the complex starts precipitating out of solution when the solubilizer concentration exceeds 0.25% making the unsubstituted BCD less useful for the preparation of solutions of alfaxalone. Substituted cyclodextrins do not form insoluble complexes with alfaxalone. The complexation constant for BCD and HPBCD are comparable in magnitude, but for HPGCD, the constant is substantially lower.The effect of temperature on thecomplexation constant was also studied at elevated temperature. Increasing the temperature results in an increased S0 (solubility without HPBCD) and a decrease in the value of the complexation constant. The net effect results in minor changes of the solubility of alfaxalone as a function of temperature. Based on regression analysis, the change in enthalpy for complex formation between alfaxalone and HPBCD is calculated as -4610 cal/mol.The results indicate that substitutedcyclodextrins are useful in the preparation of solutions of alfaxalone. Since 1 : 1 complexes are formed there is no theoretical danger for precipitation on dilution, e.g., after injection. 相似文献
2.
Fu-An Chen An-Bang Wu Chau-Yang Chen 《Journal of inclusion phenomena and macrocyclic chemistry》2003,46(1-2):111-115
The aim of this study was to investigate the characteristics ofhydroxypropyl--cyclodextrin (HPCD) on the solubility,photostability and dissolution of carprofen (CP). It was found that the solubility of carprofen increased 52-fold when16% HPCD was added to H2O (w/v). The phase-solubility diagram revealed the formation of a 1 : 1 inclusion complex of CP-HPCD with a stability constant (ks) of 487 M-1. Formation of the inclusion complex of CP-HPCD was analyzed using differential scanning calorimetry (DSC). Changes in chemical shifts of the 1H-nuclear magnetic resonance spectra of CP-HPCD demonstrated that the inclusion site of CP by HPCD was carbazolyl aromatic ring skeleton rather thanthe side chain of propanoic acid. The photostability study revealed that theCP-HPCD complex could not significantly decrease the rate of photodegradation of CP, implying that the rate-determining step of CP mainly occurredat the side chain. The dissolution rates of CP were significantly enhanced as the proportions of HPCD increasedin the prepared discs. The dissolution of the physical mixture (in a 1 : 3 molarratio) increased by about 6-fold in comparison with the parent drug. The improvement of wettability and solubility of CP by complexing to HPCD was reflected in theenhanced dissolution rate. 相似文献
3.
A. Antony Muthu Prabhu Madi Fatiha Nouar Leila T. Anantha Raj Inmaculada Navarro-González Maria Jesús Periago Maria Josefa Yáñez-Gascón Horacio Pérez-Sánchez 《Journal of solution chemistry》2018,47(3):409-429
The interactions of the neurotransmitter dopamine (DA) with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) was characterized using UV–visible, 2D fluorescence, 3D fluorescence, FT–IR, PXRD and SEM techniques. PM3, PM7 and DFT methods were used to optimize the structures of the inclusion complexes in the gas phase. The absorbance and fluorescence intensities of DA increased in the presence of CDs in aqueous solution. The binding energy, HOMO–LUMO energy gap and Mulliken atomic charges were computed for the inclusion complexes. NBO analysis revealed a greater number of intermolecular hydrogen bonds in DA:HP-β-CD. Experimental and theoretical results suggested that the DA molecule is deeply embedded in the cavities of both CDs. 相似文献
4.
K. Pitchumani M. Vellayappan 《Journal of inclusion phenomena and macrocyclic chemistry》1992,14(2):157-162
Host-guest complexation of benzoic acid, its nitro-derivatives, 1- and 2-naphthols and 1- and 2-naphthylamines with-cyclodextrin have been investigated by a spectrophotometric method. Formation constants for both the conjugate acid and base forms have been determined. Only in the case of 4-nitrobenzoic acid, is a more stable complex formed with the ionic species, compared with the undissociated one, supporting the assumption that resonance charge delocalisation and London dispersion interactions are responsible for their stability. With naphthalene derivatives, the 2-isomers give more stable complexes indicating deeper penetration into the cyclodextrin cavity. 相似文献
5.
Ana Tačić Ivan Savić Vesna Nikolić Ivana Savić Snežana Ilić-Stojanović Dušica Ilić Slobodan Petrović Mirjana Popsavin Agnes Kapor 《Journal of inclusion phenomena and macrocyclic chemistry》2014,80(1-2):113-124
Sulfanilamide belongs to the group of drugs that have a bacteriostatic effect on different pathogenic microorganisms. This activity originates from the competitive antagonism with p-aminobenzoic acid, which is an integral part of folic acid. The safe use of sulfanilamide is limited due to poor solubility in the aqueous medium. Therefore, the aim of this paper is the synthesis of sulfanilamide, as well as preparing and structural characterization of its inclusion complexes with cyclodextrins. The crude sulfanilamide was obtained in the synthesis between acetanilide and chlorosulfonic acid according to the standard procedure. The synthesized sulfanilamide was recrystallized from water in order to obtain the satisfactory purity of the substance. Sufanilamide was complexed with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin by the co-precipitation method. A molecular encapsulation of sulfanilamide was confirmed by using FTIR, 1H-NMR, XRD and DSC methods. Phase-solubility techniques were used to assess the formation of the inclusion complex between sulfanilamide and cyclodextrins. The photostability of sulfanilamide and its inclusion complexes was estimated by UVB irradiation in a photochemical reactor by applying the UV–Vis method. Based on the UV–Vis analysis, sulfanilamide:2-hydroxypropyl-β-cyclodextrin complex was presented as more photostable than sulfanilamide:β-cyclodextrin complex and sulfanilamide. The obtained results enable the potential use of these inclusion complexes for the preparation of oral formulations due to the enhanced solubility of sulfanilamide. 相似文献
6.
Esther Forgacs 《Journal of inclusion phenomena and macrocyclic chemistry》1994,18(3):229-236
The interaction of six nonionic surfactants -[4-(1,1,3,3-tetra-methylbutyl)phenyl]--hydroxypoly(oxy-1,2-ethanediyl) with hydroxypropyl--cyclodextrin (HPCD) and dimethyl--cyclodextrin (DIMEB) was studied by reversed-phase thin-layer chromatography in the presence and absence of sodium chloride. Each surfactant formed complexes with both cyclodextrin derivatives; however, the strength of interaction varied considerably. DIMEB formed more stable inclusion complexes with the surfactants than did HPCD. A longer ethyleneoxide chain decreased the strength of interaction, whereas sodium chloride exerted a negligible impact. Principal component analysis indicated that both the hydrophobicity and the specific hydrophobic surface are of the surfactant influenced the complex formation indicating the hydrophobic character of the interaction.Dedicated to Professor József Szejtli. 相似文献
7.
Anne Magali Layre Noëlle Martine Gosselet Estelle Renard Bernard Sebille Catherine Amiel 《Journal of inclusion phenomena and macrocyclic chemistry》2002,43(3-4):311-317
The ability of different cyclodextrins (CDs): CD, 2-hydroxypropyl CD to complex drugs like 3--hydroxy-11-oxoolean- 12-en-30-oic acid, 2-ethylhexyl-3-(4-methoxyphenyl)-2-propanoate and menthol was compared to that of water-soluble polymers: CD-co-epichlorhydrin polymer (pCD/EP) and CD-co-epichlorhydrin polymer partially modified with trimethylammonium groups (pCD/EPN+). 3--Hydroxy-11-oxoolean-12-en-30-oic acid was poorly solubilized by CD compared with other CD derivatives, however the determination of the complexation constants was possible for pCD/EP, K11 = 740, K12 = 4, for pCD/EPN+, K11 = 681, for CD, K11 = 16 and for hydroxypropyl CD, K11 = 114, K12 = 3.4. A significant increase of the solubility was observed for 2-ethylhexyl-3-(4-methoxyphenyl)-2-propanoate with all host molecules, it was 916 times its solubility in pure water with pCD/EPN+, 1116 and 1300 times with 2-hydroxypropyl CD and pCD/EP respectively. The association constants are K11 = 7970, K11 = 4700, K11 = 1470, K11 = 230 and K12 = 200 with pCD/EP, pCD/EPN+, CD, 2-hydroxypropyl CD respectively. An increase of the solubility of menthol was observed with all CD derivatives, up to 36–37 times, except for CD. The complexation constants are similar equal to about 200. 相似文献
8.
Yoichi Ikeda Sohko Motoune Aya Marumoto Yoh Sonoda Fumitoshi Hirayama Hidetoshi Arima Kaneto Uekama 《Journal of inclusion phenomena and macrocyclic chemistry》2002,44(1-4):141-144
The effect of 2-hydroxypropyl--cyclodextrin (HP--CyD) on the release of a water-soluble 1-selective adrenoreceptor antagonist, metoprolol (Met), from ternary Met/HP--CyD/ethylcellulose (EC) tablets was investigated. The release rate of Met from the ternary tablets was dependent on amounts of HP--CyD in the tablets, i.e., the rate decreased when small amounts of HP--CyD were added, while large amounts of HP--CyD accelerated the rate. The slowest rate was observed for the tablet consisted of a 30/10/60 weight ratio of Met/HP--CyD/EC. The analyses of the release rates by the Korsmeyer equation and their temperature dependence suggested that Met is released from the EC matrix containing HP--CyD according to the diffusion-controlled mechanism. The water penetration studies and the micro- and macroscopic observations suggested that the retarding effect of HP--CyD is attributable to a viscous gel formation in small pores on the surface of the tablets, where HP--CyD gels may work as a barrier for the water penetration into the tablets and the release of the drug from the tablets. The in-vitro release property of the ternary tablets was reflected in the in-vivo absorption profile in dogs. The results indicated that a combination of HP--CyD and EC is useful for the release control of water-soluble drugs such as Met. 相似文献
9.
Firstly, the interaction between cinnamaldehyde (CIN) and methyl-β- cyclodextrin (MBCD) was studied in aqueous solution. 1:1 inclusion complex was formed and the association constant was 187 ± 9 M?1. Then the complex of CIN–MBCD and muscone–MBCD was prepared both by sealed heating method and by supercritical carbon dioxide (sc CO2) approach. Complete complex was obtained by both methods for CIN–MBCD. Some CIN molecules was weakly associated with MBCD molecules in products by sealed heating method, all CIN molecules was strongly associated with MBCD molecules in products by sc CO2 processing. Complete complex between muscone and MBCD was not obtained. The choice for the size of guest molecule still existed for MBCD cavity in sealed heating method and sc CO2 processing. 相似文献
10.
Introduction Paclitaxel (as Taxol) is a kind of diterpenoid natural product[1] 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[2-5]. One of the major problems of paclitaxel applied to therapy is its extremely low solubility in water[6]. 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[7].Therefore, paclitaxel therapy includes a prophylactic regimen of antihistamines and corticosteroids[8] , 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[9]. 相似文献
11.
T. Gangadhar Vinod I. Bhoi S. Kumar C. N. Murthy 《Journal of inclusion phenomena and macrocyclic chemistry》2014,79(1-2):215-223
Bis-β-cyclodextrin connected via ethylene diamine on the primary side of the β-cyclodextrin was synthesized and used for the supramolecular non-covalent inclusion complex with C60 in a mixed solvent system at room temperature. The apparent association constant of the 2:2 inclusion complex determined by combination of UV–Vis absorbance and Benesi–Hildebrand equation was found to be 1.78 × 106 M?1. The product obtained was highly water-soluble and superior in stability in aqueous medium as compared to previously known β-cyclodextrin/C60 complex. The non-covalent self-assembly of bis-β-cyclodextrin and C60 was characterized and confirmed from FT-IR, UV–Vis, XRD and TGA. The supramolecular aggregation behavior and particle size of the inclusion complex was found from transmission electron microscope and static light scattering measurements. The size of the inclusion complex was found to be ~30 ± 5 nm. 相似文献
12.
CHEN Yue ZHOU Yu-lai REN Yong YAN Wei-qun 《高等学校化学研究》2005,21(6):749-752
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. 相似文献
13.
Seyed Mohammad Taghi Gharibzahedi Seyed Hadi Razavi Mohammad Mousavi 《Journal of Dispersion Science and Technology》2013,34(5):614-625
Solubilizing the potent anticancer pigments in nanoemulsion (NE) systems containing 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) is a novel and promising strategy to incorporate them into water-based drug formulations. The concentration effects of sunflower oil (SO, 5.61–17.39% w/w), surfactant mixture of Tween 80 (T80) and Span 20 (S20) (1:1 weight ratio, 3.95–14.05% w/w), and the inclusion complex of HP-β-CD with canthaxanthin (CTX) synthesized by Dietzia natronolimnaea HS-1 (2.61–14.39% w/w) were evaluated to formulate a stable NE using ultrasound-assisted emulsification. The NEs were evaluated regarding droplet size and polydispersity index (span), physical stability, turbidity, and loss of antioxidant activity (LAA). Response surface modeling showed that the NEs containing 12% T80/S20, 8.30% SO, and 12% CTX/HP-β-CD had the lowest droplet size (105.5 nm), span (0.394), droplet growth ratio (0.112), turbidity (0.139), and LAA (9.36%). The predicted values obtained were close to the experimental values, indicating the suitability of the constructed models. Transmission electron microscopy and confocal laser-scanning microscopy also demonstrated that the formed droplets of the NEs produced at optimal formulation were spherical in the range of 20–100 nm. A significant correlation was found between droplet size with stability (r = ?0.960, p < 0.01) and turbidity (r 2 = 0.876, p < 0.01) values. 相似文献
14.
Rajashree Hirlekar Vilasrao Kadam 《Journal of inclusion phenomena and macrocyclic chemistry》2009,63(3-4):219-224
Aim of the present work was to investigate the effect of methyl-β-cyclodextrin (MβCD) on the solubility and dissolution rate of carvedilol (CAR), a drug used orally for the treatment of hypertension. Phase solubility studies showed an AL-type diagram indicating the formation of inclusion complex in 1:1 molar ratio. Solid binary systems of the drug with MβCD were prepared by various methods. Physicochemical characterizations were performed using Fourier Transformation Infrared Spectroscopy, Differential Scanning Calorimetry and powder X-Ray Diffractometry. It could be concluded that CAR can form inclusion complex with MβCD. The dissolution profiles of inclusion complexes were determined and compared with those of CAR alone and the physical mixture. The dissolution rate of CAR was increased by MβCD inclusion complexation remarkably. 相似文献
15.
Miguel A. Hernández Balboa Velia Vela Arévalo Victor H. Abrego Reyes Ana M. Velázquez A. Ganem-Quintanar David Quintanar Brígida Camacho Guadalupe Nava Arzaluz M. Rosales-Hoz Marco A. Leyva Enrique Angeles 《Chromatographia》2008,67(1-2):193-196
The results of CE studies of solid inclusion complexes of chlorambucil (CHL) and trimethyl-β-cyclodextrin (TM-β-CD) are presented.
Chlorambucil has low stability in aqueous solution, so the formation of complexes with β-CD is a good way to improve its stability
and dissolution. The experimental results confirm the existence of inclusion complexes. CE can differentiate free CHL from
CHL–TM-β-CD complexes due to their different electrophoretic mobilities. 相似文献
16.
Aqueous solutions of 2-hydroxypropyl-β-cyclodextrin (HP-β-CD)at different concentrations of NaCl (0–1.90 mol) were studied
by isothermal titration calorimetry (ITC) at 298.15 K. The thermal effects obtained were analysed according to the thermodynamic
approach developed by McMillan and Mayer. The calculated enthalpic pair coefficients of HP-β-CD in water and in aqueous solutions
of NaCl were analysed taking into consideration electrostatic and structural changes caused by the presence of NaCl in solution.
This revised version was published online in July 2006 with corrections to the Cover Date. 相似文献
17.
Barbara Szafran Jan Pawlaczyk 《Journal of inclusion phenomena and macrocyclic chemistry》1995,23(4):277-288
The 1 : 1 inclusion complex involving sulfafurazole (SF) and-cyclodextrin (-CD) is prepared by the freeze-drying method and characterized on the basis of its chemical analysis, thermal behavior, infrared spectrum, X-ray powder pattern and13C NMR spectrum in DMSO-d6 solution. The stability constant of the inclusion complex was determined by the solubility method. The effect of cyclodextrin on the UV absorption spectrum of sulfafurazole was also observed. 相似文献
18.
The effect of the reaction conditions or the nature of the silylating agents on the silylation of hydroxypropyl-β-cyclodextrin with tert-butyldimethylchloro- and diphenyl-methylchlorosilanes is investigated. 相似文献
19.
Xiao-ming Chen 《化学物理学报(中文版)》2011,24(4):484-488
Cetyltrimethylammonium bromide (CTAB)/potassium bromide (KBr) micellar system has been used as a viscosity probe to study the inclusion complexation between β-cyclodextrin (β-CD) and CTAB. Viscosity measurements show that the inclusion complexation between β-CD and CTAB may cause the breakdown of CTAB/KBr wormlike micelles, resulting in the decrease of the solution viscosity. The viscosity minimum at Cβ-CD/CCTAB=2 indicate the molecular ratio of host molecule to guest molecule is 2:1 in the β-CD/CTAB inclusion complex. 相似文献
20.
Michał Nowakowski Andrzej Ejchart 《Journal of inclusion phenomena and macrocyclic chemistry》2014,79(3-4):337-342
13C NMR titration studies of inclusion complexes of bicyclic terpenoid, fenchone enantiomers with α-cyclodextrin revealed their 1:2 guest–host stoichiometry. Sequential binding constants were determined indicating a strong binding cooperativity of two α-cyclodextrin to fenchone. The overall association constants were used to calculate the Gibbs free energies of diastereomeric complex formation, which might be used as a measure of chiral recognition of fenchone by α-cyclodextrin. These results were compared with corresponding data derived for camphor, which is an isomeric bicyclic terpenoid. 相似文献