共查询到20条相似文献,搜索用时 78 毫秒
1.
Zhixuan Wang Xiaopeng Zhang Yingjie Deng Ting Wang 《Journal of inclusion phenomena and macrocyclic chemistry》2007,57(1-4):349-354
In this study, a novel method is presented for the preparation of a hydrophobic drug hydroxypropyl-β-cyclodextrin (HPβCD)
complex. Ketoprofen and nitrendipine were used as model drugs and their HPβCD complexes were prepared by lyophilization of
a tertiary butyl alcohol (TBA) system. The preparation procedure is as follows: both hydrophobic drugs and HPβCD are dissolved
in TBA and subsequently passed through a 0.22 μm millpore filter. Then the solvent is removed by lyophilization to give a
hydrophobic drug HPβCD complex in porous powder form. Based on the data obtained from FTIR, a hydrogen bond is formed between
the drug and HPβCD. DSC, SEM and XRD results show that the drugs are amorphous in freeze-dried samples. The solubility of
the hydrophobic drugs in simulated gastric juice and simulated intestinal fluid was increased markedly compared with pure
drug. An in vitro release experiment showed that the dissolution rate of drug from the HPβCD complex was markedly enhanced
compared with the pure drug and the physical mixture. This method is versatile, economic and easily scaled up. It is suitable
for heat- and water-labile drugs and is expected to have a wide application in modifying the physicochemical characteristics
of hydrophobic drugs. 相似文献
2.
M. Másson S. D. Sigfússon T. Loftsson 《Journal of inclusion phenomena and macrocyclic chemistry》2002,44(1-4):177-182
The possibility of using fish skin as model membrane tostudy drug permeation and penetration enhancement by cyclodextrins was investigated.The permeability of the skin from four species of fish, Anarhichas lupus (catfish),Pleuronectes platessa (Plaice), Hippoglossus hippoglossus (Halibut)and Anarhichas minor (Spotted catfish), was compared in a Franz diffusion cell set-up using 1% hydrocortisone aqueous solution as a donor phase. The drug fluxthrough fish skin was more than 100 times faster than the flux through hairless mouse skin and more than 10 000 times faster than through snake skin. Catfishskin was most easily accessible and was therefore used for further study. The octanol-water partition coefficient did not affect the transmembrane flux of small molecules whereas the aqueous diffusion coefficient could be correlated with the flux.The hydrocortisone flux of from aqueous hydroxypropyl--cyclodextrin solutions, which were saturated with the drug, increased with increasing cyclodextrinconcentration. From these and other observations it was concluded that small moleculesare transported through fish skin in aqueous channels. The properties of thesechannels resemble the properties of the aqueous diffusion layer present in human andanimal skin and other types of biological membranes. Previous studies have shown thatcyclodextrins will enhance drug delivery by increasing aqueous diffusion rate. Catfish skin can therefore be a good model membrane to study penetration enhancementby cyclodextrins. 相似文献
3.
R. Ambrus Z. Aigner L. Catenacci G. Bettinetti P. Szabó-Révész M. Sorrenti 《Journal of Thermal Analysis and Calorimetry》2011,104(1):291-297
In view of the poor aqueous solubility of nifluminic acid (NIF), the aim of this article was to improve its solubility and
dissolution rate through the preparation of formulations based on hydroxypropyl β-cyclodextrin (HPβCD) and polyvinylpyrrolidone
K25 (PVP K25), a combination of carriers which has been advantageously used for a similar purpose with various hydrophobic
drugs. Ternary systems of NIF, HPβCD, and PVP K25 were prepared in different drug to CD to PVP ratios by physical mixing,
kneading, microwave irradiation, and co-evaporation. Differential scanning calorimetry, thermogravimetric analysis, hot stage
microscopy, Fourier transform infrared spectroscopy, and X-ray powder diffractometry were used to investigate the resulting
solid-state interactions. The results showed that the solid state of the drug in the amorphous or crystalline ternary combinations
influenced both the solubility and the dissolution rate of NIF. 相似文献
4.
Carolina Jullian Muriel Alfaro Gerald Zapata-Torres Claudio Olea-Azar 《Journal of solution chemistry》2010,39(8):1168-1177
The formation of the complexes of galangin (GAL) with native β-cyclodextrin (βCD), and with its substituted counterparts such
as dimethyl-βCD (DMβCD) and hydroxypropyl-βCD (HPβCD), was studied by fluorescence spectra in aqueous medium. The binding
association constants (K
a) of the complexes were determined at different temperatures. The formation constants obtained have the following trend upon
complex formation at the three temperatures studied: HPβCD > DMβCD > βCD. The thermodynamic data for the inclusion of GAL
in DMβCD and HPβCD indicated that is mainly enthalpy driven whereas for βCD it is an entropy-driven process. 相似文献
5.
Fréderic Bounoure Malika Lahiani-Skiba Cécile Barbot Abdussalam Sughir Eric Mallet Soizic Jezequel Ludovic Didier Philippe Arnaud Mohamed Skiba 《Journal of inclusion phenomena and macrocyclic chemistry》2007,57(1-4):191-195
Metopimazine (MPZ) is an antiemetic drug used by oral and rectal administration. A transdermal delivery system of MPZ may
present a great advantage for the treatment of nausea and vomiting to improve therapeutic adhesion. MPZ is a lipophilic drug
with poor water solubility. Partially methyled β cyclodextrin (PMβ-CD) was tested to enhance percutaneous absorption of MPZ.
Complex MPZ/cyclodextrin was characterized by Higushi’s phase solubility, Fourier transform infrared spectroscopy (FTIR) and
differential scanning calorimetry (DSC) analyses and MPZ octanol partition coefficient was also determinated. The permeation
of free MPZ and inclusion complex through pig skin were investigated using Franz’s cells. Four concentrations of cyclodextrins,
0, 5, 10 and 20% were tested. Partition coefficient was depending on pH of the solution. At pH 5.5, MPZ ionization increased
the hydrophily (0.71) and at pH 10.3, non-ionized MPZ was the dominant form (591). The solubility of MPZ increased with the
concentration of PMβ-CD and the phase solubility diagram is an Ap type. The used characterization analyses demonstrated the formation of an inclusion complex and this complex improved percutaneous
absorption of MPZ. No MPZ flux was detected for a suspension of MPZ and it was more important with MPZ hydrochloride, 0.177 ± 0.044 μg/h/cm2.
Flux was increased to 0.570 ± 0.058 μg/h/cm2 with a concentration of 20%. The use of cyclodextrin with MPZ hydrochloride increased
also the percutaneous absorption with 0.549 ± 0.175 μg/h/cm2 for a concentration of 5%, 0.435 ± 0.031 μg/h/cm2 for a concentration
of 10% and 0.474 ± 0.054 μg/h/cm2 for a concentration of 20%. This study shows that PMβ-CD improves percutaneous penetration
of MPZ. But the absorption is not enough to allow a therapeutic effect. Cyclodextrin complex increases MPZ solubility and
this bioavailability at the skin surface, and cyclodextrin may also modify the barrier propriety of skin. 相似文献
6.
Hakon H. Sigurdsson Audur Magnusdottir Már Másson Thorsteinn Loftsson 《Journal of inclusion phenomena and macrocyclic chemistry》2002,44(1-4):163-167
Determinations of drug fluxes through semi-permeable cellophanemembranes are used to evaluate cyclodextrin complexes and cyclodextrin containingdrug formulations. In the present study we investigated how the cyclodextrin concentration,the membrane thickness and the molecular weight cut off (MWCO) of the membraneinfluence drug fluxes. The cyclodextrin used was 2-hydroxypropyl--cyclodextrin(HP--CD) and the sample drug was hydrocortisone. The MWCO ofthe membranes ranged from 500 to 14,000 and the HP--CD concentrationranged from 0 to 25% (w/v). The hydrocortisone flux from saturated solutions through the MWCO 500 membrane was unaffected by the cyclodextrin concentration. When MWCO of the membrane was greater than the molecular weight of the complex the flux fromsolutions saturated with hydrocortisone increased with increasing HP--CD concentration.This increase showed negative deviation from linearity. When the flux was correctedfor the viscosity increase with increasing HP--CD concentration then the fluxpattern could be described on the basis of Fick's first law and Stokes–Einsteinequation. However the flux did not correlate with the viscosity when it was increasedby adding polymer to the saturated drug solutions. It was shown that the observed fluxpattern was consistent with self-association of cyclodextrin complexes in the aqueousdonor phase. 相似文献
7.
R. Patel D. Bhimani J. Patel D. Patel 《Journal of inclusion phenomena and macrocyclic chemistry》2008,60(3-4):241-251
The objectives of this research were to prepare and characterize inclusion complex of Ezetimibe (EZE) with cyclodextrins (β-cyclodextrin
(β-CD) and hydroxypropyl-β-cyclodextrin (HPβ-CD)) and to study the effect of complexation on the dissolution rate of EZE,
a water insoluble drug. Phase solubility curve was classified as A
P
-type for both cyclodextrins, indicating the 2:1 stoichiometric ratio for β-CD–EZE and HPβ-CD – EZE inclusion complexes. The
inclusion complexes in the molar ratio of 2:1 (β-CD–EZE and HPβ-CD–EZE) were prepared by various methods such as kneading,
coevaporation and physical mixing. The molecular behaviors of drug in all samples were characterized by fourier-transform
infrared (FTIR) spectroscopy, differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD) studies. The results
of these studies indicated that complex prepared by kneading and coevaporation methods showed inclusion of the EZE molecule
into the cyclodextrins cavities. The highest improvement in in-vitro dissolution profiles was observed in complex prepared
with hydroxypropyl-β-cyclodextrin using co-evaporation method. Mean dissolution time and similarity factor indicated significant
difference between the release profiles of EZE from complexes and physical mixtures and from pure EZE. 相似文献
8.
Marie Piette Delphine Castagne Luc Delattre Géraldine Piel 《Journal of inclusion phenomena and macrocyclic chemistry》2007,57(1-4):101-103
In this study, preparation and evaluation of liposomes, intended for intravenous administration, encapsulating synthetic MMP
inhibitor (Ro 28-2653) – cyclodextrin complexes were realized. An increase in Ro solubility, via formation of binary (Ro/HPβCD)
or ternary (Ro/HPβCD/L-lysine) complexes, permitted a similar increase in encapsulation efficiency of liposomes (Table 1). Moreover, Ro release kinetics depend on the encapsulation efficiency. 相似文献
9.
Andrés G. León Ana I. Olives M. Antonia Martín Benito del Castillo 《Journal of inclusion phenomena and macrocyclic chemistry》2007,57(1-4):577-583
The use of cyclodextrins (CDs) in HPLC as mobile phase additives provides a flexible alternative for the separation of chemically
related compounds because these separations can be performed on conventional columns and are economically advantageous over
the use of chiral stationary phases. The present paper describes the influence of the presence of β-cyclodextrin (β-CD) and
2-hydroxypropyl-β-cyclodextrin (HPβ-CD) on the separation of the β-carboline alkaloids norharmane, harmane and harmine. The
nature of the stationary phase (reverse phases C1 and C18) affects the chromatographic separations and also the stability of the inclusion complexes that are developed. The changes
in the proportion of the organic solvents at constant concentration of CDs (3 mM for β-CD and 15 mM for HPβ-CD) modify the
retention factors (k′) for all alkaloids studied. The nature of the organic solvent in the mobile phase also changes the chromatographic parameters.
The logarithm of the capacity factor (k′) is linearly increased with the proportion of water in the hydro-organic mobile phase (ethanolic or methanolic) but the
slopes obtained vary depending on the CD added to the mobile phase. The role of competitive equilibria, i.e., chromatographic
distribution and inclusion complexes formation is discussed.
This paper was presented at XIIIth International Cyclodextrin Symposium. Torino, Italy, May, 14–17, 2006 相似文献
10.
Giangiacomo Torri Sabrina Bertini Tania Giavana Marco Guerrini Nadia Puppini Giorgio Zoppetti 《Journal of inclusion phenomena and macrocyclic chemistry》2007,57(1-4):317-321
The aim of this work is the determination of the molecular association of progesterone (P) with hydroxypropyl-β-cyclodextrin
(HPβCD) in aqueous solution. The stoichiometry and the binding constants of the inclusion complex were calculated using NMR
techniques. 相似文献
11.
《Comptes Rendus Chimie》2016,19(8):951-954
Surfactants can self-assemble in dilute aqueous solutions into a variety of microstructures, including micelles, vesicles, and bilayers. Recently, there has been an increasing interest in unilamellar vesicles, which are composed of a closed bilayer that separates an inner aqueous compartment from the outer aqueous environment. This interest is motivated by their potential to be applied as vehicles for active agents in drug delivery via several routes of administration. Active drug molecules can be encapsulated in the bilayer membrane if they are lipophilic or in the core of the vesicle if they are hydrophilic. Furthermore vesicles formed by mixing of cationic and anionic surfactants (so called ‘catanionic’ systems) can be used as models for biological membranes as they have low critical micelle concentration (cmc) and are highly biocompatible. In this work the formation of amino acid based mixed surfactant vesicles and their stabilization and biocompatibility were studied systematically using several instrumental techniques. 相似文献
12.
T Hatanaka M Inuma K Sugibayashi Y Morimoto 《Chemical & pharmaceutical bulletin》1990,38(12):3452-3459
In order to measure the contribution of lipid and pore (aqueous) pathways to the total skin permeation of drugs, and to establish a predictive method for the steady state permeation rate of drugs, the relationship between permeability through excised hairless rat skin and some physicochemical properties of several drugs were compared with those through polydimethylsiloxane (silicone) and poly(2-hydroxyethyl methacrylate) (pHEMA) membranes, as typical solution-diffusion and porous membranes, respectively. A linear relationship was found between the permeability coefficients of drugs for the silicone membrane and their octanol/water partition coefficients. For the pHEMA membrane, the permeability coefficients were almost constant independent of the partition coefficient. On the other hand, the skin permeation properties could be classified into two types: one involves the case of lipophilic drugs, where the permeability coefficient is correlated to the partition coefficient, similar to the silicone membrane; and the other involves hydrophilic drugs, where the permeability coefficients were almost constant, similar to pHEMA membrane. From the above results, the stratum corneum, the main barrier in skin, could be described as a membrane having two parallel permeation pathways: lipid and pore pathways. An equation for predicting the steady state permeation rate of drugs was derived based on this skin permeation model. 相似文献
13.
B. Malaekeh-Nikouei H. Nassirli N. Davies 《Journal of inclusion phenomena and macrocyclic chemistry》2007,59(3-4):245-250
Cyclodextrins (CDs) are cyclic oligosaccharides that form inclusion complexes with lipophilic molecules through their hydrophobic
central cavity. In this study, the effect of α-CD, hydroxylpropyl-β-CD (HP-β-CD) and mixtures of these two CDs on the aqueous
solubility of cyclosporine A (CyA) was investigated. Infrared spectroscopy and thermal analysis were used to confirm CyA-CD
complex formation. CyA aqueous solubility was increased by 10 and 80 fold in the presence of α-CD and HP β-CD, respectively.
The phase-solubility profile for HP-β-CD was linear while that for α-CD had positive deviation from linearity. In the presence
of constant concentration of α-CD (15% w/v), aqueous solubility of CyA was further increased upon addition of HP-β-CD up to
a concentration of 20% w/v. At higher HP-β-CD concentrations, aqueous solubility of CyA was observed to decrease. Addition
of sodium acetate (up to 5% w/v) to aqueous solutions containing 20% w/v HP-β-CD and increasing concentrations of α-CD resulted
in a significant reduction in CyA solubility. Complex formation between CyA and both α-CD and HP-β-CD was confirmed by differential
scanning calorimetry (DSC). No significant changes were observed in the IR spectra of either CyA or CD following complex formation
suggesting chemical interaction between CyA and the CD was unlikely. Phase-solubility studies showed that α-CD had a much
greater effect on the solubility of CyA than HP-β-CD. Addition of HP-β-CD to aqueous solutions of α-CD affected the solubility
of CyA in these systems. A mixture of 15% w/v α-CD and 20% w/v HP-β-CD was optimal for increasing aqueous solubility of CyA. 相似文献
14.
S. Leprêtre F. Boschin N. Tabary M. Bria B. Martel N. Blanchemain H. F. Hildebrand M. Morcellet E. Delcourt-Debruyne 《Journal of inclusion phenomena and macrocyclic chemistry》2007,57(1-4):297-302
In parodontology, guided tissue regeneration (GTR) is a new technique to cure periodontal lesions. Where the association of
the GTR with an antimicrobial agent does not yield optimal results, we used the properties of cyclodextrins (CDs) to improve
the membrane used in RTG to control the release and to increase the quantity of antimicrobial agent stocked on the membrane.
We successed in fixing 14%-wt of cyclodextrin polymer on polyvinylidene difluoride (PVDF) membranes thank to citric acid (CTR)
as crosslinking agent. We studied the complexation of chlorhexidine diacetate (CHX), the antiseptic agent used in this study,
with CDs in UV-spectrophotometry and ROESY NMR. We observed complexation of CHX by β, γ, hydroxypropylated (HP) βCD. We studied
the biological properties of the cyclodextrin polymer onto (PVDF) membranes and observed that the CDs-polymer is not harmful
for the cells. Moreover it stimulates their growth with native CD. A kinetic of release of the CHX was performed. Raw membranes
released all CHX stocked in few hours, whereas grafted membranes released more than tenfold this quantity during 60–80 days. 相似文献
15.
Christian Folch-Cano Claudio Olea-Azar Eduardo Sobarzo-Sánchez Carmen Alvarez-Lorenzo Angel Concheiro Francisco Otero Carolina Jullian 《Journal of solution chemistry》2011,40(11):1835-1846
The physicochemical properties of 4-hydroxy-7-methoxy-3-phenyl-2H-chromen-2-one (4HC) and β-cyclodextrins (CDs) inclusion
complexes were investigated. The phase solubility profile of 4HC with β-cyclodextrin derivatives was classified as AL-type. Stability constants for complexes with 1:1 molar ratios were calculated from the phase solubility diagrams and indicate
the following trend: DMβCD>HPβCD>βCD. The highest value of the binding constant was for 4HC-DMβCD; the binding association
constant (K
a) for this complex was determined at different temperatures and the thermodynamic data indicate that 4HC-DMβCD association
is mainly an entropically driven process. 1H NMR and ROESY were carried out, revealing that 4HC is embedded in the apolar cavity of DMβCD with the 4OH group buried in
the cyclodextrin cavity with the phenyl group outside, near the primary rim. These results are in agreement with ORACFL values; the decrease in the antioxidant activity of 4HC-DMβCD is explained by the effective protection of the hydroxyl group
due to complexation. 相似文献
16.
Cationic β-cyclodextrin polymer (CPβCD) and its complexes with butylparaben and triclosan were reported in this paper. 2D
NMR confirmed that the host-guest complexes were formed by including antibiotics inside the cavities of CPβCDs, which significantly
improved the water solubility of the antibiotics. Results of inhibition zones and shaking flask methods of antimicrobial-modified
cellulose fibres showed that both antibiotics/CPβCD complexes had excellent antimicrobial activities when applying on the
cellulose fibers whereas triclosan appeared to more effective. Morphology of untreated and treated bacteria revealed by AFM
suggested that the antibiotics/CPβCD complexes inhibited bacteria through affecting the metabolism of the bacteria instead
of damaging the cell membrane. Due to the strong electrostatic association, CPβCD polymers adsorbed on the surface of cellulose
fibres almost completely within the range of dosages investigated. 相似文献
17.
Summary The cytostatic effect of the widely used antitumor drug 1-β-D-arabinofuranosyl cytosine (ara C) can be improved by its chemical
derivatization to lipophilic prodrugs. We have incorporated these prodrugs together with lipophilic biotin derivatives into
membranes of unilamellar liposomes. Monoclonal antibodies were coupled to the biotin residues of the liposomes via avidin-biotin
complexation resulting in prodrug-liposome-antibody complexes whichin vitro preferably bind to cells selectively recognized by the immobilized antibodies. The results open a promising way of drug targeting.
The components and liposomal derivatives used for the stepwise preparation of the prodrug-liposome antibody complex are purified
by means of preparative liquid chromatography. Lipophilic membrane components are chromatographed on silica gel, antibodies
on hydroxylapatite and liposomal derivatives on Ultrogel AcA 22 columns. Concentration and desalting are achieved by ultrafiltration.
The purification process can be quantitatively pursued by labelling with radioactive components. 相似文献
18.
19.
Roberta Cavalli Francesco Trotta Wander Tumiatti 《Journal of inclusion phenomena and macrocyclic chemistry》2006,56(1-2):209-213
Nanosponges were prepared from β-cyclodextrins as nanoporous materials for possible use as carriers for drug delivery. The structure of β-cyclodextrin-based nanosponges was principally investigated by FT-IR, DSC and RX analyses. Sizes, morphology and toxicity were also examined. The capacity of the nanosponges to incorporate molecules within their structure was evaluated using drugs with different structures and solubilities. The nanosponges were found capable of carrying both lipophilic and hydrophilic drugs and of improving the solubility of poorly water-soluble molecules. 相似文献
20.
Putcharin Chittiteeranon Suganya Soontaros Piamsook Pongsawasdi 《Journal of inclusion phenomena and macrocyclic chemistry》2007,57(1-4):69-73
AHTN (7-Acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene), commercially known as fixolide or tonalide, is a synthetic
fragrance widely used in replace of natural musk odor which is more expensive. It is a popular fragrance material added in
the manufacturing of personal care and household products, such as perfumes, soaps, shampoos, detergents, and fabric softeners.
AHTN is semivolatile and is degraded under light exposure and high temperature. This work focuses on the complexation of AHTN
with cyclodextrins in the effort to stabilize the fragrance material. AHTN was complexed with β-cyclodextrin, methyl (MβCD),
and hydroxypropyl (HPβCD) derivatives in the mole ratio 1:1, 1:2, and 1:3 guest:host, and the complexes formed by physical
mixing, co-precipitation, kneading, and freeze-drying were analyzed by DSC and FTIR. Percent AHTN included in the complex
was also determined by hexane extraction and GC analysis. It was found that no inclusion complex was formed in the physical
mixture. When co-precipitation method was performed, only βCD could form inclusion complex with AHTN, while the other two
derivatives could not. Using 1:2 AHTN:βCD, no free AHTN was left in the complex as evidenced by DSC and FTIR spectrum. In
kneading and freeze-drying methods, complexes could be formed with all CDs tested. However, co-precipitation method with 1:2
AHTN:βCD and kneading method with 1:2 AHTN:MβCD provided the highest complex yield with highest amount of AHTN included in
the complex. AHTN in the complex form was more stable against high temperature and UV exposure than its free form. 相似文献