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71.
Uekama K 《Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan》2012,132(1):85-105
The α-, β-, and γ-CyDs are the most common natural CyDs, consisting of six, seven, and eight glucose units, respectively. Among the natural CyDs, bioadaptable γ-cyclodextrin (γ-CyD) is useful to improve the undesired properties of drug molecules through the formation of inclusion complex. Recently, various kinds of CyD derivatives such as hydrophilic, hydrophobic, amphiphatic and anionic CyDs have been developed, anticipating the design of CyD-based drug delivery system. The objective of this contribution is to outline our recent findings on the combinational use of γ-CyD and functional ingredients, focusing on the ability to increase the drug absorption, the ability to control the rate and time profiles of drug release, and the ability to deliver a drug to a targeted site. In addition, the multi-functional characteristic of hydroxyalkylated CyDs, in particular, 2-hydroxypropyl-β-CyD (HP-β-CyD) is applicable to design the novel pharmaceutical formulation, focusing on the ability to form hydrophilic nano-particles. Moreover, some amphiphatic CyDs such as 2,6-di-O-methyl-β-CyD (DM-β-CyD) and 2-hydroxybutyl-β-CyD (HB-β-CyD) are useful to control the crystallization and polymorphic transition of solid drugs and will provide an opportunity to isolate labile intermediate metastable polymorphs. On the basis of above-mentioned knowledge, this review explores the use of CyDs to better understand their pharmaceutical applications as well as their limitations in the approach of CyD-based drug delivery system. 相似文献
72.
Ono N Miyamoto Y Ishiguro T Motoyama K Hirayama F Iohara D Seo H Tsuruta S Arima H Uekama K 《Journal of pharmaceutical sciences》2011,100(5):1935-1943
Reduction of bitterness of antihistaminic drugs by cyclodextrin (CyD) complexation was examined. The stability constant (Kc) of the 1:1 CyD inclusion complexes with antihistaminic drugs increased in the order of 2-hydroxypropyl-β-CyD (HP-β-CyD) ≈ β-CyD > γ-CyD > α-CyD for diphenhydramine and epinastine, and HP-β-CyD ≈ β-CyD > α-CyD > γ-CyD for hydroxyzine, cetirizine, and dl-chlorpheniramine. The inclusion complexes inhibited the adsorption of antihistaminic drugs to lipid membrane using liposomes, as the magnitude of Kc increased. From human gustatory sensation tests, β-CyD and HP-β-CyD potently suppressed the bitterness of antihistaminic drugs in a dose-dependent manner. Further, an artificial taste sensor analysis revealed that β-CyD and HP-β-CyD inhibited the bitterness of antihistaminic drugs in solution. The results suggest that CyDs suppress the bitterness of antihistaminic drugs in solutions through the formation of inclusion complexes. These results may provide useful information for masking or elimination of bitterness of drugs using CyDs. 相似文献
73.
In the present study, we examined tissue distribution and the antitumor effect of doxorubicin (DOX) after intravenous injection of the pegylated liposomes entrapping the DOX complex with gamma-cyclodextrin (gamma-CyD) (complex-in-liposome) in BALB/c mice bearing colon-26 tumor cells, compared with those of DOX solution, pegylated liposomes entrapping DOX alone (DOX-in-liposome), pegylated liposomes entrapping gamma-CyD (CyD-in-liposome) and the binary system of DOX-in-liposome and CyD-in-liposome. When injected to the mice, complex-in-liposome provided the high DOX levels in plasma and solid tumors, compared with the other preparations. Reflecting the result, complex-in-liposome elicited the retardation of tumor growth and the improvement of survival rate without suppression of increase in the body weight of mice. These results suggest the potential use of pegylated liposomes entrapping the DOX complex with gamma-CyD for a promising carrier for improvement of antitumor effects of DOX. 相似文献
74.
Tavornvipas S Hirayama F Takeda S Arima H Uekama K 《Journal of pharmaceutical sciences》2006,95(12):2722-2729
Effects of cyclodextrin (CyDs) on unfolding and aggregation of lysozyme and basic fibroblast growth factor (bFGF) were investigated. CyDs inhibited the chemically induced aggregation and its inhibition was generally in the order of gamma-CyDs < alpha-CyDs < beta-CyDs. Among these CyDs, branched beta-CyDs and dimethyl-beta-CyD (DM-beta-CyD) significantly reduced the aggregation of lysozyme. Hydrophilic CyDs reduced the thermally induced unfolding of lysozyme as shown by a decrease in the thermal unfolding temperature (T(m)) value of lysozyme, suggesting that CyDs destabilize native lysozyme or stabilize the unfolded state of lysozyme. In the case of bFGF, branched beta-CyDs showed greater effects on inhibition of the chemically and thermally induced denaturation. Interestingly, sulfobutyl ether beta-CyD (SBE-beta-CyD), which was not effective in case of lysozyme, provided the inhibitory effect for bFGF on the chemically, thermally and acid-induced denaturation, suggesting that both the inclusion and electrostatic interaction may be operative in the inhibition of aggregation of the positively charged protein. The results indicated that the use of CyDs for protein stabilization is dependent not only on the structure and property of CyDs but also on the nature of the denaturing stimuli, and the most appropriate CyD should be used for the stabilization of each protein. 相似文献
75.
Nagase Y Arima H Wada K Sugawara T Satoh H Hirayama F Uekama K 《Journal of pharmaceutical sciences》2003,92(12):2466-2474
The effects of water-soluble beta-cyclodextrin derivatives (beta-CyDs), such as 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CyD) and sulfobutyl ether beta-cyclodextrin (SBE7-beta-CyD) on cytotoxicity of DY-9760e (3-[2-[4-(3-chloro-2-methylphenyl)-1-piperazinyl]ethyl]-5,6-dimethoxy-1-(4-imidazolylmethyl)-1H-indazole dihydrochloride 3.5 hydrate) toward human umbilical vein endothelial cells (HUVECs) in vitro and vascular damage of the auricular vein of rabbits by DY-9760e in vivo were investigated. The spectroscopic study revealed that of the four beta-CyDs SBE7-beta-CyD forms the most stable inclusion complex in phosphate-buffered saline, probably because of a synergetic effect of hydrophobic and electrostatic interactions. beta-CyDs inhibited DY-9760e-induced cell death toward HUVECs in an order of G(2)-beta-CyD < beta-CyD < HP-beta-CyD < SBE7-beta-CyD, which was consistent with the order of the magnitude of stability constants. When the DY-9760e solution was infused into the auricular vein of rabbits for 24 h, SBE7-beta-CyD suppressed a DY-9760e-induced irritation such as thrombus, desquamation of the endothelium vasculitis, and perivasculitis. The present data indicated that SBE7-beta-CyD formed an inclusion complex with DY-9760e in a buffer solution and possessed the protective effect on DY-9760e-induced cytotoxicity toward HUVECs and vascular damage in rabbits. These results suggested potential use of SBE7-beta-CyD as a parenteral carrier for DY-9760e. 相似文献
76.
Cyclodextrins in drug carrier systems 总被引:3,自引:0,他引:3
One of the important characteristics of cyclodextrins is the formation of an inclusion complex with a variety of drug molecules in solution and in the solid state. As a consequence of intensive basic research, exhaustive toxic studies, and realization of industrial production during the past decade, there seem to be no more barriers for the practical application of natural cyclodextrins in the biomedical field. Recently, a number of cyclodextrin derivatives and cyclodextrin polymers have been prepared to obtain better inclusion abilities than parent cyclodextrins. The natural cyclodextrins and their synthetic derivatives have been successfully utilized to improve various drug properties, such as solubility, dissolution and release rates, stability, or bioavailability. In addition, the enhancement of drug activity, selective transfer, or the reduction of side effects has been achieved by means of inclusion complexation. The drug-cyclodextrin complex is generally formed outside of the body and, after administration, it dissociates, releasing the drug into the organism in a fast and nearly uniform manner. In the biomedical application of cyclodextrins, therefore, particular attention should be directed to the magnitude of the stability constant of the inclusion complex. In the case of parenteral application, a rather limited amount of work has been done because the cyclodextrins in the drug carrier systems have to be more effectively designed to compete with various biological components in the circulatory system. However, the works published thus far apparently indicate that the inclusion phenomena of cyclodextrin analogs may allow the rational design of drug formulation and that the combination of molecular encapsulation with other carrier systems will become a very effective and valuable method for the development of a new drug delivery system in the near future. 相似文献
77.
F Hirayama T Utsuki K Uekama M Yamasaki K Harata 《Journal of pharmaceutical sciences》1992,81(8):817-822
The direct photoisomerization of (E)-4-(1-imidazoylmethyl)-cinnamic acid (IMC), a thromboxane synthetase inhibitor, to its (Z)-isomer at pH 2.0 was decelerated by beta-cyclodextrin (beta-CyD) and heptakis(2,6-di-O-methyl)-beta-cyclodextrin (DM-beta-CyD). The photostationary composition [(Z)-isomer:IMC ratio] was shifted in favor of IMC. These effects were much greater with DM-beta-CyD than with the parent beta-CyD. The quantum yield of the photoisomerization was significantly decreased by complex formation with beta-CyDs, whereas the extinction coefficient of the guest was only slightly decreased. This situation was in sharp contrast to those observed in less polar solvents and suggests that the suppressing mechanism with beta-CyD is different from that with less polar solvent systems. Spectroscopic studies (ultraviolet, circular dichroism, and nuclear magnetic resonance) indicated that IMC is tightly included in an axial mode in the cavity of DM-beta-CyD and that the rotation of the photoreactive site is sterically hindered. The results suggest that the suppressing effect of beta-CyDs on the photoisomerization of IMC results mainly from a steric origin. 相似文献
78.
79.
A crystalline complex of testosterone with gamma-cyclodextrin was evaluated for solubility and dissolution rate. Whereas these parameters were at least an order of magnitude lower than those of testosterone complexes with amorphous derivatives of cyclodextrins, the properties of the crystalline complex enabled the preparation of a suitable pharmaceutical form for the sublingual administration of hormone to humans. This is in contrast to the situation with similar beta-cyclodextrin complexes, in which such administration was ineffective. Sublingual administration of the gamma-cyclodextrin complex, as shown in previous work using amorphous complexes, avoided rapid first-pass loss of hormone and directed it effectively into the circulation; administration of the complex into the stomach resulted in much lower circulatory hormone levels. 相似文献
80.
Enhancing effects of galactosylated dendrimer/alpha-cyclodextrin conjugates on gene transfer efficiency 总被引:2,自引:0,他引:2
Wada K Arima H Tsutsumi T Hirayama F Uekama K 《Biological & pharmaceutical bulletin》2005,28(3):500-505
To improve in vitro gene transfer efficiency and/or achieve cell-specific gene delivery of polyamidoamine (PAMAM) starburst dendrimer (generation 2, G2) conjugate with alpha-cyclodextrin (alpha-CDE conjugate (G2)), we prepared alpha-CDE conjugate bearing galactose (Gal-alpha-CDE conjugates) with the various degrees of substitution of the galactose moiety (DSG) as a novel non-viral vector. The agarose gel electrophoretic studies revealed that Gal-alpha-CDE conjugates formed complexes with plasmid DNA (pDNA) and protected the degradation of pDNA by DNase I, but these effects impaired as the DSG value increased. Dendrimer and alpha-CDE conjugate exerted pDNA condensation through the complexation, but Gal-alpha-CDE conjugates did not. Gal-alpha-CDE conjugate (DSG 4) was found to have much higher gene transfer activity than dendrimer, alpha-CDE conjugate and Gal-alpha-CDE conjugates (DSG 8, 15) in HepG2, NIH3T3 and A549 cells, which are independent of the expression of the asialoglycoprotein receptor. Transfection activity of Gal-alpha-CDE conjugate (DSG 4) was insensitive to the existence of competitors (asialofetuin and galactose) and serum. In addition, no cytotoxicity after transfection of the complex of pDNA with Gal-alpha-CDE conjugate (DSG 4) was observed. These results suggest the potential use of Gal-alpha-CDE conjugate (DSG 4) as a non-viral vector in various cells. 相似文献