P-cyclodextrin complexes

Matsui and Mochida24) have determined the thermodynamic stabilities (log 1 /Kd) for a- and P-cyclodextrin complexes with a variety of alcohols (Table 2) and analyzed the results in connection with the physicochemical properties of the guest molecules by the multivariate technique. The log 1/Kd values were plotted against log Pe, where Pe is the partition coefficient of alcohol in a diethyl ether-water system. The plots for the a- and P-cyclodextrin complexes with eight 1-alkanols gave approximately straight lines with slopes of around one. 

Nishioka and Fujita 78> have determined the Kd values for a- and P-cyclodextrin complexes with m- and p-substituted phenols at pH 7.0. Taking into account the directionality in inclusion of a guest molecule, they assumed three and two probable orientational isomers for the cyclodextrin complexes with m- and p-substituted phenols respectively (Fig. 6). Then the observed Kd values were divided into two or three terms corresponding to the dissociation of the orientational isomers involved (Eqs. 16, 17) ... 

Moritz ED, Sahyun MRV (2005) Spectroscopic studies of P-cyclodextrin-complexed cyanine dyes. J Photochem Photobiol A Chem 169 211-220... 

The latter three, (4)—(6), are utilized for qualitative elucidation of the observed ICD bands in signs, and the former three, (1)—(3), are successfully applicable for quantitative calculations of the observed ICD bands in both signs and magnitudes. The ICD of P-cyclodextrin complexes with benzene derivatives or azanaphthalenes162) has been analyzed by a molecular orbital calculation, using an approximation of PPP-type, which has been compared with the theoretical spectra calculated by using the CNDO/S-CI method on the basis of the MCD spectra 16S). 

A similar complexation study supported by thermodynamic parameters was performed by the same author for mono-(6-anilino-6-deoxy)- 3-cyclodextrin and mono-[ 6-( 1 -pyridinio)-6-deoxy]-P-cyclodextrin complexation with several amino acids in zwitterionic form [24]. The inclusion complexation was enthalpy driven for the former and entropy driven for the latter host. 

Sybilska, D., Debowski, J., Jurczak, J., and Zukowski, J., The a- and P-cyclodextrin complexation as a tool for the separation of o-, m- and p-nitro-, cis- and trans-cinnamic acids by reversed-phase high-performance liquid chromatography, J. Chromatgr., 286, 163, 1984. 

Scheme 20 Formation of optically active benzoin in the p-cyclodextrin complex.

Nijhawan, R., and Agarwal, S. P. (2003), Development of an ophthalmic formulation containing ciprofloxacin-hydroxypropyl-P-cyclodextrin complex, Boll. Chim. Farm,., 142(5), 214-219. 

J. I. Seeman and H. V. Secor, Enantiomeric resolution and chiral recognition of racemic nicotine and nicotine analogues by P-cyclodextrins complexation. Structure-enantiomeric resolution relationship in host guest interaction, Anal. Chem. 60 (1988), 2120. 

Ono, N. Hirayama, F. Arima, H. Uekama, K. Determination of stability constant of P-cyclodextrin complexes using the membrane permeation technique and the permeation behavior of drug-competing agent-P-cyclodextrin ternary systems. Eur. J. Pharm. Sci. 1999, 8 (2), 133-139. 

Szente, L. Apostol, L Szejtli, J. Suppositories containing P-cyclodextrin complexes. Part 1 Stability studies. Pharmazie 1984, 39 (10), 697-699. 

Szente L, Apostol I, Gerloczy A, Szejtli J. Suppositories containing P-cyclodextrin complexes, part 2 dissolution and absorption studies. Pharmazie 1985 40 406 07. 

Figure 14 Danazol is a drug with an aqueous solubility of 10 ttg/mL. Here danazol plasma levels are plotted as a function of time after administration of three forms of the drug including a nanoparticle dispersion and a hydroxypropyl-P-cyclodextrin complex, using a suspension with a mean particle size of 10 pm as a comparator. Source From Ref. 83.

Uekama, K., Horikawa, T., Horiuchi, Y, Hirayama, F. In vitro and in vivo evaluation of delayed-release behaviour of diltiazem from its O-carboxymethyl-O-ediyl-p-cyclodextrin complex. J. Control Release 1993, 25, 99-106. 

Horiuchi, Y, Abe, K., Hirayama, F., Uekama, K. Control of dieophyl-hne by p-cyclodextrin derivatives hybridizing of hydrophihc and ionizable p-cyclodextrin complexes. J. Control Release 1991, 15, 177-182. 

Tokumura, T., Nanba, M., Tsushima, Y. et al. Enhancement of bioavailability of cinnarizine from its p-cyclodextrin complex on oral administration with DL-phenylalanine as a competing agent. J. 

Uekama, K., Otagiri, M., Uemura, Y et al Improvement of oral bioavailability of prednisolone by p-cyclodextrin complexation in humans. J. Pharmacobio-Dynam. 1983, 6, 124-127. 

Uekama, K., Matsuo, N., Hirayama, F. et al. Enhanced bioavailability of acetohexamide by p-cyclodextrin complexation. Yakugaku. Zasshi 1980, 100, 903-909. 

Horiuchi, Y, Kikuchi, M., Hirayama, F. etal. Improvement of bioavailability of menaquinone-4 by dimethyl-p-cyclodextrin complexation following oral administration. Yakugaku. Zasshi 1988,108, 1093-1100. 

Otagiri, M., Imai, T., Uekama, K. Enhanced oral bioavailability of anti-inflammatory drug flurbiprofen in rabbits by tri-O-methyl-p-cyclodextrin complexation. J. Pharmacobio-Dynam. 1982, 5, 1027-1029. 

Kikuchi, M., Uekama, K. Enhancement of antimmor activity of carmofur (HCFU) by dimethyl-p-cyclodextrin complexation in P-388 leukemia-bearing mice. Xenobiotic Metab. Dispos. 1988, 3, 267-273. 

Uekama, K., Maeda, T., Arima, H. et al. Possible utility of p-cyclodextrin complexation in the preparation of biphenylylacetic acid suppository. Yakugaku. Zasshi 1986, 106, 1126-1130. 

Irie, T., Otagiri, M., Uekama, K. et al. Alleviation of the chlorpro-mazine-induced muscular tissue damage by P-cyclodextrin complexation. J. Inclusion Phenom. 1984, 2, 637-644. 

The microenvironment created by cyclodextrins can be used to overcome the low reactivity of epoxides. Rao and coworkers have shown that in situ formation of an epoxide/p-cyclodextrin complex in water, followed by amine addition yields regioselective epoxide openings <05SL506>. Several substituted epoxides and aromatic amines were examined with isolated yields in the range of 80-90%. 

Photolyses of the solid cyclodextrin complexes 1 were carried out with a Hano-via 450-W medium-pressure Hg lamp for 3 h at room temperature in a quartz vessel under vacuum. The photolysis vessel was tumbled continuously during the irradiation to ensure homogeneous photolysis of the sample. Conversions were limited to less than 20%. After photolysis, the solid complexes were dissolved in excess water and extracted with diethyl ether and chromatographed with hexane-ethyl acetate (5 1) to isolate the products in pure form. Irradiation of solid p-cyclodextrin complexes of benzaldehyde resulted in an intramolecular reaction to give benzoin (R)-(-)-2 and 4-benzoylbenzaldehyde 3 (7 3, 80%). 

Sortino, S., Scaiano, J.C., De Guidi, G., and Monti, S., 1999a, Effect of P-cyclodextrin complexation on the photochemical and photosensitizing properties of tolmetin a steady state and time-resolved study, Photochem. Photobiol. 70, 549-556. 

Zejtli, J., Bolla-Pusztai, E., Szab6, P, and Ferenczy, T. (1980) Enhancement of stability and biological effect of cholecalciferol by P-cyclodextrin complexation, Pharmazie, 35, 779-787. 

Hadaruga NG, Hadaruga Dl, Paunescu V, Tatu C, Ordodi VL, Bandur G, Lupea AX. 2006. Thermal stability of the hnoleic acid/a- and p-cyclodextrin complexes. Food Chemistry 99(3) 500-508. 

Kurihara, M., Hirayama, F., Uekama, K. and Yamasaki, M. (1990) Improvement of some pharmaceutical properties of nocloprost by P-and P-cyclodextrin complexations. J. Incl Phenom. 8 363-373. 

Kikuchi, M., Hirayama, F. and Uekama, K. (1987) Improvement of oral and rectal bioavailability of carmofur by methylated P-cyclodextrin complexations. Int. J. Pharm. 38 191-198. 

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