V. Boldescu et al./Chem.J.Mold. 2008, 3 (1), 85-88(a)(b)Figure 3. (a) Simulated curve <strong>of</strong> the spectrophotometric titration (at 283 nm) <strong>of</strong> 0.03 mM SANG with CD inphosphate buffer-alcoholic solution (95:5 v/v) pH 8.0; (b) simulated curve <strong>of</strong> the spectrophotometric titration (at283 nm) <strong>of</strong> 0.03 mM SANG with CD in presence <strong>of</strong> 0.1% PVP, in phosphate buffer-alcoholic solution (95:5 v/v),pH 8.0(a)(b)Figure 4. Benesi-Hildebrand plots for the SANG-CD systems in the presence <strong>of</strong> 0.1 % PVP (b) and without it (a),pH 8.0(a)(b)Figure 5. Scott plots for the SANG-CD systems in the presence <strong>of</strong> 0.1% PVP (b) and without it (a), pH 8.087
V. Boldescu et al./Chem.J.Mold. 2008, 3 (1), 85-88Figure 6. Scatchard plots for the SANG-CD systems in the presence <strong>of</strong> 0.1 % PVP (b) and without it (a), pH 8.0The values <strong>of</strong> the association constants calculated by the three methods (Table 1) differ from each other not morethan by their errors. This fact suggests a satisfactory level <strong>of</strong> correlation between the obtained results.The main conclusion based on the analysis <strong>of</strong> the obtained values is a two fold increase <strong>of</strong> the association constant<strong>of</strong> SANG-CD complex in the presence <strong>of</strong> 0.1% PVP at the pH 8.0. This fact can be explained by the prevalence <strong>of</strong>the pseudobasic form <strong>of</strong> SANG (Figure 1) at this level <strong>of</strong> pH. This form is more lipophilic and, thus, it can be easierincluded inside <strong>of</strong> the hydrophobic cavity <strong>of</strong> the CD.Table 1Association constants <strong>of</strong> complexation <strong>of</strong> SANG with CD - without and in the presence <strong>of</strong> 0.1% PVP - in phosphatebuffer-alcoholic solution (95:5 v/v), pH 8.0Method <strong>of</strong> binding constantcalculationK a(SANG-CD), M -1[PVP] = 0 %K a(SANG-CD), M -1[PVP] = 0.1 %Benesi-Hildebrand 903±58 2164±132Scott 798±43 1919±100Scatchard 829±47 2005±111ConclusionsThe obtained results suggest that pharmaceutical formulations containing sanguinarine and -cyclodextrin shouldbe prepared in the weak alkaline media. Moreover, in order to improve the complexation efficiency <strong>of</strong> the cyclodextrina small amount (~0.1%) <strong>of</strong> hydrophilic polymer (polyvinylpyrrolidone) should be added.AcknowledgementsThe research described in this publication was made possible in part by Award No. MTFP-012/05 Follow-On Award <strong>of</strong> the Moldovan Research and Development Association (MRDA) and the U.S. Civilian Research &Development Foundation (CRDF).References[1] Walterová D., Ulrichová J., Válka I., Viˇcar J. Acta Univ. Palacki. Olomuc. Fac. Med. 1995, 139, 7–16;[2] Ding Z., Tang S.-C., Weerasinghe P., Yang X., Pater A., Liepins A. Biochem. Pharmacol. 2002, 63, 1415–1421;[3] Ahmad N., Gupta S., Husain M. M., Heiskanen K. M., Mukhtar H. Clin. Cancer Res. 2000, 6, 1524–1528;[4] Adhami V. M, Aziz M.H., Mukhtar H. J., Ahmad N. Clin. Ancer Res. 2003, 9, 3176 - 3182;[5] Adhami V. M, Aziz M.H., Regan-Shaw S., Nihal M., Mukhtar H., Ahmad N. Mol. Cancer Therap. 2004, 8,933-940;[6] L<strong>of</strong>tsson T., Masso M. Int. J. Pharm. 2001, 225, 15–30;[7] Szejtli J. Pure Appl. Chem. 2004, 76, 1825-1845;[8] Ling P., Tabibi S.E., Yalkowsky S.H. J. Pharm. Sci. 1998, 87, 1535-1537;[9] McCandless R., Yalkowsky S.H. 1998, 87, 1639-1642;[10] Ribeiro L., L<strong>of</strong>tsson T., Ferreira D., Veiga F. Chem. Pharm. Bull. 2003, 51, 914–922;[11] Mura P., Faucci M. T., Bettinetti G.P. Eur. J. Pharm. Sci. 2001, 113, 187–194;[12] Mura P., Faucci M. T., Manderioli A., Bramanti G. J. Incl. Phen. 2001, 39, 131–138;[13] Mura P., Maestrelli F., Cirri M. Int. J. Pharm. 2003, 260, 293–302;[14] Atwater J.A. Carbohydr. Res. 2000, 327, 219 – 221;[15] Schneider H.-J., Yatsimirsky A. Principles and Methods in Supramolecular Chemistry; John-Willey&Sons,New-York, 1999, pp 137-220.88
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