Association of 3-O-methylquercetin with β-cyclodextrin: Complex preparation, characterization and ex vivo skin permeation studies

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 62, Issue 1-2, 2008, Pages 149-159

  Schwingel, Liege ^a   Fasolo, Daniel ^a   Holzschuh, Maribete ^a   Lula, Ivana ^b   Sinisterra, Rubén ^b   Koester, Letícia ^a   Teixeira, Helder ^a   Bassani, Valquiria L ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

cyclodextrin; 3 O methylquercetin; HPMC; NMR; Phase solubility; Skin permeation

Indexed keywords

EID: 51649102269     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-008-9450-4     Document Type: Article

References (26)

1. Zhang, M.Q., Rees, D.C.: A review of recent applications of cyclodextrins for drug discovery. Expert Opin. Ther. Pat. 9(12), 1697-1717 (1999)
2. Loftsson, T., Masson, M.: Cyclodextrins in topical drug formulations: theory and practice. Int. J. Pharm. 225(1-2), 15-30 (2001)
3. Del Valle, E.M.M.: Cyclodextrins and their uses: a review. Process Biochem. 39, 1033-1046 (2004)
4. Loftsson, T., Jarho, P., Másson, M., Järvinen, T.: Cyclodextrins in drug delivery. Expert Opin. Drug Deliv. 2(2), 335-351 (2005)
5. Loftsson, T., Duchêne, D.: Cyclodextrins and their pharmaceutical applications. Int. J. Pharm. 329(1-2), 1-11 (2007)
6. Middleton, E., Jr., Kandaswami, C., Theoharides, T.C.: The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharm. Rev. 52, 673-751 (2000)
7. Vlietinck, A.J., Vanden Berghe, D.A., Van Hoof, L.M., Vrijsen, R., Boeye, A.: Antiviral activity of 3-methoxyflavones. Prog. Clin. Biol. Res. 213, 537-540 (1986)
8. Vrijsen, R., Everaert, L., Van Hoof, L.M., Vlietinck, A.J., Vanden Berghe, D.A., Boeyé, A.: The poliovirus-induced shut-off of cellular protein synthesis persists in the presence of 3-methylquercetin, a flavonoid which blocks viral protein and RNA synthesis. Antiviral Res. 7(1), 35-42 (1987)
9. Vanden Berghe, D.A.R., Haemers, A., Vlietinck, A.J.: Antiviral agents from higher plants and an example of structure-activity relationship of 3-methoxyflavones. In: Colegate, S.M., Molyneux, R.J. (eds.) Bioactive Natural Products: Detection, Isolation and Structural Determination, Chap. 17, pp. 405-440. CRC Press, London (1993)
10. Bettega, J.M.R., Teixeira, H.F., Bassani, V.L., Barardi, C.R.M., Simões, C.M.O.: Evaluation of the antiherpetic activity of standardized extracts of Achyrocline satureioides. Phytother. Res. 18(10), 819-823 (2004)
11. Bassani, V.L., Teixeira, H.F., Gonzales Ortega, G., Lemos Senna, E., Simões, C.M.O., Sonaglio, D., Petrovick, P.R.: Processo para obtenção de extratos de Achyrocline satureioides e produto obtido. INPI. BR n. PI 103468-5, 12 July 2001
12. Peppas, N.A., Sahlin, J.J.: Hydrogels as mucoadhesive and bioadhesive materials: a review. Biomaterials 17(16), 1553-1561 (1996)
13. Shojaei, A.H.: Buccal Mucosa as a route for systemic drug delivery: a review. J. Pharm. Pharm. Sci. 1(1), 15-30 (1998)
14. Backensfeld, T., Müller, B., Kolter, K.: Interaction of NSA with cyclodextrins and hydroxipropyl cyclodextrin derivatives. Int. J. Pharm. 74, 85-93 (1991)
15. Toros de Ilarduya, M., Martín, C., Goñi, M., Martínez-Ohárriz, M.: Solubilization and interaction of sulindac with β-cyclodextrin is solid state and in aqueous solution. Drug Dev. Ind. Pharm. 24(3), 301-306 (1998)
16. Perdomo-Lopez, I., Rodriguez-Perez, A.I., Yzquierdo-Peiro, J.M., White, A., Estrada, E.G., Villa, T.G., Torres-Labandeira, J.J.: Effect of cyclodextrins on the solubility and antimycotic activity of sertaconazole: experimental and computational studies. J. Pharm. Sci. 91(11), 2408-2415 (2002)
17. Tommasini, S., Raneri, D., Ficarra, R., Calabrò, M.L., Stancanelli, R., Ficarra, P.: Improvement in solubility and dissolution rate of flavonoids by complexation with β-cyclodextrin. J. Pharm. Biomed. Anal. 35, 379-387 (2004)
18. Oda, M., Saitoh, H., Kobayashi, M., Aungst, B.J.: β-Cyclodextrin as a suitable solubilizing agent for in situ absorption study of poorly water-soluble drugs. Int. J. Pharm. 280, 95-102 (2004)
19. Krishnamachari, V., Levine, L.H., Zhou, C., Pare, P.W.: In vitro flavon-3-ol oxidation mediated by a B ring hydroxylation pattern. Chem. Res. Toxicol. 17, 795-804 (2004)
20. Fasolo, D., Schwingel, L., Holzschuh, M., Bassani, V., Teixeira, H.: Validation of an isocratic LC method for determination of quercetin and methylquercetin in topical nanoemulsions. J. Pharm. Biomed. Anal. 44, 1174-1177 (2007)
21. Higuchi, T., Connors, K.: Phase-solubility techniques. Adv. Anal. Chem. Instrum. 4, 117-212 (1965)
22. ICH Steering Committee: International Conference on Harmonization of Technical Requirements for Registration of Pharmaceuticals for Human Use, Validation of Analytical Procedures: Text and Methodology. Geneva, Switzerland (2005)
23. Zheng, Y., Haworth, I.S., Zuo, Z., Chow, M.S.S., Chow, A.H.L.: Physicochemical and structural characterization of quercetin-β-cyclodextrin complexes. J. Pharm. Sci. 94(5), 1079-1089 (2005)
24. Yan, C., Li, X., Xiu, Z., Teng, H., Hao, C.: A quantum-mechanical study on the complexation of β-cyclodextrin with quercetin. J. Mol. Struct. 764, 95-100 (2006)
25. Bergonzi, M.C., Bilia, A.R., Di Bari, L., Mazzia, G., Vincieria, F.F.: Studies on the interactions between some flavonols and cyclodextrins. Bioorg. Med. Chem. Lett. 17, 5744-5748 (2007)
26. Yan, C., Xiu, Z., Li, X., Teng, H., Hao, C.: Theoretical study for quercetin/β-cyclodextrin complexes: quantum chemical calculations based on the PM3 and ONIOM2 method. J. Incl. Phenom. Macrocycl. Chem. 58, 337-344 (2007)