Studies on curcumin and curcuminoids. XXXI. Symmetric and asymmetric curcuminoids: Stability, activity and complexation with cyclodextrin

International Journal of Pharmaceutics

Volumn 338, Issue 1-2, 2007, Pages 27-34

  Tomren, M A ^a   Masson M ^b   Loftsson, T ^b   Tønnesen, H Hjorth ^a  

^a UNIVERSITY OF OSLO   (Norway)

^b UNIVERSITY OF ICELAND   (Iceland)

Author keywords

Curcumin; Curcumin derivatives; Cyclodextrin; Hydrolysis; Photostability; Radical scavenging

Indexed keywords

CURCUMIN; CURCUMINOID DERIVATIVE; CYCLODEXTRIN; HYDROXYL GROUP; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DRUG DEGRADATION; DRUG SOLUBILITY; DRUG STABILITY; PHOTOCHEMISTRY; PRIORITY JOURNAL;

CURCUMIN; CYCLODEXTRINS; DRUG STABILITY; FREE RADICAL SCAVENGERS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; PHOTOCHEMISTRY;

EID: 34248684129     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2007.01.013     Document Type: Article

References (27)

1. Baglole K.N., Boland P.G., and Wagner B.D. Fluorescense enhancement of curcumin upon inclusion into parent and modified cyclodextrins. J. Photochem. Photobiol. A 173 (2005) 230-237
2. Banerji A., Chakrabarti J., Mitra A., and Chatterjee A. Effect of curcumin on gelatinase A (MMP-2) activity in B16F10 melanoma cells. Cancer Lett. 211 (2004) 235-242
3. Barclay L.R.C., Vinquist M.R., Mukai K., Goto H., Hashimoto Y., Tokunaga A., and Uno H. Org. Lett. 2 (2000) 2841-2843
4. Chueh S.C.J., Lai M.K., Liu I.S., Teng F.C., and Chen J. Curcumin enhances the immunosuppressive activity of cyclosporine in rat cardiac allografts and in mixed lymphocyte reactions. Transplant Proc. 35 (2003) 1603-1605
5. Egan M.E., Pearson M., Weiner S., Rajendran V., Rubin D., Glöckner-Pagel J., Canny S., Du K., Lukacs G.L., and Caplan M.J. Curcumin, a major constituent of turmeric, corrects cystic fibrosis defects. Science 304 (2004) 600-602
6. Frömming K.-H., and Szejtli J. Cyclodextrins in Pharmacy (1994), Kluwer Academic Publishers, Dordrecht
7. Gao X., Kuo J., Jiang H., Deeb D., Liu Y., Divine G., Chapman R.A., Dulchavsky S.A., and Gautam S.C. Immunomodulatory activity of curcum: suppression of lymphocyte proliferation, development of cell-mediated cytotoxicity, and cytokine production in vitro. Biochem. Pharmacol. 68 (2004) 51-61
8. Litwinienko G., and Ingold K.U. Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer. J. Org. Chem. 69 (2004) 5888-5896
9. Loftsson T., Másson M., and Brewster M.E. Self-association of cyclodextrins and cyclodextrin complexes. J. Pharm. Sci. 93 (2004) 1091-1099
10. Loftsson T., Jarho P., Másson M., and Jarvinen T. Cyclodextrins in drug delivery. Exp. Opin. Drug Deliv. 2 (2005) 335-351
11. Másson M., Sigurdardóttir B.V., Matthiasson K., and Loftsson T. Investigation of drug-cyclodextrin complexes by a phase-distribution method: some theoretical and practical considerations. Chem. Pharm. Bull. 53 (2005) 958-964
12. Masuda T., Maekawa T., Hidaka K., Bando H., Takeda Y., and Yamaguchi H. Chemical studies on antioxidant mechanism of curcumin: analysis of oxidative coupling products from curcumin and linoleate. J. Agric. Food. Chem. 49 (2001) 2539-2547
13. Mazumder A., Raghavan K., Weinstein J., Kohn K.W., and Pommier Y. Inhibition of human immunodeficiency virus type-1 integrase by curcumin. Biochem. Pharmacol. 49 (1995) 1165-1170
14. Pabon H. A synthesis of curcumin and related compounds. Rec. Trav. Chim. Pays-Bas 83 (1964) 379-386
15. Priyadarsini K.I., Maity D.K., Naik G.H., Kumar M.S., Unnikrishnan M.K., Satav J., and Mohan H. Role of phenolic OH and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin. Free Rad. Biol. Med. 35 (2003) 475-484
16. Qi A.-D., Li L., and Liu Y. The binding ability and inclusion complexation behavior of curcumin with natural alpha-, beta-, gamma-cyclodextrins and organoselenium-bridges bis(beta-cyclodextrin). J. Chin. Pharm. Sci. 12 (2003) 15-20
17. Sui Z., Salto R., Li J., Craik C., and Ortiz de Montellano P.R. Inhibition of the HIV-1 and HIV-2 proteases by curcumin and curcumin boron complexes. Bioorg. Med. Chem. 1 (1993) 415-422
18. Sun Y.-M., Zhang H.-Y., Chen D.-Z., and Liu C.-B. Theoretical elucidation on the antioxidant mechanism of curcumin: a DFT study. Org. Lett. 4 (2002) 2909-2911
19. Syng-ai C., Kumari A.L., and Khar A. Effect of curcumin on normal and tumor cells: role of glutathione and bcl-2. Mol. Cancer. Ther. 3 (2004) 1101-1108
20. Tang B., Ma L., Wang H.-Y., and Zhang G.-Y. Study on the supramolecular interaction of curcumin and beta-cyclodextrin by spectrophotometry and its analytical application. J. Agric. Food Chem. 50 (2002) 1355-1361
21. Tønnesen H.H. Studies on curcumin and curcuminoids XXVIII. Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Pharmazie 57 (2002) 820-824
22. Tønnesen H.H., Arrieta A., and Lerner D. Studies on curcumin and curcuminoids XXIV. Characterization of the spectroscopic properties of the naturally occurring curcuminoids and selected derivatives. Pharmazie 50 (1995) 689-693
23. Tønnesen H.H., and Karlsen J. Studies on Curcumin and Curcuminoids VI. Kinetics of curcumin degradation in aqueous solution. Z. Lebensm. Unters. Forsch. 180 (1985) 402-404
24. Tønnesen H.H., and Karlsen J. Studies on curcumin and curcuminoids. V. Alkaline degradation of curcumin. Z. Lebensm. Unters. Forsch. 180 (1985) 132-134
25. Tønnesen H.H., Karlsen J., and van Henegouwen G.B. Studies on curcumin and curcuminoids VIII. Photochemical stability of curcumin. Z. Lebens. Unters. Forsch. 183 (1986) 116-122
26. Tønnesen H.H., Masson M., and Loftsson T. Studies of Curcumin and Curcuminoids XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability. Int. J. Pharm. 244 (2002) 127-135
27. Venkatesan P., and Rao M. Structure-activity relationship for the inhibition of lipid peroxidation and the scavenging of free radicals by synthetic symmetrical curcumin analogues. J. Pharm. Pharmacol. 52 (2000) 1123-1128