Shikonin-loaded liposomes as a new drug delivery system: Physicochemical characterization and in vitro cytotoxicity

European Journal of Lipid Science and Technology

Volumn 113, Issue 9, 2011, Pages 1113-1123

  Kontogiannopoulos, Konstantinos N ^a   Assimopoulou, Andreana N ^a   Dimas, Konstantinos ^b   Papageorgiou, Vassilios P ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b UNIVERSITY OF THESSALY   (Greece)

Author keywords

Alkannin; Antitumor activity; Cancer; Controlled release; Naphthoquinones

Indexed keywords

EID: 80052651429     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201100104     Document Type: Article

References (54)

1. Papageorgiou, V. P., Assimopoulou, A. N., Samanidou, V. F., Papadoyannis, I. N., Recent advances in chemistry, biology and biotechnology of alkannins and shikonins. Curr. Org. Chem. 2006, 10, 2123- 2142.
2. Papageorgiou, V. P., Assimopoulou, A. N., Couladouros, E. A., Hepworth, D., Nicolaou, K. C., The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products. Angew. Chem., Int. Ed. 1999, 38, 270- 300.
3. Papageorgiou, V. P., Naturally occurring isohexenylnaphthazarin pigments: A new class of drugs. Planta Med. 1980, 38, 193- 203.
4. Papageorgiou, V. P., Assimopoulou, A. N., Ballis, A. C., Alkannins and shikonins: A new class of would healing agents. Curr. Med. Chem. 2008, 15, 3248- 3267.
5. Chen, X., Yang, L., Oppenheim, J. J., Howard, O. M. Z., Cellular pharmacology studies of shikonin derivatives. Phytother. Res. 2002, 16, 199- 209.
6. Lee, H. J., Lee, H. J., Magesh, V., Nam, D. et al., Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in Lewis lung carcinoma-bearing mice. Yakugaku Zasshi. 2008, 128, 1681- 1688.
7. Zeng, Y., Liu, G., Zhou, L. M., Inhibitory effect of acetylshikonin on human gastric carcinoma cell line SGC-7901 in vitro and in vivo. World J. Gastroenterol. 2009, 15, 1816- 1820.
8. Yao, Y., Zhou, Q., A novel antiestrogen agent Shikonin inhibits estrogen-dependent gene transcription in human breast cancer cells. Breast Cancer Res. Treat. 2010, 121, 233- 240.
9. Yang, H. J., Zhou, P., Huang, H. B., Chen, D. et al., Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo. Int. J. Cancer. 2009, 124, 2450- 2459.
10. Komi, Y., Suzuki, Y., Shimamura, M., Kajimoto, S. et al., Mechanism of inhibition of tumor angiogenesis by beta-hydroxyisovalerylshikonin. Cancer Sci. 2009, 100, 269- 277.
11. He, J., Complex of shikonin and beta-cyclodextrins by using supercritical carbon dioxide. J. Inclusion Phenomena Macrocyclic Chem. 2009, 63, 249- 255.
12. Cheng, H. W., Chen, F. A., Hsu, H. C., Chen, C. Y., Photochemical decomposition of alkannin/shikonin enantiomers. Int. J. Pharm. 1995, 120, 137- 144.
13. Papageorgiou, V. P., Assimopoulou, A. N., Kyriacou, G., Determination of naturally occurring hydroxynaphthoquinone polymers by size-exclusion chromatography. Chromatographia 2002, 55, 423- 430.
14. Assimopoulou, A. N., Papageorgiou, V. P., Study on polymerization of the pharmaceutical substances isohexenylnaphthazarins. Biomed. Chromatogr. 2004, 18, 492- 500.
15. Assimopoulou, A. N., Papageorgiou, V. P., Study on isohexenylnaphthazarins polymerization in alkaline media. Biomed. Chromatogr. 2004, 18, 508- 522.
16. Alexis, F., Rhee, J. W., Richie, J. P., Radovic-Moreno, A. F. et al., New frontiers in nanotechnology for cancer treatment. Urol. Oncol. Semin. Orig. Investig. 2008, 26, 74- 85.
17. Edwards, K. A., Baeumner, A. J., Analysis of liposomes. Talanta 2006, 68, 1432- 1441.
18. New, R. R. C., Liposomes: A Practical Approach, Oxford University Press, New York (USA) 1990.
19. Lasic, D. D., Needham, D., The "Stealth" liposome: A prototypical biomaterial. Chem. Rev. 1995, 95, 2601- 2628.
20. Drummond, D. C., Meyer, O., Hong, K., Kirpotin, D. B., Papahadjopoulos, D., Optimizing liposomes for delivery of chemotherapeutic agents to solid tumors. Pharmacol. Rev. 1999, 51, 691- 743.
21. Matsingou, C., Hatziantoniou, S., Georgopoulos, A., Dimas, K. et al., Labdane-type diterpenes: Thermal effects on phospholipid bilayers, incorporation into liposomes and biological activity. Chem. Phys. Lipids 2005, 138, 1- 11.
22. Yang, T., Choi, M. K., Cui, F. D., Kim, J. S. et al., Preparation and evaluation of paclitaxel-loaded PEGylated immunoliposome. J. Control. Release 2007, 120, 169- 177.
23. Woodle, M. C., Sterically stabilized liposome therapeutics. Adv. Drug Deliv. Rev. 1995, 16, 249- 265.
24. Pinto-Alphandary, H., Andremont, A., Couvreur, P., Targeted delivery of antibiotics using liposomes and nanoparticles: Research and applications. Int. J. Antimicrob. Agents 2000, 13, 155- 168.
25. Abraham, S. A., Waterhouse, D. N., Mayer, L. D., Cullis, P. R. et al., The liposomal formulation of doxorubicin. Liposomes Pt E 2005, 391, 71- 97.
26. Meselhy, M. R., Kadota, S., Tsubono, K., Hattori, M., Namba, T., Biotransformation of shikonin by human intestinal bacteria. Tetrahedron 1994, 50, 3081- 3098.
27. Meselhy, M. R., Kadota, S., Tsubono, K., Kusai, A. et al., Shikometabolins A, B, C and D, novel dimeric naphthoquinone metabolites obtained from shikonin by human intestinal bacteria. Tetrahedron Lett. 1994, 35, 583- 586.
28. Assimopoulou, A. N., Papageorgiou, V. P., Preparation and release studies of alkannin-containing microcapsules. J. Microencapsul. 2004, 21, 161- 173.
29. Assimopoulou, A. N., Papageorgiou, V. P., Kiparissides, C., Synthesis and release studies of shikonin-containing microcapsules prepared by the solvent evaporation method. J. Microencapsul. 2003, 20, 581- 596.
30. Assimopoulou, A. N., Papageorgiou, V. P., Encapsulation of isohexenylnaphthazarins in cyclodextrins. Biomed. Chromatogr. 2004, 18, 240- 247.
31. Kontogiannopoulos, K. N., Assimopoulou, A. N., Tsivintzelis, I., Panayiotou, C., Papageorgiou, V. P., Electrospun fiber mats containing shikonin and derivatives with potential biomedical application. Int. J. Pharm. 2011, 409, 216- 228.
32. Assimopoulou, A. N., Sturm, S., Stuppner, H., Papageorgiou, V. P., Preparative isolation and purification of alkannin/shikonin derivatives from natural products by high-speed counter-current chromatography. Biomed. Chromatogr. 2009, 23, 182- 198.
33. Bangham, A. D., Standish, M. M., Watkins, J. C., Diffusion of univalent ions across the lamellae of swollen phospholipids. J. Mol. Biol. 1965, 13, 238- 252.
34. Washington, C., Drug release from microdisperse systems: A critical review. Int. J. Pharm. 1990, 58, 1- 12.
35. Liu, J., Lee, H., Huesca, M., Young, A., Allen, C., Liposome formulation of a novel hydrophobic aryl-imidazole compound for anti-cancer therapy. Cancer Chemother. Pharmacol. 2006, 58, 308- 316.
36. Dimas, K., Papadaki, A., Tsimplouli, C., Hatziantoniou, S. et al., Labd-14-ene-8, 13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs. Biomed. Pharmacother. 2006, 60, 127- 133.
37. Dimas, K., Hatziantoniou, S., Tseleni, S., Khan, H. et al., Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice. Apoptosis 2007, 12, 685- 694.
38. Broto, P., Moreau, G., Vandycke, C., Molecular structures - perception, auto-correlation descriptor and SAR studies - system of atomic contributions for the calculation of the normal-octanol water partition-coefficients. Eur. J. Med. Chem. 1984, 19, 71- 78.
39. Ghose, A. K., Crippen, G. M., Atomic physicochemical parameters for three-dimensional-structure-directed quantitative structure-activity relationships. 2. Modeling dispersive and hydrophobic interactions. J. Chem. Inf. Comp. Sci. 1987, 27, 21- 35.
40. Ceruti, M., Crosasso, P., Brusa, P., Arpicco, S. et al., Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing water-soluble prodrugs of paclitaxel. J. Control. Release 2000, 63, 141- 153.
41. Crosasso, P., Ceruti, M., Brusa, P., Arpicco, S. et al., Preparation, characterization and properties of sterically stabilized paclitaxel-containing liposomes. J. Control. Release 2000, 63, 19- 30.
42. Cocera, M., Lopez, O., Coderch, L., Parra, J. L., Maza, Adl., Permeability investigations of phospholipid liposomes by adding cholesterol. Colloids Surf. A. Physicochem. Eng. Asp. 2003, 221, 9- 17.
43. Gregoriadis, G., Drug entrapment in liposomes. FEBS Lett. 1973, 36, 292- 296.
44. Mohammed, A. R., Weston, N., Coombes, A. G. A., Fitzgerald, M., Perrie, Y., Liposome formulation of poorly water soluble drugs: Optimisation of drug loading and ESEM analysis of stability. Int. J. Pharm. 2004, 285, 23- 34.
45. Al-Angary, A. A., Bayomi, M. A., Khidr, S. H., Al-Meshal, M. A., Al-Dardiri, M., Characterization, stability and in vivo targeting of liposomal formulations containing cyclosporin. Int. J. Pharm. 1995, 114, 221- 225.
46. Hathout, R. M., Mansour, S., Mortada, N. D., Guinedi, A. S., Optimizing liposomes for delivery of chemotherapeutic agents to solid tumors. AAPS PharmSciTech 2007, 8, E1- E12.
47. Immordino, M. L., Brusa, P., Arpicco, S., Stella, B. et al., Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing docetaxel. J. Control. Release. 2003, 91, 417- 429.
48. Müller, R. H., Colloidal Carriers for Controlled Drug Delivery and Targeting: Modification, Characterization, and In Vivo Distribution, CRC Press, Inc., Boca Raton, Florida (USA) 1991.
49. Gardikis, K., Hatziantoniou, S., Bucos, M., Fessas, D. et al., New drug delivery nanosystem combining liposomal and dendrimeric technology (Liposomal locked-in dendrimers) for cancer therapy, J. Pharm. Sci. 2010, 99, 3561- 3571.
50. Cho, E. C., Lim, H. J., Shim, J., Kim, J., Chang, I. S., Improved stability of liposome in oil/water emulsion by association of amphiphilic polymer with liposome and its effect on bioactive skin permeation. Colloids Surf. A Physicochem. Eng. Aspects 2007, 299, 160- 168.
51. Fatouros, D. G., Antimisiaris, S. G., Effect of amphiphilic drugs on the stability and zeta-potential of their liposome formulations: A study with prednisolone, diazepam, and griseofulvin, J. Colloid Interface Sci. 2002, 251, 271- 277.
52. Margalit, R., Alon, R., Linenberg, M., Rubin, I. et al., Liposomal drug delivery: thermodynamic and chemical kinetic considerations. J. Control. Release 1991, 17, 285- 296.
53. Yang, T., Choi, M. K., Cui, F. D., Lee, S. J., et al., Antitumor effect of paclitaxel-loaded PEGylated immunoliposomes against human breast cancer cells, Pharm. Res. 2007, 24, 2402- 2411.
54. Yang, T., Cui, F. D., Choi, M. K., Cho, J. W., Chung, S. J., Shim, C. K., Kim, D. D., Enhanced solubility and stability of PEGylated liposomal paclitaxel: In vitro and in vivo evaluation. Int. J. Pharm. 2007, 338, 317- 326.