Nanoemulsion formulation of fisetin improves bioavailability and antitumour activity in mice

International Journal of Pharmaceutics

Volumn 427, Issue 2, 2012, Pages 452-459

  Ragelle, Héloïse ^a   Crauste Manciet, Sylvie ^a   Seguin, Johanne ^a   Brossard, Denis ^a   Scherman, Daniel ^a   Arnaud, Philippe ^a   Chabot, Guy G ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Antitumour activity; Bioavailability; Fisetin; Flavonoids; Nanoemulsion; Pharmacokinetics

Indexed keywords

ALPHA TOCOPHERYL ACID SUCCINATE ESTER; CAPTEX; CARTHAME OIL; DECANOIC ACID; FISETIN; IMWITOR; LABRAFAC; LABRASOL; LIPID; LIPOID E80; LONG CHAIN TRIACYLGLYCEROL; MACROGOL 10000; MACROGOL STEARATE; MEDIUM CHAIN FATTY ACID; MEDIUM CHAIN TRIACYLGLYCEROL; MIGLYOL; OCTANOIC ACID; OCTANOIN; OIL; OLEIC ACID ETHYL ESTER; PEGLICOL 5 OLEATE; POLYSORBATE 80; SHORT CHAIN FATTY ACID; SOLVENT; SORBITAN TRIOLEATE; SOYBEAN OIL; SURFACTANT; UNCLASSIFIED DRUG; WATER; WATER OIL CREAM;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CELL STRUCTURE; CHEMICAL COMPOSITION; CONTROLLED STUDY; DISPERSION; DOSE RESPONSE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG DOSAGE FORM COMPARISON; DRUG DOSE COMPARISON; DRUG EFFECT; DRUG EFFICACY; DRUG ELIMINATION; DRUG FORMULATION; DRUG HALF LIFE; DRUG SOLUBILITY; DRUG STABILITY; ENDOTHELIUM CELL; FEMALE; HUMAN; HUMAN CELL; LEWIS CARCINOMA; MAXIMUM PLASMA CONCENTRATION; MEAN RESIDENCE TIME; MOUSE; NANOEMULSION; NANOPHARMACEUTICS; NONHUMAN; PHASE SEPARATION; PRIORITY JOURNAL; SOLVENT EFFECT; ZETA POTENTIAL;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; AREA UNDER CURVE; BIOLOGICAL AVAILABILITY; CARCINOMA, LEWIS LUNG; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG STABILITY; EMULSIONS; ENDOTHELIAL CELLS; EXCIPIENTS; FEMALE; FLAVONOIDS; HALF-LIFE; HUMANS; INJECTIONS, INTRAPERITONEAL; INJECTIONS, INTRAVENOUS; MICE; MICE, INBRED C57BL; NANOPARTICLES; PARTICLE SIZE; SOLUBILITY; SOLVENTS; SURFACE-ACTIVE AGENTS;

EID: 84859106379     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2012.02.025     Document Type: Article

References (52)

1. Y. Arai, S. Watanabe, M. Kimira, K. Shimoi, R. Mochizuki, and N. Kinae Dietary intakes of flavonols, flavones and isoflavones by Japanese women and the inverse correlation between quercetin intake and plasma LDL cholesterol concentration J. Nutr. 130 2000 2243 2250
2. P. Becher Technique of emulsification Emulsions: Theory and Practice 1965 Reinhold Publishing Corp New York pp. 267-325
3. M. Böhl, S. Tietze, A. Sokoll, S. Madathil, F. Pfennig, J. Apostolakis, K. Fahmy, and H.O. Gutzeit Flavonoids affect actin functions in cytoplasm and nucleus Biophys. J. 93 2007 2767 2780
4. I. Capek Degradation of kinetically-stable o/w emulsions Adv. Colloid Interface Sci. 107 2004 125 155
5. C.S. Chien, K.H. Shen, J.S. Huang, S.C. Ko, and Y.W. Shih Antimetastatic potential of fisetin involves inactivation of the PI3K/Akt and JNK signaling pathways with downregulation of MMP-2/9 expressions in prostate cancer PC-3 cells Mol. Cell. Biochem. 333 2010 169 180
6. A. Constantinou, R. Mehta, C. Runyan, K. Rao, A. Vaughan, and R. Moon Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships J. Nat. Prod. 58 1995 217 225
7. A.A. Date, and M.S. Nagarsenker Parenteral microemulsions: an overview Int. J. Pharm. 355 2008 19 30
8. C.J. Edgell, C.C. McDonald, and J.B. Graham Permanent cell line expressing human factor VIII-related antigen established by hybridization Proc. Natl. Acad. Sci. U. S. A. 80 1983 3734 3737
9. A.G. Floyd Top ten considerations in the development of parenteral emulsions Pharm. Sci. Technol. Today 4 1999 134 143
10. T. Fotsis, M.S. Pepper, E. Aktas, S. Breit, S. Rasku, H. Adlercreutz, K. Wahala, R. Montesano, and L. Schweigerer Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis Cancer Res. 57 1997 2916 2921
11. S.C. Gad, C.D. Cassidy, N. Aubert, B. Spainhour, and H. Robbe Nonclinical vehicle use in studies by multiple routes in multiple species Int. J. Toxicol. 25 2006 499 521
12. S. Ganta, J.W. Paxton, B.C. Baguley, and S. Garg Pharmacokinetics and pharmacodynamics of chlorambucil delivered in parenteral emulsion Int. J. Pharm. 360 2008 115 121
13. M. Gibaldi, and D. Perrier Noncompartmental analysis based on statistical moment theory J. Swarbrick, Pharmacokinetics 1982 Marcel Dekker, Inc. New York and Basel 409 417
14. M.R. Guzzo, M. Uemi, P.M. Donate, S. Nikolaou, A.E. Machado, and L.T. Okano Study of the complexation of fisetin with cyclodextrins J. Phys. Chem. A 110 2006 10545 10551
15. M. Han, C.X. He, Q.L. Fang, X.C. Yang, Y.Y. Diao, D.H. Xu, Q.J. He, Y.Z. Hu, W.Q. Liang, B. Yang, and J.Q. Gao A novel camptothecin derivative incorporated in nano-carrier induced distinguished improvement in solubility, stability and anti-tumor activity both in vitro and in vivo Pharm. Res. 26 2009 926 935
16. B.H. Havsteen The biochemistry and medical significance of the flavonoids Pharmacol. Ther. 96 2002 67 202
17. Z. Hu, R. Tawa, T. Konishi, N. Shibata, and K. Takada A novel emulsifier, labrasol, enhances gastrointestinal absorption of gentamicin Life Sci. 69 2001 2899 2910
18. J. Jankun, S.H. Selman, J. Aniola, and E. Skrzypczak-Jankun Nutraceutical inhibitors of urokinase: potential applications in prostate cancer prevention and treatment Oncol. Rep. 16 2006 341 346
19. P. Kan, Z.B. Chen, C.J. Lee, and I.M. Chu Development of nonionic surfactant/phospholipid o/w emulsion as a paclitaxel delivery system J. Control. Release 58 1999 271 278
20. S. Kawakami, F. Yamashita, and M. Hashida Disposition characteristics of emulsions and incorporated drugs after systemic or local injection Adv. Drug Deliv. Rev. 45 2000 77 88
21. R.G. Kelmann, G. Kuminek, H.F. Teixeira, and L.S. Koester Carbamazepine parenteral nanoemulsions prepared by spontaneous emulsification process Int. J. Pharm. 342 2007 231 239
22. N. Khan, M. Asim, F. Afaq, Z.M. Abu, and H. Mukhtar A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice Cancer Res. 68 2008 8555 8563
23. M. Kimira, Y. Arai, K. Shimoi, and S. Watanabe Japanese intake of flavonoids and isoflavonoids from foods J. Epidemiol. 8 1998 168 175
24. T.R. Kommuru, B. Gurley, M.A. Khan, and I.K. Reddy Self-emulsifying drug delivery systems (SEDDS) of coenzyme Q10: formulation development and bioavailability assessment Int. J. Pharm. 212 2001 233 246
25. G. Leonarduzzi, G. Testa, B. Sottero, P. Gamba, and G. Poli Design and development of nanovehicle-based delivery systems for preventive or therapeutic supplementation with flavonoids Curr. Med. Chem. 17 2010 74 95
26. M. Lopez-Lazaro Flavonoids as anticancer agents: structure-activity relationship study Curr. Med. Chem. Anticancer Agents 2 2002 691 714
27. H. Lu, D.J. Chang, B. Baratte, L. Meijer, and U. Schulze-Gahmen Crystal structure of a human cyclin-dependent kinase 6 complex with a flavonol inhibitor, fisetin J. Med. Chem. 48 2005 737 743
28. X. Lu, J. Jung, H.J. Cho, D.Y. Lim, H.S. Lee, H.S. Chun, D.Y. Kwon, and J.H. Park Fisetin inhibits the activities of cyclin-dependent kinases leading to cell cycle arrest in HT-29 human colon cancer cells J. Nutr. 135 2005 2884 2890
29. E. Middleton Jr., C. Kandaswami, and T.C. Theoharides The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer Pharmacol. Rev. 52 2000 673 751
30. N. Mignet, J. Seguin, M. Ramos Romano, L. Brullé, Y.S. Touil, D. Scherman, M. Bessodes, and G.G. Chabot Development of a liposomal formulation of the natural flavonoid fisetin Int. J. Pharm. 423 2012 69 76
31. G. Mulak, and J. Cotty Solubilité et constante diélectrique Sci. Technol. Pharm. 4 1975 281 288
32. R.H. Müller, S. Schmidt, I. Buttle, A. Akkar, J. Schmitt, and S. Brömer SolEmuls-novel technology for the formulation of i.v. emulsions with poorly soluble drugs Int. J. Pharm. 269 2004 293 302
33. Y. Nishioka, and H. Yoshino Lymphatic targeting with nanoparticulate system Adv. Drug Deliv. Rev. 47 2001 55 64
34. A.O. Nornoo, D.W. Osborne, and D.S. Chow Cremophor-free intravenous microemulsions for paclitaxel I: formulation, cytotoxicity and hemolysis Int. J. Pharm. 349 2008 108 116
35. A.J. Olaharski, S.T. Mondrala, and D.A. Eastmond Chromosomal malsegregation and micronucleus induction in vitro by the DNA topoisomerase II inhibitor fisetin Mutat. Res. 582 2005 79 86
36. H.H. Park, S. Lee, J.M. Oh, M.S. Lee, K.H. Yoon, B.H. Park, J.W. Kim, H. Song, and S.H. Kim Anti-inflammatory activity of fisetin in human mast cells (HMC-1) Pharmacol. Res. 55 2007 31 37
37. S. Poullain-Termeau, S. Crauste-Manciet, D. Brossard, S. Muhamed, G. Nicolaos, R. Farinotti, C. Barthelemy, H. Robert, and P. Odou Effect of oil-in-water submicron emulsion surface charge on oral absorption of a poorly water-soluble drug in rats Drug Deliv. 15 2008 503 514
38. P.R. Reddy, and V. Venkateswarlu Pharmacokinetics and tissue distribution of etoposide delivered in long circulating parenteral emulsion J. Drug Target. 13 2005 543 553
39. D.K. Sarker Engineering of nanoemulsions for drug delivery Curr. Drug Deliv. 2 2005 297 310
40. D. Soma, J. Kitayama, H. Ishigami, S. Kaisaki, and H. Nagawa Different tissue distribution of paclitaxel with intravenous and intraperitoneal administration J. Surg. Res. 155 2009 142 146
41. R.G. Strickley Solubilizing excipients in oral and injectable formulations Pharm. Res. 21 2004 201 230
42. B. Sung, M.K. Pandey, and B.B. Aggarwal Fisetin, an inhibitor of cyclin-dependent kinase 6, down-regulates nuclear factor-kappaB-regulated cell proliferation, antiapoptotic and metastatic gene products through the suppression of TAK-1 and receptor-interacting protein-regulated IkappaBalpha kinase activation Mol. Pharmacol. 71 2007 1703 1714
43. Y.J. Surh Cancer chemoprevention with dietary phytochemicals Nat. Rev. Cancer 3 2003 768 780
44. T. Tadros, P. Izquierdo, J. Esquena, and C. Solans Formation and stability of nano-emulsions Adv. Colloid Interface Sci. 108-109 2004 303 318
45. J.B. Tagne, S. Kakumanu, and R.J. Nicolosi Nanoemulsion preparations of the anticancer drug dacarbazine significantly increase its efficacy in a xenograft mouse melanoma model Mol. Pharm. 5 2008 1055 1063
46. S. Tamilvanan Oil-in-water lipid emulsions: implications for parenteral and ocular delivering systems Prog. Lipid Res. 43 2004 489 533
47. Y.S. Touil, A. Fellous, D. Scherman, and G.G. Chabot Flavonoid-induced morphological modifications of endothelial cells through microtubule stabilization Nutr. Cancer 61 2009 310 321
48. Y.S. Touil, J. Seguin, D. Scherman, and G.G. Chabot Improved antiangiogenic and antitumour activity of the combination of the natural flavonoid fisetin and cyclophosphamide in Lewis lung carcinoma-bearing mice Cancer Chemother. Pharmacol. 68 2011 445 455
49. R. Tripathi, T. Samadder, S. Gupta, A. Surolia, and C. Shaha Anticancer activity of a combination of cisplatin and fisetin in embryonal carcinoma cells and xenograft tumors Mol. Cancer Ther. 10 2011 255 268
50. J.J. Wang, K.C. Sung, O.Y. Hu, C.H. Yeh, and J.Y. Fang Submicron lipid emulsion as a drug delivery system for nalbuphine and its prodrugs J. Control. Release 115 2006 140 149
51. J.E. Willson, D.E. Brown, and E.K. Timmens A toxicologic study of dimethyl sulfoxide Toxicol. Appl. Pharmacol. 7 1965 104 112
52. O.L. Woodman, and E.C. Chan Vascular and anti-oxidant actions of flavonols and flavones Clin. Exp. Pharmacol. Physiol. 31 2004 786 790