Nanoemulsion-based delivery systems for poorly water-soluble bioactive compounds: Influence of formulation parameters on polymethoxyflavone crystallization

Food Hydrocolloids

Volumn 27, Issue 2, 2012, Pages 517-528

  Li, Yan ^a   Zheng, Jinkai ^a   Xiao, Hang ^a   McClements, David Julian ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

Bioavailability; Crystallization; Delivery systems; Emulsion; Functional foods; Nanoemulsion; Nutraceuticals; PMF; Polymethoxyflavones; Poorly water soluble drugs

Indexed keywords

CITRUS; ZEA MAYS;

EID: 84855194898     PISSN: 0268005X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodhyd.2011.08.017     Document Type: Article

References (62)

1. Acosta E. Bioavailability of nanoparticles in nutrient and nutraceutical delivery. Current Opinion in Colloid & Interface Science 2009, 14(1):3-15.
2. Ali W., Williams A.C., Rawlinson C.F. Stochiometrically governed molecular interactions in drug: poloxamer solid dispersions. International Journal of Pharmaceutics 2010, 391(1-2):162-168.
3. Araya H., Tomita M., Hayashi M. The novel formulation design of O/W microemulsion for improving the gastrointestinal absorption of poorly water soluble compounds. International Journal of Pharmaceutics 2005, 305(1-2):61-74.
4. Barakat N.S. Self-emulsifying system for improving drug dissolution and bioavailability: invitro/invivo evaluation. Drug Development Research 2010, 71(2):149-158.
5. Bevernage J., Brouwers J., Clarysse S., Vertzoni M., Tack J., Annaert P., et al. Drug supersaturation in simulated and human intestinal fluids representing different nutritional states. Journal of Pharmaceutical Sciences 2010, 99(11):4525-4534.
6. Bovicelli P., D'Angelo V., Collalto D., Verzina A., D'Antona N., Lambusta D. Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones. Journal of Pharmacy and Pharmacology 2007, 59(12):1697-1701.
7. Brouwers J., Brewster M.E., Augustijns P. Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability?. Journal of Pharmaceutical Sciences 2009, 98(8):2549-2572.
8. Burcham D.L., Maurin M.B., Hausner E.A., Huang S.M. Improved oral bioavailability of the hypocholesterolemic DMP 565 in dogs following oral dosing in oil and glycol solutions. Biopharmaceutics & Drug Disposition 1997, 18(8):737-742.
9. Chakraborty S., Shukla D., Mishra B., Singh S. Lipid - an emerging platform for oral delivery of drugs with poor bioavailability. European Journal of Pharmaceutics and Biopharmaceutics 2009, 73(1):1-15.
10. Dong P., Qiu P., Zhu Y., Li S., Ho C.T., McClements D.J., et al. Simultaneous determination of four 5-hydroxy polymethoxyflavones by reversed-phase high performance liquid chromatography with electrochemical detection. Journal of Chromatography A 2010, 1217(5):642-647.
11. Feltham D.L., Garside J. Amathematical model of crystallization in an emulsion. Journal of Chemical Physics 2005, 122(17).
12. Fredrick E., Walstra P., Dewettinck K. Factors governing partial coalescence in oil-in-water emulsions. Advances in Colloid and Interface Science 2010, 153(1-2):30-42.
13. Gao P., Rush B.D., Pfund W.P., Huang T., Bauer J.M., Morozowich W., et al. Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability. Journal of Pharmaceutical Sciences 2003, 92(12):2386-2398.
14. Hageman M.J. Preformulation designed to enable discovery and assess developability. Combinatorial Chemistry & High Throughput Screening 2010, 13(2):90-100.
15. He C.X., He Z.G., Gao J.Q. Microemulsions as drug delivery systems to improve the solubility and the bioavailability of poorly water-soluble drugs. Expert Opinion on Drug Delivery 2010, 7(4):445-460.
16. Hirata T., Fujii M., Akita K., Yanaka N., Ogawa K., Kuroyanagi M., et al. Identification and physiological evaluation of the components from Citrus fruits as potential drugs for anti-corpulence and anticancer. Bioorganic & Medicinal Chemistry 2009, 17(1):25-28.
17. Jafari S., He Y., Bhandari B. Optimization of nano-emulsions production by microfluidization. European Food Research and Technology 2007, 225(5):733-741.
18. Jafari S.M., Assadpoor E., He Y.H., Bhandari B. Re-coalescence of emulsion droplets during high-energy emulsification. Food Hydrocolloids 2008, 22(7):1191-1202.
19. Kabalnov A. Ostwald ripening and related phenomena. Journal of Dispersion Science and Technology 2001, 22(1):1-12.
20. Kawakami K., Yoshikawa T., Moroto Y., Kanaoka E., Takahashi K., Nishihara Y., et al. Microemulsion formulation for enhanced absorption of poorly soluble drugs: I. Prescription design. Journal of Controlled Release 2002, 81(1-2):65-74.
21. Kinoshita T., Firman K. Highly oxygenated flavonoids from Murraya paniculata. Phytochemistry 1996, 42(4):1207-1210.
22. Kleberg K., Jacobsen J., Mullertz A. Characterising the behaviour of poorly water soluble drugs in the intestine: application of biorelevant media for solubility, dissolution and transport studies. Journal of Pharmacy and Pharmacology 2010, 62(11):1656-1668.
23. Kohli K., Chopra S., Dhar D., Arora S., Khar R.K. Self-emulsifying drug delivery systems: an approach to enhance oral bioavailability. Drug Discovery Today 2010, 15(21-22):958-965.
24. Kohno H., Yoshitani S., Tsukio Y., Murakami A., Koshimizu K., Yano M., et al. Dietary administration of citrus nobiletin inhibits azoxymethane-induced colonic aberrant crypt foci in rats. Life Sciences 2001, 69(8):901-913.
25. Kourniatis L.R., Spinelli L.S., Piombini C.R., Mansur C.R.E. Formation of orange oil-in-water nanoemulsions using nonionic surfactant mixtures by high pressure homogenizer. Colloid Journal 2010, 72(3):396-402.
26. Lai C.-S., Li S., Chai C.-Y., Lo C.-Y., Dushenkov S., Ho C.-T., et al. Anti-inflammatory and antitumor promotional effects of a novel urinary metabolite, 3',4'-didemethylnobiletin, derived from nobiletin. Carcinogenesis 2008, 29(12):2415-2424.
27. Lai C.-S., Li S., Chai C.-Y., Lo C.-Y., Ho C.-T., Wang Y.-J., et al. Inhibitory effect of citrus 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone on 12-O-tetradecanoylphorbol 13-acetate-induced skin inflammation and tumor promotion in mice. Carcinogenesis 2007, 28(12):2581-2588.
28. Li S., Lo C.-Y., Ho C.-T. Hydroxylated polymethoxyflavones and methylated flavonoids in sweet orange (Citrus sinensis) peel. Journal of Agricultural and Food Chemistry 2006, 54(12):4176-4185.
29. Li S., Pan M.-H., Lai C.-S., Lo C.-Y., Dushenkov S., Ho C.-T. Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines. Bioorganic & Medicinal Chemistry 2007, 15(10):3381-3389.
30. Li S., Pan M.-H., Lo C.-Y., Tan D., Wang Y., Shahidi F., et al. Chemistry and health effects of polymethoxyflavones and hydroxylated polymethoxyflavones. Journal of Functional Foods 2009, 1(1):2-12.
31. Li S., Wang Z., Sang S., Huang M.-T., Ho C.-T. Identification of nobiletin metabolites in mouse urine. Molecular Nutrition & Food Research 2006, 50(3):291-299.
32. Lindfors L., Forssen S., Westergren J., Olsson U. Nucleation and crystal growth in supersaturated solutions of a model drug. Journal of Colloid and Interface Science 2008, 325(2):404-413.
33. McClements D.J. Food emulsions: Principles, practice, and techniques 2005, CRC Press, Boca Raton. 2nded.
34. McClements D.J. Emulsion design to improve the delivery of functional lipophilic components. In Annual Review of Food Science and Technology 2010, 1:241-269.
35. McClements D.J. Edible nanoemulsions: fabrication, properties, and functional performance. Soft Matter 2011.
36. McClements D.J., Li Y. Structured emulsion-based delivery systems: Controlling the digestion and release of lipophilic food components. Advances in Colloid and Interface Science 2010, 159(2):213-228.
37. McClements D.J., Rao J. Food-grade nanoemulsions: formulation, fabrication, properties, performance, biological fate, and potential toxicity. Critical Reviews in Food Science and Nutrition 2011, 51(4):285-330.
38. Muller R.H., Mader K., Gohla S. Solid lipid nanoparticles (SLN) for controlled drug delivery - a review of the state of the art. European Journal of Pharmaceutics and Biopharmaceutics 2000, 50(1):161-177.
39. Müllertz A., Ogbonna A., Ren S., Rades T. New perspectives on lipid and surfactant based drug delivery systems for oral delivery of poorly soluble drugs. Journal of Pharmacy and Pharmacology 2010, 62(11):1622-1636.
40. Neslihan Gursoy R., Benita S. Self-emulsifying drug delivery systems (SEDDS) for improved oral delivery of lipophilic drugs. Biomedecine & Pharmacotherapy 2004, 58(3):173-182.
41. Okuno Y., Miyazawa M. Biotransformation of nobiletin by Aspergillus niger and the antimutagenic activity of a metabolite, 4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone. Journal of Natural Products 2004, 67(11):1876-1878.
42. Porter C.J.H., Trevaskis N.L., Charman W.N. Lipids and lipid-based formulations: optimizing the oral delivery of lipophilic drugs. Nature Reviews Drug Discovery 2007, 6(3):231-248.
43. Poullain-Termeau S., Crauste-Manciet S., Brossard D., Muhamed S., Nicolaos G., Farinotti R., et al. Effect of oil-in-water submicron emulsion surface charge on oral absorption of a poorly water-soluble drug in rats. Drug Delivery 2008, 15(8):503-514.
44. Pouton C.W. Formulation of poorly water-soluble drugs for oral administration: physicochemical and physiological issues and the lipid formulation classification system. European Journal of Pharmaceutical Sciences 2006, 29(3-4):278-287.
45. Pouton C.W., Porter C.J.H. Formulation of lipid-based delivery systems for oral administration: Materials, methods and strategies. Advanced Drug Delivery Reviews 2008, 60(6):625-637.
46. Qian C., McClements D. Formation of nanoemulsions stabilized by model food-grade emulsifiers using high pressure homogenization: factors affecting particle size. Food Hydrocolloids 2010.
47. Rhee Y.S., Mansour H.M. Nanopharmaceuticals I: nanocarrier systems in drug delivery. International Journal of Nanotechnology 2011, 8(1-2):84-114.
48. Rousseau D. Fat crystals and emulsion stability - a review. Food Research International 2000, 33(1):3-14.
49. Sato K. Solidification and phase transformation behaviour of food fats - a review. Fett-Lipid 1999, 101(12):467-474.
50. Sergeev I.N., Ho C.-T., Li S., Colby J., Dushenkov S. Apoptosis-inducing activity of hydroxylated polymethoxyflavones and polymethoxyflavones from orange peel in human breast cancer cells. Molecular Nutrition & Food Research 2007, 51(12):1478-1484.
51. Sergeev I.N., Li S., Colby J., Ho C.-T., Dushenkov S. Polymethoxylated flavones induce Ca2+-mediated apoptosis in breast cancer cells. Life Sciences 2006, 80(3):245-253.
52. Setthacheewakul S., Mahattanadul S., Phadoongsombut N., Pichayakorn W., Wiwattanapatapee R. Development and evaluation of self-microemulsifying liquid and pellet formulations of curcumin, and absorption studies in rats. European Journal of Pharmaceutics and Biopharmaceutics 2010, 76(3):475-485.
53. Sinha S., Baboota S., Ali M., Kumar A., Ali J. Solid dispersion: an alternative technique for bioavailability enhancement of poorly soluble drugs. Journal of Dispersion Science & Technology 2009, 30(10):1458-1473.
54. Sjöström B., Bergenståhl B., Kronberg B. Amethod for the preparation of submicron particles of sparingly water-soluble drugs by precipitation in oil-in-water emulsions. II: influence of the emulsifier, the solvent, and the drug substance. Journal of Pharmaceutical Sciences 1993, 82(6):584-589.
55. Sjöstrom B., Kronberg B., Carlfors J. Amethod for the preparation of submicron particles of sparingly water-soluble drugs by precipitation in oil-in-water emulsions. I: influence of emulsification and surfactant concentration. Journal of Pharmaceutical Sciences 1993, 82(6):579-583.
56. Tsukayama M., Kusunoki E., Hossain M.M., Kawamura Y., Hayashi S. Microwave-assisted efficient synthesis of polymethoxyacetophenones and natural polymethoxyflavones, and their inhibitory effects on melanogenesis. Heterocycles 2007, 71(7):1589-1600.
57. Wang D., Wang J., Huang X., Tu Y., Ni K. Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques. Journal of Pharmaceutical and Biomedical Analysis 2007, 44(1):63-69.
58. Warren D.B., Benameur H., Porter C.J.H., Pouton C.W. Using polymeric precipitation inhibitors to improve the absorption of poorly water-soluble drugs: a mechanistic basis for utility. Journal of Drug Targeting 2010, 18(10):704-731.
59. Wissing S.A., Kayser O., Muller R.H. Solid lipid nanoparticles for parenteral drug delivery. Advanced Drug Delivery Reviews 2004, 56(9):1257-1272.
60. Wooster T., Golding M., Sanguansri P. Impact of oil type on nanoemulsion formation and Ostwald ripening stability. Langmuir 2008, 24(22):12758-12765.
61. Xiao H., Yang C.S., Li S., Jin H., Ho C.-T., Patel T. Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel Inhibit growth of human lung cancer cells by apoptosis. Molecular Nutrition & Food Research 2009, 53(3):398-406.
62. Yoo J., Shanmugam S., Thapa P., Lee E.-S., Balakrishnan P., Baskaran R., et al. Novel self-nanoemulsifying drug delivery system for enhanced solubility and dissolution of lutein. Archives of Pharmacal Research 2010, 33(3):417-426.