Lecithin-based novel cationic nanocarriers (Leciplex) II: Improving therapeutic efficacy of quercetin on oral administration

Molecular Pharmaceutics

Volumn 8, Issue 3, 2011, Pages 716-726

  Date, Abhijit A ^a   Nagarsenker, Mangal S ^a   Patere, Shilpa ^a   Dhawan, Vivek ^a   Gude, R P ^b   Hassan, P A ^c   Aswal, V ^c   Steiniger, Frank ^d   Thamm, Jana ^d   Fahr, Alfred ^d  

^a BOMBAY COLLEGE OF PHARMACY   (India)

^b TATA MEMORIAL HOSPITAL   (India)

^c BHABHA ATOMIC RESEARCH CENTRE   (India)

^d FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

antitumorigenic activity; lecithin; lipid nanoparticles; oral delivery; phospholipids; poor solubility; quercetin

Indexed keywords

PHOSPHATIDYLCHOLINE; QUERCETIN; SODIUM HYDROXIDE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG STABILITY; FEMALE; FLUORESCENCE SPECTROSCOPY; HUMAN; HUMAN CELL; IN VITRO STUDY; MELANOMA; MOUSE; NANOENCAPSULATION; NEUTRON SCATTERING; NONHUMAN; PARTICLE SIZE; PAW EDEMA; PRIORITY JOURNAL; RAT; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY; ZETA POTENTIAL;

ADMINISTRATION, ORAL; ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYOELECTRON MICROSCOPY; FEMALE; LECITHINS; MICROSCOPY, ELECTRON, TRANSMISSION; NANOPARTICLES; PHOSPHOLIPIDS; QUERCETIN; RATS; RATS, SPRAGUE-DAWLEY; SPECTROMETRY, FLUORESCENCE;

EID: 79958251735     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100305h     Document Type: Article

References (51)

1. Boots, A. W.; Haenen, G. R.; Bast, A. Health Effects of Quercetin: from Antioxidant to Nutraceutical Eur. J. Pharmacol. 2008, 585, 325-337
2. Harwood, M.; Danielewska-Nikiel, B.; Borzelleca, J. F.; Flamm, G. W.; Williams, G. M.; Lines, T. C. A Critical Review of the Data Related to the Safety of Quercetin and Lack of Evidence of In Vivo Toxicity, Including Lack of Genotoxic/Carcinogenic Properties Food Chem. Toxicol. 2007, 45, 2179-2205 (Pubitemid 47451573)
3. Ruiz, M. J.; Fernández, M.; Picó, Y.; Mañes, J.; Asensi, M.; Carda, C.; Asensio, G.; Estrela, J. M. Dietary Administration of High Doses of Pterostilbene and Quercetin to Mice is Not Toxic J. Agric. Food Chem. 2009, 57, 3180-3186
4. Rotelli, A. E.; Guardia, T.; Juárez, A. O.; de la Rocha, N. E.; Pelzer, L. E. Comparative Study of Flavonoids in Experimental Models of Inflammation Pharmacol. Res. 2003, 48, 601-606 (Pubitemid 38352778)
5. Joshi, D.; Naidu, P. S.; Singh, A.; Kulkarni, S. K. Protective Effect of Quercetin on Alcohol Abstinence-Induced Anxiety and Convulsions J. Med. Food 2005, 8, 392-396 (Pubitemid 41502425)
6. Lee, E. S.; Lee, H. E.; Shin, J. Y.; Yoon, S.; Moon, J. O. The Flavonoid Quercetin Inhibits Dimethylnitrosamine Induced Liver Damage in Rats J. Pharm. Pharmacol. 2003, 55, 1169-1174 (Pubitemid 36998660)
7. Ramos, S. Effects of Dietary Flavonoids on Apoptotic Pathways Related to Cancer Chemoprevention J. Nutr. Biochem. 2007, 18, 427-442 (Pubitemid 46874924)
8. Yuan, Z. P.; Chen, L. J.; Fan, L. Y.; Tang, M. H.; Yang, G. L.; Yang, H. S.; Du, X. B.; Wang, G. Q.; Yao, W. X.; Zhao, Q. M.; Ye, B.; Wang, R.; Diao, P.; Zhang, W.; Wu, H. B.; Zhao, X.; Wei, Y. Q. Liposomal Quercetin Efficiently Suppresses Growth of Solid Tumors in Murine Models Clin. Cancer Res. 2006, 12, 3193-3199 (Pubitemid 43837369)
9. Drewa, G.; Woźqak, A.; Pałgan, K.; Schachtschabel, D. O.; Grzanka, A.; Sujkowska, R. Influence of Quercetin on B16 Melanotic Melanoma Growth in C57BL/6 Mice and on Activity of Some Acid Hydrolases in Melanoma Tissue Neoplasma 2001, 8, 12-18 (Pubitemid 32167701)
10. Khaled, K. A.; El-Sayed, Y. M.; Al-Hadiya, B. M. Disposition of the Flavonoid Quercetin in Rats after Single Intravenous and Oral Doses Drug Dev. Ind. Pharm. 2003, 29, 397-403 (Pubitemid 36528607)
11. Gao, Y.; Wang, Y.; Ma, Y.; Yu, A.; Cai, F.; Shao, W.; Zhai, G. Formulation Optimization and in situ Absorption in Rat Intestinal Tract of Quercetin-Loaded Microemulsion Colloids Surf., B 2009, 71, 306-314
12. Kale, R.; Saraf, M.; Juvekar, A.; Tayade, P. Decreased B16F10 Melanoma Growth and Impaired Tumour Vascularization In BDF1Mice with Quercetin- Cyclodextrin Binary System J. Pharm. Pharmacol. 2006, 58, 1351-1358 (Pubitemid 44580565)
13. Li, H.; Zhao, X.; Ma, Y.; Zhai, G.; Li, L.; Lou, H. Enhancement of Gastrointestinal Absorption of Quercetin by Solid Lipid Nanoparticles J. Controlled Release 2009, 133, 238-244
14. Azuma, K.; Ippoushi, K.; Ito, H.; Higashio, H.; Terao, J. Combination of Lipids and Emulsifiers Enhances the Absorption of Orally Administered Quercetin in Rats J. Agric. Food Chem. 2002, 50, 1706-1712 (Pubitemid 34233251)
15. Takahashi, M.; Uechi, S.; Takara, K.; Asikin, Y.; Wada, K. Evaluation of an Oral Carrier System in Rats: Bioavailability and Antioxidant Properties of Liposome-Encapsulated Curcumin J. Agric. Food Chem. 2009, 57, 9141-9146
16. Chen, C. C.; Tsai, T. H.; Huang, Z. R.; Fang, J. Y. Effects of Lipophilic Emulsifiers on the Oral Administration of Lovastatin From Nanostructured Lipid Carriers: Physicochemical Characterization and Pharmacokinetics Eur. J. Pharm. Biopharm. 2010, 74, 474-482
17. Date, A. A.; Nagarsenker, M. S.; Srivastava, D.; Mulherkar, R.; Panicker, L.; Aswal, V. K.; Hassan, P. A.; Steiniger, F.; Thamm, J.; Fahr, A. Phospholipid Based Novel Cationic Nanocarriers (Leciplex) I: Fabrication, Characterization and Evaluation. Nanomedicine 2011, in press.
18. Wu, T. H.; Yen, F. L.; Lin, L. T.; Tsai, T. R.; Lin, C. C.; Cham, T. M. Preparation, Physicochemical Characterization, and Antioxidant Effects of Quercetin Nanoparticles Int. J. Pharm. 2008, 346, 160-168
19. Redkar, M.; Hassan, P. A.; Aswal, V.; Devarajan, P. Onion Phases of PEG-8 Distearate J. Pharm. Sci. 2007, 96, 2436-2445 (Pubitemid 47477898)
20. Ramadan, M. F. Quercetin Increases Antioxidant Activity of Soy Lecithin in a Triolein Model System LWT Food Sci. Technol. 2008, 41, 581-587
21. Liu, W.; Guo, R. Interaction of Flavonoid, Quercetin with Organized Molecular Assemblies of Nonionic Surfactant Colloids Surf., A 2006, 274, 192-199 (Pubitemid 43129431)
22. Leung, M. H.; Colangelo, H.; Kee, T. W. Encapsulation of Curcumin in Cationic Micelles Suppresses Alkaline Hydrolysis Langmuir 2008, 24, 5672-5675
23. Tyukavkina, N. A.; Pogodaeva, N. N. Ultraviolet Absorption of Flavonoids VIII. Ionization Constants of Kaempferol and Quercetin Chem. Nat. Compd. 1975, 11, 741-743
24. Nifli, A. P.; Theodoropoulos, P. A.; Munier, S.; Castagnino, C.; Roussakis, E.; Katerinopoulos, H. E.; Vercauteren, J.; Castanas, E. Quercetin Exhibits a Specific Fluorescence in Cellular Milieu: a Valuable Tool for the Study of its Intracellular Distribution J. Agric. Food Chem. 2007, 55, 2873-2878 (Pubitemid 46668292)
25. Khumsupan, P.; Ramirez, R.; Khumsupan, D.; Narayanaswami, V. Apolipoprotein E LDL Receptor-Binding Domain-Containing High-Density Lipoprotein: a Nanovehicle to Transport Curcumin, an Antioxidant and Anti-Amyloid Bioflavonoid Biochim. Biophys. Acta 2011, 1808, 352-359
26. Liu, H. B.; Yu, D.; Shin, S. C.; Park, H. R.; Park, J. K.; Bark, K. M. Spectroscopic Properties of Quercetin Derivatives, Quercetin-3-O-rhamnoside and Quercetin-3-O-rutinoside, in Hydro-Organic Mixed Solvents Photochem. Photobiol. 2009, 85, 934-942
27. Sengupta, B.; Sengupta, P. K. Binding of Quercetin with Human Serum Albumin: a Critical Spectroscopic Study Biopolymers 2003, 72, 427-434 (Pubitemid 37413220)
28. Schmiedel, H.; Almásy, L.; Klose, G. Multilamellarity, Structure and Hydration of Extruded POPC Vesicles by SANS Eur. Biophys. J. 2006, 35, 181-189 (Pubitemid 43221177)
29. Grillo, I.; Penfold, J.; Tucker, I.; Cousin, F. Spontaneous Formation of Nanovesicles in Mixtures of Nonionic and Dialkyl Chain Cationic Surfactants Studied by Surface Tension And SANS Langmuir 2009, 25, 3932-3943
30. Yue, B.; Huang, C. Y.; Nieh, M. P.; Glinka, C. J.; Katsaras, J. Highly Stable Phospholipid Unilamellar Vesicles from Spontaneous Vesiculation: A DLS and SANS Study J. Phys. Chem. B 2005, 109, 609-616 (Pubitemid 40121007)
31. Aswal, V. K.; Haldar, J.; De, S.; Goyald, P. S.; Bhattacharya, S. Characterization of Vesicles From Ion-Paired Gemini Surfactants by Small Angle Neutron Scattering Phys. Chem. Chem. Phys. 2003, 5, 907-910
32. Zheng, Y.; Haworth, I. S.; Zuo, Z.; Chow, M. S.; Chow, A. H. Physicochemical and Structural Characterization of Quercetin-Beta-Cyclodextrin Complexes J. Pharm. Sci. 2005, 94, 1079-1089 (Pubitemid 40780774)
33. Yang, L. J.; Li, P.; Gao, Y. J.; Wu, D. C. Qualitative Observation of Chemical Change Rate for Quercetin in Basic Medium Characterized by Time Resolved UV-Vis Spectroscopy J. Mol. Liq. 2010, 151, 134-137
34. Caltagirone, S.; Rossi, C.; Poggi, A.; Ranelletti, F. O.; Natali, P. G.; Brunetti, M.; Aiello, F. B.; Piantelli, M. Flavonoids Apigenin and Quercetin Inhibit Melanoma Growth and Metastatic Potential Int. J. Cancer 2000, 87, 595-600 (Pubitemid 30639822)
35. Chen, C.; Han, D.; Cai, C.; Tang, X. An Overview of Liposome Lyophilization and its Future Potential J. Controlled Release 2010, 142, 299-311
36. Canty, D. J.; Zeisel, S. H. Lecithin and Choline in Human Health and Disease Nutr. Rev. 1994, 52, 327-339 (Pubitemid 24349550)
37. Gershanik, T.; Benita, S. Positively Charged Self-Emulsifying Oil Formulation for Improving Oral Bioavailability of Progesterone Pharm. Dev. Technol. 1996, 1, 147-157
38. Gershanik, T.; Benzeno, S.; Benita, S. Interaction of a Self-Emulsifying Lipid Drug Delivery System with the Everted Rat Intestinal Mucosa as a Function of Droplet Size and Surface Charge Pharm. Res. 1998, 15, 863-869 (Pubitemid 28307827)
39. Jain, V.; Prasad, V.; Jadhav, P.; Mishra, P. R. Preparation and Performance Evaluation of Saquinavir Laden Cationic Submicron Emulsions Drug Deliv. 2009, 16, 37-44
40. Liu, D.; Liu, C.; Zou, W.; Zhang, N. Enhanced Gastrointestinal Absorption of N3- O -Toluylfluorouracil by Cationic Solid Lipid Nanoparticles J. Nanoparticle Res. 2010, 57, 284-290
41. Bala, I.; Bhardwaj, V.; Hariharan, S.; Kharade, S. V.; Roy, N.; Ravi Kumar, M. N. Sustained Release Nanoparticulate Formulation Containing Antioxidant-Ellagic Acid as Potential Prophylaxis System for Oral Administration J. Drug Target. 2006, 14, 27-34
42. Delongeas, J. L.; de Conchard, G. V.; Beamonte, A.; Bertheux, H.; Spire, C.; Maisonneuve, C.; Becourt-Lhote, N.; Goldfain-Blanc, F.; Claude, N. Assessment of Labrasol(R)/Labrafil(R)/Transcutol(R) (4/4/2, V/V/V) as a Non-Clinical Vehicle for Poorly Water-Soluble Compounds after 4-Week Oral Toxicity Study in Wistar Rats Regul. Toxicol. Pharmacol. 2010, 12, 975-984
43. Yin, Y. M.; Cui, F. D.; Mu, C. F.; Choi, M. K.; Kim, J. S.; Chung, S. J.; Shim, C. K.; Kim, D. D. Docetaxel Microemulsion for Enhanced Oral Bioavailability: Preparation and In Vitro and In Vivo Evaluation J. Controlled Release 2009, 140, 86-94
44. Shishu, R. S. Kamalpreet; Development of Novel Microemulsion-Based Topical Formulations of Acyclovir for the Treatment of Cutaneous Herpetic Infections AAPSPharmSciTech 2009, 10, 559-565
45. Bhardwaj, V.; Ankola, D. D.; Gupta, S. C.; Schneider, M.; Lehr, C. M.; Kumar., M. N. PLGA Nanoparticles Stabilized with Cationic Surfactant: Safety Studies and Application in Oral Delivery of Paclitaxel to Treat Chemical-Induced Breast Cancer in Rat Pharm. Res. 2009, 26, 2495-2503
46. Cui, Z.; Qiu, F.; Sloat, B. R. Lecithin-based Cationic Nanoparticles as a Potential DNA Delivery System Int. J. Pharm. 2006, 313, 206-213
47. Nait Chabane, M.; Al Ahmad, A.; Peluso, J.; Muller, C. D.; Ubeaud, G. Quercetin and Naringenin Transport Across Human Intestinal Caco-2 Cells J. Pharm. Pharmacol. 2009, 61, 1473-1483
48. Wen, X.; Walle, T. Methylated Flavonoids Have Greatly Improved Intestinal Absorption and Metabolic Stability Drug Metab. Dispos. 2006, 34, 1786-1792 (Pubitemid 44427483)
49. Rogerio, A. P.; Dora, C. L.; Andrade, E. L.; Chaves, J. S.; Silva, L. F.; Lemos-Senna, E.; Calixto, J. B. Anti-Inflammatory Effect of Quercetin-Loaded Microemulsion in the Airways Allergic Inflammatory Model in Mice Pharmacol. Res. 2010, 61, 288-297
50. Rothwell, J. A.; Day, A. J.; Morgan, M. R. Experimental Determination of Octanol-Water Partition Coefficients of Quercetin and Related Flavonoids J. Agric. Food Chem. 2005, 53, 4355-4360 (Pubitemid 40855457)
51. Nishimukai, M.; Hara, H.; Aoyama, Y. Enteral Administration of Soybean Lecithin Enhanced Lymphatic Absorption of Triacylglycerol in Rats Br. J. Nutr. 2003, 90, 565-571 (Pubitemid 37168355)