Stearic acid-g-chitosan polymeric micelle for oral drug delivery: In vitro transport and in vivo absorption

Molecular Pharmaceutics

Volumn 8, Issue 1, 2011, Pages 225-238

  Yuan, Hong ^a   Lu, Lin Juan ^a   Du, Yong Zhong ^a   Hu, Fu Qiang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Amino substitution degree; Caco 2 cells; Chitosan; Micelles; Oral delivery; P glycoprotein

Indexed keywords

CHITOSAN DERIVATIVE; DOXORUBICIN; DRUG VEHICLE; STEARIC ACID DERIVATIVE; STEARIC ACID G CHITOSAN; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; CELL TRANSPORT; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; CYTOTOXICITY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DELIVERY SYSTEM; DRUG PENETRATION; DRUG TRANSPORT; ELECTRIC RESISTANCE; GASTROINTESTINAL TRACT; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; IN VIVO STUDY; MALE; MICELLE; MONOLAYER CULTURE; NONHUMAN; PARTICLE SIZE; PH; PINOCYTOSIS; PRIORITY JOURNAL; RAT; SYNTHESIS; TEMPERATURE; TIGHT JUNCTION; TRANSCYTOSIS; TRANSEPITHELIAL ELECTRICAL RESISTANCE; ZETA POTENTIAL;

CACO-2 CELLS; CELL SURVIVAL; CHITOSAN; DOXORUBICIN; DRUG CARRIERS; HUMANS; HYDROGEN-ION CONCENTRATION; MICELLES; MICROSCOPY, ELECTRON, TRANSMISSION; P-GLYCOPROTEIN; POLYMERS; STEARIC ACIDS;

EID: 79952950503     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100289v     Document Type: Article

References (62)

1. Nishiyama, N.; Kataoka, K. Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery. Pharmacol. Ther. 2006, 112, 630-648. (Pubitemid 44592613)
2. Nakanishi, T.; Fukushima, S.; Okamoto, K.; Suzuki, M.; Matsumura, Y.; Yokoyama, M.; Okano, T.; Sakurai, Y.; Kataoka, K. Development of the polymer micelle carrier system for doxorubicin. J. Controlled Release 2001, 74, 295-302. (Pubitemid 32727635)
3. Rijcken, C. J. F.; Soga, O.; Hennink, W. E.; van Nostrum, C. F. Triggered de-stabilisation of polymeric micelles and vesicles by changing polymers polarity: An attractive tool for drug delivery. J. Controlled Release 2007, 120, 131-148. (Pubitemid 47058635)
4. Discher, D. E.; Eisenberg, A. Polymer vesicles. Science 2002, 297, 967-973. (Pubitemid 34856022)
5. Mathot, F.; van Beijsterveldt, L.; Preat, V.; Brewster, M.; Arien, A. Intestinal uptake and biodistribution of novel polymeric micelles after oral administration. J. Controlled Release 2006, 111, 47-55. (Pubitemid 43289994)
6. Sant, V. P.; Smith, D.; Leroux, J. C. Enhancement of oral bioavailability of poorly water-soluble drugs by poly (ethylene glycol)-block-poly(alkyl- acrylate-co-methacrylic acid)self-assemblies. J. Controlled Release 2005, 104, 289-300. (Pubitemid 40724930)
7. Gaucher, G.; Satturwar, P.; Jones, M. C.; Furtos, A.; Leroux, J. C. Polymeric micelles for oral drug delivery. Eur. J. Pharm. Sci. 2010, 76, 147-158.
8. Francis, M. F.; Cristea, M.; Winnik, F. M. Polymeric micelles for oral drug delivery: why and how. Pure Appl. Chem. 2004, 76, 1321-1335.
9. Gaucher, G.; Dufresne, M. H.; Sant, V. P.; Kang, N.; Maysinger, D. J.; Leroux, C. Block copolymer micelles: preparation, characterization and application in drug delivery. J. Controlled Release 2005, 109, 169-188. (Pubitemid 41742123)
10. Grabovac, V.; Guggi, D.; Bernkop-Schnurch, A. Comparison of the mucoadhesive properties of various polymers. Adv. Drug Delivery Rev. 2005, 57, 1713-1723. (Pubitemid 41443475)
11. Hejazi, R.; Amiji, M. Chitosan-based gastrointestinal delivery systems. J. Controlled Release 2003, 89, 151-165. (Pubitemid 36507012)
12. Lee, E.; Lee, J.; Lee, I. H.; Yu, M.; Kim, H.; Chae, S. Y.; Jon, S. Conjugated chitosan as a novel platform for oral delivery of paclitaxel. J. Med. Chem. 2008, 51, 6442-6449.
13. Hernandez-Lauzardo, A. N.; Bautista-Banos, S.; Velazquez-del Valle, M. G.; Mendez-Montealvo, M. G.; Sanchez-Rivera, M. M.; Bello-Perez, L. A. Antifungal effects of chitosan with different molecular weights on in vitro development of Rhizopus stolonifer (Ehrenb: Fr.) Vuill. Carbohydr. Polym. 2008, 73, 541-547. (Pubitemid 351658955)
14. Opanasopit, P.; Ngawhirunpat, T.; Chaidedgumjorn, A.; Rojanarata, T.; Apirakaramwong, A.; Phongying, S.; Choochottiros, C.; Chirachanchai, S. Incorporation of camptothecin into N-phthaloyl chitosan-mPEG self-assembly micellar system. Eur. J. Pharm. Biopharm. 2006, 64, 269-276. (Pubitemid 44585206)
15. Zhang, C.; Ping, Q. N.; Zhang, H. Self-assembly and characterization of paclitaxe-loaded N-octyl-O-sulfate chitosan micellar system. Colloids Surf., B 2004, 39, 69-75. (Pubitemid 39473356)
16. Hu, F. Q.; Zhao, M. D.; Yuan, H.; You, J. A novel chitosan oligosaccharide-stearic acid micelles for gene delivery: properties and in vitro transfection studies. Int. J. Pharm. 2006, 315, 158-166. (Pubitemid 43674116)
17. Hu, F. Q.; Ren, G. F.; Yuan, H.; Du, Y. Z.; Zeng, S. Shell cross-linked stearic acid grafted chitosan oligosaccharide self-aggregated micelles for controlled release of paclitaxel. Colloids Surf., B 2006, 50, 97-103. (Pubitemid 43946659)
18. Hu, F. Q.; Liu, L. N.; Du, Y. Z.; Yuan, H. Synthesis and antitumor activity of doxorubicin conjugated stearic acid-g-chitosan oligosaccharide polymeric micelles. Biomaterials 2009, 30, 6955-6963.
19. Camenisch, G.; Alsenz, J.; vande Waterbeemd, H.; Folkers, G. Estimation of permeability by passive diffusion through Caco-2 cell monolayers using the drugs' lipophilicity and molecular weight. Eur. J. Pharm. Sci. 1998, 6, 313-319. (Pubitemid 28468539)
20. Van der Sandt, I.C. J.; Blom-Roosemalen, M.C M.; Boer, A. G.; Breimer, D. D. Specificity of doxorubicin versus rhodamine-123 in assessing P-glycoprotein functionality in the LLC-PK1, LLCPK1: MDR1 and Caco-2 cell lines. Eur. J. Pharm. Sci. 2000, 11, 207-214. (Pubitemid 30616443)
21. Huang, M.; Ma, Z.; Khor, E.; Lim, L. Y. Uptake of FITC-chitosan nanoparticles by A549 cells. Pharm. Res. 2002, 19, 1488-1494. (Pubitemid 35266553)
22. Kohori, F.; Yokoyama, M.; Sakai, K.; Okanob, T. Process design for efficient and controlled drug incorporation into polymeric micelle carrier systems. J. Controlled Release 2002, 78, 155-163. (Pubitemid 34081861)
23. Hu, F. Q.; Wu, X. L.; Du, Y. Z.; You, J.; Yuan, H. Cellular uptake and cytotoxicity of shell cross-linked stearic acid-grafted chitosan oligosaccharide micelles encapsulating doxorubicin. Eur. J. Pharm. Biopharm. 2008, 69, 117-125. (Pubitemid 351467161)
24. Panyam, J.; Zhou, W. Z.; Prabha, S.; Sahoo, S. K.; Labhasetwar, V. Rapid endo-lysosomal escape of poly(D,L-lactide-co-glycolide) nanoparticle; Implication for drug and gene delivery. J. FASEB 2002, 16, 1217-1226. (Pubitemid 34815409)
25. Paruchuri, V. K.; Nguyen, A. V.; Miller, J. D. Zeta-potentials of self assembled surface micelles of ionic surfactants adsorbed at hydrophobic graphite surfaces. Colloids Surf., A 2004, 250, 519-526. (Pubitemid 39610831)
26. Sandri, G.; Bonferoni, M. C.; Rossi, S.; Ferrari, F.; Gibin, S.; Zambito, Y.; Colo, D. G.; Caramella, C. Nanoparticles based on N-trimethylchitosan: Evaluation of absorption properties using in vitro (Caco-2 cells) and ex-vivo (excised rat jejunum) models. Eur. J. Pharm. Biopharm. 2007, 65, 68-77. (Pubitemid 44827693)
27. Behrens, I.; Kissel, T. Do cell culture conditions influence the carrier-mediated transport of peptides in Caco-2 cell monolayers? Eur. J. Pharm. Sci. 2003, 19, 433-442. (Pubitemid 36952405)
28. Moyes, S. M.; Morris, J. F.; Carr, K. E. Culture conditions and treatments affect Caco-2 characteristics and particle uptake. Int. J. Pharm. 2010, 387, 7-18.
29. Wang, X. D.; Meng, M. X.; Gao, L. B. Permeation of astilbin and taxifolin in Caco-2 cell and their effects on the P-gp. Int. J. Pharm. 2009, 378, 1-8.
30. Mathot, F.; Beijsterveldt, L.; Preat, V.; Brewster, M. Intestinal uptake and bio-distribution of novel polymeric micelles after oral administration. J. Controlled Release 2006, 111, 47-55. (Pubitemid 43289994)
31. Unezaki, S.; Maruyama, K.; Hosoda, J. I.; Nagae, I.; Koyanagi, Y.; Nakata, M.; Ishida, O.; Iwatsuru, M.; Tsuchiya, S. Direct measurement of the extravasation of polyethyleneglycol-coated liposomes into solid tumor tissue by in vivo fluorescence microscopy. Int. J. Pharm. 1996, 144, 11-17. (Pubitemid 27039339)
32. Gabizon, A. A.; Shmeeda, H.; Zalipsky, S. Pros and cons of the liposome platform in cancer drug targeting. J. Lipid Res. 2006, 16, 175-183. (Pubitemid 44358991)
33. Bruesewitz, C.; Funke, A.; Kuhland, U.; Wagner, T.; Lipp, R. Comparison of permeation enhancing strategies for an oral factor Xa inhibitor using the Caco-2 cell monolayer model. Eur. J. Pharm. Biopharm. 2006, 64, 229-237. (Pubitemid 44291995)
34. Chaumeil, J. C. Micronization: a method of improving the bioavailability of poorly soluble drugs, Methods Find. Exp. Clin. Pharmacol. 1998, 20, 211-215. (Pubitemid 28255411)
35. Serajuddin, A. T. M. Salt formation to improve drug solubility. Adv. Drug Delivery Rev. 2007, 59, 603-616. (Pubitemid 47285406)
36. Stella, V.J. K.; Nti-Addae, W. Prodrug strategies to overcome poor water solubility. Adv. Drug Delivery Rev. 2007, 59, 677-694.
37. Yin, Y.; Chen, D.; Qiao, M.; Lu, Z.; Hu, H. Preparation and evaluation of lectin conjugates PLGA nanoparticles for oral delivery of thymopentin. J. Controlled Release 2006, 116, 337-345. (Pubitemid 44827411)
38. Alphandary, P. H.; Aboubakar, M.; Jaillard, D.; Couvreur, P.; Vauthier, C. Visualization of insulin-loaded nanocapsules: in vitro and in vivo studies after oral administration to rats. Pharm. Res. 2003, 20, 1071-1084. (Pubitemid 36774279)
39. Alonso-Romanowski, S.; Chiaramoni, N. S.; Lioy, V. S.; Gargini, R. A.; Viera, L. I.; Taira, M. C. Characterization of diacetylenic liposomes as carriers for oral vaccines. Chem. Phys. Lipids 2003, 122, 191-203. (Pubitemid 36207526)
40. Okada, J.; Cohen, S.; Langer, R. In vitro evaluation of polymerized liposomes as an oral drug delivery system. Pharm. Res. 1995, 12, 576-582.
41. Liu, J.; Zeng, F.; Allen, C. In vivo fate of unimers and micelles of poly (ethylene glycol)-block-poly (caprolactone) copolymer in mice following intravenous administration. Eur. J. Pharm. Biopharm. 2007, 65, 309-319.
42. Yu, Q. H.; Yang, Q. Diversity of tight junctions (TJs) between gastrointestinal epithelial cells and their function in maintaining the mucosal barrier. Cell Biol. Int. 2009, 33, 78-82.
43. Peng, Q.; Zhang, Z. R.; Sun, X.; Zuo, J.; Zhao, D.; Gong, T. Mechanisms of phospholipid complex loaded nanoparticles enhancing the oral bioavailability. Mol. Pharmaceutics 2010, 7, 565-575.
44. Armstrong, J. K.; Chowdry, B. Z.; Snowden, M. J.; Dong, J.; Leharne, S. A. The effect of pH and concentration upon aggregation transitions in aqueous solutions of poloxamine T701. Int. J. Pharm. 2001, 22, 57-66. (Pubitemid 32972081)
45. Dong, J.; Chowdry, B. Z.; Leharne, S. A. Solubilisation of polyaromatic hydrocarbons in aqueous solutions of poloxamine T803. Colloids Surf., A 2004, 246, 91-98. (Pubitemid 39330374)
46. Diamond, J. M. The epithelial junction: bridge, gate, and fence. Physiologist 1977, 20, 10-18.
47. Yang, J.; Kim, K. J.; Lee, V. H. L. Role of P-glycoprotein in restricting propranolol transport in cultured rabbit conjunctival epithelial cell layers. Pharm. Res. 2000, 17, 533-538. (Pubitemid 30416390)
48. Orlowski, S.; Mir, J.; Belehradek, J.; Garrigos, M. Effects of steroids and verapamil on P-glycoprotein ATPase activity: progesterone, desoxycorticosterone, corticosterone and verapamil are mutually non-exclusive modulator. Biochem. J. 1996, 317, 515-522. (Pubitemid 26253990)
49. Lin, Y. H.; Chung, C. K.; Chen, C. T.; Liang, H. F.; Chen, S. C.; Sung, H. W. Preparation of nanoparticles composed of chitosan/poly-gamma-glutamic acid and evaluation of their permeability through Caco-2 cells. Biomacromolecules 2005, 6, 1104-1112.
50. Luo, L.; Tam, J.; Maysinger, D.; Eisenberg, A. Cellular internalization of poly(ethyleneoxide)-b-poly(ε-caprolactone) diblock copolymer micelles. Bioconjugate Chem. 2002, 13, 1259-1265. (Pubitemid 35420018)
51. Pho, M. T.; Ashok, A.; Atwood, W. J. Virus enters human glial cells by clathrin-dependent receptor-mediated endocytosis. J. Virology 2000, 74, 2288-2292. (Pubitemid 30091483)
52. Nam, Y. S.; Kang, H. S.; Park, J. Y.; Park, T. G.; Han, S. H.; Chang, I. S. New micelle-like polymer aggregates made from PEIPLGA di-block copolymers: micellar characteristics and cellular uptake. Biomaterials 2003, 24, 2053-2059. (Pubitemid 36298776)
53. Wang, L. H.; Rothberg, K. G.; Anderson, R. G. Mis-assembly of clathrin lattices on endosomes reveals a regulatory switch for coated pit formation. J. Cell Biol. 1993, 123, 1107-1117. (Pubitemid 23352421)
54. Joki-Korpela, P.; Marjomaki, V.; Krogerus, C. Entry of human parechovirus 1. J. Virology 2001, 75, 1958-1967. (Pubitemid 32110186)
55. Gabrielson, N. P.; Pack, D. W. Efficient poly-ethyleniminemediated gene delivery proceeds via a caveolar pathway in HeLa cells. J. Controlled Release 2009, 136, 54-61.
56. Damke, H.; Baba, T.; Bliek, A. M. V.; Schmid, S. L. Clathrinindependent pinocytosis is induced in cells over expressing a temperature-sensitive mutant of dynamin. J. Cell Biol. 1995, 131, 69-80.
57. Kitchens, K. M.; Foraker, A. B.; Kolhatkar, R. B.; Swaan, P. W.; Eddington, N. D.; Ghandehari, H. Endocytosis and interaction of poly(amidoamine) dendrimers with Caco-2 cells. Pharm. Res. 2007, 24, 2138-2145. (Pubitemid 47493582)
58. Emieux, B. L.; Percival, M. D.; Falgueyret, J. F. Quantitation of lysomotropic character of cationic amphiphilic drugs using the fluorescent basic amine red DND-99. Anal. Biochem. 2004, 327, 247-251. (Pubitemid 38402194)
59. Goldman, R. The effect of cytochalasin B and colchicines on concovalin A induced vacuolization in mouse peritoneal macrophage. Exp. Cell Res. 1976, 99, 385-394.
60. Togle, M.; Wiche, G.; Propst, F. Novel features of light chain of microtubule associated protein, MAP1B: regulation by the heavy Chain. J. Cell Biol. 1998, 143, 695-707.
61. Nagele, R. G.; Kosciuk, M. C.; Hunter, E. T. Immuno electron microscopic localization of actin is a component of granular, microtubule associated cross bridges. J. Brain Res. 1998, 474, 279-286.
62. Sun, F.; Li, Y. X.; Ling, Y.; Liang, L.; Chen, S.; Chen, H. P. Experimental approaches and the development of virus entry. Microbiol. China 2010, 37, 103-111.