Development and characterization of a novel lipid nanocapsule formulation of Sn38 for oral administration

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 79, Issue 1, 2011, Pages 181-188

  Roger, Emilie ^a,b   Lagarce, Frédéric ^b,c   Benoit, Jean Pierre ^b,c  

^a Ethypharm   (France)

^b INSERM   (France)

^c ANGERS UNIVERSITY HOSPITAL   (France)

Author keywords

Caco 2; Lipid nanocapsule; Nanotechnology; Oral administration; Sn38; Stability

Indexed keywords

7 ETHYL 10 HYDROXYCAMPTOTHECIN; LIPID NANOCAPSULE; NANOCAPSULE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN CACO 2; CELL TRANSPORT; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG PENETRATION; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; DRUG STORAGE; EMULSION; HUMAN; HUMAN CELL; INTESTINE FLUID; PARTICLE SIZE; SURFACE CHARGE;

ADMINISTRATION, ORAL; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BODY FLUIDS; CACO-2 CELLS; CAMPTOTHECIN; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; DRUG EVALUATION, PRECLINICAL; DRUG STABILITY; ELECTRIC CONDUCTIVITY; EXCIPIENTS; HUMANS; LIPIDS; NANOCAPSULES; PARTICLE SIZE; SOLUBILITY; TOPOISOMERASE I INHIBITORS; TRANSENDOTHELIAL AND TRANSEPITHELIAL MIGRATION;

EID: 80052264440     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2011.01.021     Document Type: Article

References (54)

1. Y.H. Hsiang, M.G. Lihou, and L.F. Liu Arrest of replication forks by drug-stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin Cancer Res. 49 1989 5077 5082 (Pubitemid 19239347)
2. Y.H. Hsiang, and L.F. Liu Identification of mammalian DNA topoisomerase I as an intracellular target of the anticancer drug camptothecin Cancer Res. 48 1988 1722 1726
3. Y.H. Hsiang, L.F. Liu, M.E. Wall, M.C. Wani, A.W. Nicholas, G. Manikumar, S. Kirschenbaum, R. Silber, and M. Potmesil DNA topoisomerase I-mediated DNA cleavage and cytotoxicity of camptothecin analogues Cancer Res. 49 1989 4385 4389 (Pubitemid 19208330)
4. Y. Kawato, M. Aonuma, Y. Hirota, H. Kuga, and K. Sato Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT-11, in the antitumor effect of CPT-11 Cancer Res. 51 1991 4187 4191
5. R.L. Drengler, J.G. Kuhn, L.J. Schaaf, G.I. Rodriguez, M.A. Villalona-Calero, L.A. Hammond, J.A. Stephenson Jr., S. Hodges, M.A. Kraynak, B.A. Staton, G.L. Elfring, P.K. Locker, L.L. Miller, D.D. Von Hoff, and M.L. Rothenberg Phase I and pharmacokinetic trial of oral irinotecan administered daily for 5 days every 3 weeks in patients with solid tumors J. Clin. Oncol. 17 1999 685 696 (Pubitemid 29075258)
6. S. Guichard, I. Hennebelle, R. Bugat, and P. Canal Cellular interactions of 5-fluorouracil and the camptothecin analogue CPT-11 (irinotecan) in a human colorectal carcinoma cell line Biochem. Pharmacol. 55 1998 667 676 (Pubitemid 28077825)
7. F. Koizumi, M. Kitagawa, T. Negishi, T. Onda, S. Matsumoto, T. Hamaguchi, and Y. Matsumura Novel SN-38-incorporating polymeric micelles, NK012, eradicate vascular endothelial growth factor-secreting bulky tumors Cancer Res. 66 2006 10048 10056 (Pubitemid 44672058)
8. Y. Matsumura Poly (amino acid) micelle nanocarriers in preclinical and clinical studies Adv. Drug Deliv. Rev. 60 2008 899 914
9. T.E. Nakajima, M. Yasunaga, Y. Kano, F. Koizumi, K. Kato, T. Hamaguchi, Y. Yamada, K. Shirao, Y. Shimada, and Y. Matsumura Synergistic antitumor activity of the novel SN-38-incorporating polymeric micelles, NK012, combined with 5-fluorouracil in a mouse model of colorectal cancer, as compared with that of irinotecan plus 5-fluorouracil Int. J. Cancer 122 2008 2148 2153 (Pubitemid 351441208)
10. C.L. Peng, P.S. Lai, F.H. Lin, S. Yueh-Hsiu Wu, and M.J. Shieh Dual chemotherapy and photodynamic therapy in an HT-29 human colon cancer xenograft model using SN-38-loaded chlorin-core star block copolymer micelles Biomaterials 30 2009 3614 3625
11. M. Sumitomo, F. Koizumi, T. Asano, A. Horiguchi, K. Ito, T. Asano, T. Kakizoe, M. Hayakawa, and Y. Matsumura Novel SN-38-incorporated polymeric micelle, NK012, strongly suppresses renal cancer progression Cancer Res. 68 2008 1631 1635 (Pubitemid 351416546)
12. S. Lei, P.Y. Chien, S. Sheikh, A. Zhang, S. Ali, and I. Ahmad Enhanced therapeutic efficacy of a novel liposome-based formulation of SN-38 against human tumor models in SCID mice Anticancer Drugs 15 2004 773 778 (Pubitemid 39281301)
13. V. Peikov, S. Ugwu, M. Parmar, A. Zhang, and I. Ahmad pH-dependent association of SN-38 with lipid bilayers of a novel liposomal formulation Int. J. Pharm. 299 2005 92 99 (Pubitemid 40962410)
14. Y. Sadzuka, H. Takabe, and T. Sonobe Liposomalization of SN-38 as active metabolite of CPT-11 J. Control. Release 108 2005 453 459 (Pubitemid 41608676)
15. J.A. Zhang, T. Xuan, M. Parmar, L. Ma, S. Ugwu, S. Ali, and I. Ahmad Development and characterization of a novel liposome-based formulation of SN-38 Int. J. Pharm. 270 2004 93 107 (Pubitemid 38077091)
16. J. Williams, R. Lansdown, R. Sweitzer, M. Romanowski, R. LaBell, R. Ramaswami, and E. Unger Nanoparticle drug delivery system for intravenous delivery of topoisomerase inhibitors J. Control. Release 91 2003 167 172 (Pubitemid 37288887)
17. G. Liu, E. Franssen, M.I. Fitch, and E. Warner Patient preferences for oral versus intravenous palliative chemotherapy J. Clin. Oncol. 15 1997 110 115 (Pubitemid 27021524)
18. B. Heurtault, P. Saulnier, B. Pech, J.E. Proust, and J.P. Benoit A novel phase inversion-based process for the preparation of lipid nanocarriers Pharm. Res. 19 2002 875 880 (Pubitemid 34692585)
19. J. Hureaux, F. Lagarce, F. Gagnadoux, M.C. Rousselet, V. Moal, T. Urban, and J.P. Benoit Toxicological study and efficacy of blank and paclitaxel-loaded lipid nanocapsules after i.v. administration in mice Pharm. Res. 27 2010 421 430
20. S. Peltier, J.M. Oger, F. Lagarce, W. Couet, and J.P. Benoit Enhanced oral paclitaxel bioavailability after administration of paclitaxel-loaded lipid nanocapsules Pharm. Res. 23 2006 1243 1250 (Pubitemid 43946146)
21. E. Roger, F. Lagarce, and J.P. Benoit The gastrointestinal stability of lipid nanocapsules Int. J. Pharm. 379 2009 260 265
22. E. Roger, F. Lagarce, E. Garcion, and J.P. Benoit Lipid nanocarriers improve paclitaxel transport throughout human intestinal epithelial cells by using vesicle-mediated transcytosis J. Control. Release 140 2009 174 181
23. US Pharmacopeia XXIV, Rockville, MD, 2006.
24. E. Jantratid, N. Janssen, C. Reppas, and J.B. Dressman Dissolution media simulating conditions in the proximal human gastrointestinal tract: an update Pharm. Res. 25 2008 1663 1676
25. P. Artursson, and R.T. Borchardt Intestinal drug absorption and metabolism in cell cultures: Caco-2 and beyond Pharm. Res. 14 1997 1655 1658 (Pubitemid 28062907)
26. P. Artursson, and J. Karlsson Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells Biochem. Biophys. Res. Commun. 175 1991 880 885
27. P. Larger, M. Altamura, R.M. Catalioto, S. Giuliani, C.A. Maggi, C. Valenti, and A. Triolo Simultaneous LC-MS/MS determination of reference pharmaceuticals as a method for the characterization of the Caco-2 cell monolayer absorption properties Anal. Chem. 74 2002 5273 5281 (Pubitemid 35215356)
28. E. Jantratid, N. Janssen, H. Chokshi, K. Tang, and J.B. Dressman Designing biorelevant dissolution tests for lipid formulations: case example - lipid suspension of RZ-50 Eur. J. Pharm. Biopharm. 69 2008 776 785
29. J.B. Dressman, G.L. Amidon, C. Reppas, and V.P. Shah Dissolution testing as a prognostic tool for oral drug absorption: immediate release dosage forms Pharm. Res. 15 1998 11 22 (Pubitemid 28080861)
30. R.B. Kolhatkar, P. Swaan, and H. Ghandehari Potential oral delivery of 7-ethyl-10-hydroxy-camptothecin (SN-38) using poly(amidoamine) dendrimers Pharm. Res. 25 2008 1723 1729
31. E. Allard, C. Passirani, E. Garcion, P. Pigeon, A. Vessieres, G. Jaouen, and J.P. Benoit Lipid nanocapsules loaded with an organometallic tamoxifen derivative as a novel drug-carrier system for experimental malignant gliomas J. Control. Release 130 2008 146 153
32. F. Lacoeuille, F. Hindre, F. Moal, J. Roux, C. Passirani, O. Couturier, P. Cales, J.J. Le Jeune, A. Lamprecht, and J.P. Benoit In vivo evaluation of lipid nanocapsules as a promising colloidal carrier for paclitaxel Int. J. Pharm. 344 2007 143 149 (Pubitemid 47464828)
33. A. Lamprecht, and J.P. Benoit Etoposide nanocarriers suppress glioma cell growth by intracellular drug delivery and simultaneous P-glycoprotein inhibition J. Control. Release 112 2006 208 213
34. A. Lamprecht, J.L. Saumet, J. Roux, and J.P. Benoit Lipid nanocarriers as drug delivery system for ibuprofen in pain treatment Int. J. Pharm. 278 2004 407 414 (Pubitemid 38759512)
35. M. Cirri, P. Mura, and P.C. Mora Liquid spray formulations of xibornol by using self-microemulsifying drug delivery systems Int. J. Pharm. 340 2007 84 91 (Pubitemid 47049783)
36. D.C. Drummond, C.O. Noble, Z. Guo, K. Hong, J.W. Park, and D.B. Kirpotin Development of a highly active nanoliposomal irinotecan using a novel intraliposomal stabilization strategy Cancer Res. 66 2006 3271 3277
37. J.S. Woo, T.S. Kim, J.H. Park, and S.C. Chi Formulation and biopharmaceutical evaluation of silymarin using SMEDDS Arch. Pharm. Res. 30 2007 82 89
38. A. Beduneau, P. Saulnier, N. Anton, F. Hindre, C. Passirani, H. Rajerison, N. Noiret, and J.P. Benoit Pegylated nanocapsules produced by an organic solvent-free method: evaluation of their stealth properties Pharm. Res. 23 2006 2190 2199
39. R.P. Hertzberg, M.J. Caranfa, K.G. Holden, D.R. Jakas, G. Gallagher, M.R. Mattern, S.M. Mong, J.O. Bartus, R.K. Johnson, and W.D. Kingsbury Modification of the hydroxy lactone ring of camptothecin: inhibition of mammalian topoisomerase I and biological activity J. Med. Chem. 32 1989 715 720 (Pubitemid 19075732)
40. L. Zufia, A. Aldaz, and J. Giraldez Separation methods for camptothecin and related compounds J. Chromatogr. B Biomed. Sci. Appl. 764 2001 141 159 (Pubitemid 33044663)
41. P. de Bruijn, J. Verweij, W.J. Loos, K. Nooter, G. Stoter, and A. Sparreboom Determination of irinotecan (CPT-11) and its active metabolite SN-38 in human plasma by reversed-phase high-performance liquid chromatography with fluorescence detection J. Chromatogr. B: Biomed. Sci. Appl. 698 1997 277 285 (Pubitemid 27412531)
42. S. Ragot, P. Marquet, F. Lachatre, A. Rousseau, E. Lacassie, J.M. Gaulier, J.L. Dupuy, and G. Lachatre Sensitive determination of irinotecan (CPT-11) and its active metabolite SN-38 in human serum using liquid chromatography-electrospray mass spectrometry J. Chromatogr. B Biomed. Sci. Appl. 736 1999 175 184
43. C. Dulieu, and D. Bazile Influence of lipid nanocapsules composition on their aptness to freeze-drying Pharm. Res. 22 2005 285 292 (Pubitemid 40487213)
44. E. Roger, F. Lagarce, E. Garcion, and J.P. Benoit Biopharmaceutical parameters to consider in order to alter the fate of nanocarriers after oral delivery Nanomedicine (Lond) 5 2010 287 306
45. P.V. Balimane, and S. Chong Cell culture-based models for intestinal permeability: a critique Drug Discov. Today 10 2005 335 343 (Pubitemid 40313585)
46. A.R. Hilgers, R.A. Conradi, and P.S. Burton Caco-2 cell monolayers as a model for drug transport across the intestinal mucosa Pharm. Res. 7 1990 902 910 (Pubitemid 20349761)
47. T. Itoh, S. Itagaki, Y. Sumi, T. Hirano, I. Takemoto, and K. Iseki Uptake of irinotecan metabolite SN-38 by the human intestinal cell line Caco-2 Cancer Chemother. Pharmacol. 55 2005 420 424 (Pubitemid 40568970)
48. K. Kobayashi, B. Bouscarel, Y. Matsuzaki, S. Ceryak, S. Kudoh, and H. Fromm pH-dependent uptake of irinotecan and its active metabolite, SN-38, by intestinal cells Int. J. Cancer 83 1999 491 496 (Pubitemid 29489864)
49. K. Kobayashi, S. Ceryak, Y. Matsuzaki, S. Kudoh, and B. Bouscarel Effect of bile acids on the uptake of irinotecan and its active metabolite, SN-38, by intestinal cells Biochim. Biophys. Acta 1525 2001 125 129 (Pubitemid 32149984)
50. T. Bansal, G. Mishra, M. Jaggi, R.K. Khar, and S. Talegaonkar Effect of P-glycoprotein inhibitor, verapamil, on oral bioavailability and pharmacokinetics of irinotecan in rats Eur. J. Pharm. Sci. 2008
51. H. Takeuchi, H. Yamamoto, T. Niwa, T. Hino, and Y. Kawashima Mucoadhesion of polymer-coated liposomes to rat intestine in vitro Chem. Pharm. Bull. (Tokyo) 42 1994 1954 1956 (Pubitemid 24315522)
52. E. Garcion, A. Lamprecht, B. Heurtault, A. Paillard, A. Aubert-Pouessel, B. Denizot, P. Menei, and J.P. Benoit A new generation of anticancer, drug-loaded, colloidal vectors reverses multidrug resistance in glioma and reduces tumor progression in rats Mol. Cancer Ther. 5 2006 1710 1722 (Pubitemid 44323239)
53. L.E. Buckingham, M. Balasubramanian, A.R. Safa, H. Shah, P. Komarov, R.M. Emanuele, and J.S. Coon Reversal of multi-drug resistance in vitro by fatty acid-PEG-fatty acid diesters Int. J. Cancer 65 1996 74 79 (Pubitemid 26030939)
54. J.S. Coon, W. Knudson, K. Clodfelter, B. Lu, and R.S. Weinstein Solutol HS 15, nontoxic polyoxyethylene esters of 12-hydroxystearic acid, reverses multidrug resistance Cancer Res. 51 1991 897 902