Self-assembled micelles of monosialogangliosides as nanodelivery vehicles for taxanes

Journal of Controlled Release

Volumn 162, Issue 3, 2012, Pages 619-627

  Leonhard, Victoria ^a,b   Alasino, Roxana V ^a,b   Bianco, Ismael D ^a,b,c   Garro, Ariel G ^a   Heredia, Valeria ^a   Beltramo, Dante M ^a,b,d  

^a Tecnología e Innovación   (Argentina)

^b Consejo Nacional de Investigaciones Científicas y Técnicas ^*  (Argentina)

^c Universidad Nacional de La Rioja   (Argentina)

^d UNIVERSIDAD CATÓLICA DE CÓRDOBA   (Argentina)

Author keywords

Docetaxel; Drug delivery; Gangliosides; Micelles; Paclitaxel

Indexed keywords

ACID TREATMENTS; ALKALINE PH; CERAMIDES; CRYSTALLINE STATE; DOCETAXEL; FREEZE-THAWING; GANGLIOSIDES; HUMAN BLOODS; HUMAN SERUM ALBUMINS; IN-VITRO; INTERNAL STRUCTURE; MIXED MICELLES; MOLAR RATIO; NANOMICELLES; PACLITAXEL; PLATELET AGGREGATION; POLAR HEADGROUPS; PRE-TREATMENT; ROOM TEMPERATURE; SELF-ASSEMBLED; SIALIC ACIDS; SOLUBILIZATION CAPACITIES; STRUCTURAL REORGANIZATION; TAXANES; UNILAMELLAR VESICLE; WATER SOLUBILITIES;

ALKALINITY; AMIDES; CRYSTALLINE MATERIALS; DRUG PRODUCTS; FATTY ACIDS; LOADING; SOLUBILITY; X RAY POWDER DIFFRACTION;

MICELLES;

ACETIC ACID DERIVATIVE; CERAMIDE; DICHLOROACETYL; DOCETAXEL; FATTY ACID; GANGLIOSIDE GM1; GANGLIOSIDE GM2; GANGLIOSIDE GM3; MONOSIALOGANGLIOSIDE; NANOPARTICLE; PACLITAXEL; SIALIC ACID; UNCLASSIFIED DRUG; WATER;

ALKALINITY; ANIMAL CELL; ARTICLE; CELL VACUOLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; CYTOTOXICITY; DIFFUSION; DRUG DELIVERY SYSTEM; DRUG SOLUBILITY; DRUG STABILITY; FREEZE THAWING; HUMAN; HUMAN CELL; HYDROLYSIS; KINETICS; LYOPHILISATE; MICELLE; NONHUMAN; PRIORITY JOURNAL; ROOM TEMPERATURE; SOLUBILIZATION; X RAY POWDER DIFFRACTION;

ANTINEOPLASTIC AGENTS; BLOOD PLATELETS; CELLS, CULTURED; DRUG CARRIERS; DRUG STABILITY; ERYTHROCYTES; GANGLIOSIDES; HEMOLYSIS; HUMANS; MICELLES; NANOSTRUCTURES; PACLITAXEL; PLATELET AGGREGATION; SOLUBILITY; TAXOIDS;

EID: 84865824194     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2012.07.031     Document Type: Article

References (47)

1. M.C. Wani, H.L. Taylor, M.E. Wall, P. Coggon, and A.T. McPhail Plant antitumor agents VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia J. Am. Chem. Soc. 93 1971 2325 2327
2. E.K. Rowinsky, and R.C. Donehower Paclitaxel (Taxol) N. Engl. J. Med. 332 1995 1004 1014
3. R.T. Liggins, W.L. Hunger, and H.M. Burt Solid-state characterization of paclitaxel J. Pharm. Sci. 86 1997 1458 1463
4. E.K. Rowinsky The taxanes: dosing and scheduling considerations Oncology 11 1997 7 19
5. F.A. Greco, and T.M. Hainsworth One-hour paclitaxel infusions: a review of safety and efficacy Cancer J. Sci. Am. 5 1999 179 191
6. S.M. Moghimi, A.C. Hunter, and J.C. Murray Long-circulating and target-specific nanoparticles: theory to practice Pharmacol. Rev. 53 2001 283 318
7. M.L. Adams, A. Lavasanifar, and G.S. Kwon Amphiphilic block copolymers for drug delivery J. Pharm. Sci. 92 2003 1343 1355
8. Z.G. Gao, A.N. Lukyanov, A. Singhal, and V.P. Torchilin Diacyllipid-polymer micelles as nanocarriers for poorly soluble anticancer drugs Nano Lett. 2 2002 979 982
9. N.K. Ibrahim, N. Desai, S. Legha, P. Soon-Shiong, R.L. Theriault, E. Rivera, B. Esmaeli, S.E. Ring, A. Bedikian, G.N. Hortobagyi, and J.A. Ellerhorst Phase I and pharmacokinetic study of ABI-007, a Cremophor-free, protein-stabilized, nanoparticle formulation of paclitaxel Clin. Cancer Res. 8 2002 1038 1044
10. W.J. Gradishar Albumin-bound paclitaxel: a next-generation taxane Expert Opin. Pharmacother. 7 2006 1041 1053
11. B. Mishra, B.B. Patel, and S. Tiwari Colloidal nanocarriers: a review on formulation technology, types and applications toward targeted drug delivery Nanomedicine 6 2010 9 24
12. Y. Matsumura Poly (amino acid) micelle nanocarriers in preclinical and clinical studies Adv. Drug Deliv. Rev. 60 2008 899 914
13. H. Maeda, J. Wu, T. Sawa, Y. Matsumura, and K. Hori Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review J. Control. Release 65 2000 271 284
14. R.B. Weiss, R.C. Donehower, P.H. Wiernik, T. Ohnuma, R.J. Gralla, D.L. Trump, J.R. Baker Jr.; D.A. Van Echo, D.D. Von Hoff, and B. Leyland-Jones Hypersensitivity reactions from taxol J. Clin. Oncol. 8 1990 1263 1268
15. R. Kunstfeld, G. Wickenhauser, U. Michaelis, M. Teifel, W. Umek, K. Naujoks, K. Wolff, and P. Petzelbauer Paclitaxel encapsulated in cationic liposomes diminishes tumor angiogenesis and melanoma growth in a humanized SCID mouse model J. Invest. Dermatol. 120 2003 476 482
16. D.C. Drummond, O. Meyer, K. Hong, D.B. Kirpotin, and D. Papahadjopoulos Optimizing liposomes for delivery of chemotherapeutic agents to solid tumors Pharmacol. Rev. 51 1999 691 743
17. D. Papahadjopoulos, T.M. Allen, A. Gabizon, E. Mayhew, K. Matthay, S.K. Huang, K.D. Lee, M.C. Woodle, D.D. Lasic, and C. Redemann Sterically stabilized liposomes: improvements in pharmacokinetics and antitumor therapeutic efficacy Proc. Natl. Acad. Sci. 88 1991 11460 11464
18. J.A. O'Shaughnessy Pegylated liposomal doxorubicin in the treatment of breast cancer Clin. Breast Cancer 4 2003 318 328
19. A. Sharma, and R.M. Straubinger Novel taxol formulations: preparation and characterization of taxol-containing liposomes Pharm. Res. 11 1994 889 896
20. R.M. Straubinger, A. Sharma, M. Murray, and E. Mayhew Novel taxol formulation: taxol-containing liposomes J. Natl. Cancer Inst. Monogr. 15 1993 69 78
21. V.P. Torchilin Micellar nanocarriers: pharmaceutical perspectives Pharm. Res. 24 2007 1 16
22. V. Leonhard, D.M. Beltramo, R.V. Alasino, and I.D. Bianco Water-soluble pharmaceutical composition comprising at least one therapeutically active substance having hydrophobic properties and at least one compound selected from among sialoglycosphingolipids, glycosphingolipids or a mixture of sialoglycosphingolipids and glycosphingolipids 2011 WO 2011/113981 A1
23. T. Miettinen, and I.T. Takki-Luukkainen Use of butyl acetate in determination of sialic acid Acta Chem. Scand. 13 1959 856 858
24. B. Ulrich-Bott, and H. Wiegandt Micellar properties of glycosphingolipids in aqueous media J. Lipid Res. 25 1984 1233 1245
25. S. Sonnino, L. Cantú, M. Corti, D. Acquotti, and B. Venerando Aggregative properties of gangliosides in solution Chem. Phys. Lipids 71 1994 21 45
26. 4Cer) containing an acetyl group as acyl moiety Chem. Phys. Lipids 56 1 1990 49 57
27. P. Brocca, L. Cantú, M. Corti, E. Del Favero, and A. Raudino Collective phenomena in confined micellar systems of gangliosides Physica A 304 2002 117 190
28. L. Cantú, M. Corti, E. Del Favero, E. Muller, A. Raudino, and S. Sonnino Thermal hysteresis in ganglioside micelles investigated by differential scanning calorimetry and light-scattering Langmuir 15 1999 4975 4980
29. D. Orthaber, and O. Glatter Time and temperature dependent aggregation behaviour of the ganglioside GM1 in aqueous solution Chem. Phys. Lipids 92 1 1998 53 62
30. M. Hirai, and T. Takizawa Intensive extrusion and occlusion of water in ganglioside micelles with thermal reversibility Biophys. J. 74 1998 3010 3014
31. T. Hayakawa, and M. Hirai Hydration and thermal reversibility of glycolipids depending on sugar chains Eur. Biophys. J. 31 1 2002 62 72
32. V.P. Torchilin Micellar nanocarriers: pharmaceutical perspectives Pharmacol. Res. 24 1 2007
33. G. Gaucher, M.H. Dufresne, V.P. Sant, N. Kang, D. Maysinger, and J.C. Leroux Block copolymer micelles: preparation, characterization and application in drug delivery J. Control. Release 109 2005 169 188
34. A.N. Lukyanov, and V.P. Torchilin Micelles from lipid derivatives of water-soluble polymers as delivery systems for poorly soluble drugs Adv. Drug Deliv. Rev. 56 2004 1273 1289
35. S. Formisano, M.L. Johnson, G. Lee, S.M. Aloj, and H. Edelhoch Critical micelle concentrations of gangliosides Biochemistry 18 6 1979
36. H.A. Guglielmone, J.J. Daniele, I.D. Bianco, E.J. Fernandez, and G.D. Fidelio Inhibition of human platelet aggregation by gangliosides Thromb. Res. 98 1 2000 51 57
37. S. Sonnino, L. Mauri, V. Chigorno, and A. Prinetti Gangliosides as components of lipid membrane domains Glycobiology 17 1 2006 1R 13R
38. C.R. Partington, and J.W. Daly Effect of gangliosides on adenylate cyclase activity in rat cerebral cortical membranes Mol. Pharmacol. 15 1979 484 491
39. E.G. Bremer, S. Hakomori, D.F. Bowen-Pope, E. Raines, and R. Ross Ganglioside-mediated modulation of cell growth, growth factor binding, and receptor phosphorylation J. Biol. Chem. 259 1984 6818 6825
40. D. Acquotti, and S. Sonnino Use of nuclear magnetic resonance spectroscopy in evaluation of ganglioside structure, conformation and dynamics Methods Enzymol. 312 2000 247 272
41. K.M. Huh, S.C. Lee, Y.W. Cho, J. Lee, J.H. Jeong, and K. Park Hydrotropic polymer micelle system for delivery of paclitaxel J. Control. Release 101 1 2005 59 68
42. J. Lee, S.C. Lee, G. Acharya, C.J. Chang, and K. Park Hydrotropic solubilization of paclitaxel: analysis of chemical structures for hydrotropic property Pharm. Res. 20 7 2003 1022 1030
43. M. Fukunaga-Kalabis, and M. Herlyn Unraveling mysteries of the multifunctional protein SPARC J. Invest. Dermatol. 127 2007 2497 2498
44. J. Wang, D. Mongayt, and V.P. Torchilin Polymeric micelles for delivery of poorly soluble drugs: preparation and anticancer activity in vitro of paclitaxel incorporated into mixed micelles based on poly(ethylene glycol)-lipid conjugate and positively charged lipids J. Drug Target. 13 1 2005 73 80
45. F. Danhier, N. Magotteaux, B. Ucakar, N. Lecouturier, M. Brewster, and V. Préat Novel self-assembling PEG-p-(CL-co-TMC) polymeric micelles as safe and effective delivery system for Paclitaxel Eur. J. Pharm. Biopharm. 73 2009 230 238
46. Q. Zha, Y. Ruan, T. Hartmann, K. Beyreuther, and D. Zhang GM1 ganglioside regulates the proteolysis of amyloid precursor protein Mol. Psychiatry 9 2004 946 952
47. T.V. Sokolova, I.O. Zakharova, V.V. Furaev, M.P. Rychova, and N.F. Avrova Neuroprotective effect of ganglioside GM1 on the cytotoxic action of hydrogen peroxide and amyloid β-peptide in PC12 cells Neurochem. Res. 32 2007 1302 1313