Morphological and physicochemical characterization of liposomes loading cucurbitacin E, an anti-proliferative natural tetracyclic triterpene

Chemistry and Physics of Lipids

Volumn 177, Issue , 2014, Pages 64-70

  Habib, Lamice ^a,b   Jraij, Alia ^a   Khreich, Nathalie ^a   Fessi, Hatem ^b   Charcosset, Catherine ^b   Greige Gerges, Hélène ^a  

^a LEBANESE UNIVERSITY   (Lebanon)

^b CPE LYON   (France)

Author keywords

Abbreviations; AFM; atomic force microscopy; Cho; cholesterol; Cuc D; Cuc E; cucurbitacin D; cucurbitacin E; differential scanning calorimetry; dipalmitoylphosphatidylcholine; dipalmitoylphosphatidylethanolamine; dipalmitoylphosphatidylglycerol; DLS; DPPC; DPPE; DPPG; DSC; dynamic light scattering; large unilamellar vesicles; LE; loading efficiency; LUV; MLV; multilamellar vesicles; TEM; transmission electron microscopy

Indexed keywords

CUCURBITACIN E; DIPALMITOYLPHOSPHATIDYLCHOLINE; DIPALMITOYLPHOSPHATIDYLETHANOLAMINE; DIPALMITOYLPHOSPHATIDYLGLYCEROL; LIPOSOME; TRITERPENOID; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL PARAMETERS; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DETERMINATION; FILM; HYDRATION; LIPID MEMBRANE; MEMBRANE STRUCTURE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; THERMODYNAMICS; TRANSMISSION ELECTRON MICROSCOPY;

AFM; ATOMIC FORCE MICROSCOPY; CHO; CHOLESTEROL; CUC D; CUC E; CUCURBITACIN D; CUCURBITACIN E; DIFFERENTIAL SCANNING CALORIMETRY; DIPALMITOYLPHOSPHATIDYLCHOLINE; DIPALMITOYLPHOSPHATIDYLETHANOLAMINE; DIPALMITOYLPHOSPHATIDYLGLYCEROL; DLS; DPPC; DPPE; DPPG; DSC; DYNAMIC LIGHT SCATTERING; LARGE UNILAMELLAR VESICLES; LE; LIPOSOMES; LOADING EFFICIENCY; LUV; MLV; MULTILAMELLAR VESICLES; TEM; TRANSMISSION ELECTRON MICROSCOPY;

ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; CELL PROLIFERATION; LIPOSOMES; PHYSICOCHEMICAL PROCESSES; TRITERPENES;

EID: 84889973366     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2013.11.006     Document Type: Article

References (56)

1. S. Abbas, J.-B. Vincourt, L. Habib, P. Netter, H. Greige-Gerges, and J. Magdalou The cucurbitacins E, D and I: investigation of their cytotoxicity toward human chondrosarcoma SW 1353 cell line and their biotransformation in man liver Toxicol. Lett. 216 2013 189 199
2. A. Agil, M. Miró, J. Jimenez, J. Aneiros, M.D. Caracuel, A. García-Granados, and M.C. Navarro Isolation of anti-hepatotoxic principle from the juice of Ecballium elaterium Planta Med. 65 1999 673 675 (Pubitemid 29503243)
3. N. Albon, and J.M. Sturtevant Nature of the gel to liquid crystal transition of synthetic phosphatidylcholines Proc. Natl. Acad. Sci. U.S.A. 75 1978 2258 2260 (Pubitemid 8349418)
4. E. Attard, M.P. Brincat, and A. Cushieri Immunomodulatory activity of cucurbitacin E isolated from Ecballium elateium Fitoterapia 76 2005 439 441 (Pubitemid 40922604)
5. G. Balliano, O. Caputo, F. Viola, L. Delprino, and L. Cattel The Transformation of 10α-Cucurbita-5,24-dien-3β-ol into Cucurbitacin C by Seedlings of Cucumis sativus Phytochemistry 22 1983 909 913
6. A.D. Bangham, M.M. Standish, and J.C. Watkins Diffusion of univalent ions across the lamellae of swollen phospholipids J. Mol. Biol. 13 1965 238 252
7. Y. Barenholz Liposome application: problems and prospects Curr. Opin. Colloid Interface Sci. 6 2001 66 77 (Pubitemid 32233069)
8. Y. Barenholz, C. Bombelli, M.G. Bonicelli, P. di Profio, L. Giansanti, G. Mancini, and F. Pascale Influence of lipid composition on the thermotropic behavior and size distribution of mixed cationic liposomes J. Colloid Interface Sci. 356 2011 46 53
9. A. Berquand, N. Fa, Y.F. Dufrêne, and M.-P. Mingeot-Leclercq Interaction of the macrolide antibiotic azithromycin with lipid bilayers: effect on membrane organization, fluidity and permeability Pharm. Res. 22 2005 465 475 (Pubitemid 40575656)
10. R.L. Biltonen A statistical-thermodynamic view of cooperative structural changes in phospholipid bilayer membranes: their potential role in biological function J. Chem. Thermodyn. 22 1990 1 19
11. M.A. Blaskovich, J. Sun, A. Cantor, J. Turkson, R. Jove, and S.M. Sebti Discovery of JSI-124 (Cucurbitacin I), a selective janus kinase/signal transducer and activator of transcription 3 signaling pathway inhibitor with potent antitumor activity against human and murine cancer cells in mice Cancer Res. 63 2003 1270 1279 (Pubitemid 36348705)
12. C.J. Chang, C.H. Chiang, W.S. Song, S.K. Tsai, L.C. Woung, C.H. Chang, S.Y. Jeng, C.Y. Tsai, C.C. Hsu, H.F. Lee, C.S. Huang, M.C. Yung, J.H. Liu, and K.H. Lu Inhibition of phosphorylated STAT3 by cucurbitacin I enhances chemoradiosensitivity in medulloblastoma-derived cancer stem cells Childs Nerv. Syst. 28 2012 363 373
13. W. Cong, Q. Liu, Q. Liang, Y. Wang, and G. Luo Investigation on the interactions between pirarubicin and phospholipids Biophys. Chem. 143 2009 154 160
14. C. Delporte, O. Muñoz, J. Rojas, M. Ferrándiz, M. Payá, S. Erazo, R. Negrete, S. Maldonado, F.A. San, and N. Backhouse Pharmaco-toxicological study of Kageneckia oblonga, Rosaceae Z. Naturforsch. C. 57 2002 100 108 (Pubitemid 34234340)
15. W.-x. Ding, X.-r. Qi, P. Li, Y. Maitani, and T. Nagai Cholesteryl hemisuccinate as a membrane stabilizer in dipalmitoylphosphatidylcholine liposomes containing saikosaponin-d Int. J. Pharm. 300 2005 38 47 (Pubitemid 41112165)
16. K.L. Duncan, M.D. Duncan, M.C. Alley, and E.A. Sausville Cucurbitacin E-induced disruption of the actin and vimentin cytoskeleton in prostate carcinoma cells Biochem. Pharmacol. 52 1996 1553 1560 (Pubitemid 26375461)
17. H. Greige-Gerges, R. Abou Khalil, E. Abou Mansour, J. Magdalou, R. Chahine, and N. Ouaini Cucurbitacins from Ecballium elaterium juice increase the binding of bilirubin and ibuprofen to albumin in human plasma Chem-Biol. Interact. 169 2007 53 62 (Pubitemid 47042710)
18. L. Habib, N. Khreich, A. Jraij, S. Abbas, J. Magdalou, C. Charcosset, and H. Greige-Gerges Preparation and characterization of liposomes incorporating cucurbitacin E, a natural cytotoxic triterpene Int. J. Pharm. 448 2013 313 319
19. B. Jayaprakasam, N.P. Seeram, and M.G. Nair Anticancer and anti-inflammatory activities of cucurbitacins from Cucurbita andreana Cancer Lett. 189 2003 11 16 (Pubitemid 35351514)
20. K. Jorgensen, J.H. Ipsen, O.G. Mouritsen, and M.J. Zuckermann The effect of anaesthetics on the dynamic heterogeneity of lipid membranes Chem. Phys. Lipids 65 1993 205 216 (Pubitemid 23306200)
21. J. Katsaras, S. Tristram-Nagle, Y. Liu, R.L. Headrick, E. Fontes, P.C. Mason, and J.F. Nagle Clarification of the ripple phase of lecithin bilayers using fully hydrated, aligned samples Phys. Rev. E 61 2000 5668 5677
22. N. Khreich, P. Lamourette, H. Boutal, K. Devilliers, C. Créminon, and H. Volland Detection of Staphylococcus enterotoxin B using fluorescent immunoliposomes as label for immunochromatographic testing Anal. Biochem. 377 2008 182 188
23. R. Koynova, and M. Caffrey Phases and phase transitions of the phosphatidylcholines Biochim. Biophys. Acta 1376 1998 91 145 (Pubitemid 28321526)
24. S. Kumar, and J.H. Hoh Direct visualization of vesicle bilayer complexes by atomic force microscopy Langmuir 16 2000 9936 9940 (Pubitemid 32085578)
25. I. Kyrikou, S.K. Hadjikakou, D. Kovala-Demertzi, K. Viras, and T. Mavromoustakos Effects of non-steroid anti-inflammatory drugs in membrane bilayers Chem. Phys. Lipids 132 2004 157 169 (Pubitemid 39536141)
26. I. Kyrikou, I. Daliani, T. Mavromoustakos, H. Maswadeh, C. Demetzos, S. Hatziantoniou, S. Giatrellis, and G. Nounesis The modulation of thermal properties of vinblastine by cholesterol in membrane bilayers Biochim. Biophys. Acta 1661 2004 1 8 (Pubitemid 38201566)
27. D.H. Lee, N.H. Thoennissen, C. Goff, G.B. Iwanski, C. Forscher, N.B. Doan, J.W. Said, and P. Koeffler Synergistic effect of low-dose cucurbitacin B and low-dose methotrexate for treatment of human osteosarcoma Cancer Lett. 306 2011 161 170
28. X. Liang, G. Mao, and K.Y. Ng Mechanical properties and stability measurement of cholesterol containing liposomes on mica by atomic force microscopy J. Colloid Interface Sci. 278 2004 53 62 (Pubitemid 39094475)
29. D.Z. Liu, W.Y. Chen, L.M. Tasi, and S.P. Yang The effects of cholesterol on the release of free lipids and physical stability of lecithin liposomes J. Chin. Inst. Chem. Eng. 31 2000 269 276
30. T. Liu, H. Peng, M. Zhang, Y. Deng, and Z. Wu Cucurbitacin B, a small molecule inhibitor of the Stat3 signaling pathway, enhances the chemosensitivity of laryngeal squamous cell carcinoma cells to cisplatin Eur. J. Pharmacol. 641 2010 15 22
31. A. Mahmud, S. Patel, O. Molavi, P. Choi, J. Samuel, and A. Lavasanifar Self-associating poly(ethylene oxide)-b-poly(r-cholesteryl carboxylate-É- caprolactone) block copolymer for the solubilization of STAT-3 inhibitor cucurbitacin I Biomacromolecules 10 2009 471 478
32. G. Mao, X. Liang, and K.Y. Ng Direct force measurement of liposomes by atomic force microscopy Dekker Encyclopedia of Nanoscience and Nanotechnology 2004 933 942
33. T. Mavromoustakos, E. Theodoropoulou, and D.P. Yang The use of high-resolution solid-state NMR spectroscopy and differential scanning calorimetry to study interactions of anaesthetic steroids with membrane Biochim. Biophys. Acta 1328 1997 65 73 (Pubitemid 27344898)
34. T.P. McMullen, and R.N. McElhaney New aspects of the interaction of cholesterol with dipalmitoylphosphatidylcholine bilayers as revealed by high-sensitivity differential scanning calorimetry Biochim. Biophys. Acta 1234 1995 90 98
35. O. Molavi, Z. Ma, A. Mahmud, A. Alshamsan, J. Samuel, R. Lai, G. Kwon, and A. Lavasanifar Polymeric micelles for the solubilization and delivery of STAT3 inhibitor cucurbitacins in solid tumors Int. J. Pharm. 347 2008 118 127 (Pubitemid 350180319)
36. D.J. Muller, and A. Engel The height of biomolecules measured with the atomic force microscope depends on electrostatic interactions Biophys. J. 73 1997 1633 1644 (Pubitemid 27360752)
37. K. Nakano, Y. Tozuka, H. Yamamoto, Y. Kawashima, and H. Takeuchi A novel method for measuring rigidity of submicron-size liposomes with atomic force microscopy Int. J. Pharm. 355 2008 203 209
38. C.M. Paleos, D. Tsiourvas, and Z. Sideratou Hydrogen bonding interactions of liposomes simulating cell-cell recognition. A review Orig. Life 34 2004 195 213 (Pubitemid 38171051)
39. J. Prades, O. VÖgler, R. Alemany, M. Gomez-Florit, S. Funari, V. Ruiz-Gutierrez, and F. Barcelo Plant pentacyclic triterpenic acids as modulators of lipid membrane physical properties Biochim. Biophys. Acta 1808 2011 752 760
40. K.A. Ramirez-Aguilar, and K.L. Rowlen Tip characterization from AFM images of nanometric spherical particles Langmuir 14 1998 2562 2566 (Pubitemid 128567723)
41. M.C. Recio, M. Prieto, M. Bonucelli, C. Orsi, S. Máñez, R.M. Giner, M. Cerdá-Nicolás, and J.L. Ríos Antiinflammatory activity of two cucurbitacins isolated from Cayaponia tayuya roots Planta Med. 70 2004 414 420 (Pubitemid 38716473)
42. I. Reviakine, and A. Brisson Formation of supported phospholipid bilayers from unilamellar vesicles investigated by atomic force microscopy Langmuir 16 2000 1806 1815 (Pubitemid 30590688)
43. M. Saade, J. Magdalou, N. Ouaini, and H. Greige-Gerges Stability of cucurbitacin E in human plasma: chemical hydrolysis and role of plasma esterases Biopharm. Drug Dispos. 30 2009 389 397
44. A. Schanck, M.P. Mingeot-Leclercq, P.M. Tulkens, D. Carrier, I.C. Smith, and H.C. Jarrell Interactions of aminoglycoside antibiotics with phospholipids. A deuterium nuclear magnetic resonance study Chem. Phys. Lipids 62 1992 153 163
45. G. Sessa, and G. Weissmann Phospholipids spherules (liposomes) as a model for biological membranes J. Lipid Res. 9 1968 310 318
46. T. Shibata-Seki, J. Masai, T. Tagawa, T. Sorin, and S. Kondo In-situ atomic force microscopy study of lipid vesicles adsorbed on a substrate Thin Solid Films 273 1996 297 303 (Pubitemid 126348082)
47. J.M. Sturtevant A scanning calorimetric study of small molecule-lipid bilayer mixtures Proc. Natl. Acad. Sci. U.S.A. 79 1982 3963 3967
48. J. Sun, M.A. Blaskovish, R. Jove, S.K. Livingston, D. Coppola, and S.M. Sebti Cucurbitacin Q: a selective STAT3 activation inhibitor with potent antitumor activity Oncogene 24 2005 3236 3245 (Pubitemid 40695105)
49. T. Tannin-spitz, M. Bergman, and S. Grossman Cucurbitacin glucosides: antioxydant and free radical scavenging activities Biochem. Biophys. Res. Commun. 364 2007 181 186 (Pubitemid 47599438)
50. L.-P. Tseng, H.-J. Liang, T.-W. Chung, Y.-Y. Huang, and D.-Z. Liu Liposomes incorporated with cholesterol for drug release triggered by magnetic field J. Med. Biol. Eng. 27 2007 29 34 (Pubitemid 46724808)
51. D. Tyteca, A. Schanck, Y.F. Dufrene, M. Deleu, P.J. Courtoy, P.M. Tulkens, and M.P. Mingeot-Leclercq The macrolide antibiotic azithromycin interacts with lipids and affects membrane organization and fluidity: studies on Langmuir-Blodgett monolayers, liposomes and J774 macrophages J. Membr. Biol. 192 2003 203 215 (Pubitemid 37020920)
52. J.J. Wenz, and F.J. Barrantes Steroid structural requirements for stabilizing or disrupting lipid domains Biochemistry 42 2003 14267 14276 (Pubitemid 37499424)
53. P.L. Wu, F.W. Lin, T.S. Wu, C.S. Kuoh, K.H. Lee, and S.J. Lee Cytotoxic and Anti-HIV principles from the rhizomes of begonia nantoensis Chem. Pharm. Bull. 52 2004 345 349
54. P.A. Yoshida, D. Yokota, M.A. Foglio, R.A.F. Rodrigues, and S.C. Pinho Liposomes incorporating essential oil of Brazilian cherry (Eugenia uniflora L.): characterization of aqueous dispersions and lyophilized formulations J. Microencapsul. 27 2010 416 425
55. L. Zhao, and S.-S. Feng Effects of lipid chain unsaturation and headgroup type on molecular interactions between paclitaxel and phospholipid within model biomembrane J. Colloid Interface Sci. 285 2005 326 335 (Pubitemid 41350444)
56. P. Zoumpoulakis, I. Daliani, M. Zervou, I. Kyrikou, E. Siapi, G. Lamprinidis, E. Mikros, and T. Mavromoustakos Losartan's molecular basis of interaction with membranes and AT1 receptor Chem. Phys. Lipids 125 2003 13 25 (Pubitemid 37414802)