Steric Stabilizers for Cubic Phase Lyotropic Liquid Crystal Nanodispersions (Cubosomes)

Advances in Planar Lipid Bilayers and Liposomes

Volumn 21, Issue , 2015, Pages 131-187

  Chong, Josephine Y T ^a,b,c   Mulet, Xavier ^b   Boyd, Ben J ^a   Drummond, Calum J ^b,c  

^a MONASH UNIVERSITY   (Australia)

^b CSIRO   (Australia)

^c RMIT UNIVERSITY   (Australia)

Author keywords

Bicontinuous cubic; Colloidal; Cubosome; Lytropic liquid crystal; Nanodispersion; Self assembly; Stabilizer; Steric stabilization

Indexed keywords

EID: 84925260628     PISSN: 15544516     EISSN: None     Source Type: Book Series    
DOI: 10.1016/bs.adplan.2014.11.001     Document Type: Chapter

References (224)

1. Luzzati V., et al. La structure des colloïdes d'association. I. Les phases liquide-cristallines des systèmes amphiphile-eau. Acta Crystallogr. 1960, 13:660-667.
2. Luzzati V., Spegt P.A. Polymorphism of lipids. Nature 1967, 215:701-704.
3. Luzzati V., et al. Structure of cubic phases of lipid-water systems. Nature 1968, 220:485-488.
4. Tardieu A., Luzzati V. Polymorphism of lipids: a novel cubic phase-a cage-like network of rods with enclosed spherical micelles. Biochim. Biophys. Acta 1970, 219:11-17.
5. Longley W., McIntosh T.J. A bicontinuous tetrahedral structure in a liquid-crystalline lipid. Nature 1983, 303:612-614.
6. Caffrey M. Kinetics and mechanism of transitions involving the lamellar, cubic, inverted hexagonal and fluid isotropic phases of hydrated monoacylglycerides monitored by time-resolved X-ray diffraction. Biochemistry 1987, 26:6349-6363.
7. Mariani P., Luzzati V., Delacroix H. Cubic phases of lipid-containing systems: structure analysis and biological implications. J. Mol. Biol. 1988, 204:165-189.
8. Maddaford P.J., Toprakcioglu C. Structure of cubic phases in the ternary system didodecyldimethylammonium bromide/water/hydrocarbon. Langmuir 1993, 9:2868-2878.
9. Diat O., Porte G., Berret J.-F. Orientation and twins separation in a micellar cubic crystal under oscillating shear. Phys. Rev. B 1996, 54:14869-14872.
10. Balmbra R.R., Clunie J.S., Goodman J.F. Cubic mesomorphic phases. Nature 1969, 222:1159-1160.
11. Luzzati V., et al. Lipid polymorphism: a correction. The structure of the cubic phase of extinction symbol Fd-consists of two types of disjointed reverse micelles embedded in a three-dimensional hydrocarbon matrix. Biochemistry 1992, 31:279-285.
12. Mariani P., et al. Polymorphism of a lipid extract from Pseudomonas fluorescens: structure analysis of a hexagonal phase and of a novel cubic phase of extinction symbol Fd. Biochemistry 1990, 29:6799-6810.
13. Charvolin J., Sadoc J.F. Periodic-systems of frustrated fluid films and micellar cubic structures in liquid crystals. J. Phys. 1988, 49:521-526.
14. Delacroix H., Gulik-Krzywicki T., Seddon J.M. Freeze fracture electron microscopy of lyotropic lipid systems: quantitative analysis of the inverse micellar cubic phase of space group Fd3m (Q227). J. Mol. Biol. 1996, 258:88-103.
15. Shearman G.C., et al. A 3-D hexagonal inverse micellar lyotropic phase. J. Am. Chem. Soc. 2009, 131:1678-1679.
16. Schwarz H.A. Gesammelte matematische Abhandlung 1890, vol. 1. Springer-Verlag, Berlin.
17. Schoen A.H. Infinite periodic minimal surfaces without self-intersections. NASA Technical Note, TD-5541, Springfield 1970.
18. Scriven L.E. Equilibrium bicontinuous structure. Nature 1976, 263:123-125.
19. Enlow J.D. Mathematical Modelling of Surfactant Liquid Crystal X-ray Diffraction 2001, 222. Department of Mathematics and Statistics, University of Otago, New Zealand.
20. Yang D., Armitage B., Marder S.R. Cubic liquid-crystalline nanoparticles. Angew. Chem. Int. Ed. Engl. 2004, 43:4402-4409.
21. Angelov B. Modulation of nanochannels hydration in lipid cubic phases studied by SANS and SAXS 2007, 5-8.
22. Angelov B., et al. Diamond-type lipid cubic phase with large water channels. J. Am. Chem. Soc. 2003, 125:7188-7189.
23. Israelachvili J.N., Mitchell D.J., Ninham B.W. Theory of self-assembly of lipid bilayers and vesicles. Biochim. Biophys. Acta 1977, 470:185-201.
24. Luzzati V., Tardieu A. Lipid phases-structure and structural transitions. Annu. Rev. Phys. Chem. 1974, 25:79-94.
25. Malmsten M. Surfactants and Polymers in Drug Delivery. Drugs and the Pharmaceutical Sciences 2002, vol. 122. Marcel Dekker, New York, NY.
26. Figueiredo Neto A.M., Salinas S.R.A. The Physics of Lyotropic Liquid Crystals: Phase Transitions and Structural Properties. Monographs on the Physics & Chemistry of Materials 2005, Oxford University Press, New York, NY.
27. Winsor P.A. Binary and multicomponent solutions of amphiphilic compounds. Solubilization and the formation, structure, and theoretical significance of liquid crystalline solutions. Chem. Rev. 1968, 68:1-40.
28. Tiddy G.J.T. Surfactant-water liquid crystal phases. Phys. Rep. 1980, 57:1-46.
29. Charvolin J. Crystals of interfaces-the cubic phases of amphiphile water-systems. J. Geophys. Res. 1985, 46:173-190.
30. Fontell K. Cubic phases in surfactant and surfactant-like lipid systems. Colloid Polym. Sci. 1990, 268:264-285.
31. Fong C., Le T., Drummond C.J. Lyotropic liquid crystal engineering-ordered nanostructured small molecule amphiphile self-assembly materials by design. Chem. Soc. Rev. 2012, 41:1297-1322.
32. Kaasgaard T., Drummond C.J. Ordered 2-D and 3-D nanostructured amphiphile self-assembly materials stable in excess solvent. Phys. Chem. Chem. Phys. 2006, 8:4957-4975.
33. Conn C.E., Drummond C.J. Nanostructured bicontinuous cubic lipid self-assembly materials as matrices for protein encapsulation. Soft Matter 2013, 9:3449-3464.
34. Chang H.-I., Yeh M.-K. Clinical development of liposome-based drugs: formulation, characterization, and therapeutic efficacy. Int. J. Nanomed. 2012, 7:49-60.
35. Zhang J.-X., et al. Application of liposomes in drug development-focus on gastroenterological targets. Int. J. Nanomed. 2013, 8:1325-1334.
36. Rizwan S.B., et al. Characterisation of bicontinuous cubic liquid crystalline systems of phytantriol and water using cryo field emission scanning electron microscopy (cryo FESEM). Micron 2007, 38:478-485.
37. Yaghmur A., Glatter O. Characterization and potential applications of nanostructured aqueous dispersions. Adv. Colloid Interface Sci. 2009, 147-148:333-342.
38. Barauskas J., Johnsson M., Tiberg F. Self-assembled lipid superstructures: beyond vesicles and liposomes. Nano Lett. 2005, 5:1615-1619.
39. Mulet X., et al. High throughput preparation and characterisation of amphiphilic nanostructured nanoparticulate drug delivery vehicles. Int. J. Pharm. 2010, 395:290-297.
40. Fong W.-K., et al. Controlling the nanostructure of gold nanorod-lyotropic liquid-crystalline hybrid materials using near-infrared laser irradiation. Langmuir 2012, 28:14450-14460.
41. Lee K.W.Y., et al. Nanostructure of liquid crystalline matrix determines in vitro sustained release and in vivo oral absorption kinetics for hydrophilic model drugs. Int. J. Pharm. 2009, 365:190-199.
42. Negrini R., Mezzenga R. Diffusion, molecular separation, and drug delivery from lipid mesophases with tunable water channels. Langmuir 2012, 28:16455-16462.
43. Clogston J., et al. Controlling release from the lipidic cubic phase by selective alkylation. J. Control. Release 2005, 102:441-461.
44. Clogston J., Caffrey M. Controlling release from the lipidic cubic phase. Amino acids, peptides, proteins and nucleic acids. J. Control. Release 2005, 107:97-111.
45. Zabara A., Mezzenga R. Modulating the crystal size and morphology of in meso-crystallized lysozyme by precisely controlling the water channel size of the hosting mesophase. Soft Matter 2013, 9:1010-1014.
46. Mezzenga R., et al. Polysaccharide-induced order-to-order transitions in lyotropic liquid crystals. Langmuir 2005, 21:6165-6169.
47. Morsi N.M., Abdelbary G.A., Ahmed M.A. Silver sulfadiazine based cubosome hydrogels for topical treatment of burns: development and in vitro/in vivo characterization. Eur. J. Pharm. Biopharm. 2014, 86:178-189.
48. Kwon T.K., Kim J.-C. Preparation and in vitro skin permeation of cubosomes containing Hinokitiol. J. Dispers. Sci. Technol. 2010, 31:1004-1009.
49. Kwon T., et al. In vitro skin permeation of cubosomes containing water soluble extracts of Korean barberry. Colloid J. 2010, 72:205-210.
50. Rattanapak T., et al. Transcutaneous immunization using microneedles and cubosomes: mechanistic investigations using Optical Coherence Tomography and Two-Photon Microscopy. J. Control. Release 2013, 172:894-903.
51. Seo S.R., et al. In vivo hair growth-promoting efficacies of herbal extracts and their cubosomal suspensions. J. Ind. Eng. Chem. 2013, 19:1331-1339.
52. Sherif S., Bendas E.R., Badawy S. The clinical efficacy of cosmeceutical application of liquid crystalline nanostructured dispersions of alpha lipoic acid as anti-wrinkle. Eur. J. Pharm. Biopharm. 2014, 86:251-259.
53. Rattanapak T., et al. Comparative study of liposomes, transfersomes, ethosomes and cubosomes for transcutaneous immunisation: characterisation and in vitro skin penetration. J. Pharm. Pharmacol. 2012, 64:1560-1569.
54. Kwon T.K., Hong S.K., Kim J.C. In vitro skin permeation of cubosomes containing triclosan. J. Ind. Eng. Chem. 2012, 18:563-567.
55. Hong S.K., Ma J.Y., Kim J.-C. In vitro skin permeation enhancement of KIOM-MA-128 by monoolein cubosomes. J. Dispers. Sci. Technol. 2012, 33:1503-1508.
56. Kwon T.K., Kim J.-C. In vitro skin permeation and anti-atopic efficacy of lipid nanocarriers containing water soluble extracts of Houttuynia cordata. Drug Dev. Ind. Pharm. 2014, 40:1350-1357.
57. Thapa R.K., et al. Preparation, characterization, and release study of Tacrolimus-loaded liquid crystalline nanoparticles. J. Dispers. Sci. Technol. 2013, 34:72-77.
58. Esposito E., et al. Clotrimazole nanoparticle gel for mucosal administration. Mater. Sci. Eng. C 2013, 33:411-418.
59. Gan L., et al. Self-assembled liquid crystalline nanoparticles as a novel ophthalmic delivery system for dexamethasone: improving preocular retention and ocular bioavailability. Int. J. Pharm. 2010, 396:179-187.
60. Han S., et al. Novel vehicle based on cubosomes for ophthalmic delivery of flurbiprofen with low irritancy and high bioavailability. Acta Pharmacol. Sin. 2010, 31:990-998.
61. Chen Y., et al. Ocular delivery of cyclosporine A based on glyceryl monooleate/poloxamer 407 liquid crystalline nanoparticles: preparation, characterization, in vitro corneal penetration and ocular irritation. J. Drug Target. 2012, 20:856-863.
62. Gong X., et al. Nanostructured self-assembly materials from neat and aqueous solutions of C18 lipid pro-drug analogues of capecitabine-a chemotherapy agent. Focus on nanoparticulate cubosomes (TM) of the oleyl analogue. Soft Matter 2011, 7:5764-5776.
63. Tu Y.S., et al. Preparation, characterisation and evaluation of curcumin with piperine-loaded cubosome nanoparticles. J. Microencapsul. 2014, 31:551-559.
64. Yang Z., et al. Optimization of the preparation process for an oral phytantriol-based amphotericin B cubosomes. J. Nanomater. 2011, 2011. 10.1155/2011/308016.
65. Yang Z., et al. Development of amphotericin B-loaded cubosomes through the SolEmuls technology for enhancing the oral bioavailability. AAPS PharmSciTech 2012, 13:1483-1491.
66. Nguyen T.-H., et al. Nanostructured liquid crystalline particles provide long duration sustained-release effect for a poorly water soluble drug after oral administration. J. Control. Release 2011, 153:180-186.
67. Lai J., et al. Pharmacokinetics and enhanced oral bioavailability in beagle dogs of cyclosporine A encapsulated in glyceryl monooleate/poloxamer 407 cubic nanoparticles. Int. J. Nanomed. 2010, 5:13-23.
68. Dian L., et al. Cubic phase nanoparticles for sustained release of ibuprofen: formulation, characterization, and enhanced bioavailability study. Int. J. Nanomed. 2013, 8:845-854.
69. Chung H., et al. Self-assembled "nanocubicle" as a carrier for peroral insulin delivery. Diabetologia 2002, 45:448-451.
70. Jin X., et al. A nanostructured liquid crystalline formulation of 20(S)-protopanaxadiol with improved oral absorption. Fitoterapia 2013, 84:64-71.
71. Jin X., et al. Enhanced oral absorption of 20(S)-protopanaxadiol by self-assembled liquid crystalline nanoparticles containing piperine: in vitro and in vivo studies. Int. J. Nanomed. 2013, 8:641-652.
72. Lai J., et al. Glyceryl monooleate/poloxamer 407 cubic nanoparticles as oral drug delivery systems: I. In vitro evaluation and enhanced oral bioavailability of the poorly water-soluble drug Simvastatin. AAPS PharmSciTech 2009, 10:960-966.
73. Tamayo-Esquivel D., et al. Evaluation of the enhanced oral effect of omapatrilat-monolein nanoparticles prepared by the emulsification-diffusion method. J. Nanosci. Nanotechnol. 2006, 6:3134-3138.
74. Swarnakar N.K., Thanki K., Jain S. Lyotropic liquid crystalline nanoparticles of CoQ10: implication of lipase digestibility on oral bioavailability, in vivo antioxidant activity, and in vitro-in vivo relationships. Mol. Pharm. 2014, 11:1435-1449.
75. Zeng N., et al. Lipid-based liquid crystalline nanoparticles as oral drug delivery vehicles for poorly water-soluble drugs: cellular interaction and in vivo absorption. Int. J. Nanomed. 2012, 7:3703-3718.
76. Hong S.K., Ma J.Y., Kim J.-C. Preparation and characterization of cubosomal KIOM-C suspension and investigation on in vitro small intestinal absorption of Baicalin. J. Dispers. Sci. Technol. 2013, 34:252-258.
77. Hong S.K., Ma J.Y., Kim J.-C. In vitro small intestinal absorption enhancement of S-164 by monoolein cubic phase nanoparticles. J. Dispers. Sci. Technol. 2013, 34:511-515.
78. Wu H., et al. A novel small odorranalectin-bearing cubosomes: preparation, brain delivery and pharmacodynamic study on amyloid-beta(25-35)-treated rats following intranasal administration. Eur. J. Pharm. Biopharm. 2012, 80:368-378.
79. Esposito E., et al. Cubosome dispersions as delivery systems for percutaneous administration of Indomethacin. Pharm. Res. 2005, 22:2163-2173.
80. Esposito E., et al. Nanoparticulate lipid dispersions for bromocriptine delivery: characterization and in vivo study. Eur. J. Pharm. Biopharm. 2012, 80:306-314.
81. Rizwan S.B., et al. Cubosomes containing the adjuvants imiquimod and monophosphoryl lipid A stimulate robust cellular and humoral immune responses. J. Control. Release 2013, 165:16-21.
82. Gordon S., et al. Chitosan hydrogels containing liposomes and cubosomes as particulate sustained release vaccine delivery systems. J. Liposome Res. 2012, 22:193-204.
83. Jain V., et al. Paclitaxel loaded PEGylated gleceryl monooleate based nanoparticulate carriers in chemotherapy. Biomaterials 2012, 33:7206-7220.
84. Johnsson M., et al. Physicochemical and drug delivery aspects of lipid-based liquid crystalline nanoparticles: a case study of intravenously administered propofol. J. Nanosci. Nanotechnol. 2006, 6:3017-3024.
85. Cervin C., et al. A combined in vitro and in vivo study on the interactions between somatostatin and lipid-based liquid crystalline drug carriers and bilayers. Eur. J. Pharm. Sci. 2009, 36:377-385.
86. Liu H., et al. Protein-bearing cubosomes prepared by liquid precursor dilution: inner ear delivery and pharmacokinetic study following intratympanic administration. J. Biomed. Nanotechnol. 2013, 9:1784-1793.
87. Rizwan S.B., et al. Preparation of phytantriol cubosomes by solvent precursor dilution for the delivery of protein vaccines. Eur. J. Pharm. Biopharm. 2011, 79:15-22.
88. Angelov B., et al. Protein-containing PEGylated cubosomic particles: freeze-fracture electron microscopy and synchrotron radiation circular dichroism study. J. Phys. Chem. B 2012, 116:7676-7686.
89. Angelov B., et al. Multicompartment lipid cubic nanoparticles with high protein upload: millisecond dynamics of formation. ACS Nano 2014, 8:5216-5226.
90. Shen H.-H., et al. Targeted detection of phosphatidylserine in biomimetic membranes and in vitro cell systems using annexin V-containing cubosomes. Biomaterials 2013, 34:8361-8369.
91. Esposito E., et al. Curcumin containing monoolein aqueous dispersions: a preformulative study. Mater. Sci. Eng. C 2013, 33:4923-4934.
92. Murgia S., et al. Drug-loaded fluorescent cubosomes: versatile nanoparticles for potential theranostic applications. Langmuir 2013, 29:6673-6679.
93. Caltagirone C., et al. Cancer-cell-targeted theranostic cubosomes. Langmuir 2014, 30:6228-6236.
94. Bei D., Marszalek J., Youan B.B.C. Formulation of dacarbazine-loaded cubosomes-Part I: influence of formulation variables. AAPS PharmSciTech 2009, 10:1032-1039.
95. Bei D., Marszalek J., Youan B.B.C. Formulation of dacarbazine-loaded cubosomes-Part II: influence of process parameters. AAPS PharmSciTech 2009, 10:1040-1047.
96. Bei D., et al. Formulation of dacarbazine-loaded cubosomes. Part III. Physicochemical characterization. AAPS PharmSciTech 2010, 11:1243-1249.
97. Efrat R., et al. Solubilization of hydrophobic guest molecules in the monoolein discontinuous Q(L) cubic mesophase and its soft nanoparticles. Langmuir 2009, 25:1316-1326.
98. Boyd B.J. Characterisation of drug release from cubosomes using the pressure ultrafiltration method. Int. J. Pharm. 2003, 260:239-247.
99. Gong X., et al. Lyotropic liquid crystalline self-assembly material behavior and nanoparticulate dispersions of a phytanyl pro-drug analogue of capecitabine-a chemotherapy agent. ACS Appl. Mater. Interfaces 2011, 3:1552-1561.
100. Le T.C., et al. Predicting the complex phase behavior of self-assembling drug delivery nanoparticles. Mol. Pharm. 2013, 10:1368-1377.
101. Mangiapia G., et al. Cubosomes for ruthenium complex delivery: formulation and characterization. Soft Matter 2011, 7:10577-10580.
102. Barauskas J., et al. Interactions of lipid-based liquid crystalline nanoparticles with model and cell membranes. Int. J. Pharm. 2010, 391:284-291.
103. Bode J.C., et al. Interaction of dispersed cubic phases with blood components. Int. J. Pharm. 2013, 448:87-95.
104. Rizwan S.B., et al. Bicontinuous cubic liquid crystals as sustained delivery systems for peptides and proteins. Expert Opin. Drug Deliv. 2010, 7:1133-1144.
105. Lawrence M.J. Surfactant systems: their use in drug delivery. Chem. Soc. Rev. 1994, 23:417-424.
106. Mulet X., Boyd B.J., Drummond C.J. Advances in drug delivery and medical imaging using colloidal lyotropic liquid crystalline dispersions. J. Colloid Interface Sci. 2013, 393:1-20.
107. Liu G.Z., et al. Colloidal amphiphile self-assembly particles composed of gadolinium oleate and myverol: evaluation as contrast agents for magnetic resonance imaging. Langmuir 2010, 26:2383-2391.
108. Muir B.W., et al. Metal-free and MRI visible theranostic lyotropic liquid crystal nitroxide-based nanoparticles. Biomaterials 2012, 33:2723-2733.
109. Fraser S.J., et al. Development of cubosomes as a cell-free biosensing platform. Aust. J. Chem. 2011, 64:46-53.
110. Amar-Yuli I., et al. Solubilization of food bioactives within lyotropic liquid crystalline mesophases. Curr. Opin. Colloid Interface Sci. 2009, 14:21-32.
111. Larsson K. Lyotropic liquid crystals and their dispersions relevant in foods. Curr. Opin. Colloid Interface Sci. 2009, 14:16-20.
112. Nadiminti P.P., et al. Nanostructured liquid crystalline particles as an alternative delivery vehicle for plant agrochemicals. ACS Appl. Mater. Interfaces 2013, 5:1818-1826.
113. Boyd B.J., Dong Y.D., Rades T. Nonlamellar liquid crystalline nanostructured particles: advances in materials and structure determination. J. Liposome Res. 2009, 19:12-28.
114. Guo C., et al. Lyotropic liquid crystal systems in drug delivery. Drug Discov. Today 2010, 15:1032-1040.
115. Ljusberg-Wahern H., Nyberg L., Larsson K. Dispersion of the cubic liquid crystalline phase-structure preparation and functionality aspects. Chim. Oggi 1996, 14:40-43.
116. Libster D., et al. Soft matter dispersions with ordered inner structures, stabilized by ethoxylated phytosterols. Colloids Surf. B 2009, 74:202-215.
117. Amar-Yuli I., et al. Hexosome and hexagonal phases mediated by hydration and polymeric stabilizer. Langmuir 2007, 23:3637-3645.
118. Chong J.Y.T., et al. Accelerated stability assay (ASA) for colloidal systems. ACS Comb. Sci. 2014, 16:205-210.
119. Larsson K. Cubic lipid-water phases-structures and biomembrane aspects. J. Phys. Chem. 1989, 93:7304-7314.
120. Tilley A.J., Drummond C.J., Boyd B.J. Disposition and association of the steric stabilizer Pluronic (R) F127 in lyotropic liquid crystalline nanostructured particle dispersions. J. Colloid Interface Sci. 2013, 392:288-296.
121. Lindell K., et al. Influence of a charged phospholipid on the release pattern of timolol maleate from cubic liquid crystalline phases. The Colloid Science of Lipids 1998, 111-118. Steinkopff. B. Lindman, B.W. Ninham (Eds.).
122. Nishikawa K., Arai H., Inoue K. Scavenger receptor-mediated uptake and metabolism of lipid vesicles containing acidic phospholipids by mouse peritoneal macrophages. J. Biol. Chem. 1990, 265:5226-5231.
123. Funato K., Yoda R., Kiwada H. Contribution of complement system on destabilization of liposomes composed of hydrogenated egg phosphatidylcholine in rat fresh plasma. Biochim. Biophys. Acta 1992, 1103:198-204.
124. Senior J. Fate and behavior of liposomes in vivo: a review of controlling factors. Crit. Rev. Ther. Drug Carrier Syst. 1987, 3:123-193.
125. Chonn A., Cullis P., Devine D. The role of surface charge in the activation of the classical and alternative pathways of complement by liposomes. J. Immunol. 1991, 146:4234-4241.
126. Immordino M.L., Dosio F., Cattel L. Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential. Int. J. Nanomed. 2006, 1:297-315.
127. Wattendorf U., Merkle H.P. PEGylation as a tool for the biomedical engineering of surface modified microparticles. J. Pharm. Sci. 2008, 97:4655-4669.
128. Ostuni E., et al. A survey of structure-property relationships of surfaces that resist the adsorption of protein. Langmuir 2001, 17:5605-5620.
129. Harris J.M., Martin N., Modi M. Pegylation. Clin. Pharmacokinet. 2001, 40:539-551.
130. Harris J.M., Chess R.B. Effect of pegylation on pharmaceuticals. Nat. Rev. Drug Discov. 2003, 2:214-221.
131. Torchilin V.P. Immunoliposomes and PEGylated immunoliposomes: possible use for targeted delivery of imaging agents. Immunomethods 1994, 4:244-258.
132. Klibanov A.L., et al. Amphipathic polyethyleneglycols effectively prolong the circulation time of liposomes. FEBS Lett. 1990, 268:235-237.
133. Gref R., et al. 'Stealth' corona-core nanoparticles surface modified by polyethylene glycol (PEG): influences of the corona (PEG chain length and surface density) and of the core composition on phagocytic uptake and plasma protein adsorption. Colloids Surf. B 2000, 18:301-313.
134. Morra M. On the molecular basis of fouling resistance. J. Biomater. Sci. Polym. Ed. 2000, 11:547-569.
135. Jeon S.I., Andrade J.D. Protein-surface interactions in the presence of polyethylene oxide: II. Effect of protein size. J. Colloid Interface Sci. 1991, 142:159-166.
136. Jeon S.I., et al. Protein-surface interactions in the presence of polyethylene oxide: I. Simplified theory. J. Colloid Interface Sci. 1991, 142:149-158.
137. Halperin A. Polymer brushes that resist adsorption of model proteins: design parameters. Langmuir 1999, 15:2525-2533.
138. Zhu B., et al. Chain-length dependence of the protein and cell resistance of oligo(ethylene glycol)-terminated self-assembled monolayers on gold. J. Biomed. Mater. Res. 2001, 56:406-416.
139. Prime K.L., Whitesides G.M. Adsorption of proteins onto surfaces containing end-attached oligo(ethylene oxide): a model system using self-assembled monolayers. J. Am. Chem. Soc. 1993, 115:10714-10721.
140. McPherson T., et al. Prevention of protein adsorption by tethered poly(ethylene oxide) layers: experiments and single-chain mean-field analysis. Langmuir 1998, 14:176-186.
141. Malmsten M., Emoto K., Van Alstine J.M. Effect of chain density on inhibition of protein adsorption by poly(ethylene glycol) based coatings. J. Colloid Interface Sci. 1998, 202:507-517.
142. Kingshott P., Thissen H., Griesser H.J. Effects of cloud-point grafting, chain length, and density of PEG layers on competitive adsorption of ocular proteins. Biomaterials 2002, 23:2043-2056.
143. Pasche S., et al. Poly(l-lysine)-graft-poly(ethylene glycol) assembled monolayers on niobium oxide surfaces: a quantitative study of the influence of polymer interfacial architecture on resistance to protein adsorption by ToF-SIMS and in situ OWLS. Langmuir 2003, 19:9216-9225.
144. Jokerst J.V., et al. Nanoparticle PEGylation for imaging and therapy. Nanomedicine 2011, 6:715-728.
145. Thies C. Adsorption of styrene/butadiene copolymers and stabilization of silica dispersed in perchloroethylene. J. Colloid Interface Sci. 1976, 54:13-21.
146. Heller W., Pugh T.L. "Steric protection" of hydrophobic colloidal particles by adsorption of flexible macromolecules. J. Chem. Phys. 1954, 22:1778.
147. Lee J., Martic P.A., Tan J.S. Protein adsorption on pluronic copolymer-coated polystyrene particles. J. Colloid Interface Sci. 1989, 131:252-266.
148. Neff J.A., Caldwell K.D., Tresco P.A. A novel method for surface modification to promote cell attachment to hydrophobic substrates. J. Biomed. Mater. Res. 1998, 40:511-519.
149. Dong Y.-D., et al. Bulk and dispersed aqueous phase behavior of phytantriol: effect of vitamin E acetate and F127 polymer on liquid crystal nanostructure. Langmuir 2006, 22:9512-9518.
150. Boyd B.J., et al. Self-assembled geometric liquid-crystalline nanoparticles imaged in three dimensions: hexosomes are not necessarily flat hexagonal prisms. Langmuir 2007, 23:12461-12464.
151. Muller F., Salonen A., Glatter O. Phase behavior of phytantriol/water bicontinuous cubic Pn3m cubosomes stabilized by laponite disc-like particles. J. Colloid Interface Sci. 2010, 342:392-398.
152. Zhai J., et al. Revisiting β-casein as a stabilizer for lipid liquid crystalline nanostructured particles. Langmuir 2011, 27:14757-14766.
153. Kojarunchitt T., et al. Development and characterisation of modified poloxamer 407 thermoresponsive depot systems containing cubosomes. Int. J. Pharm. 2011, 408:20-26.
154. Shen H.H., et al. The influence of dipalmitoyl phosphatidylserine on phase behaviour of and cellular response to lyotropic liquid crystalline dispersions. Biomaterials 2010, 31:9473-9481.
155. Conn C.E., et al. Enhanced uptake of an integral membrane protein, the dopamine D2L receptor, by cubic nanostructured lipid nanoparticles doped with Ni(II) chelated EDTA amphiphiles. Soft Matter 2011, 7:567-578.
156. Shen H.H., et al. The interaction of cubosomes with supported phospholipid bilayers using neutron reflectometry and QCM-D. Soft Matter 2011, 7:8041-8049.
157. Fraser S.J., et al. Surface immobilization of bio-functionalized cubosomes: sensing of proteins by quartz crystal microbalance. Langmuir 2012, 28:620-627.
158. Hartnett T.E., et al. Size and phase control of cubic lyotropic liquid crystal nanoparticles. J. Phys. Chem. B 2014, 118:7430-7439.
159. Fraser S.J., et al. Controlling nanostructure and lattice parameter of the inverse bicontinuous cubic phases in functionalised phytantriol dispersions. J. Colloid Interface Sci. 2013, 408:117-124.
160. Chong J.Y.T., et al. Steric stabilisation of self-assembled cubic lyotropic liquid crystalline nanoparticles: high throughput evaluation of triblock polyethylene oxide-polypropylene oxide-polyethylene oxide copolymers. Soft Matter 2011, 7:4768-4777.
161. Uyama M., et al. Useful modified cellulose polymers as new emulsifiers of cubosomes. Langmuir 2009, 25:4336-4338.
162. Abraham T., Hato M., Hirai M. Glycolipid based cubic nanoparticles: preparation and structural aspects. Colloids Surf. B 2004, 35:107-118.
163. Abraham T., Hato M., Hirai M. Polymer-dispersed bicontinuous cubic glycolipid nanoparticles. Biotechnol. Prog. 2005, 21:255-262.
164. de Campo L., et al. Reversible phase transitions in emulsified nanostructured lipid systems. Langmuir 2004, 20:5254-5261.
165. Yaghmur A., et al. Oil-loaded monolinolein-based particles with confined inverse discontinuous cubic structure (Fd3m). Langmuir 2005, 22:517-521.
166. Yaghmur A., et al. Emulsified microemulsions and oil-containing liquid crystalline phases. Langmuir 2004, 21:569-577.
167. Salonen A., Guillot S., Glatter O. Determination of water content in internally self-assembled monoglyceride-based dispersions from the bulk phase. Langmuir 2007, 23:9151-9154.
168. Guillot S., et al. Direct and indirect thermal transitions from hexosomes to emulsified micro-emulsions in oil-loaded monoglyceride-based particles. Colloids Surf. A 2006, 291:78-84.
169. Yaghmur A., et al. Control of the internal structure of MLO-based isasomes by the addition of diglycerol monooleate and soybean phosphatidylcholine. Langmuir 2006, 22:9919-9927.
170. Yaghmur A., et al. Self-assembly in monoelaidin aqueous dispersions: direct vesicles to cubosomes transition. PLoS One 2008, 3:e3747.
171. Esposito E., et al. Lipid-based supramolecular systems for topical application: a preformulatory study. AAPS PharmSci 2003, 5:62-76.
172. Gustafsson J., et al. Cubic lipid-water phase dispersed into submicron particles. Langmuir 1996, 12:4611-4613.
173. Gustafsson J., et al. Submicron particles of reversed lipid phases in water stabilized by a nonionic amphiphilic polymer. Langmuir 1997, 13:6964-6971.
174. Larsson K. Colloidal dispersions of ordered lipid-water phases. J. Dispers. Sci. Technol. 1999, 20:27-34.
175. Larsson K. Aqueous dispersions of cubic lipid-water phases. Curr. Opin. Colloid Interface Sci. 2000, 5:64-69.
176. Larsson K. Bicontinuous cubic lipid-water particles and cubosomal dispersions. Studies in Surface Science and Catalysis 2004, 41-51. Elsevier. T. Osamu (Ed.).
177. Neto C., et al. Imaging soft matter with the atomic force microscope: cubosomes and hexosomes. J. Phys. Chem. B 1999, 103:3896-3899.
178. Spicer P.T., et al. Novel process for producing cubic liquid crystalline nanoparticles (cubosomes). Langmuir 2001, 17:5748-5756.
179. Barauskas J., et al. Cubic phase nanoparticles (cubosome): principles for controlling size, structure, and stability. Langmuir 2005, 21:2569-2577.
180. Monduzzi M., Ljusberg-Wahren H., Larsson K. A 13C NMR study of aqueous dispersions of reversed lipid phases. Langmuir 2000, 16:7355-7358.
181. Nakano M., et al. Small-angle X-ray scattering and 13C NMR investigation on the internal structure of "cubosomes". Langmuir 2001, 17:3917-3922.
182. Svensson O., Thuresson K., Arnebrant T. Interactions between chitosan-modified particles and mucin-coated surfaces. J. Colloid Interface Sci. 2008, 325:346-350.
183. Svensson O., Thuresson K., Arnebrant T. Interactions between drug delivery particles and mucin in solution and at interfaces. Langmuir 2008, 24:2573-2579.
184. Vandoolaeghe P., et al. Adsorption of cubic liquid crystalline nanoparticles on model membranes. Soft Matter 2008, 4:2267-2277.
185. Vandoolaeghe P., et al. Neutron reflectivity studies of the interaction of cubic-phase nanoparticles with phospholipid bilayers of different coverage. Langmuir 2009, 25:4009-4020.
186. Vandoolaeghe P., et al. Adsorption of intact cubic liquid crystalline nanoparticles on hydrophilic surfaces: lateral organization, interfacial stability, layer structure, and interaction mechanism. J. Phys. Chem. C 2009, 113:4483-4494.
187. Landh T. Phase-behavior in the system pine oil monoglycerides-poloxamer-407-water at 20-degrees-C. J. Phys. Chem. 1994, 98:8453-8467.
188. Gupta A., et al. Nanoassemblies of Gd-DTPA-monooleyl and glycerol monooleate amphiphiles as potential MRI contrast agents. J. Mater. Chem. B 2014, 2:1225-1233.
189. Siekmann B., et al. Preparation and structural investigations of colloidal dispersions prepared from cubic monoglyceride-water phases. Int. J. Pharm. 2002, 244:33-43.
190. Nakano M., et al. Dispersions of liquid crystalline phases of the monoolein/oleic acid/Pluronic F127 system. Langmuir 2002, 18:9283-9288.
191. Popescu G., et al. Liquid crystalline phases and their dispersions in aqueous mixtures of glycerol monooleate and glyceryl monooleyl ether. Langmuir 2006, 23:496-503.
192. Salonen A., Muller F., Glatter O. Dispersions of internally liquid crystalline systems stabilized by charged disklike particles as pickering emulsions: basic properties and time-resolved behavior. Langmuir 2008, 24:5306-5314.
193. Muller F., Salonen A., Glatter O. Monoglyceride-based cubosomes stabilized by laponite: separating the effects of stabilizer, pH and temperature. Colloids Surf. A 2010, 358:50-56.
194. Salonen A., et al. Material transfer in cubosome-emulsion mixtures: effect of alkane chain length. Langmuir 2010, 26:10670-10676.
195. Sagalowicz L., et al. Influence of vitamin E acetate and other lipids on the phase behavior of mesophases based on unsaturated monoglycerides. Langmuir 2013, 29:8222-8232.
196. Nilsson C., et al. PEGylation of phytantriol-based lyotropic liquid crystalline particles-the effect of lipid composition, PEG chain length, and temperature on the internal nanostructure. Langmuir 2014, 30:6398-6407.
197. Koynova R., Tenchov B., Rapp G. Effect of PEG-lipid conjugates on the phase behavior of phosphatidylethanolamine dispersions. Colloids Surf. A 1999, 149:571-575.
198. Koynova R., Tenchov B., Rapp G. Low amounts of PEG-lipid induce cubic phase in phosphatidylethanolamine dispersions. Biochim. Biophys. Acta 1997, 1326:167-170.
199. Johnsson M., Barauskas J., Tiberg F. Cubic phases and cubic phase dispersions in a phospholipid-based system. J. Am. Chem. Soc. 2005, 127:1076-1077.
200. Johnsson M., Edwards K. Phase behavior and aggregate structure in mixtures of dioleoylphosphatidylethanolamine and poly(ethylene glycol)-lipids. Biophys. J. 2001, 80:313-323.
201. Chong J.Y.T., et al. Novel steric stabilizers for lyotropic liquid crystalline nanoparticles: PEGylated-phytanyl copolymers. Langmuir 2014, 10.1021/la501471z.
202. Rangelov S., Almgren M. Particulate and bulk bicontinuous cubic phases obtained from mixtures of glyceryl monooleate and copolymers bearing blocks of lipid-mimetic anchors in water. J. Phys. Chem. B 2005, 109:3921-3929.
203. Chong J.Y.T., et al. High-throughput discovery of novel steric stabilizers for cubic lyotropic liquid crystal nanoparticle dispersions. Langmuir 2012, 28:9223-9232.
204. Angelov B., et al. Earliest stage of the tetrahedral nanochannel formation in cubosome particles from unilamellar nanovesicles. Langmuir 2012, 28:16647-16655.
205. Zeng N., et al. Preparation and characterization of paclitaxel-loaded DSPE-PEG-liquid crystalline nanoparticles (LCNPs) for improved bioavailability. Int. J. Pharm. 2012, 424:58-66.
206. Almgren M., Rangelov S. Polymorph dispersed particles from the bicontinuous cubic phase of glycerol monooleate stabilized by PEG-copolymers with lipid-mimetic hydrophobic anchors. J. Dispers. Sci. Technol. 2006, 27:599-609.
207. Chong J.Y.T., et al. Novel RAFT amphiphilic brush copolymer steric stabilisers for cubosomes: poly(octadecyl acrylate)-block-poly(polyethylene glycol methyl ether acrylate). Soft Matter 2014, 10:6666-6676.
208. Gustafsson J., et al. Phase behavior and aggregate structure in aqueous mixtures of sodium cholate and glycerol monooleate. J. Colloid Interface Sci. 1999, 211:326-335.
209. Spicer P.T., et al. Dry powder precursors of cubic liquid crystalline nanoparticles (cubosomes). J. Nanopart. Res. 2002, 4:297-311.
210. Salonen A., Muller F.o., Glatter O. Internally self-assembled submicrometer emulsions stabilized by spherical nanocolloids: finding the free nanoparticles in the aqueous continuous phase. Langmuir 2010, 26:7981-7987.
211. Alexandridis P. Amphiphilic copolymers and their applications. Curr. Opin. Colloid Interface Sci. 1996, 1:490-501.
212. Mori A., et al. Influence of the steric barrier activity of amphipathic poly(ethyleneglycol) and ganglioside GM1 on the circulation time of liposomes and on the target binding of immunoliposomes in vivo. FEBS Lett. 1991, 284:263-266.
213. Martina M.-S., et al. The in vitro kinetics of the interactions between PEG-ylated magnetic-fluid-loaded liposomes and macrophages. Biomaterials 2007, 28:4143-4153.
214. Martina M.-S., Wilhelm C., Lesieur S. The effect of magnetic targeting on the uptake of magnetic-fluid-loaded liposomes by human prostatic adenocarcinoma cells. Biomaterials 2008, 29:4137-4145.
215. Patton J., Carey M. Watching fat digestion. Science 1979, 204:145-148.
216. Lindström M., et al. Aqueous lipid phases of relevance to intestinal fat digestion and absorption. Lipids 1981, 16:749-754.
217. Buchheim W., Larsson K. Cubic lipid-protein-water phases. J. Colloid Interface Sci. 1987, 117:582-583.
218. Almgren M., et al. Dispersed lipid liquid crystalline phases stabilized by a hydrophobically modified cellulose. Langmuir 2007, 23:2768-2777.
219. Luo Y., et al. Dry coating, a novel coating technology for solid pharmaceutical dosage forms. Int. J. Pharm. 2008, 358:16-22.
220. Kablitz C.D., Kappl M., Urbanetz N.A. Parameters influencing polymer particle layering of the dry coating process. Eur. J. Pharm. Biopharm. 2008, 69:760-768.
221. Konno H., et al. Effect of polymer type on the dissolution profile of amorphous solid dispersions containing felodipine. Eur. J. Pharm. Biopharm. 2008, 70:493-499.
222. Driever C.D., et al. Layer-by-layer polymer coating on discrete particles of cubic lyotropic liquid crystalline dispersions (cubosomes). Langmuir 2013, 29:12891-12900.
223. Angelov B., et al. DNA/fusogenic lipid nanocarrier assembly: millisecond structural dynamics. J. Phys. Chem. Lett. 2013, 4:1959-1964.
224. Du J.D., et al. A novel approach to enhance the mucoadhesion of lipid drug nanocarriers for improved drug delivery to the buccal mucosa. Int. J. Pharm. 2014, 471:358-365.