Characterization of oil-free and oil-loaded liquid-crystalline particles stabilized by negatively charged stabilizer citrem

Langmuir

Volumn 28, Issue 32, 2012, Pages 11755-11766

  Nilsson, Christa ^a   Edwards, Katarina ^b,c   Eriksson, Jonny ^b   Larsen, Susan Weng ^a   Østergaard, Jesper ^a   Larsen, Claus ^a   Urtti, Arto ^d   Yaghmur, Anan ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UPPSALA UNIVERSITY   (Sweden)

^c UNIVERSITY OF FREIBURG   (Germany)

^d UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS DISPERSIONS; CRYOGENIC TRANSMISSION ELECTRON MICROSCOPY (CRYO-TEM); DISPERSED PARTICLE; EMULSIFIED MICROEMULSION; FUNCTIONALIZED; GLYCERYL MONOOLEATE; HEXOSOMES; HYDROPHILIC CORES; HYDROPHILIC DOMAINS; HYDROPHOBIC TAILS; INTERFACIAL AREAS; LIPID MOLECULES; LIQUID-CRYSTALLINE PHASIS; MICROEMULSION SYSTEMS; NANO CHANNELS; PHYTANTRIOL; POSITIVELY CHARGED; SIGNIFICANT IMPACTS; STABILIZING AGENTS; SYNCHROTRON SMALL-ANGLE X-RAY SCATTERINGS;

CRYSTALLINE MATERIALS; DISPERSIONS; EMULSIFICATION; HYDROPHILICITY; LIQUIDS; NANOSTRUCTURES; TRANSMISSION ELECTRON MICROSCOPY;

MICROEMULSIONS;

3,7,11,15 TETRAMETHYL 1,2,3 HEXADECANETRIOL; 3,7,11,15-TETRAMETHYL-1,2,3-HEXADECANETRIOL; ACYLGLYCEROL; ALPHA TOCOPHEROL; CITRIC ACID; EMULSIFYING AGENT; FATTY ALCOHOL; GLYCEROL OLEATE; NANOMATERIAL; OIL; OLEIC ACID; TRIACYLGLYCEROL; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; LIQUID CRYSTAL;

ALPHA-TOCOPHEROL; CITRATES; EMULSIFYING AGENTS; FATTY ALCOHOLS; GLYCERIDES; LIQUID CRYSTALS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NANOSTRUCTURES; OILS; OLEIC ACIDS; TRIGLYCERIDES; WATER;

EID: 84865173797     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la3021244     Document Type: Article

References (84)

1. Angelova, A.; Angelov, B.; Mutafchieva, R.; Lesieur, S.; Couvreur, P. Self-Assembled Multicompartment Liquid Crystalline Lipid Carriers for Protein, Peptide, and Nucleic Acid Drug Delivery Acc. Chem. Res. 2011, 44, 147-156
2. Shah, M. H.; Paradkar, A. Cubic Liquid Crystalline Glyceryl Monooleate Matrices for Oral Delivery of Enzyme Int. J. Pharm. 2005, 294, 161-171 (Pubitemid 40462332)
3. Yaghmur, A.; Glatter, O. Characterization and Potential Applications of Nanostructured Aqueous Dispersions Adv. Colloid Interface Sci. 2009, 147-148, 333-342
4. Drummond, C. J.; Fong, C. Surfactant Self-Assembly Objects as Novel Drug Delivery Vehicles Curr. Opin. Colloid Interface Sci. 1999, 4, 449-456 (Pubitemid 30449773)
5. Guo, C. Y.; Wang, J.; Cao, F. L.; Lee, R. J.; Zhai, G. X. Lyotropic Liquid Crystal Systems in Drug Delivery Drug Discovery Today 2010, 15, 1032-1040
6. Larsson, K. Lyotropic Liquid Crystals and Their Dispersions Relevant in Foods Curr. Opin. Colloid Interface Sci. 2009, 14, 16-20
7. 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
8. Luzzati, V. Biological Significance of Lipid Polymorphism: the Cubic Phases Curr. Opin. Struct. Biol. 1997, 7, 661-668 (Pubitemid 27472585)
9. Faivre, V.; Rosilio, V. Interest of Glycolipids in Drug Delivery: From Physicochemical Properties to Drug Targeting Expert Opin. Drug Delivery 2010, 7, 1031-1048
10. Larsson, K. Cubic Lipid-Water Phases: Structures and Biomembrane Aspects J. Phys. Chem. 1989, 93, 7304-7314
11. Hyde, S.; Andersson, S.; Larsson, K.; Blum, Z.; Landh, T.; Lidin, S.; Ninham, B. W. The Language of Shape: The Role of Curvature in Condensed Matter: Physics, Chemistry, Biology; Elsevier: Amsterdam, 1997.
12. Yaghmur, A.; Larsen, S. W.; Schmitt, M.; Østergaard, J.; Larsen, C.; Jensen, H.; Urtti, A.; Rappolt, M. In Situ Characterization of Lipidic Bupivacaine-Loaded Formulations Soft Matter 2011, 7, 8291-8295
13. Yaghmur, A.; Rappolt, M.; Østergaard, J.; Larsen, C.; Weng Larsen, S. Characterization of Bupivacaine-Loaded Formulations Based on Liquid Crystalline Phases and Microemulsions: The Effect of Lipid Composition Langmuir 2012, 28, 2881-2889
14. de Campo, L.; Yaghmur, A.; Sagalowicz, L.; Leser, M. E.; Watzke, H.; Glatter, O. Reversible Phase Transitions in Emulsified Nanostructured Lipid Systems Langmuir 2004, 20, 5254-5261
15. Qiu, H.; Caffrey, M. The Phase Diagram of the Monoolein/Water System: Metastability and Equilibrium Aspects Biomaterials 2000, 21, 223-234
16. Barauskas, J.; Landh, T. Phase Behavior of the Phytantriol/Water System Langmuir 2003, 19, 9562-9565
17. Angelov, B.; Angelova, A.; Vainio, U.; Garamus, V. M.; Lesieur, S.; Willumeit, R.; Couvreur, P. Long-Living Intermediates During a Lamellar to a Diamond-Cubic Lipid Phase Transition: A Small-Angle X-ray Scattering Investigation Langmuir 2009, 25, 3734-3742
18. Yaghmur, A.; Sartori, B.; Rappolt, M. The Role of Calcium in Membrane Condensation and Spontaneous Curvature Variations in Model Lipidic Systems Phys. Chem. Chem. Phys. 2011, 13, 3115-3125
19. 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
20. 2 Phase Transition Monitored by Combined Rapid Mixing and Time-Resolved Synchrotron SAXS PLoS ONE 2008, 3, e2072
21. Yaghmur, A.; Laggner, P.; Almgren, M.; Rappolt, M. Self-Assembly in Monoelaidin Aqueous Dispersions: Direct Vesicles to Cubosomes Transition PLoS ONE 2008, 3, e3747
22. Shah, J. C.; Sadhale, Y.; Chilukuri, D. M. Cubic Phase Gels as Drug Delivery Systems Adv. Drug Delivery Rev. 2001, 47, 229-250 (Pubitemid 32324116)
23. Boyd, B. J.; Whittaker, D. V.; Khoo, S. M.; Davey, G. Lyotropic Liquid Crystalline Phases Formed from Glycerate Surfactants as Sustained Release Drug Delivery Systems Int. J. Pharm. 2006, 309, 218-226 (Pubitemid 43129485)
24. Engstrom, S.; Norden, T. P.; Nyquist, H. Cubic Phases for Studies of Drug Partition into Lipid Bilayers Eur. J. Pharm. Sci. 1999, 8, 243-254 (Pubitemid 29325016)
25. Almsherqi, Z. A.; Landh, T.; Kohlwein, S. D.; Deng, Y. R. Cubic Membranes: The Missing Dimension of Cell Membrane Organization Int. Rev. Cell Mol. Biol. 2009, 274, 275-342
26. Snapp, E. L.; Hegde, R. S.; Francolini, M.; Lombardo, F.; Colombo, S.; Pedrazzini, E.; Borgese, N.; Lippincott-Schwartz, J. Formation of Stacked ER Cisternae by Low Affinity Protein Interactions J. Cell Biol. 2003, 163, 257-269 (Pubitemid 37363127)
27. Gustafsson, J.; Ljusberg-Wahren, H.; Almgren, M.; Larsson, K. Cubic Lipid-Water Phase Dispersed into Submicron Particles Langmuir 1996, 12, 4611-4613
28. Yaghmur, A.; Rappolt, M. Liquid Crystalline Nanoparticles as Drug Nanocarriers. In Colloids in Drug Delivery; Fanun, M., Ed.; CRC Press/Taylor & Francis: Boca Raton, FL, 2010; pp 339-355.
29. Nguyen, T. H.; Hanley, T.; Porter, C. J. H.; Boyd, B. J. Nanostructured Liquid Crystalline Particles Provide Long Duration Sustained-Release Effect for a Poorly Water Soluble Drug After Oral Administration J. Controlled Release 2011, 153, 180-186
30. Chang, C. M.; Bodmeier, R. Low Viscosity Monoglyceride-Based Drug Delivery Systems Transforming into a Highly Viscous Cubic Phase Int. J. Pharm. 1998, 173, 51-60 (Pubitemid 29027760)
31. Malmsten, M. Phase Transformations in Self-Assembly Systems for Drug Delivery Applications J. Dispersion Sci. Technol. 2007, 28, 63-72 (Pubitemid 44869307)
32. Esposito, E.; Cortesi, R.; Drechsler, M.; Paccamiccio, L.; Mariani, P.; Contado, C.; Stellin, E.; Menegatti, E.; Bonina, F.; Puglia, C. Cubosome Dispersions as Delivery Systems for Percutaneous Administration of Indomethacin Pharm. Res. 2005, 22, 2163-2173 (Pubitemid 41821596)
33. Lopes, L. B.; Ferreira, D. A.; de Paula, D.; Garcia, M. T. J.; Thomazini, J. A.; Fantini, M. C. A.; Bentley, M. V. L. B. Reverse Hexagonal Phase Nanodispersion of Monoolein and Oleic Acid for Topical Delivery of Peptides: in Vitro and in Vivo Skin Penetration of Cyclosporin A Pharm. Res. 2006, 23) 1332-1342 (Pubitemid 43946155)
34. Zeng, N. F.; Hu, Q. F.; Liu, Z. F.; Gao, X. F.; Hu, R. F.; Song, Q. F.; Gu, G. F.; Xia, H. F.; Yao, L. F.; Pang, Z. F.; Jiang, X. F.; Chen, J. F.; Fang, L. Preparation and Characterization of Paclitaxel-Loaded DSPE-PEG-Liquid Crystalline Nanoparticles (LCNPs) for Improved Bioavailability Int. J. Pharm. 2012, 424, 58-66
35. Esposito, E.; Mariani, P.; Ravani, L.; Contado, C.; Volta, M.; Bido, S.; Drechsler, M.; Mazzoni, S.; Menegatti, E.; Morari, M.; Cortesi, R. Nanoparticulate Lipid Dispersions for Bromocriptine Delivery: Characterization and in Vivo Study Eur. J. Pharm. Biopharm. 2012, 80, 306-314
36. Boyd, B. J.; Whittaker, D. V.; Khoo, S. M.; Davey, G. Hexosomes Formed from Glycerate Surfactants-Formulation as a Colloidal Carrier for Irinotecan Int. J. Pharm. 2006, 318, 154-162 (Pubitemid 43977801)
37. Mulet, X.; Kennedy, D. F.; Conn, C. E.; Hawley, A.; Drummond, C. J. High Throughput Preparation and Characterisation of Amphiphilic Nanostructured Nanoparticulate Drug Delivery Vehicles Int. J. Pharm. 2010, 395, 290-297
38. Barauskas, J.; Johnsson, M.; Tiberg, F. Self-Assembled Lipid Superstructures: Beyond Vesicles and Liposomes Nano Lett. 2005, 5, 1615-1619 (Pubitemid 41251697)
39. Libster, D.; Aserin, A.; Yariv, D.; Shoham, G.; Garti, N. Soft Matter Dispersions with Ordered Inner Structures, Stabilized by Ethoxylated Phytosterols Colloids Surf., B 2009, 74, 202-215
40. 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
41. 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. Disper. Sci. Technol. 2006, 27, 599-609 (Pubitemid 43878655)
42. Dulle, M.; Glatter, O. Internally Self-Assembled Submicrometer Emulsions Stabilized with a Charged Polymer or with Silica Particles Langmuir 2012, 28, 1136-1141
43. Almgren, M.; Borne, J.; Feitosa, E.; Khan, A.; Lindman, B. Dispersed Lipid Liquid Crystalline Phases Stabilized by a Hydrophobically Modified Cellulose Langmuir 2007, 23, 2768-2777 (Pubitemid 46383699)
44. Gustafsson, J.; Nylander, T.; Almgren, T.; Ljusberg-Wahren, H. Phase Behavior and Aggregate Structure in Aqueous Mixtures of Sodium Cholate and Glycerol Monooleate J. Colloid Interface Sci. 1999, 211, 326-335 (Pubitemid 29394633)
45. Uyama, M. F.; Nakano, M. F.; Yamashita, J. F.; Handa, T. Useful Modified Cellulose Polymers as New Emulsifiers of Cubosomes Langmuir 2009, 25, 4336-4338
46. Fong, C.; Wells, D.; Krodkiewska, I.; Hartley, P. G.; Drummond, C. J. New Role for Urea as a Surfactant Headgroup Promoting Self-Assembly in Water Chem. Mater. 2006, 18, 594-597 (Pubitemid 43260091)
47. Yaghmur, A.; de Campo, L.; Sagalowicz, L.; Leser, M. E.; Glatter, O. Control of the Internal Structure of MLO-Based Isasomes by the Addition of Diglycerol Monooleate and Soybean Phosphatidylcholine Langmuir 2006, 22, 9919-9927 (Pubitemid 46079268)
48. Nakano, M.; Teshigawara, T.; Sugita, A.; Leesajakul, W.; Taniguchi, A.; Kamo, T.; Matsuoka, H.; Handa, T. Dispersions of Liquid Crystalline Phases of the Monoolein/Oleic Acid/Pluronic F127 System Langmuir 2002, 18, 9283-9288 (Pubitemid 35458187)
49. Larsson, K. Colloidal Dispersions of Ordered Lipid-Water Phases J. Dispersion Sci. Technol. 1999, 20, 27-34
50. Amar-Yuli, I.; Wachtel, E.; Ben Shoshan, E.; Danino, D.; Aserin, A.; Garti, N. Hexosome and Hexagonal Phases Mediated by Hydration and Polymeric Stabilizer Langmuir 2007, 23, 3637-3645 (Pubitemid 46581888)
51. Barauskas, J.; Johnsson, M.; Johnson, F.; Tiberg, F. Cubic Phase Nanoparticles (Cubosome): Principles for Controlling Size, Structure, and Stability Langmuir 2005, 21, 2569-2577 (Pubitemid 40421910)
52. Spicer, P. T.; Hayden, K. L.; Lynch, M. L.; Ofori-Boateng, A.; Burns, J. L. Novel Process for Producing Cubic Liquid Crystalline Nanoparticles (Cubosomes) Langmuir 2001, 17, 5748-5756 (Pubitemid 35330732)
53. Yaghmur, A.; de Campo, L.; Sagalowicz, L.; Leser, M. E.; Glatter, O. Emulsified Microemulsions and Oil-Containing Liquid Crystalline Phases Langmuir 2005, 21, 569-577 (Pubitemid 40168841)
54. Yaghmur, A.; de Campo, L.; Salentinig, S.; Sagalowicz, L.; Leser, M. E.; Glatter, O. Oil-Loaded Monolinolein-Based Particles with Confined Inverse Discontinuous Cubic Structure (Fd 3 m) Langmuir 2006, 22, 517-521 (Pubitemid 43164784)
55. Dong, Y. D.; Larson, I.; Hanley, T.; Boyd, B. J. 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 (Pubitemid 44826357)
56. Chong, J.; Mulet, X.; Waddington, L. J.; Boyd, B. J.; Drummond, C. J. Steric Stabilsation 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
57. 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
58. 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
59. Murgia, S.; Falchi, A. M.; Mano, M.; Lampis, S.; Angius, R.; Carnerup, A. M.; Schmidt, J.; Diaz, G.; Giacca, M.; Talmon, Y.; Monduzzi, M. Nanoparticles from Lipid-Based Liquid Crystals: Emulsifier Influence on Morphology and Cytotoxicity J. Phys. Chem. B 2010, 114, 3518-3525
60. Moghimi, S. M.; Hunter, A. C. Poloxamers and Poloxamines in Nanoparticle Engineering and Experimental Medicine Trends Biotechnol. 2000, 18, 412-420
61. 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 (Pubitemid 40228662)
62. Zhai, J.; Waddington, L.; Wooster, T. J.; Aguilar, M. I.; Boyd, B. J. Revisiting β-Casein as a Stabilizer for Lipid Liquid Crystalline Nanostructured Particles Langmuir 2011, 27, 14757-14766
63. Berton, C.; Genot, C.; Ropers, M. H. Quantification of Unadsorbed Protein and Surfactant Emulsifiers in Oil-in-Water Emulsions J. Colloid Interface Sci. 2011, 354, 739-748
64. Antipova, A. S.; Semenova, M. G.; Belyakova, L. E.; Il'in, M. M. On Relationships Between Molecular Structure, Interaction and Surface Behavior in Mixture: Small-Molecule Surfactant+Protein Colloids Surf., B 2001, 21, 217-230 (Pubitemid 32500321)
65. Gudipati, V.; Sandra, S.; McClements, D. J.; Decker, E. A. Oxidative Stability and in Vitro Digestibility of Fish Oil-in-Water Emulsions Containing Multilayered Membranes J. Agric. Food Chem. 2010, 58, 8093-8099
66. Berton, C.; Ropers, M. H.; Viau, M.; Genot, C. Contribution of the Interfacial Layer to the Protection of Emulsified Lipids Against Oxidation J. Agric. Food Chem. 2011, 59, 5052-5061
67. Arnebrant, T.; Bergenstahl, B.; Bos, M. A.; Euston, S. R.; Golding, M.; Hartel, R.; Hasenhuettl, G. L.; McSweeney, S. L.; Narsimhan, G.; Nylander, T.; Orthoefer, F.; Pelan, E.; Wang, Z.; Wassell, P.; Weyland, M.; Wilde, P.; Young, N. Food Emulsifiers and Their Applications, 2 nd ed.; Springer: New York, 2008.
68. Berton, C.; Genot, C.; Guibert, D.; Ropers, M. H. Effect of Lateral Heterogeneity in Mixed Surfactant-Stabilized Interfaces on the Oxidation of Unsaturated Lipids in Oil-in-Water Emulsions J. Colloid Interface Sci. 2012, 377, 244-250
69. Knaapila, M.; Svensson, C.; Barauskas, J.; Zackrisson, M.; Nielsen, S. S.; Toft, K. N.; Vestergaard, B.; Arleth, L.; Olsson, U.; Pedersen, J. S.; Cerenius, Y. A New Small-Angle X-ray Scattering Set-Up on the Crystallography Beamline I711 at MAX-Lab J. Synchrotron Radiat. 2009, 16, 498-504
70. Almgren, M.; Edwards, K.; Karlsson, G. Cryo Transmission Electron Microscopy of Liposomes and Related Structures Colloids Surf., A 2000, 174, 3-21 (Pubitemid 30628959)
71. Hyde, S. T. Bicontinuous Structure in Lyotropic Liquid Crystals and Crystalline Hyperbolic Surfaces Curr. Opin. Solid State Mater. Sci. 1996, 1, 653-662 (Pubitemid 126415798)
72. Larsson, K.; Tiberg, F. Periodic Minimal Surface Structures in Bicontinuous Lipid-Water Phases and Nanoparticles Curr. Opin. Colloid Interface Sci. 2005, 9, 365-369 (Pubitemid 40797712)
73. Israelachvili, J. N.; Mitchell, D. J.; Ninham, B. W. Theory of Self-Assembly of Hydrocarbon Amphiphiles into Micelles and Bilayers J. Chem. Soc. 1976, 72, 1525-1568
74. Yaghmur, A.; Laggner, P.; Zhang, S.; Rappolt, M. Tuning Curvature and Stability of Monoolein Bilayers by Designer Lipid-Like Peptide Surfactants PLoS ONE 2007, 2, e479
75. Angelova, A.; Angelov, B.; Papahadjopoulos-Sternberg, B.; Bourgaux, C.; Couvreur, P. Protein Driven Patterning of Self-Assembled Cubosomic Nanostructures: Long Oriented Nanoridges J. Phys. Chem. B 2005, 109, 3089-3093 (Pubitemid 40352267)
76. Masum, S. M.; Li, S. J.; Tamba, Y.; Yamashita, Y.; Tanaka, T.; Yamazaki, M. Effect of de Novo Designed Peptides Interacting with the Lipid-Membrane Interface on the Stability of the Cubic Phases of the Monoolein Membrane Langmuir 2003, 19, 4745-4753
77. Masum, S. M.; Li, S. J.; Awad, T. S.; Yamazaki, M. Effect of Positively Charged Short Peptides on Stability of Cubic Phases of Monoolein/ Dioleoylphosphatidic Acid Mixtures Langmuir 2005, 21, 5290-5297 (Pubitemid 40850611)
78. Borne, J.; Nylander, T.; Khan, A. Phase Behavior and Aggregate Formation for the Aqueous Monoolein System Mixed with Sodium Oleate and Oleic Acid Langmuir 2001, 17, 7742-7751 (Pubitemid 35330942)
79. Yaghmur, A.; Kriechbaum, M.; Amenitsch, H.; Steinhart, M.; Laggner, P.; Rappolt, M. Effects of Pressure and Temperature on the Self-Assembled Fully Hydrated Nanostructures of Monoolein-Oil Systems Langmuir 2010, 26, 1177-1185
80. Barauskas, J.; Misiunas, A.; Gunnarsson, T.; Tiberg, F.; Johnsson, M. Sponge Nanoparticle Dispersions in Aqueous Mixtures of Diglycerol Monooleate, Glycerol Dioleate, and Polysorbate 80 Langmuir 2006, 22, 6328-6334 (Pubitemid 44140333)
81. Gustafsson, J.; Ljusberg-Wahren, H.; Almgren, M.; Larsson, K. Submicron Particles of Reversed Lipid Phases in Water Stabilized by a Nonionic Amphiphilic Polymer Langmuir 1997, 13, 6964-6971 (Pubitemid 127601886)
82. Johnsson, M.; Lam, Y.; Barauskas, J.; Tiberg, F. Aqueous Phase Behavior and Dispersed Nanoparticles of Diglycerol Monooleate/Glycerol Dioleate Mixtures Langmuir 2005, 21, 5159-5165 (Pubitemid 40795341)
83. Sørensen Moltke, A.-D.; Haahr, A.-M.; Becker, M. E.; Skibsted, H. L.; Bergenståhl, B.; Nilsson, L.; Jacobsen, C. Interactions between Iron, Phenolic Compounds, Emulsifiers, and pH in Omega-3-Enriched Oil-in-Water Emulsions J. Agric. Food Chem. 2008, 56, 1740-1750 (Pubitemid 351506888)
84. Haahr, A.-M.; Jacobsen, C. Emulsifier Type, Metal Chelation and pH Affect Oxidative Stability of n -3-Enriched Emulsions Eur. J. Lipid Sci. Technol. 2008, 110, 949-961