Manipulating the Ordered Nanostructure of Self-Assembled Monoolein and Phytantriol Nanoparticles with Unsaturated Fatty Acids

Langmuir

Volumn 34, Issue 8, 2018, Pages 2764-2773

  Tran, Nhiem ^a,b   Mulet, Xavier ^b   Hawley, Adrian M ^c   Fong, Celesta ^a,b   Zhai, Jiali ^a   Le, Tu C ^a   Ratcliffe, Julian ^b   Drummond, Calum J ^a  

^a RMIT UNIVERSITY   (Australia)

^b CSIRO   (Australia)

^c AUSTRALIAN SYNCHROTRON   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; CHARACTERIZATION; CONTROLLED DRUG DELIVERY; FATTY ACIDS; MICROEMULSIONS; NANOPARTICLES; NANOSTRUCTURES; STEREOCHEMISTRY; TARGETED DRUG DELIVERY; UNSATURATED FATTY ACIDS; X RAY SCATTERING;

CHARACTERIZATION METHODS; CONTROLLED MANIPULATIONS; DRUG DELIVERY SYSTEM; LYOTROPIC LIQUID CRYSTALLINE; MESOPHASE STRUCTURES; MICELLAR CUBIC PHASIS; ORDERED NANOSTRUCTURES; SELF-ASSEMBLED SYSTEMS;

DRUG DELIVERY;

3,7,11,15-TETRAMETHYL-1,2,3-HEXADECANETRIOL; ACYLGLYCEROL; FATTY ALCOHOL; GLYCEROL OLEATE; NANOMATERIAL; UNSATURATED FATTY ACID;

CHEMISTRY; PARTICLE SIZE; SURFACE PROPERTY;

FATTY ACIDS, UNSATURATED; FATTY ALCOHOLS; GLYCERIDES; NANOSTRUCTURES; PARTICLE SIZE; SURFACE PROPERTIES;

EID: 85042408607     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.7b03541     Document Type: Article

References (59)

1. 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 10.1016/j.jcis.2012.10.014
2. Angelov, B.; Angelova, A.; Filippov, S. K.; Drechsler, M.; Štěpánek, P.; Lesieur, S. Multicompartment Lipid Cubic Nanoparticles with High Protein Upload: Millisecond Dynamics of Formation ACS Nano 2014, 8, 5216-5226 10.1021/nn5012946
3. 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. 2010, 44, 147-156 10.1021/ar100120v
4. Clogston, J.; Caffrey, M. Controlling release from the lipidic cubic phase. Amino acids, peptides, proteins and nucleic acids J. Controlled Release 2005, 107, 97-111 10.1016/j.jconrel.2005.05.015
5. 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 10.1016/j.jconrel.2011.03.033
6. Tarahovsky, Y. S.; Koynova, R.; MacDonald, R. C. DNA release from lipoplexes by anionic lipids: correlation with lipid mesomorphism, interfacial curvature, and membrane fusion Biophys. J. 2004, 87, 1054-1064 10.1529/biophysj.104.042895
7. Koltover, I.; Salditt, T.; Rädler, J. O.; Safinya, C. R. An inverted hexagonal phase of cationic liposome-DNA complexes related to DNA release and delivery Science 1998, 281, 78-81 10.1126/science.281.5373.78
8. 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 10.1039/c1cs15148g
9. Fong, W.-K.; Hanley, T.; Boyd, B. J. Stimuli responsive liquid crystals provide "on-demand" drug delivery in vitro and in vivo J. Controlled Release 2009, 135, 218-226 10.1016/j.jconrel.2009.01.009
10. Fong, W.-K.; Negrini, R.; Vallooran, J. J.; Mezzenga, R.; Boyd, B. J. Responsive self-assembled nanostructured lipid systems for drug delivery and diagnostics J. Colloid Interface Sci. 2016, 484, 320-339 10.1016/j.jcis.2016.08.077
11. Meikle, T. G.; Yao, S.; Zabara, A.; Conn, C. E.; Drummond, C. J.; Separovic, F. Predicting the release profile of small molecules from within the ordered nanostructured lipidic bicontinuous cubic phase using translational diffusion coefficients determined by PFG-NMR Nanoscale 2017, 9, 2471-2478 10.1039/c6nr07382d
12. Phan, S.; Fong, W.-K.; Kirby, N.; Hanley, T.; Boyd, B. J. Evaluating the link between self-assembled mesophase structure and drug release Int. J. Pharm. 2011, 421, 176-182 10.1016/j.ijpharm.2011.09.022
13. Falchi, A. M.; Rosa, A.; Atzeri, A.; Incani, A.; Lampis, S.; Meli, V.; Caltagirone, C.; Murgia, S. Effects of monoolein-based cubosome formulations on lipid droplets and mitochondria of HeLa cells Toxicol. Res. 2015, 4, 1025-1036 10.1039/c5tx00078e
14. 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 10.1021/jp9098655
15. Shen, H.-H.; Crowston, J. G.; Huber, F.; Saubern, S.; McLean, K. M.; Hartley, P. G. The influence of dipalmitoyl phosphatidylserine on phase behaviour of and cellular response to lyotropic liquid crystalline dispersions Biomaterials 2010, 31, 9473-9481 10.1016/j.biomaterials.2010.08.030
16. Tran, N.; Mulet, X.; Hawley, A. M.; Hinton, T. M.; Mudie, S. T.; Muir, B. W.; Giakoumatos, E. C.; Waddington, L. J.; Kirby, N. M.; Drummond, C. J. Nanostructure and Cytotoxicity of Self-Assembled Monoolein-Capric Acid Lyotropic Liquid Crystalline Nanoparticles RSC Adv. 2015, 5, 26785-26795 10.1039/c5ra02604k
17. Zhai, J.; Suryadinata, R.; Luan, B.; Tran, N.; Hinton, T. M.; Ratcliffe, J.; Hao, X.; Drummond, C. J. Amphiphilic brush polymers produced using the RAFT polymerisation method stabilise and reduce the cell cytotoxicity of lipid lyotropic liquid crystalline nanoparticles Faraday Discuss. 2016, 191, 545-563 10.1039/c6fd00039h
18. Tran, N.; Bye, N.; Moffat, B. A.; Wright, D. K.; Cuddihy, A.; Hinton, T. M.; Hawley, A. M.; Reynolds, N. P.; Waddington, L. J.; Mulet, X.; Turnley, A. M.; Morganti-Kossmann, M. C.; Muir, B. W. Dual-modality NIRF-MRI cubosomes and hexosomes: High throughput formulation and in vivo biodistribution Mater. Sci. Eng. C 2016, 71, 584-593 10.1016/j.msec.2016.10.028
19. Briggs, J.; Chung, H.; Caffrey, M. The temperature-composition phase diagram and mesophase structure characterization of the monoolein/water system J. Phys. II 1996, 6, 723-751 10.1051/jp2:1996208
20. Kulkarni, C. V.; Wachter, W.; Iglesias-Salto, G.; Engelskirchen, S.; Ahualli, S. Monoolein: a magic lipid? Phys. Chem. Chem. Phys. 2011, 13, 3004-3021 10.1039/c0cp01539c
21. Hato, M.; Yamashita, J.; Shiono, M. Aqueous phase behavior of lipids with isoprenoid type hydrophobic chains J. Phys. Chem. B 2009, 113, 10196-10209 10.1021/jp902883q
22. Barauskas, J.; Landh, T. Phase behavior of the phytantriol/water system Langmuir 2003, 19, 9562-9565 10.1021/la0350812
23. Luzzati, V.; Spegt, P. A. Polymorphism of lipids Nature 1967, 215, 701-704 10.1038/215701a0
24. Seddon, J. M.; Templer, R. H. Polymorphism of lipid-water systems Handb. Biol. Phys. 1995, 1, 97-160 10.1016/s1383-8121(06)80020-5
25. Hyde, S. T. Identification of lyotropic liquid crystalline mesophases. Handbook of Applied Surface and Colloid Chemistry; Wiley, 2001; Vol. 2, pp 299-332.
26. Shearman, G. C.; Ces, O.; Templer, R. H.; Seddon, J. m. Inverse lyotropic phases of lipids and membrane curvature J. Phys.: Condens. Matter 2006, 18, S1105 10.1088/0953-8984/18/28/s01
27. van't Hag, L.; Gras, S. L.; Conn, C. E.; Drummond, C. J. Lyotropic liquid crystal engineering moving beyond binary compositional space-ordered nanostructured amphiphile self-assembly materials by design Chem. Soc. Rev. 2017, 46, 2705-2731 10.1039/c6cs00663a
28. Borné, 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 10.1021/la010650w
29. Caboi, F.; Amico, G. S.; Pitzalis, P.; Monduzzi, M.; Nylander, T.; Larsson, K. Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior Chem. Phys. Lipids 2001, 109, 47-62 10.1016/s0009-3084(00)00200-0
30. Angelov, B.; Angelova, A.; Ollivon, M.; Bourgaux, C.; Campitelli, A. Diamond-type lipid cubic phase with large water channels J. Am. Chem. Soc. 2003, 125, 7188-7189 10.1021/ja034578v
31. Negrini, R.; Mezzenga, R. Diffusion, molecular separation, and drug delivery from lipid mesophases with tunable water channels Langmuir 2012, 28, 16455-16462 10.1021/la303833s
32. 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 10.1021/la061706v
33. Yaghmur, A.; Sartori, B.; Rappolt, M. Self-assembled nanostructures of fully hydrated monoelaidin-elaidic acid and monoelaidin-oleic acid systems Langmuir 2012, 28, 10105-10119 10.1021/la3019716
34. Aota-Nakano, Y.; Li, S. J.; Yamazaki, M. Effects of electrostatic interaction on the phase stability and structures of cubic phases of monoolein/oleic acid mixture membranes Biochim. Biophys. Acta 1999, 1461, 96-102 10.1016/s0005-2736(99)00156-x
35. Salentinig, S.; Sagalowicz, L.; Glatter, O. Self-Assembled Structures and pKa Value of Oleic Acid in Systems of Biological Relevance Langmuir 2010, 26, 11670-11679 10.1021/la101012a
36. Tran, N.; Mulet, X.; Hawley, A. M.; Conn, C. E.; Zhai, J.; Waddington, L. J.; Drummond, C. J. First Direct Observation of Stable Internally Ordered Janus Nanoparticles Created by Lipid Self-Assembly Nano Lett. 2015, 15, 4229-4233 10.1021/acs.nanolett.5b01751
37. Zhai, J.; Tran, N.; Sarkar, S.; Fong, C.; Mulet, X.; Drummond, C. J. Self-assembled Lyotropic Liquid Crystalline Phase Behavior of Monoolein-Capric Acid-Phospholipid Nanoparticulate Systems Langmuir 2017, 33, 2571-2580 10.1021/acs.langmuir.6b04045
38. Razumas, V.; Talaikytedot, Z.; Barauskasa, J.; Larsson, K.; Miezis, Y.; Nylander, T. Effects of distearoylphosphatidylglycerol and lysozyme on the structure of the monoolein-water cubic phase: X-ray diffraction and Raman scattering studies Chem. Phys. Lipids 1996, 84, 123-138 10.1016/s0009-3084(96)02629-1
39. Tran, N.; Hawley, A. M.; Zhai, J.; Muir, B. W.; Fong, C.; Drummond, C. J.; Mulet, X. High-throughput screening of saturated fatty acid influence on nanostructure of lyotropic liquid crystalline lipid nanoparticles Langmuir 2016, 32, 4509-4520 10.1021/acs.langmuir.5b03769
40. Funari, S. S.; Barceló, F.; Escribá, P. V. Effects of oleic acid and its congeners, elaidic and stearic acids, on the structural properties of phosphatidylethanolamine membranes J. Lipid Res. 2003, 44, 567-575 10.1194/jlr.m200356-jlr200
41. Roach, C.; Feller, S. E.; Ward, J. A.; Shaikh, S. R.; Zerouga, M.; Stillwell, W. Comparison of cis and trans fatty acid containing phosphatidylcholines on membrane properties Biochemistry 2004, 43, 6344-6351 10.1021/bi049917r
42. Seddon, J. M.; Squires, A. M.; Conn, C. E.; Ces, O.; Heron, A. J.; Mulet, X.; Shearman, G. C.; Templer, R. H. Pressure-jump X-ray studies of liquid crystal transitions in lipids Philos. Trans. R. Soc., A 2006, 364, 2635-2655 10.1098/rsta.2006.1844
43. 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 10.1021/la026297r
44. Ridell, A.; Ekelund, K.; Evertsson, H.; Engström, S. On the water content of the solvent/monoolein/water sponge (L3) phase Colloids Surf., A 2003, 228, 17-24 10.1016/s0927-7757(03)00299-1
45. Cherezov, V.; Clogston, J.; Papiz, M. Z.; Caffrey, M. Room to move: crystallizing membrane proteins in swollen lipidic mesophases J. Mol. Biol. 2006, 357, 1605-1618 10.1016/j.jmb.2006.01.049
46. Angelov, B.; Angelova, A.; Mutafchieva, R.; Lesieur, S.; Vainio, U.; Garamus, V. M.; Jensen, G. V.; Pedersen, J. S. SAXS investigation of a cubic to a sponge (L3) phase transition in self-assembled lipid nanocarriers Phys. Chem. Chem. Phys. 2011, 13, 3073-3081 10.1039/c0cp01029d
47. Duesing, P. M.; Templer, R. H.; Seddon, J. M. Quantifying packing frustration energy in inverse lyotropic mesophases Langmuir 1997, 13, 351-359 10.1021/la960602p
48. Shearman, G. C.; Khoo, B. J.; Motherwell, M.-L.; Brakke, K. A.; Ces, O.; Conn, C. E.; Seddon, J. M.; Templer, R. H. Calculations of and evidence for chain packing stress in inverse lyotropic bicontinuous cubic phases Langmuir 2007, 23, 7276-7285 10.1021/la700355a
49. Qiu, H.; Caffrey, M. The phase diagram of the monoolein/water system: metastability and equilibrium aspects Biomaterials 2000, 21, 223-234 10.1016/s0142-9612(99)00126-x
50. Anderson, D. M.; Gruner, S. M.; Leibler, S. Geometrical aspects of the frustration in the cubic phases of lyotropic liquid crystals Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5364-5368 10.1073/pnas.85.15.5364
51. Tilley, A. J.; Drummond, C. J.; Boyd, B. J. Disposition and association of the steric stabilizer Pluronic F127 in lyotropic liquid crystalline nanostructured particle dispersions J. Colloid Interface Sci. 2013, 392, 288-296 10.1016/j.jcis.2012.09.051
52. Hyde, S. T. Bicontinuous structures in lyotropic liquid crystals and crystalline hyperbolic surfaces Curr. Opin. Solid State Mater. Sci. 1996, 1, 653-662 10.1016/s1359-0286(96)80047-7
53. Larsson, K.; Tiberg, F. Periodic minimal surface structures in bicontinuous lipid-water phases and nanoparticles Curr. Opin. Colloid Interface Sci. 2005, 9, 365-369 10.1016/j.cocis.2004.12.002
54. Larsson, K. Two cubic phases in monoolein-water system Nature 1983, 304, 664 10.1038/304664c0
55. 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 10.1021/la970566+
56. Abraham, T.; Hato, M.; Hirai, M. Polymer-Dispersed Bicontinuous Cubic Glycolipid Nanoparticles Biotechnol. Prog. 2005, 21, 255-262 10.1021/bp0498544
57. 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 10.1021/la061303v
58. Rizwan, S. B.; Dong, Y.-D.; Boyd, B. J.; Rades, T.; Hook, S. 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 10.1016/j.micron.2006.08.003
59. Rizwan, S. B.; Assmus, D.; Boehnke, A.; Hanley, T.; Boyd, B. J.; Rades, T.; Hook, S. Preparation of phytantriol cubosomes by solvent precursor dilution for the delivery of protein vaccines Eur. J. Pharm. Biopharm. 2011, 79, 15-22 10.1016/j.ejpb.2010.12.034