||Fabrication of vesicular structures from didodecyl-chained ion pair amphiphile with additives by using a semi-spontaneous process
||Department of Chemical Engineering
Ion Pair Amphiphile
In this study, ion pair amphiphile (IPA), dodecyltrimethylammonium-dodecylsulfate (DTMA-DS), composed of anionic surfactant, sodium dodecylsulfate (SDS), and cationic surfactant, dodecyltrimethylammonium bromide (DTMAB), was successfully fabricated. Then, catanionic vesicles were prepared from the IPA by a semispontaneous approach. The effects of added cholesterol and cationic surfactants, dihexadecyldimethylammonium (DHDAB) and ditetradecyldimethylammonium bromide (DTDAB), DTMA-DS/cholesterol vesicles on the physical properties and stability of the catanionic vesicles were evaluated. Without the addition of cationic surfactants, a negative charge character of the vesicle surfaces was detected, in contrast with the addition of cationic surfactants. A fluorescence polarization study was performed to investigate the bilayer packing characteristics of the vesicles.
Physical stability of the catanionic vesicles determined by visual and vesicle size was monitored with time at room temperature. The mean sizes of the vesicles ranged from 156 to 224 nm with narrow distributions. Negatively charged characteristic of the vesicles was confirmed based on the zeta potential values varying from -21 to -37 mV. The zeta potential of the vesicles with added cationic surfactants (DHDAB or DTDAB) varied from 50 to 132 mV. Incorporation of cholesterol and the homogenizing time were found to be crucial in the formation of stable DTMA-DS/DHDAB and DTMA-DS/ DTDAB catanionic vesicles.
DTDAB was found to provide a positively charged characteristic for the catanionic vesicles, which induced the repulsive interaction between vesicles and thus inhibited the fusion or aggregation of the vesicles. The presence of cholesterol in the DTMA-DS/DTDAB bilayers would increase the distance between the charged headgroups and decrease the counterion binding on the bilayer surfaces, which could explain the cholesterol-enhanced charge character of the catanionic vesicles. The addition of ethanol in the DTMA-DS/DTDAB vesicle system did not enhance the stability of the vesicles, probably because the solvophobic effect of the headgroups tend to diminish the vesicular structures. Transmission electron microscopy (TEM) images have confirmed the spherical structures of the vesicles.
Keyword: Catanionic vesicles; Intra-vesicular approach; Inter-vesicular approach;Ion pair amphiphile; Semi-spontaneous process
TABLE OF CONTENTS
TABLE OF CONTENTS v
LIST OF TABLES vii
LIST OF FIGURES ix
CHAPTER I INTRODUCTION 1
1.1. Background 1
1.2. Research Motivation 6
CHAPTER II LITERATURE REVIEW 8
2.1. Drug Delivery 8
2.1.1 High-Density Charged Surface 9
2.1.2 Reduction of Disulphide Bridges 10
2.1.3 Zeta Potential Changing Methodology 11
2.2 Ion Pair Amphiphile 13
2.3 Formation of Catanionic Vesicles 17
2.4 The Packing Parameter 21
2.5 Additional Charged Surfactant 30
2.6 Effects of Cholesterol 34
2.7 Effect of Ethanol 38
CHAPTER III EXPERIMENTAL 45
3.1. Materials 45
3.2. Equipments 45
3.2.1 Homogenizer 45
3.2.2 Particle Size/ Zeta Potential Analyzer 51
3.2.3 Laser Doppler Electrophoresis Zeta Potential Analyzer 52
3.2.4 Transmission Electron Microscope 53
3.2.5 Multi-Mode Microplate Reader 54
3.3. Methodology 54
3.3.1 Preparation of DTMA-DS 54
3.3.2 Preparation of Catanionic Vesicles 55
3.3.3 Size Distribution of Catanionic Vesicles 56
3.3.4 Zeta Potential of Catanionic Vesicles 56
3.3.5 Transmission Electron Microscope Observation 56
3.3.6 Fluorescence Polarization Measurement 57
CHAPTER 4 RESULTS AND DISCUSSION 62
4.1. Formation Of Catanionic Vesicles 62
4.1.1 Catanionic Vesicles Formed by DTMA-DS 62
4.1.2 Catanionic Vesicles Formed by DTMA-DS/Cholesterol in Buffer Solution 67
4.1.3 FP Analysis Result 81
4.1.4 Temperature Effect Analysis on the Vesicular Structure 84
4.2 Catanionic Vesicles Formed by DTMA-DS/DHDAB /Cholesterol 87
4.2.1 Zeta Potential Result 98
4.2.2 FP Analysis Result 100
4.2.3. Temperature Effect on The Vesicular Structure 102
4.2.4 Effect of Added Ethanol on the Modified Catanionic Vesicles. 104
CHAPTER V SUMMARY 108
Abdulkarim, M., N. Agulló, B. Cattoz, P. Griffiths, A. Bernkop-Schnürch, S. G. Borros and M. Gumbleton (2015). "Nanoparticle diffusion within intestinal mucus: Three-dimensional response analysis dissecting the impact of particle surface charge, size and heterogeneity across polyelectrolyte, pegylated and viral particles." European Journal of Pharmaceutics and Biopharmaceutics 97: 230-238.
Andersson, M., T. Curstedt, H. Jörnvall and J. Johansson (1995). "An amphipathic helical motif common to tumourolytic polypeptide NK-lysin and pulmonary surfactant polypeptide SP-B." FEBS letters 362(3): 328-332.
Andrews, G. P., T. P. Laverty and D. S. Jones (2009). "Mucoadhesive polymeric platforms for controlled drug delivery." European Journal of Pharmaceutics and Biopharmaceutics 71(3): 505-518.
Antunes, F. E., E. F. Marques, M. G. Miguel and B. Lindman (2009). "Polymer–vesicle association." Advances in Colloid and Interface Science 147: 18-35.
Atuma, C., V. Strugala, A. Allen and L. Holm (2001). "The adherent gastrointestinal mucus gel layer: thickness and physical state in vivo." American Journal of Physiology-Gastrointestinal and Liver Physiology 280(5): G922-G929.
Azmin, M., A. Florence, R. Handjani‐Vila, J. Stuart, G. Vanlerberghe and J. Whittaker (1985). "The effect of non‐ionic surfactant vesicle (niosome) entrapment on the absorption and distribution of methotrexate in mice." Journal of Pharmacy and Pharmacology 37(4): 237-242.
Balazs, D. A. and W. Godbey (2011). "Liposomes for use in gene delivery." Journal of drug delivery 2011.
Bansil, R. and B. S. Turner (2006). "Mucin structure, aggregation, physiological functions and biomedical applications." Current opinion in colloid & interface science 11(2-3): 164-170.
Barry, J. A. and K. Gawrisch (1995). "Effects of ethanol on lipid bilayers containing cholesterol, gangliosides, and sphingomyelin." Biochemistry 34(27): 8852-8860.
Bhattacharya, S., S. De and M. Subramanian (1998). "Synthesis and vesicle formation from hybrid bolaphile/amphiphile ion-pairs. Evidence of membrane property modulation by molecular design." The Journal of Organic Chemistry 63(22): 7640-7651.
Boudier, A., P. Castagnos, E. Soussan, G. Beaune, H. Belkhelfa, C. Ménager, V. Cabuil, L. Haddioui, C. Roques and I. Rico-Lattes (2011). "Polyvalent catanionic vesicles: exploring the drug delivery mechanisms." International journal of pharmaceutics 403(1-2): 230-236.
Bramer, T., N. Dew and K. Edsman (2007). "Pharmaceutical applications for catanionic mixtures." Journal of Pharmacy and Pharmacology 59(10): 1319-1334.
Carmona-Ribeiro, A. and B. Midmore (1992). "Surface potential in charged synthetic amphiphile vesicles." The Journal of Physical Chemistry 96(8): 3542-3547.
Carrion, F., A. De La Maza and J. Parra (1994). "The influence of ionic strength and lipid bilayer charge on the stability of liposomes." Journal of colloid and interface science 164(1): 78-87.
Chandra, N. and V. Tyagi (2013). "Synthesis, properties, and applications of amino acids based surfactants: a review." Journal of Dispersion Science and Technology 34(6): 800-808.
Chater, P. I., M. D. Wilcox and J. P. Pearson (2018). "Efficacy and safety concerns over the use of mucus modulating agents for drug delivery using nanoscale systems." Advanced drug delivery reviews 124: 184-192.
Chiruvolu, S., J. Israelachvili, E. Naranjo, Z. Xu, J. Zasadzinski, E. Kaler and K. Herrington (1995). "Measurement of forces between spontaneous vesicle-forming bilayers." Langmuir 11(11): 4256-4266.
Cone, R. A. (2009). "Barrier properties of mucus." Advanced drug delivery reviews 61(2): 75-85.
Cullum, D. (1994). Ion exchange. Introduction to Surfactant Analysis, Springer: 77-104.
DeMaris, E. E. (1991). High speed rotational dispersion device using short shear path, Google Patents.
Desai, P., R. R. Patlolla and M. Singh (2010). "Interaction of nanoparticles and cell-penetrating peptides with skin for transdermal drug delivery." Molecular membrane biology 27(7): 247-259.
Dhankhar, P. (2014). "Homogenization fundamentals." IOSR Journal of Engineering 4(5): 01-08.
Dhawan, V. V. and M. S. Nagarsenker (2017). "Catanionic systems in nanotherapeutics–Biophysical aspects and novel trends in drug delivery applications." Journal of Controlled Release 266: 331-345.
Discher, B. M., W. R. Schief, V. Vogel and S. B. Hall (1999). "Phase separation in monolayers of pulmonary surfactant phospholipids at the air–water interface: composition and structure." Biophysical journal 77(4): 2051-2061.
Discher, B. M., Y.-Y. Won, D. S. Ege, J. C. Lee, F. S. Bates, D. E. Discher and D. A. Hammer (1999). "Polymersomes: tough vesicles made from diblock copolymers." Science 284(5417): 1143-1146.
Dumay, E., D. Chevalier-Lucia, L. Picart-Palmade, A. Benzaria, A. Gràcia-Julià and C. Blayo (2013). "Technological aspects and potential applications of (ultra) high-pressure homogenisation." Trends in Food Science & Technology 31(1): 13-26.
Elizondo, E., E. Moreno, I. Cabrera, A. Cordoba, S. Sala, J. Veciana and N. Ventosa (2011). Liposomes and other vesicular systems: structural characteristics, methods of preparation, and use in nanomedicine. Progress in molecular biology and translational science, Elsevier. 104: 1-52.
Engberts, J. B. and J. Kevelam (1996). "Formation and stability of micelles and vesicles." Current Opinion in Colloid & Interface Science 1(6): 779-789.
Feitosa, E. and W. Brown (1997). "Fragment and vesicle structures in sonicated dispersions of dioctadecyldimethylammonium bromide." Langmuir 13(18): 4810-4816.
Feitosa, E., G. Karlsson and K. Edwards (2006). "Unilamellar vesicles obtained by simply mixing dioctadecyldimethylammonium chloride and bromide with water." Chemistry and physics of lipids 140(1-2): 66-74.
Gallová, J., D. Uhríková, N. Kučerka, J. Teixeira and P. Balgavý (2008). "Hydrophobic thickness, lipid surface area and polar region hydration in monounsaturated diacylphosphatidylcholine bilayers: SANS study of effects of cholesterol and β-sitosterol in unilamellar vesicles." Biochimica et Biophysica Acta (BBA)-Biomembranes 1778(11): 2627-2632.
Guha, P., B. Roy, G. Karmakar, P. Nahak, S. Koirala, M. Sapkota, T. Misono, K. Torigoe and A. K. Panda (2015). "Ion-pair amphiphile: a neoteric substitute that modulates the physicochemical properties of biomimetic membranes." The Journal of Physical Chemistry B 119(11): 4251-4262.
Hays, L. M., J. H. Crowe, L. M. Crowe, R. E. Feeney and A. E. Oliver (1999). Prevention of leakage and phase separation during thermotropic phase transition in liposomes and biological cells, Google Patents.
Hiromitsu, I. and L. Kevan (1987). "Effect of cholesterol on the solubilization site and the photoionization efficiency of chlorophyl a in dipalmitoylphosphatidylcholine vesicle solutions as studied by electron spin resonance and optical absorption spectroscopies." Journal of the American Chemical Society 109(15): 4501-4507.
Hopkins, T. (1991). "Physical and chemical cell disruption for the recovery of intracellular proteins." Bioprocess Technol 12: 57-83.
Huang, J.-B., B.-Y. Zhu, G.-X. Zhao and Z.-Y. Zhang (1997). "Vesicle formation of a 1: 1 catanionic surfactant mixture in ethanol solution." Langmuir 13(21): 5759-5761.
Huang, Z.-L., J.-Y. Hong, C.-H. Chang and Y.-M. Yang (2009). "Gelation of charged catanionic vesicles prepared by a semispontaneous process." Langmuir 26(4): 2374-2382.
Jiang, L., Y. Cao, X. Ni, M. Zhang and G. Cao (2018). "Influences of the concentration and the molar ratio of mixed surfactants on the performance of vesicle pseudostationary phase." Electrophoresis 39(14): 1794-1801.
Jiang, Y., Y. Luan, F. Qin, L. Zhao and Z. Li (2012). "Catanionic vesicles from an amphiphilic prodrug molecule: a new concept for drug delivery systems." RSC Advances 2(17): 6905-6912.
Jurašin, D. D., S. Šegota, V. Čadež, A. Selmani and M. D. Sikirć (2017). "Recent Advances in Catanionic Mixtures." Application and Characterization of Surfactants: 33.
Kaler, E. W., K. L. Herrington, A. K. Murthy and J. A. Zasadzinski (1992). "Phase behavior and structures of mixtures of anionic and cationic surfactants." The Journal of Physical Chemistry 96(16): 6698-6707.
Khelashvili, G. and D. Harries (2013). "How cholesterol tilt modulates the mechanical properties of saturated and unsaturated lipid membranes." The Journal of Physical Chemistry B 117(8): 2411-2421.
Knight, J. and R. House (1959). "Analysis of surfactant mixtures. I." Journal of the American Oil Chemists' Society 36(5): 195-200.
KONG, L.-l., J.-f. HU and N.-h. CHEN (2012). "Advances in pharmacology and toxicology of coumarins [J]." Chinese Pharmacological Bulletin 2.
Kuo, A.-T. and C.-H. Chang (2013). "Cholesterol-induced condensing and disordering effects on a rigid catanionic bilayer: A molecular dynamics study." Langmuir 30(1): 55-62.
Kuo, A.-T. and C.-H. Chang (2016). "Recent strategies in the development of catanionic vesicles." Journal of oleo science: ess15249.
Kuo, A.-T., C.-L. Tu, Y.-M. Yang and C.-H. Chang (2018). "Enhanced physical stability of mixed ion pair amphiphile/double-chained cationic surfactant vesicles in the presence of cholesterol." Journal of oleo science: ess18008.
Kuo, A.-T., C.-L. Tu, Y.-M. Yang and C.-H. Chang (2018). "Enhanced physical stability of positively charged catanionic vesicles: Role of cholesterol-adjusted molecular packing." Journal of the Taiwan Institute of Chemical Engineers 92: 29-35.
Lai, S. K., Y.-Y. Wang and J. Hanes (2009). "Mucus-penetrating nanoparticles for drug and gene delivery to mucosal tissues." Advanced drug delivery reviews 61(2): 158-171.
Lawaczeck, R., P. K. Nandi and C. Nicolau (1987). "Interaction of negatively charged liposomes with nuclear membranes: adsorption, lipid mixing and lysis of the vesicles." Biochimica et Biophysica Acta (BBA)-Biomembranes 903(1): 123-131.
Lee, J. and C.-H. Chang (2014). "DNA association-enhanced physical stability of catanionic vesicles composed of ion pair amphiphile with double-chain cationic surfactant." Colloids and Surfaces B: Biointerfaces 121: 171-177.
Lee, W.-H., Y.-L. Tang, T.-C. Chiu and Y.-M. Yang (2015). "Synthesis of ion-pair amphiphiles and calorimetric study on the gel to liquid-crystalline phase transition behavior of their bilayers." Journal of Chemical & Engineering Data 60(4): 1119-1125.
Li, J., X. Wang, T. Zhang, C. Wang, Z. Huang, X. Luo and Y. Deng (2015). "A review on phospholipids and their main applications in drug delivery systems." Asian journal of pharmaceutical sciences 10(2): 81-98.
Liang, C.-H. and T.-H. Chou (2009). "Effect of chain length on physicochemical properties and cytotoxicity of cationic vesicles composed of phosphatidylcholines and dialkyldimethylammonium bromides." Chemistry and physics of lipids 158(2): 81-90.
Liu, M., J. Zhang, W. Shan and Y. Huang (2015). "Developments of mucus penetrating nanoparticles." asian journal of pharmaceutical sciences 10(4): 275-282.
Liu, Y.-S., C.-F. Wen and Y.-M. Yang (2012). "Development of ethosome-like catanionic vesicles for dermal drug delivery." Journal of the Taiwan Institute of Chemical Engineers 43(6): 830-838.
Lonez, C., M. Vandenbranden and J.-M. Ruysschaert (2008). "Cationic liposomal lipids: from gene carriers to cell signaling." Progress in lipid research 47(5): 340-347.
Lopes, G., Y.-L. Wu, I. Kudaba, D. Kowalski, B. C. Cho, G. Castro, V. Srimuninnimit, I. Bondarenko, K. Kubota and G. M. Lubiniecki (2018). Pembrolizumab (pembro) versus platinum-based chemotherapy (chemo) as first-line therapy for advanced/metastatic NSCLC with a PD-L1 tumor proportion score (TPS)≥ 1%: Open-label, phase 3 KEYNOTE-042 study, American Society of Clinical Oncology.
Mannan, A. and F. Unnisa (2019). "Role of biochemicals and other factors affecting biotransformation and drug absorption."
Marques, E. F., R. O. Brito, S. G. Silva, J. E. Rodríguez-Borges, M. L. s. d. Vale, P. Gomes, M. J. Araújo and O. Söderman (2008). "Spontaneous vesicle formation in catanionic mixtures of amino acid-based surfactants: chain length symmetry effects." Langmuir 24(19): 11009-11017.
Marques, E. F., O. Regev, A. Khan, M. d. G. Miguel and B. Lindman (1999). "Interactions between catanionic vesicles and oppositely charged polyelectrolytes phase behavior and phase structure." Macromolecules 32(20): 6626-6637.
Martínez-Monteagudo, S. I., B. Yan and V. Balasubramaniam (2017). "Engineering process characterization of high-pressure homogenization—from laboratory to industrial scale." Food Engineering Reviews 9(3): 143-169.
Martinez-Sanchez, M. (2004). Effect of homogenisation on milk fouling in a tubular heat exchanger: a thesis presented in partial fulfilment for the requirements for the degree of Master of Food Engineering, Massey University, Palmerston North, New Zealand, Massey University.
Marui, N., M. K. Offermann, R. Swerlick, C. Kunsch, C. A. Rosen, M. Ahmad, R. W. Alexander and R. M. Medford (1993). "Vascular cell adhesion molecule-1 (VCAM-1) gene transcription and expression are regulated through an antioxidant-sensitive mechanism in human vascular endothelial cells." The Journal of clinical investigation 92(4): 1866-1874.
McMullen, T. P. and R. N. McElhaney (1996). "Physical studies of cholesterol-phospholipid interactions." Current Opinion in Colloid & Interface Science 1(1): 83-90.
Mozafari, M. (2010). Nanoliposomes: preparation and analysis. Liposomes, Springer: 29-50.
Pandolfe, W. D. (1981). "Effect of dispersed and continuous phase viscosity on droplet size of emulsions generated by homogenization." Journal of Dispersion Science and Technology 2(4): 459-474.
Pandolfe, W. D. (1982). "Development of the new Gaulin Micro-Gap™ homogenizing valve." Journal of Dairy Science 65(10): 2035-2044.
Patra, J. K., G. Das, L. F. Fraceto, E. V. R. Campos, M. del Pilar Rodriguez-Torres, L. S. Acosta-Torres, L. A. Diaz-Torres, R. Grillo, M. K. Swamy and S. Sharma (2018). "Nano based drug delivery systems: recent developments and future prospects." Journal of nanobiotechnology 16(1): 71.
Pavlovich, J. G. (1993). "Ion pairing of nucleotides with surfactants for enhanced sensitivity in liquid matrix assisted secondary ion mass spectrometry."
Pelaseyed, T., J. H. Bergström, J. K. Gustafsson, A. Ermund, G. M. Birchenough, A. Schütte, S. van der Post, F. Svensson, A. M. Rodríguez‐Piñeiro and E. E. Nyström (2014). "The mucus and mucins of the goblet cells and enterocytes provide the first defense line of the gastrointestinal tract and interact with the immune system." Immunological reviews 260(1): 8-20.
Peng, X.-H., X. Qian, H. Mao and A. Y. Wang (2008). "Targeted magnetic iron oxide nanoparticles for tumor imaging and therapy." International journal of nanomedicine 3(3): 311.
Porte, G. and C. Ligoure (1995). "Mixed amphiphilic bilayers: bending elasticity and formation of vesicles." The Journal of chemical physics 102(10): 4290-4298.
Poste, G., D. Papahadjopoulos and W. J. Vail (1976). Lipid vesicles as carriers for introducing biologically active materials into cells. Methods in cell biology, Elsevier. 14: 33-71.
Pucci, C., L. Pérez, C. La Mesa and R. Pons (2014). "Characterization and stability of catanionic vesicles formed by pseudo-tetraalkyl surfactant mixtures." Soft Matter 10(48): 9657-9667.
Renoncourt, A. (2005). Study of supra-aggregates in catanionic surfactant systems.
Róg, T., M. Pasenkiewicz-Gierula, I. Vattulainen and M. Karttunen (2009). "Ordering effects of cholesterol and its analogues." Biochimica et Biophysica Acta (BBA)-Biomembranes 1788(1): 97-121.
Rosen, M. J. and J. T. Kunjappu (2012). Surfactants and interfacial phenomena, John Wiley & Sons.
Safran, S., P. Pincus, D. Andelman and F. MacKintosh (1991). "Stability and phase behavior of mixed surfactant vesicles." Physical Review A 43(2): 1071.
Samad, A., Y. Sultana and M. Aqil (2007). "Liposomal drug delivery systems: an update review." Current drug delivery 4(4): 297-305.
Sankaram, M. B. and T. E. Thompson (1990). "Modulation of phospholipid acyl chain order by cholesterol. A solid-state deuterium nuclear magnetic resonance study." Biochemistry 29(47): 10676-10684.
Sarma, N., J. M. Borah, S. Mahiuddin, H. A. R. Gazi, B. Guchhait and R. Biswas (2011). "Influence of chain length of alcohols on Stokes’ shift dynamics in catanionic vesicles." The Journal of Physical Chemistry B 115(29): 9040-9049.
Schwierz, N., D. Horinek and R. R. Netz (2013). "Anionic and cationic Hofmeister effects on hydrophobic and hydrophilic surfaces." Langmuir 29(8): 2602-2614.
Sein, A. and J. B. Engberts (1995). "Micelle to lamellar aggregate transition of an anionic surfactant in dilute aqueous solution induced by alkali metal chloride and tetraalkylammonium chloride salts." Langmuir 11(2): 455-465.
Sigurdsson, H. H., J. Kirch and C.-M. Lehr (2013). "Mucus as a barrier to lipophilic drugs." International journal of pharmaceutics 453(1): 56-64.
Simons, K. and W. L. Vaz (2004). "Model systems, lipid rafts, and cell membranes." Annu. Rev. Biophys. Biomol. Struct. 33: 269-295.
Smaby, J. M., M. M. Momsen, H. L. Brockman and R. E. Brown (1997). "Phosphatidylcholine acyl unsaturation modulates the decrease in interfacial elasticity induced by cholesterol." Biophysical journal 73(3): 1492-1505.
Smart, J. D. (1993). "Drug delivery using buccal-adhesive systems." Advanced Drug Delivery Reviews 11(3): 253-270.
Soussan, E., S. Cassel, M. Blanzat and I. Rico‐Lattes (2009). "Drug delivery by soft matter: matrix and vesicular carriers." Angewandte Chemie International Edition 48(2): 274-288.
Srinivasan, V. and D. Blankschtein (2003). "Effect of counterion binding on micellar solution behavior: 2. Prediction of micellar solution properties of ionic surfactant− electrolyte systems." Langmuir 19(23): 9946-9961.
Stahl, P. H. and C. G. Wermuth (2002). Pharmaceutical salts: Properties, selection and use, John wiley & sons.
Suchaoin, W., I. P. de Sousa, K. Netsomboon, H. T. Lam, F. Laffleur and A. Bernkop-Schnürch (2016). "Development and in vitro evaluation of zeta potential changing self-emulsifying drug delivery systems for enhanced mucus permeation." International journal of pharmaceutics 510(1): 255-262.
Tomašić, V. and T. Mihelj (2017). "The review on properties of solid catanionic surfactants: Main applications and perspectives of new catanionic surfactants and compounds with catanionic assisted synthesis." Journal of Dispersion Science and Technology 38(4): 515-544.
Tondre, C. and C. Caillet (2001). "Properties of the amphiphilic films in mixed cationic/anionic vesicles: a comprehensive view from a literature analysis." Advances in colloid and interface science 93(1-3): 115-134.
Uchegbu, I. F. and A. T. Florence (1995). "Non-ionic surfactant vesicles (niosomes): physical and pharmaceutical chemistry." Advances in colloid and interface science 58(1): 1-55.
Verma, A. and F. Stellacci (2010). "Effect of surface properties on nanoparticle–cell interactions." Small 6(1): 12-21.
Vermani, K. and S. Garg (2000). "The scope and potential of vaginal drug delivery." Pharmaceutical science & technology today 3(10): 359-364.
Vigderman, L., B. P. Khanal and E. R. Zubarev (2012). "Functional gold nanorods: synthesis, self‐assembly, and sensing applications." Advanced materials 24(36): 4811-4841.
Vist, M. R. and J. H. Davis (1990). "Phase equilibria of cholesterol/dipalmitoylphosphatidylcholine mixtures: deuterium nuclear magnetic resonance and differential scanning calorimetry." Biochemistry 29(2): 451-464.
Walker, S. A., M. T. Kennedy and J. A. Zasadzinski (1997). "Encapsulation of bilayer vesicles by self-assembly." Nature 387(6628): 61.
Wang, P., Y. Ma, Z. Liu, Y. Yan, X. Sun and J. Zhang (2016). "Vesicle formation of catanionic mixtures of CTAC/SDS induced by ratio: A coarse-grained molecular dynamic simulation study." RSC Advances 6(16): 13442-13449.
Watts, A., D. Marsh and P. F. Knowles (1978). "Characterization of dimyristoylphosphatidylcholine vesicles and their dimensional changes through the phase transition: molecular control of membrane morphology." Biochemistry 17(9): 1792-1801.
Wong, S. P. (2014). Synthesis, characterization and biological properties of palm catanionic surfactants/Wong Siew Pui, University of Malaya.
Wu, C.-J., A.-T. Kuo, C.-H. Lee, Y.-M. Yang and C.-H. Chang (2014). "Fabrication of positively charged catanionic vesicles from ion pair amphiphile with double-chained cationic surfactant." Colloid and Polymer Science 292(3): 589-597.
Wu, D. Y., S. Meure and D. Solomon (2008). "Self-healing polymeric materials: A review of recent developments." Progress in polymer science 33(5): 479-522.
Wu, K.-C., Z.-L. Huang, Y.-M. Yang, C.-H. Chang and T.-H. Chou (2007). "Enhancement of catansome formation by means of cosolvent effect: Semi-spontaneous preparation method." Colloids and Surfaces A: Physicochemical and Engineering Aspects 302(1-3): 599-607.
Xu, D., Z. Li, G. Wang, X. Li, X. Lv, Y. a. Zhang, Y. Fan and B. Xiong (2017). "Phase transformation and microstructure evolution of an ultra-high strength Al-Zn-Mg-Cu alloy during homogenization." Materials Characterization 131: 285-297.
Yang, J. (2002). "Viscoelastic wormlike micelles and their applications." Current opinion in colloid & interface science 7(5-6): 276-281.
Yeagle, P. L. (1985). "Cholesterol and the cell membrane." Biochimica et Biophysica Acta (BBA)-Reviews on Biomembranes 822(3-4): 267-287.
Yeh, S.-J., Y.-M. Yang and C.-H. Chang (2005). "Cosolvent effects on the stability of catanionic vesicles formed from ion-pair amphiphiles." Langmuir 21(14): 6179-6184.
Yousefi, A., S. Javadian, H. Gharibi, J. Kakemam and M. Rashidi-Alavijeh (2011). "Cosolvent effects on the spontaneous formation of nanorod vesicles in catanionic mixtures in the rich cationic region." The Journal of Physical Chemistry B 115(25): 8112-8121.
Yu, W.-Y., Y.-M. Yang and C.-H. Chang (2005). "Cosolvent effects on the spontaneous formation of vesicles from 1: 1 anionic and cationic surfactant mixtures." Langmuir 21(14): 6185-6193.