The role of lipid geometry in designing liposomes for the solubilisation of poorly water soluble drugs

International Journal of Pharmaceutics

Volumn 453, Issue 1, 2013, Pages 225-232

  Ali, M Habib ^a   Moghaddam, Behfar ^a   Kirby, Daniel J ^a   Mohammed, Afzal R ^a   Perrie, Yvonne ^a  

^a ASTON UNIVERSITY   (United Kingdom)

Author keywords

Bilayer drug loading; Liposomes; Low soluble drugs; Monolayer studies; Solubilisation

Indexed keywords

ALKYL GROUP; CHOLESTEROL; IBUPROFEN; LIPID; LIPOSOME; MIDAZOLAM; PHOSPHOLIPID; PROPOFOL; RIFAMPICIN;

ARTICLE; CHEMICAL STRUCTURE; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SOLUBILITY; DRUG TARGETING; GEOMETRY; LIPID BILAYER; LIPID MONOLAYER; LIPOPHILICITY; MOLECULAR SIZE; MOLECULAR STABILITY; PRIORITY JOURNAL; SOLUBILIZATION;

EID: 84884166695     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2012.06.056     Document Type: Article

References (34)

1. Ali, M.H., Kirby, D.J., Mohammed, A.R., Perrie, Y., 2010. Solubilisation of drugs within liposomal bilayers: alternatives to cholesterol as a membrane stabilising agent. J. Pharm. Pharmacol. 62, 1646-1655.
2. Arnarson, T., Elworthy, P.H., 1980. Effect of structural variations of non-ionic surfactants on micellar properties and solubilisation: surfactants based on erucyl and behenyl (C22) alcohols. J. Pharm. Pharmacol. 32, 381-386.
3. Bangham, A.D., Standish, M.M., Watkins, J.C., 1965. Diffusion of univalent ions across the lamellae of swollen phospholipids. J. Mol. Biol. 13, 325-328.
4. Barnes, G.T., Gentle, I.R., 2005. Interfacial Science: An Introduction. Oxford University Press Inc., UK.
5. Bennati, C.R., Epand, R.M., Lamy, M.T., 2007. Low cholesterol solubility in DODAB liposomes. Chem. Phys. Lipids 145, 27-36. (Pubitemid 44855749)
6. Brzustowicz, M.R., Cherezo, V., Zerouga, M., Caffrey, M., Stillwell, W., Wassall, S.R., 2002. Controlling membrane cholesterol content. A role for polyunsaturated (docosahexaenoate) phospholipids. Biochemistry 41, 12509-12519.
7. Dan, 2007. Lipid tail chain asymmetry and the strength of membrane-induced interactions between membrane proteins. Biochim. Biophys. Acta 1768, 2393-2399.
8. Daneshpour, N., Griffin, M., Collighan, R., Perrie, Y., 2011. Targeted delivery of a novel group of site-directed transglutaminase inhibitors to the liver using liposomes: a new approach for the potential treatment of liver fibrosis. J. Drug Target. 8, 624-631.
9. Davies, J.T., Rideal, E.K., 1963. Interfacial Phenomena. Academic Press Inc., New York, USA.
10. Devaraj, G.N., Parakh, S.R., Devraj, R., Apte, S.S., Ramesg Rao, B., Rambhau, D., 2002. Release studies on niosomes containing fatty alcohols as bilayer stabilisers instead of cholesterol. J. Colloid Interface Sci. 251, 360-365.
11. Dougherty, D.A., Stauffer, D.A., 1990. Acetylcholine binding by a synthetic receptor: implications for biological recognition. Science 250, 1558-1560. (Pubitemid 120034365)
12. Dynarowicz-Latka, P., Hac-Wydro, K., 2004. Interactions between phosphatidylcholines and cholesterol in monolayers at the air/water interface. Colloid Surf. B Biointerf. 37, 21-25. (Pubitemid 39164190)
13. Fatouros, D.G., Antimisiaris, S.G., 2002. Effect of amphiphilic drugs on the stability and zeta-potential of their liposome formulations: a study with prednisolone, diazepam, and griseofulvin. J. Colloid Interface Sci. 251, 271-277. (Pubitemid 34775392)
14. 31P NMR study. Biochim. Biophys. Acta 1234, 235-243.
15. Gaines, G.L., 1966. Insoluble Monolayers at Liquid-Gas Interfaces. John Wiley & Sons Inc., New York.
16. Garau, C., Frontera, A., Quinonero, D., Ballester, P., Costa, A., Deya, P.M., 2004. Cation-π vs. anion-π interactions: a complete π-orbital analysis. Chem. Phys. Lett. 399, 220-225. (Pubitemid 40017608)
17. Gregoriadis, G., 1973. Drug entrapment in liposomes. FEBS Lett. 36, 292-296.
18. Gregoriadis, G., Davis, C., 1979. Stability of liposomes in vivo and in vitro is promoted by their cholesterol content in the presence of blood cells. Biochim. Biophys. Res. Commun. 90, 1287-1293.
19. Hac-Wydro, K., Wydro, P., 2007. The influence of fatty acids on model cholesterol/phospholipid membranes. Chem. Phys. Lipids 150, 66-81. (Pubitemid 47538550)
20. Hamada, F., Higuchi, Y., Kondo, Y., Kabuto, C., Iki, N., 2006. Supramolecular assembly based on π-π stacking π-cation interactions between thiacalixarene and DMF. Tetrahedron Lett. 47, 5591-5593. (Pubitemid 43928996)
21. Ismail, A.A., Gouda, M.W., Motawi, M.M., 1970. Micellar solubilisation of barbiturates I: solubilities of certain barbiturates in polysorbates of varying hydrophobic chain length. J. Pharm. Sci. 59, 220-224.
22. Kirby, C., Gregoriadis, G., 1980. Effect of the cholesterol content of small unilamellar liposomes on their stability in vivo and in vitro. Biochem. J. 186, 591-598.
23. Kragh-Hansen, U., le Maire, M., Moller, J.V., 1998. The mechanism of detergent solubilization of liposomes and protein-containing membranes. Biophys. J. 75, 2932-2946. (Pubitemid 28548962)
24. Ma, J.C., Dougherty, D.A., 1997. The cation-π interaction. Chem. Rev. 97, 1303-1324.
25. Moghaddam, B., McNeil, S.E., Zheng, Q., Mohammed, A.R., Perrie, Y., 2011a. Exploring the correlation between lipid packaging in Lipoplexes and their transfection efficiency. Pharmaceutics 3, 848-864.
26. Moghaddam, B., Ali, M.H., Wilkhu, J., Kirby, D.J., Mohammed, A.R., Zheng, Q., Perrie, Y., 2011b. The application of monolayer studies in the understanding of liposomal formulations. Int. J. Pharm. 417, 235-244.
27. Mohammed, A.R., Weston, N., Coombes, A.G.A., Fitzgerald, M., Perrie, Y., 2004. Liposome formulation of poorly water soluble drugs: optimisation of drug loading and ESEM analysis of stability. Int. J. Pharm. 285, 23-34. (Pubitemid 39361533)
28. Nounou, M., El-Khordagui, L.K., Khalafallah, N.A., Khalil, S.A., 2006. In vitro release of hydrophilic and hydrophobic duugs from liposomal dispersions and gels. Acta Pharm. 56, 311-324. (Pubitemid 44422511)
29. Rangel-Yagui, C.O., Pessoa Jr., A., Tavares, L.C., 2005. Micellar solubilization of drugs. J. Pharm. Pharm. Sci. 8, 147-163. (Pubitemid 41521911)
30. Taylor, K.M.G., Taylor, G., Kellaway, I.W., Stevens, J., 1990. Drug entrapment and release from multilamellar and reverse-phase evaporation liposomes. Int. J. Pharm. 58, 49-55. (Pubitemid 20034227)
31. Uchegbu, I.F., Florence, A.T., 1995. Non-ionic surfactant vesicles (niosomes): physical and pharmaceutical chemistry. Adv. Colloid Interface Sci. 58, 1-55.
32. Vilcheze, C., McMullen, T.P.W., McElhaney, R.N., Bittman, R., 1996. The effect of side-chain analogues of cholesterol on the thermotropic phase behaviour of 1-stearoyl-2-oleoylphosphatidylcholine bilayers: a differential scanning calorimetric study. Biochim. Biophys. Acta 1279, 235-242. (Pubitemid 26080855)
33. Wishart, D.S., Knox, C., Guo, A.C., Shrivastava, S., Hassanali, M., Stothard, P., Chang, Z., Woolsey, J., January 2006. DrugBank: a comprehensive resource for in silico drug discovery and exploration. Nucl. Acids Res. 1, D668-D672 (Database issue).
34. Yoshioka, T., Sternberg, B., Florence, A.T., 1994. Preparation and properties of vesicles (niosomes) of sorbitan monoesters (Span 20, 40, 60 and 80) and a sorbitan triester (Span 85). Int. J. Pharm. 105, 1-6. (Pubitemid 24087666)