Effect of vesicle's membrane packing behaviour on skin penetration of model lipophilic drug

References

• Aripin NFK, Park JW, Park HJ. Preparation of vesicles drug carrier from palm oil- and palm kernel oil-based glycosides. Colloids Surf B 2012; 95: 144–53
   PubMed Web of Science ®Google Scholar
• Bangham AD, Standish MM, Watkins JC. Diffusion of univalent ions across the lamellae of swollen phospholipids. J Mol Biol 1965; 13: 238–52
   PubMed Web of Science ®Google Scholar
• Brooks NJ, Hamid HAA, Hashim R, Heidelberg T, Seddon JM, Conn CE, Mirzadeh Husseini SM, Zahid NI, Duali Hussen RS. Thermotropic and lyotropic liquid crystalline phases of Guerbet branched-chain β-D-glucosides. Liq Cryst 2011; 38: 1725–34
   Web of Science ®Google Scholar
• Chester MA. Nomenclature of glycolipids (IUPAC Recommendations 1997). Pure Appl Chem 1997; 69: 2475–87
   Web of Science ®Google Scholar
• Choi MJ, Maibach HI. Liposomes and niosomes as topical drug delivery systems. Skin Pharm Phys 2005; 18: 209–19
   PubMed Web of Science ®Google Scholar
• Cook AG, Wardell JL, Imrie CT. Carbohydrate liquid crystals: Synthesis and characterisation of the methyl-6-O-(n-acyl)-α-d-glucopyranosides. Chem Phys Lipids 2011; 164: 118–24
   PubMed Web of Science ®Google Scholar
• Cosco D, Celia C, Cilurzo F, Trapasso E, Paolino D. Colloidal carriers for the enhanced delivery through the skin. Expert Opin Drug Deliv 2008; 5: 737–55
   PubMed Web of Science ®Google Scholar
• El Maghraby GM, Barry BW, Williams AC. Liposomes and skin: From drug delivery to model membranes. Eur J Pharm Sci 2008; 34: 203–22
   PubMed Web of Science ®Google Scholar
• El Maghraby GM, Williams AC. Vesicular systems for delivering conventional small organic molecules and larger macromolecules to and through human skin. Expert Opin Drug Deliv 2009; 6: 149–63
   PubMed Web of Science ®Google Scholar
• Faivre V, Rosilio V. Interest of glycolipids in drug delivery: From physicochemical properties to drug targeting. Expert Opin Drug Deliv 2010; 7: 1031–48
   PubMed Web of Science ®Google Scholar
• Goodby JW, Görtz V, Cowling SJ, Mackenzie G, Martin P, Plusquellec D, Benvegnu T, Boullanger P, Lafont D, Queneau Y, et al. Thermotropic liquid crystalline glycolipids. Chem Soc Rev 2007; 36: 1971–2032
   PubMed Web of Science ®Google Scholar
• Hashim R, Hassan Abdalla Hashim H, Mohd. Rodzi NZ, Duali Hussen RS, Heidelberg T. Branched chain glycosides: Enhanced diversity for phase behavior of easily accessible synthetic glycolipids. Thin Solid Films 2006; 509: 27–35
   Web of Science ®Google Scholar
• Hashim R, Sugimura A, Minamikawa H, Heidelberg T. Nature-like synthetic alkyl branched-chain glycolipids: A review on chemical structure and self-assembly properties. Liq Cryst 2012; 39: 1–17
   Web of Science ®Google Scholar
• Hatanaka T, Shimoyama M, Sugibayashi K, Morimoto Y. Effect of vehicle on the skin permeability of drugs: Polyethylene glycol 400-water and ethanol-water binary solvents. J Control Release 1993; 23: 247–60
   Web of Science ®Google Scholar
• Hato M, Minamikawa H, Tamada K, Baba T, Tanabe Y. Self-assembly of synthetic glycolipid/water systems. Adv Colloid Interface Sci 1999; 80: 233–70
   PubMed Web of Science ®Google Scholar
• Katahira N, Murakami T, Kugai S, Yata N, Takano M. Enhancement of topical delivery of a lipophilic drug from charged multilamellar liposomes. J Drug Target 1999a; 6: 405–14
   PubMed Web of Science ®Google Scholar
• Kirjavainen M, Urtti A, Jääskeläinen I, Suhonen TM, Paronen P, Valjakka-Koskela R, Kiesvaara J, Mönkkönen J. Interaction of liposomes with human skin in vitro – The influence of lipid composition and structure. Biochim Biophys Acta 1996; 1304: 179–89
   PubMed Web of Science ®Google Scholar
• Kong M, Chen XG, Kweon DK, Park HJ. Investigations on skin permeation of hyaluronic acid based nanoemulsion as transdermal carrier. Carbohydr Polym 2011; 86: 837–43
   Web of Science ®Google Scholar
• Manconi M, Sinico C, Valenti D, Lai F, Fadda AM. Niosomes as carriers for tretinoin III. A study into the in vitro cutaneous delivery of vesicle-incorporated tretinoin. Int J Pharm 2006; 311: 11–19
   PubMed Web of Science ®Google Scholar
• Mura S, Pirot F, Manconi M, Franson F, Fadda AM. Liposomes and niosomes as potential carriers for dermal delivery of minoxidil. J Drug Target 2007; 15: 101–8
   PubMed Web of Science ®Google Scholar
• Nainggolan I, Radiman S, Hamzah AS, Hashim R. The effect of the head group on branched-alkyl chain surfactants in glycolipid/n-octane/water ternary system. Colloids Surf B 2009; 73: 84–91
   PubMed Web of Science ®Google Scholar
• Nystrom RF, Brown WG. Reduction of organic compounds by lithium aluminium hydride. I. Aldehydes, ketones, esters, acid chlorides and acid anhydrides. J Am Chem Soc 1947; 69: 1197–9
   Web of Science ®Google Scholar
• Ogiso T, Yamaguchi T, Iwaki M, Tanino T, Miyake Y. Effect of positively and negatively charged liposomes on skin permeation of drugs. J Drug Target 2001; 9: 49–59
   PubMed Web of Science ®Google Scholar
• Ph. Eur. 6.0. 2008. European pharmacopoeia 6.0. Strasbourg, France: European Directorate for Quality of Medicines, Council of Europe.
   Google Scholar
• Sabah K, Heidelberg T, Hashim R. Novel crown ethers on glucose based glycolipids. Carbohydr Res 2011; 346: 891–6
   PubMed Web of Science ®Google Scholar
• Savić S, Tamburić S, Savić MM. From conventional towards new-natural surfactants in drug delivery systems design: Current status and perspectives. Expert Opin Drug Deliv 2010; 7: 353–69
   PubMed Web of Science ®Google Scholar
• Schramlova J, Blazek K, Bartackova M, Otova B, Mardesicova L, Zizkovsky V, Hulinska D. Electron microscopic demonstration of the penetration of liposomes through skin. Folia Biol 1997; 43: 165–9
   PubMed Web of Science ®Google Scholar
• Sheihet L, Chandra P, Batheja P, Devore D, Kohn J, Michniak B. Tyrosine-derived nanospheres for enhanced topical skin penetration. Int J Pharm 2008; 350: 312–19
   PubMed Web of Science ®Google Scholar
• Sinico C, Manconi M, Peppi M, Lai F, Valenti D, Fadda AM. Liposomes as carriers for dermal delivery of tretinoin: In vitro evaluation of drug permeation and vesicle–skin interaction. J Control Release 2005; 103: 123–36
   PubMed Web of Science ®Google Scholar
• Song YK, Kim CK. Topical delivery of low-molecular-weight heparin with surface-charged flexible liposomes. Biomaterials 2006; 27: 271–80
   PubMed Web of Science ®Google Scholar
• Steber J, Guhl W, Stelter N, Schröder FR. Ecological evaluation of alkyl polyglucosides. Alkyl polyglucosides technology, properties and applications, K Hill, W von Rybinski, G Stoll. VCH, Weinheim 1997; 177–90
   Google Scholar
• Uchegbu IF, Vyas SP. Non-ionic surfactant based vesicles (niosomes) in drug delivery. Int J Pharm 1998; 172: 33–70
   Web of Science ®Google Scholar
• van Hal DA, Bouwstra JA, van Rensen A, Jeremiasse E, de Vringer T, Junginger HE. Preparation and characterization of non-ionic surfactant vesicles. J Colloid Interface Sci 1996; 178: 263–73
   Web of Science ®Google Scholar
• van Kuijk-Meuwissen MEMJ, Junginger HE, Bouwstra JA. Interactions between liposomes and human skin in vitro, a confocal laser scanning microscopy study. Biochim Biophys Acta 1998; 1371: 31–9
   PubMed Web of Science ®Google Scholar
• Verma DD, Verma S, Blume G, Fahr A. Particle size of liposomes influences dermal delivery of substances into skin. Int J Pharm 2003; 258: 141–51
   PubMed Web of Science ®Google Scholar
• Vill V, Hashim R. Carbohydrate liquid crystals: Structure–property relationship of thermotropic and lyotropic glycolipids. Curr Opin Colloid Interface Sci 2002; 7: 395–409
   Web of Science ®Google Scholar
• von Minden HM, Brandenburg K, Seydel U, Koch MHJ, Garamus V, Willumeit R, Vill V. Thermotropic and lyotropic properties of long chain alkyl glycopyranosides. Part II. Disaccharide headgroups. Chem Phys Lipids 2000; 106: 157–79
   PubMed Web of Science ®Google Scholar
• von Rybinski W, Hill K. Alkyl polyglucosides – Properties and applications of a new class of surfactants. Angew Chem Int Ed 1998; 37: 1328–45
   PubMed Web of Science ®Google Scholar
• Walker RB, Smith EW. The role of percutaneous penetration enhancers. Adv Drug Deliv Rev 1996; 18: 295–301
   Web of Science ®Google Scholar
• Yoo J, Shanmugam S, Song CK, Kim DD, Choi HG, Yong CS, Woo JS, Yoo BK. Skin penetration and retention of l-ascorbic acid 2-phosphate using multilamellar vesicles. Arch Pharm Res 2008; 31: 1652–8
   PubMed Web of Science ®Google Scholar
• Zahid NI, Abou-Zied OK, Hashim R, Heidelberg T. Characterization of the head group and the hydrophobic regions of a glycolipid lyotropic hexagonal phase using fluorescent probes. J Phys Chem C 2011; 115: 19805–10
   Web of Science ®Google Scholar