Charged liposomes as carriers to enhance the permeation through the skin

Expert Opinion on Drug Delivery

Volumn 8, Issue 7, 2011, Pages 857-871

  Gonzalez Rodriguez M L ^a   Rabasco, A M ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

charged liposome; dicetyl phosphate; DOTAP; liposome; stearylamine; surfactant; transdermal delivery

Indexed keywords

(1,3 DI OLEOYLOXY 2 (6 CARBOXY SPERMYL) PROPYLAMID); (N [1 (2,3 DIOLEOYLOXY)PROPYL] N,N,NTRIMETHYLAMMONIUM); 1,2 DIHEXADECANOYL SN GLYCERO 3 [PHOSPHO (1 GLYCEROL)]; ALCOHOL; ANTIVIRUS AGENT; CARBOXYMETHYL BETA CYCLODEXTRIN; CHITOSAN; CHOLESTEROL; DICETYL PHOSPHATE; DIDECYLDIMETHYLAMMONIUM BROMIDE; DNA; DRUG CARRIER; EDETIC ACID; EUDRAGIT; FATTY ACID; GALLIDERMIN; HEPATITIS B SURFACE ANTIGEN; LIPOSOME; MINOXIDIL; NIOSOME; OCTADECYLAMINE; PALMITOYLOLEOYL PHOSPHATIDYLCHOLINE; PALMITOYLOLEOYL PHOSPHATIDYLGLYCEROL; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; POLYVINYL ALCOHOL; PROTAMINE; SPAN; SPERMINE; SPHINGOMYELIN; TERPENE; TRANSFERSOME; TWEEN; UNCLASSIFIED DRUG;

ABSCESS; DRUG PENETRATION; DRUG RELEASE; ENDOCARDITIS; GENE THERAPY; HUMAN; HYDROPHILICITY; IN VITRO STUDY; IN VIVO STUDY; LAMELLAR BODY; NONHUMAN; OVARY FOLLICLE STRATUM GRANULOSUM; REVIEW; SKIN INFECTION; SKIN PERMEABILITY; STRATUM CORNEUM; TRANSDERMAL DRUG ADMINISTRATION;

ADMINISTRATION, CUTANEOUS; DRUG CARRIERS; HUMANS; LIPOSOMES; PERMEABILITY; SKIN ABSORPTION;

EID: 79959227506     PISSN: 17425247     EISSN: 17447593     Source Type: Journal    
DOI: 10.1517/17425247.2011.574610     Document Type: Review

References (107)

1. Rabasco AM, Gonzalez-Rodriguez ML. Lipids in pharmaceutical and cosmetic preparations. Grasas y aceites 2000;51(1-2):74-96
2. Meyer RR. Delivery system handbook for personal care and cosmetic products: technology, applications and formulations, William Andrew Inc., USA; 2005
3. Otberg N, Richter H, Schaefer H, et al. Variations of hair follicle size and distribution in different body sites. J Invest Dermatol 2004;122:14-9 (Pubitemid 38114633)
4. Bos JD, Meinardi MHM. The 500 dalton rule for the skin penetration of chemical compounds and drugs. Exp Dermatol 2000;9(3):165-9 (Pubitemid 30255378)
5. Martin GP, Lloyd AW. Basic principles of liposomes for drug use. In: Braun-Falco O, Korting HC, Maibach HI, editors, Liposome Dermatics, Springer-Verlag, Germany; p. 21-26
6. Mura P, Maestrelli F, Gonzalez-Rodriguez ML, et al. Development, characterization and in vivo evaluation of benzocaine-loaded liposomes. Eur J Pharm Biopharm 2007;67:86-95 (Pubitemid 46991345)
7. Berger N, Sachse A, Bender J, et al. Filter extrusion of liposomes using different devices: comparison of liposome size, encapsulation efficiency, and process characteristics. Int J Pharm 2001;223(1-2):55-68 (Pubitemid 32640878)
8. Maestrelli F, Gonzalez-Rodriguez ML, Rabasco AM, et al. Effect of preparation technique on the properties of liposomes encapsulating ketoprofen-cyclodextrin complexes aimed for transdermal delivery. Int J Pharm 2006;312(1-2):53-60
9. Massing U, Cicko S, Ziroli V. Dual asymmetric centrifugation (DAC) - A new technique for liposome preparation. J Control Release 2008;125(1):16-24 (Pubitemid 350198678)
10. Silva R, Ferreira H, Little C, et al. Effect of ultrasound parameters for unilamellar liposome preparation. Ultrason Sonochem 2010;17(3):628-32
11. Coderch L, Fonollosa J, de Pera M, et al. Influence of cholesterol on liposome fluidity by EPR. Relationship with percutaneous absorption. J Control Release 2000;68(1):85-95 (Pubitemid 30407064)
12. Liu H, Pan WS, Tang R, et al. Topical delivery of different acyclovir palmitate liposome formulations through rat skin in vitro. Pharmazie 2004;59(3):203-6 (Pubitemid 38391425)
13. Manosroi A, Kongkaneramit L, Manosroi J. Stability and transdermal absorption of topical amphotericin B liposome formulations. Int J Pharm 2004;270(1-2):279-86 (Pubitemid 38077107)
14. Bouwstra JA, Honeywell-Nguyen PL. Skin structure and mode of action of vesicles, Adv Drug Deliv Rev 2002;54:41-55
15. Fresta M, Puglisi G. Application of liposomes as potential cutaneous drug delivery systems. In vitro and in vivo investigation with radioactively labelled vesicles. J Drug Target 1996;4(2):95-101 (Pubitemid 26381471)
16. Puglia C, Bonina F, Rizza L, et al. Evaluation of percutaneous absorption of naproxen from different liposomal formulations. J Pharm Sci 2010;99(6):2819-29
17. Cevc G, Vierl U. Nanotechnology and the transdermal route. A state of the art review and critical appraisal. J Control Release 2010;141:277-99
18. Sinico C, Fadda AM. Vesicular carriers for dermal drug delivery. Expert Opin Drug Deliv 2009;6:813-25
19. Cevc G, Blume G. Lipid vesicles penetrate into intact skin owing to the transdermal osmotic gradients and hydration force. Biochim Biophys Acta 1992;1104:226-32
20. Cevc G, Blume G, Schatzlein A, et al. The skin: a pathway for systemic treatment with patches and lipid-based agent carriers. Adv Drug Deliv Rev 1996;18:349-78 (Pubitemid 26063309)
21. El Maghraby GM, Williams AC, Barry BW. Oestradiol skin delivery from ultradeformable liposomes: refinement of surfactant concentration. Int J Pharm 2000;196:63-74 (Pubitemid 30089515)
22. Cevc G, Blume G. New, highly efficient formulation of diclofenac for the topical, transdermal administration in ultradeformable drug carriers: Transfersomes. Biochim Biophys Acta 2001;1514:191-205 (Pubitemid 32831008)
23. Cevc G, Blume G. Biological activity and characteristics of triamcinolone-acetonide formulated with the self-regulating drug carriers: Transfersomes. Biochim Biophys Acta 2003;1614:156-64 (Pubitemid 36929979)
24. Cevc G, Blume G. Hydrocortisone and dexamethasone in very deformable drug carriers have increased biological potency, prolonged effect, and reduced therapeutic dosage. Biochim Biophys Acta 2004;1663:61-73 (Pubitemid 38625580)
25. Lee EH, Kim A, Oh YK, et al. Effect of edge activators on the formation and transfection efficiency of ultradeformable liposomes. Biomaterials 2005;26:205-10 (Pubitemid 38789103)
26. El Maghraby GM, Williams AC, Barry BW. Interactions of surfactants (edge activators) and skin penetration enhancers with liposomes. Int J Pharm 2004;276:143-61 (Pubitemid 38542995)
27. Cevc G, Blume G, Schatzlein A. Transdermal drug carriers: basic properties, optimization and transfer efficiency in the case of epicutaneously applied peptides. J Control Release 1995;36:3-16
28. Choi MJ, Maibach HI. Liposomes and niosomes as topical drug delivery systems. Skin Pharmacol Physiol 2005;18(5):209-19 (Pubitemid 41159952)
29. Hao Y, Zhao F, Li N, et al. Studies on a high encapsulation of colchicine by a niosome system. Int J Pharm 2002;244(1-2):73-80 (Pubitemid 35245447)
30. Nasseri B. Effect of cholesterol and temperature on the elastic properties of niosomal membranes. Int J Pharm 2005;300(1-2):95-101 (Pubitemid 41112171)
31. Balakrishnan P, Shanmugam S, Lee WS, et al. Formulation and in vitro assessment of minoxidil niosomes for enhanced skin delivery. Int J Pharm 2009;377(1-2):1-8
32. Paolino D, Muzzalupo R, Ricciardi A, et al. In vitro and in vivo evaluation of Bola-surfactant containing niosomes for transdermal delivery, Biomed. Microdevices 2007;9(4):421-33
33. Manosroi A, Jantrawut P, Manosroi J. Anti-inflammatory activity of gel containing novel elastic niosomes entrapped with diclofenac diethylammonium. Int J Pharm 2008;360:156-63
34. Manosroi A, Khanrin P, Lohcharoenkal W, et al. Transdermal absorption enhancement through rat skin of gallidermin loaded in niosomes. Int J Pharm 2010;392:304-10
35. Alsarra IA, Bosela AA, Ahmed SM, et al. Proniosomes as a drug carrier for transdermal delivery of ketorolac. Eur J Pharm Biopharm 2005;59(3):485-90 (Pubitemid 40342523)
36. Mokhtar M, Sammour OA, Hammad MA, et al. Effect of some formulation parameters on flurbiprofen encapsulation and release rates of niosomes prepared from proniosomes. Int J Pharm 2008;361(1-2):104-11
37. El-Laithy HM, Shoukry O, Mahran LG. Novel sugar esters proniosomes for transdermal delivery of vinpocetine: preclinical and clinical studies. Eur J Pharm Biopharm 2011;77(1):43-55
38. Touitou E, Dayan N, Bergelson L, et al. Ethosomes-novel vesicular carriers for enhanced delivery: characterization and skin penetration properties. J Control Release 2000;65:403-18 (Pubitemid 30122942)
39. Lopez-Pinto JM, Gonzalez-Rodriguez ML, Rabasco AM. Effect of cholesterol and ethanol on dermal delivery from DPPC liposomes. Int J Pharm 2005;298(1):1-12 (Pubitemid 40828324)
40. Elsayed MMA, Abdallah OY, Naggar VF, et al. Deformable liposomes and ethosomes: Mechanism of enhanced skin delivery. Int J Pharm 2006;322(1-2):60-6 (Pubitemid 44348860)
41. Fang YP, Tsai YH, Wu PC, et al. Comparison of 5-aminolevulinic acidencapsulated liposome versus ethosome for skin delivery for photodynamic therapy. Int J Pharm 2008;356(1-2):144-52
42. Foldvari M, Gesztes A, Mezei M, et al. Topical liposomal local anesthetics: design, optimization and evaluation of formulations. Drug Dev Ind Pharm 1993;19:2499-517 (Pubitemid 23337901)
43. Dubey V, Mishra D, Dutta T, et al. Dermal and transdermal delivery of an anti-psoriatic agent via ethanolic liposomes. J Control Release 2007;123(2):148-54 (Pubitemid 47562141)
44. Maestrelli F, Gonzalez-Rodriguez ML, Rabasco AM, et al. New drug-in cyclodextrin-in deformable liposomes formulations to improve the therapeutic efficacy of local anaesthetics. Int J Pharm 2010;395:222-31
45. Dayan N, Touitou E. Carriers for skin delivery of trihexyphenidyl HCl: ethosomes vs. liposomes. Biomaterials 2000;21:1879-85 (Pubitemid 30398506)
46. Elsayed MM, Abdallah OY, Naggar VF, et al. Deformable liposomes and ethosomes as carriers for skin delivery of ketotifen. Pharmazie 2007;62(2):133-7 (Pubitemid 46279965)
47. Maestrelli F, Capasso G, Gonzalez-Rodriguez ML, et al. Effect of preparation technique on the properties and in vivo efficacy of benzocaine-loaded ethosomes. J Liposome Res 2009;19(4):253-60
48. Ainbinder D, Touitou E. Testosterone ethosomes for enhanced transdermal delivery. Drug Deliv 2005;12:297-303 (Pubitemid 41356186)
49. Jain S, Umamaheshwari R, Bhadra D, et al. Ethosomes: a novel vesicular carries for enhanced transdermal delivery of an anti HIV agent. Indian J Pharm Sci 2004;66:72-81
50. Van den Bergh BAI, Vroom J, Gerritsen H, et al. Interactions of elastic and rigid vesicles with human skin in vitro: electron microscopy and two-photon excitation microscopy. Biochim Biophys Acta 1999;1461:155-73 (Pubitemid 30077471)
51. Dragicevic-Curic N, Scheglmann D, Albrecht V, et al. Development of different temoporfin-loaded invasomes-novel nanocarriers of temoporfin: characterization, stability and in vitro skin penetration studies. Colloids Surf B Biointerfaces 2009;70:198-206
52. Phayre AN, Farfano HMV, Hayes MA. Effects of pH gradients on liposomal charge states examined by capillary electrophoresis. Langmuir 2002;18(17):6499-503 (Pubitemid 35383279)
53. Owen RL, Strasters JK, Breyer ED. Lipid vesicles in capillary electrophoretic techniques: characterization of structural properties and associated membrane-molecule interactions. Electrophoresis 2005;26(4-5):735-51 (Pubitemid 40424906)
54. Zellmer S, Pfeil W, Lasch J. Interaction of phosphatidylcholine liposomes with the human stratum corneum. Biochim Biophys Acta (BBA) - Biomembr 1995;1237:176-82
55. Kirjavainen M, Urtti A, Jaaskelainen I, et al. Interaction of liposomes with human skin in vitro-the influence of lipid composition and structure. Biochim Biophys Acta 1996;1304:179-89 (Pubitemid 26426990)
56. Liu Y, Yan ECY, Eisenthal KB. Effects of bilayer surface charge density on molecular adsorption and transport across liposome bilayers. Biophys J 2001;80:1004-12 (Pubitemid 32128351)
57. Murthy SN, Zhao YL, Hui SW, et al. Synergistic effect of anionic lipid enhancer and electroosmosis for transcutaneous delivery of insulin. Int J Pharm 2006;326(1-2):1-6
58. Martin GT, Pliquett UF, Weaver JC. Theoretical analysis of localized heating in human skin subjected to high voltage pulses. Bioelectrochemistry 2002;57:55-62
59. Pliquett U, Gallo SA, Hui SW, et al. Local and transient structural changes in stratum corneum at high electric field: contribution of Joule heating. Bioelectrochemistry 2005;67:37-46 (Pubitemid 40828415)
60. Sen A, Zhao Y, Zhang L, et al. Enhanced transdermal transport by electroporation using anionic lipids. J Control Release 2002;82(2-3):399-405 (Pubitemid 34880193)
61. Mateescu E, Jeppepsen C, Pincus R. Overcharging of a spherical macroion by an oppositely charged polyelectrolyte. Europhys Lett 1999;46:493-8
62. Nguyen TT, Shklovskii BI. Overcharging of macroion by an oppositely charged polyelectrolyte. Physica A 2001;293:324-38 (Pubitemid 32385096)
63. Dobrynin AV, Deshkovski A, Rubinstein M. Adsorption of polyelectrolytes at oppositely charged surface. Phys Rev Lett 2000;84:3101-4
64. Guo J, Ping Q, Jiang G, et al. Chitosan-coated liposomes: characterization and interaction with leuprolide. Int J Pharm 2003;260:167-73 (Pubitemid 36773915)
65. Rengel RG, Barisic KP. High efficiency entrapment of superoxide dismutase into mucoadhesive chitosan-coated liposome. Eur J Pharm Sci 2002;15:441-8
66. Takeuchi H, Kojima H, Yamamoto H. Polymer coating of liposomes with a modified polyvinyl alcohol and their systemic circulation and RES uptake in rats. J Control Release 2000;68:195-205 (Pubitemid 30488897)
67. Hasanovic A, Hollick C, Fischinger K, et al. Improvement in physicochemical parameters of DPPC liposomes and increase in skin permeation of aciclovir and minoxidil by the addition of cationic polymers. Eur J Pharm Biopharm 2010;75:148-53
68. Sashiwa H, Shigemasa Y. Chemical modification of chitin and chitosan 2: preparation and water soluble property of N-acylated or N-alkylated partially deacetylated chitins. Carbohydr Polym 1999;39(2):127-38
69. Park IK, Park YH. Preparation and structural characterization of water-soluble o-hydroxypropyl chitin derivatives. J Appl Polym Sci 2001;80:2624-32
70. Muzzarelli RAA. Carboxymethylated chitins and chitosans. Carbohydr Polym 1988;8:1-21
71. Li N, Zhuanga C, Wanga M, et al. Liposome coated with low molecular weight chitosan and its potential use in ocular drug delivery. Int J Pharm 2009;379:131-138
72. Kubota N, Tatsumoto N, Sano T, et al. A simple preparation of half N-acetylated chitosan highly soluble in water and aqueous organic solvents. Carbohydr Res 2000;324:268-74 (Pubitemid 30114453)
73. Gonzalez-Rodriguez ML, Barros LB, Palma J, et al. Application of statistical experimental design to study the formulation variables influencing the coating process of lidocaine liposomes. Int J Pharm 2007;337(1-2):336-45 (Pubitemid 46778957)
74. Hasanovic A, Zehl M, Reznicek G, et al. Chitosan-TPP nanoparticles as a possible skin drug delivery system for acyclovir with enhanced stability. J Pharm Pharmacol 2009;61:1609-16
75. Takeuchi H, Yamamoto H, Niwa T, et al. Enteral absorption of insulin in rats from mucoadhesive chitosan-coated liposomes. Pharm Res 1996;13:896-901 (Pubitemid 26227747)
76. Mady MM, Darwish MM. Effect of chitosan coating on the characteristics of DPPC liposomes. J Adv Res 2010;1(3):187-91
77. Valenta C, Auner BG. The use of polymers for dermal and transdermal delivery. Eur J Pharm Biopharm 2004;58:279-89 (Pubitemid 39037235)
78. Biruss B, Valenta C. Skin permeation of different steroid hormones from polymeric coated liposomal formulations. Eur J Pharm Biopharm 2006;62(2):210-9 (Pubitemid 43143274)
79. Bernkop-Schnurch A, Krajicek ME. Mucoadhesive polymers as platforms for peroral peptide delivery and absorption: synthesis and evaluation of different chitosan-EDTA conjugates. J Control Release 1998;50:215-23 (Pubitemid 28044116)
80. Smith JM. Chitosan and transdermal drug delivery. Retinoids 2003;19:72-5
81. Valenta C, Christen A, Bernkop-Schnurch A. Chitosan-EDTA conjugate: a novel polymer for topical gels. J Pharm Pharmacol 1998;50:445-52 (Pubitemid 28241129)
82. Kitagawa S, Kasamaki M. Enhanced delivery of retinoic acid to skin by cationic liposomes. Chem Pharm Bull 2006;54(2):242-4 (Pubitemid 43200608)
83. Ham I, Kim M, Kim J. Enhanced transfollicular delivery of adriamycin with a liposome and iontophoresis. Exper Dermatol 2004;13:86-92 (Pubitemid 38247866)
84. Song YK, Kim CK. Topical delivery of low-molecular-weight heparin with surface-charged flexible liposomes. Biomaterials 2006;27:271-80
85. Hong-Yu W, Kashani-Sabet M, Liggitt D, et al. Topical gene delivery to murine skin. J Invest Dermatol 1999;112:370-5 (Pubitemid 29125115)
86. Kim A, Lee EH, Choi SH, et al. In vitro and in vivo transfection efficiency of a novel ultradeformable cationic liposome. Biomaterials 2004;25:305-13 (Pubitemid 37329720)
87. Babiuk S, Baca-Estrada ME, Pontarrollo R, et al. Topical delivery of plasmid DNA using biphasic lipid vesicles (Biphasix). J Pharm Pharmacol 2002;54:1609-14 (Pubitemid 36018808)
88. Akita H, Kudo A, Minoura A, et al. Multi-layered nanoparticles for penetrating the endosome and nuclear membrane via a step-wise membrane fusion process. Biomaterials 2009;30:2940-9
89. Geusens B, Sanders N, Prow T, et al. Cutaneous short-interfering RNA therapy. Expert Opin Drug Deliv 2009;6:1333-49
90. Tran R, Ho S, Dea P. Effects of ethanol on lipid bilayers with and without cholesterol: the distearoylphosphatidylcholine system. Biophys Chem 2004;110(1-2):39-47 (Pubitemid 38829135)
91. Geusens B, Van Gele M, Braat S, et al. Flexible nanosomes (SECosomes) enable efficient siRNA delivery in cultures primary skin cells and in the viable epidermis of ex vivo human skin. Adv Funct Mater 2010;20:4077-90
92. Kupper TS, Fuhlbrigge RC. Immune surveillance in the skin: mechanisms and clinical consequences. Nat Rev Immunol 2004;4:211-22 (Pubitemid 38339087)
93. Bal SM, Ding Z, Van Riet E, et al. Advances in transcutaneous vaccine delivery: do all ways lead to Rome? J Control Release 2010;148:266-82
94. Babiuk S, Baca-Estrada ME, Babiuk LA, et al. Cutaneous vaccination: the skin as an immunologically active tissue and the challenge of antigen delivery. J Control Release 2000;66(2-3):199-214 (Pubitemid 30160857)
95. Filion MC, Phillips NC. Toxicity and immunomodulatory activity of liposomal vectors formulated with cationic lipids toward immune effector cells. Biochim Biophys Acta 1997;1329:345-56 (Pubitemid 27466823)
96. Wattiaux R, Jadot M, Warnier-Pirotte MT, et al. Cationic lipids destabilize lysosomal membrane in vitro. FEBS Lett 1997;417:199-202 (Pubitemid 27491732)
97. Mishra D, Dubey V, Abhay A, et al. Elastic liposomes mediated transcutaneous immunization against Hepatitis B. Vaccine 2006;24(22):4847-55 (Pubitemid 43776800)
98. Ding Z, Bal SM, Romeijn S, et al. Transcutaneous immunization studies in mice using diphtheria toxoid-loaded vesicle formulations and a microneedle array. Pharm Res 2011;28(1):145-58
99. Hubbard A. Electrophoresis of liposomes. In: Encyclopedia of Surface and Colloid Science, Marcel Dekker, New York (2002)
100. Villasmil-Sanchez S, Dhrimeur W, Salas SC, et al. Positively and negatively charged liposomes as carriers for transdermal delivery of sumatriptan: in vitro characterization. Drug Dev Ind Pharm 2010;36(6):666-75
101. Casals E, Soler M, Gallardo M, et al. Electrophoretic behaviour of stearylamine containing liposomes. Langmuir 1998;14(26):7522-6 (Pubitemid 128585055)
102. Dragicevic-Curic N, Grafe S, Gitter B, et al. Surface charged temoporfin-loaded flexible vesicles: in vitro skin penetration studies and stability. Int J Pharm 2010;384:100-8
103. Katahira N, Murakami T, Kugai S, et al. Enhancement of topical delivery of a lipophilic drug from charged multilamellar liposomes. J Drug Target 1999;6:405-14 (Pubitemid 29452684)
104. Montenegro L, Panico AM, Ventimiglia A, et al. In vitro retinoic acid release and skin permeation from different liposome formulations. Int J Pharm 1996;113:89-96 (Pubitemid 26160838)
105. Puglia C, Rizza L, Bonina F, et al. Effect of charge and lipid concentration on in-vivo percutaneous absorption of methyl nicotinate from liposomal vesicles. J Pharm Pharmacol 2005;57(9):1169-76 (Pubitemid 41391775)
106. Ogiso T, Yamaguchi T, Iwaki M, et al. Effect of positively and negatively charged liposomes on skin permeation of drugs. J Drug Target 2001;9:49-59 (Pubitemid 32496450)
107. Azeem A, Ahmad FJ, Khan ZI, et al. Nonionic surfactant vesicles as a carrier for transdermal delivery of frusemide. J Dispers Sci Technol 2008;29(5):723-30 (Pubitemid 351584083)