Oil-frozen W1/O/W2 double emulsions for dermal biomacromolecular delivery containing ethanol as chemical penetration enhancer

Journal of Pharmaceutical Sciences

Volumn 100, Issue 4, 2011, Pages 1398-1406

  Jaimes Lizcano, Yuly A ^a   Lawson, Louise B ^b   Papadopoulos, Kyriakos D ^a  

^a Tulane University   (United States)

^b TULANE UNIVERSITY HEALTH SCIENCES CENTER   (United States)

Author keywords

Emulsion; Formulation; Macromolecular drug delivery; Permeation enhancers; Transdermal drug delivery

Indexed keywords

ALCOHOL; BOVINE SERUM ALBUMIN; FLUORESCEIN ISOTHIOCYANATE; OIL; DRUG VEHICLE; EMULSION; FLUORESCEIN ISOTHIOCYANATE BOVINE SERUM ALBUMIN; WATER;

ANIMAL TISSUE; ANTIGEN ANTIBODY COMPLEX; AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; DERMAL BIOMACROMOLECULAR DRUG DELIVERY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG PENETRATION; EMULSION; ENZYME LINKED IMMUNOSORBENT ASSAY; EPIDERMIS; FREEZE THAWING; IN VITRO STUDY; NONHUMAN; OIL FROZEN WATER IN OIL IN WATER DOUBLE EMULSION; SKIN PENETRATION; SWINE; TRANSDERMAL DRUG ADMINISTRATION; ANALOGS AND DERIVATIVES; ANIMAL; BOVINAE; CHEMISTRY; FREEZING; INTRADERMAL DRUG ADMINISTRATION; METABOLISM; SKIN; SKIN ABSORPTION;

ADMINISTRATION, CUTANEOUS; ANIMALS; CATTLE; EMULSIONS; ETHANOL; FLUORESCEIN-5-ISOTHIOCYANATE; FREEZING; OILS; PHARMACEUTICAL VEHICLES; SERUM ALBUMIN, BOVINE; SKIN; SKIN ABSORPTION; SWINE; WATER;

EID: 79951892016     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22362     Document Type: Article

References (61)

1. Prausnitz MR, Langer R. 2008. Transdermal drug delivery. Nat Biotechnol 26:1261-1268.
2. World Health Organization. 2009. In World Health Statistics; Gollogly L, Ed. 1st ed. Geneva World Health Organization
3. Benson HA, Namjoshi S. 2008. Proteins and peptides: Strategies for delivery to and across the skin. J Pharm Sci 97:3591-3610.
4. Gill HS, Prausnitz MR. 2007. Coated microneedles for transdermal delivery. J Control Release 117:227-237.
5. Karande P, Jain A, Ergun K, Kispersky V, Mitragotri S. 2005. Design principles of chemical penetration enhancers for transdermal drug delivery. Proc Natl Acad Sci U S A 102:4688-4693.
6. Tahara Y, Honda S, Kamiya N, Piao H, Hirata A, Hayakawa E, Fujii T, Goto M. 2008. A solid-in-oil nanodispersion for transcutaneous protein delivery. J Control Release 131:14-18.
7. Mitragotri S. 2000. Synergistic effect of enhancers for transdermal drug delivery. Pharm Res 17:1354-1359.
8. Foldvari M. 2000. Non-invasive administration of drugs through the skin: Challenges in delivery system design. J Pharm Sci Technol 3:417-425.
9. Bouwstra JA, Honeywell-Nguyen PL, Gooris GS, Ponec M. 2003. Structure of the skin barrier and its modulation by vesicular formulations. Prog Lipid Res 42:1-36.
10. Warner RR, Stone KJ, Boissy YL. 2003. Hydration disrupts human stratum corneum ultrastructure. J Invest Dermatol 120:275-284.
11. Tan G, Xu P, Lawson LB, He J, Freytag LC, Clements J, John VT. 2010. Hydration effects on skin microstructure as probed by high-resolution cryo-scanning electron microscopy and mechanistic implications to enhanced transcutaneous delivery of biomacromolecules. J Pharm Sci 99:730-740.
12. Van Hal DA, Jeremiasse E, Junginger HE, Spies F, Bouwstra JA. 1996. Structure of fully hydrated human stratum corneum: A freeze-fracture electron microscopy study. J Invest Dermatol 106:89-95.
13. Kasting GB, Namrata DB, Wang T-F, Nitsche JM. 2003. Mobility of water in human stratum corneum. J Pharm Sci 92:2326-2340.
14. Ting W, Vest C, Sontheimer R. 2004. Review of traditional and novel modalities that enhance the permeability of local therapeutics across the stratum corneum. Int J Dermatol 43:538-547.
15. Williams AC, Barry BW. 2004. Penetration enhancers. Adv Drug Deliv Rev 56:603-618.
16. Jakasa I, Verberk MM, Bunge AL, Kruse J, Kezic S. 2006. Increased permeability for polyethylene glycols through skin compromised by sodium lauryl sulphate. Exp Dermatol 15:801-807.
17. Sinha VR, Kaur MP. 2000. Permeation enhancers for transdermal drug delivery. Drug Dev Ind Pharm 26:1131-1140.
18. Rissmann R, Oudshoorn M, Hennink W, Ponec M, Bouwstra J. 2009. Skin barrier disruption by acetone: Observations in a hairless mouse skin model. Arch Dermatol Res 301:609-613.
19. Lu MY, Lee D, Rao GS. 1992. Percutaneous absorption enhancement of leuprolide. Pharm Res 9:1575-1579.
20. Langkjær L, Brange J, Grodsky GM, Guy RH. 1998. Iontophoresis of monomeric insulin analogues in vitro: Effects of insulin charge and skin pretreatment. J Control Release 51:47-56.
21. Chen Y, Shen Y, Guo X, Zhang C, Yang W, Ma M, Liu S, Zhang M, Wen LP. 2006. Transdermal protein delivery by a coadministered peptide identified via phage display. Nat Biotechnol 24:455-460.
22. Hadgraft J. 1999. Passive enhancement strategies in topical and transdermal drug delivery. Int J Pharm 184:1-6.
23. Leichtnam M-L, Rolland H, Wüthrich P, Guy RH. 2006. Formulation and evaluation of a testosterone transdermal spray. J Pharm Sci 95:1693-1702.
24. Nicolazzo JA, Morgan TM, Reed BL, Finnin BC. 2005. Synergistic enhancement of testosterone transdermal delivery. J Control Release 103:577-585.
25. Kim YC, Park JH, Ludovice PJ, Prausnitz MR. 2008. Synergistic enhancement of skin permeability by N-lauroylsarcosine and ethanol. Int J Pharm 352:129-138.
26. Narishetty ST, Panchagnula R. 2005. Effect of L-menthol and 1, 8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine. J Control Release 102:59-70.
27. Kim YC, Late S, Banga AK, Ludovice PJ, Prausnitz MR. 2008. Biochemical enhancement of transdermal delivery with magainin peptide: Modification of electrostatic interactions by changing pH. Int J Pharm 362:20-28.
28. Cui Z, Fountain W, Clark M, Jay M, Mumper RJ. 2003. Novel ethanol-in-fluorocarbon microemulsions for topical genetic immunization. Pharm Res 20:16-23.
29. Chaudhuri SR, Gajjar RM, Krantz WB, Kasting GB. 2009. Percutaneous absorption of volatile solvents following transient liquid exposures II. Ethanol. Chem Eng Sci 64:1665-1672.
30. Bommannan D, Potts RO, Guy RH. 1991. Examination of the effect of ethanol on human stratum corneum in vivo using infrared spectroscopy. J Control Release 16:299-304.
31. Bromberg LE, Klibanov AM. 1995. Transport of proteins dissolved in organic solvents across biomimetic membranes. Proc Natl Acad Sci U S A 92:1262-1266.
32. Babiuk S, Baca-Estrada M, Babiuk LA, Ewen C, Foldvari M. 2000. Cutaneous vaccination: The skin as an immunologically active tissue and the challenge of antigen delivery. J Control Release 66:199-214.
33. Lawson LB, Freytag LC, Clements JD. 2007. Use of nanocarriers for transdermal vaccine delivery. Clin Pharmacol Ther 82:641-643.
34. Glenn GM, Scharton-Kersten T, Alving CR. 1999. Advances in vaccine delivery: Transcutaneous immunisation. Expert Opin Investig Drugs 8:797-805.
35. Glenn GM, Taylor DN, Li X, Frankel S, Montemarano A, Alving CR. 2000. Transcutaneous immunization: A human vaccine delivery strategy using a patch. Nat Med 6:1403-1406.
36. Pays K, Giermanska-Kahn J, Pouligny B, Bibette J, Leal-Calderon F. 2002. Double emulsions: How does release occur? J Control Release 79:193-205.
37. Aserin A, Ed. 2008. Multiple emulsions: Technology and applications. 1st ed. Hoboken, NJ: Wiley, pp 350.
38. Jiao J, Rhodes DG, Burgess DJ. 2002. Multiple emulsion stability: Pressure balance and interfacial film strength. J Colloid Interface Sci 250:444-450.
39. Rojas EC, Papadopoulos KD. 2007. Induction of instability in water-in-oil-in-water double emulsions by freeze-thaw cycling. Langmuir 23:6911-6917.
40. Rojas EC, Staton JA, John VT, Papadopoulos KD. 2008. Temperature-induced protein release from water-in-oil-in-water double emulsions. Langmuir 24:7154-7160.
41. 2 globules stabilized with Span 80 and Tween 80. Colloid Surf A Physiochem Eng Asp 125:181-187.
42. Pays K, Giermanska-Kahn J, Pouligny B, Bibette J, Leal-Calderon F. 2001. Coalescence in surfactant-stabilized double emulsions. Langmuir 17:7758-7769.
43. Villa CH, Lawson LB, Li Y, Papadopoulos KD. 2003. Internal coalescence as a mechanism of instability in water-in-oil-in-water double-emulsion globules. Langmuir 19:244-249.
44. Florence AT, Omotosho JA, Whateley TL. 1989. Multiple w/o/w emulsions as drug vehicles. In Controlled release of drugs: Polymers and aggregate systems; Rosoff M, Ed. New York: VCH Publisher INC, pp 163-184.
45. Conway BR, Alpar OH. 1996. Double emulsion microencapsulation of proteins as model antigens using polylactide polymers: Effect of emulsifier on the microsphere characteristics and release kinetics. Eur J Pharm Biopharm 42:42-48.
46. Bozkir A, Hayta G. 2004. Preparation and evaluation of multiple emulsions water-in-oil-in-water (w/o/w) as delivery system for influenza virus antigens. J Drug Target 12:157-164.
47. Bozkir A, Hayta G, Saka OM. 2004. Comparison of biodegradable nanoparticles and multiple emulsions (water-in-oil-in-water) containing influenza virus antigen on the in vivo immune response in rats. Pharmazie 59:723-725.
48. Picard A, Daniel I, Montagnac G, Oger P. 2007. In situ monitoring by quantitative Raman spectroscopy of alcoholic fermentation by Saccharomyces cerevisiae under high pressure. Extremophiles 11:445-452.
49. Alvarez-Román R, Naik A, Kalia YN, Fessi H, Guy RH. 2004. Visualization of skin penetration using confocal laser scanning microscopy. Eur J Pharm Biopharm 58:301-316.
50. Magdassi S, Garti N. 1987. Formation of water/oil/water multiple emulsions with solid oil phase. J Colloid Interface Sci 120:537-539.
51. Herhold AB, Ertas D, Levine AJ, King HE. 1999. Impurity mediated nucleation in hexadecane-in-water emulsions. Phys Rev E 59:6946.
52. 16) systems: methanol + decane, ethanol +tetradecane, and ethanol + hexadecane. Fluid Phase Equilib 224:31-37.
53. Mulholland WJ, Arbuthnott EAH, Bellhouse BJ, Cornhill JF, Austyn JM, Kendall MA, Cui Z, Tirlapur UK. 2006. Multiphoton high-resolution 3D imaging of Langerhans cells and keratinocytes in the mouse skin model adopted for epidermal powdered immunization. J Invest Dermatol 126:1541-1548.
54. Nelson DL, Cox MM. 2000. Lehninger principles of biochemistry. 3rd ed. New York: Worth Publishers, pp 192.
55. Brandts JF, Hunt L. 1967. Thermodynamics of protein denaturation. III. Denaturation of ribonuclease in water and in aqueous urea and aqueous ethanol mixtures. J Am Chem Soc 89:4826-4838.
56. Choi WS, Krishna Murthy GG, Edwards DA, Langer R, Klibanov AM. 2001. Inhalation delivery of proteins from ethanol suspensions. Proc Natl Acad Sci U S A 98:11103-11107.
57. Michnik A, Drzazga Z. 2007. Effect of ethanol on the thermal stability of human serum albumin. J Therm Anal Calorim 88:449-454.
58. Martin SR, Esposito V, De Los Rios P, Pastore A, Temussi PA. 2008. Cold denaturation of yeast frataxin offers the clue to understand the effect of alcohols on protein stability. J Am Chem Soc 130:9963-9970.
59. Melnikova YI, Odintsov SG, Kravchuk ZI, Martsev SP. 2000. Antigen-binding activity of monoclonal antibodies after incubation with organic solvents. Biochemistry 65:1488-1499.
60. Rehan M, Younus H. 2006. Effect of organic solvents on the conformation and interaction of catalase and anticatalase antibodies. Int J Biol Macromol 38:289-295.
61. Lardinois OM, Detweiler CD, Tomer KB, Mason RP, Deterding LJ. 2008. Identifying the site of spin trapping in proteins by a combination of liquid chromatography, ELISA, and off-line tandem mass spectrometry. Free Radic Biol Med 44:893-906.