Recent advances in predicting skin permeability of hydrophilic solutes

Advanced Drug Delivery Reviews

Volumn 65, Issue 2, 2013, Pages 295-305

  Chen, Longjian ^a,b   Han, Lujia ^a,b   Lian, Guoping ^c  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b State Key Laboratory of Animal Nutrition   (China)

^c UNILEVER RESEARCH   (United Kingdom)

Author keywords

Aqueous porous pathway; Brick and mortar; Hydrophilic; Quantitative structure permeability relationships; Skin permeability; Stratum corneum; Transdermal permeation

Indexed keywords

BRICK-AND-MORTAR; HYDROPHILIC; POROUS PATHWAY; QUANTITATIVE STRUCTURE-PERMEABILITY RELATIONSHIPS; SKIN PERMEABILITY; STRATUM CORNEUM; TRANSDERMAL PERMEATION;

FORECASTING; HYDROPHILICITY; MECHANICAL PERMEABILITY; SKIN;

CONTROLLED DRUG DELIVERY;

LIPID;

AQUEOUS SOLUTION; BIOLOGICAL MODEL; DIFFUSION; HUMAN; HYDROPHILICITY; HYDROPHOBICITY; MECHANISTIC MODEL; MOLECULAR WEIGHT; NONHUMAN; PHYSICAL CHEMISTRY; POROSITY; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE PERMEABILITY RELATIONSHIP MODEL; REVIEW; SKIN CELL; SKIN PERMEABILITY; SKIN PROTECTION; SKIN STRUCTURE; SOLUTE; STATISTICAL MODEL; STATISTICAL PARAMETERS;

ADMINISTRATION, CUTANEOUS; DRUG DELIVERY SYSTEMS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, THEORETICAL; PERMEABILITY; PHARMACEUTICAL PREPARATIONS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SKIN; SKIN ABSORPTION;

EID: 84873526733     PISSN: 0169409X     EISSN: 18728294     Source Type: Journal    
DOI: 10.1016/j.addr.2012.05.001     Document Type: Review

References (143)

1. Tezel A., Sens A., Mitragotri S. Description of transdermal transport of hydrophilic solutes during low-frequency sonophoresis based on a modified porous pathway model. J. Pharm. Sci. 2003, 92:381-393.
2. Chen Y., Shen Y., Guo X., Zhang C., Yang W., Ma M., Liu S., Zhang M., Wen L.-P. Transdermal protein delivery by a coadministered peptide identified via phage display. Nat Biotechnol. 2006, 24:455-460.
3. Nicoli S., Zani F., Bilzi S., Bettini R., Santi P. Association of nicotinamide with parabens: effect on solubility, partition and transdermal permeation. Eur. J. Pharm. Biopharm. 2008, 69:613-621.
4. Brand R.M., Mueller C. Transdermal penetration of atrazine, alachlor, and trifluralin: effect of formulation. Toxicol. Sci. 2002, 68:18-23.
5. Kielhorn J., Melching-Kollmuss S., Mangelsdorf I. Environmental Health Criteria 235: Dermal Absorption 2006, World Health Organization, Geneva, Switzerland.
6. Bouwman T., Cronin M.T.D., Bessems J.G., van de Sandt J.J. Improving the applicability of (Q)SARs for percutaneous penetration in regulatory risk assessment. Hum. Exp. Toxicol. 2008, 27:269-276.
7. Polat B.E., Seto J.E., Blankschtein D., Langer R. Application of the aqueous porous pathway model to quantify the effect of sodium lauryl sulfate on ultrasound-induced skin structural perturbation. J. Pharm. Sci. 2011, 100:1387-1397.
8. Kushner J., Blankschtein D., Langer R. Evaluation of the porosity, the tortuosity, and the hindrance factor for the transdermal delivery of hydrophilic permeants in the context of the aqueous pore pathway hypothesis using dual-radiolabeled permeability experiments. J. Pharm. Sci. 2007, 96:3263-3282.
9. Mitragotri S. Modeling skin permeability to hydrophilic and hydrophobic solutes based on four permeation pathways. J. Control. Release 2003, 86:69-92.
10. Zhang G.J., Moore D.J., Sloan K.B., Flach C.R., Mendelsohn R. Imaging the prodrug-to-drug transformation of a 5-fluorouracil derivative in skin by confocal Raman microscopy. J. Invest. Dermatol. 2007, 127:1205-1209.
11. Prausnitz M.R., Langer R. Transdermal drug delivery. Nat. Biotechnol. 2008, 26:1261-1268.
12. Polat B.E., Figueroa P.L., Blankschtein D., Langer R. Transport pathways and enhancement mechanisms within localized and non-localized transport regions in skin treated with low-frequency sonophoresis and sodium lauryl sulfate. J. Pharm. Sci. 2011, 100:512-529.
13. Kushner J., Blankschtein D., Langer R. Experimental demonstration of the existence of highly permeable localized transport regions in low-frequency sonophoresis. J. Pharm. Sci. 2004, 93:2733-2745.
14. Prausnitz M.R., Mitragotri S., Langer R. Current status and future potential of transdermal drug delivery. Nat. Rev. Drug Discov. 2004, 3:115-124.
15. Williams A.C., Barry B.W. Penetration enhancers. Adv. Drug Deliv. Rev. 2004, 56:603-618.
16. Purdon C.H., Azzi C.G., Zhang J., Smith E.W., Maibach H.I. Penetration enhancement of transdermal delivery-current permutations and limitations. Crit. Rev. Ther. Drug Carrier Syst. 2004, 21:97-132.
17. Hathout R.M., Mansour S., Mortada N.D., Geneidi A.S., Guy R.H. Uptake of microemulsion components into the stratum corneum and their molecular effects on skin barrier function. Mol. Pharm. 2010, 7:1266-1273.
18. Kalia Y.N., Naik A., Garrison J., Guy R.H. Iontophoretic drug delivery. Adv. Drug Deliv. Rev. 2004, 56:619-658.
19. Cross S.E., Roberts M.S. Physical enhancement of transdermal drug application: is delivery technology keeping up with pharmaceutical development?. Curr. Drug Deliv. 2004, 1:81-92.
20. Lavon I., Kost J. Ultrasound and transdermal drug delivery. Drug Discov. Today 2004, 9:670-676.
21. Alvarez-Roman R., Merino G., Kalia Y.N., Naik A., Guy R.H. Skin permeability enhancement by low frequency sonophoresis: lipid extraction and transport pathways. J. Pharm. Sci. 2003, 92:1138-1146.
22. Mitragotri S., Anissimov Y.G., Bunge A.L., Frasch H.F., Guy R.H., Hadgraft J., Kasting G.B., Lane M.E., Roberts M.S. Mathematical models of skin permeability: an overview. Int. J. Pharm. 2011, 418:115-129.
23. Russell L.M., Guy R.H. Measurement and prediction of the rate and extent of drug delivery into and through the skin. Expert Opin. Drug Deliv. 2009, 6:355-369.
24. Geinoz S., Guy R.H., Testa B., Carrupt P.A. Quantitative structure-permeation relationships (QSPeRs) to predict skin permeation: a critical evaluation. Pharm. Res. 2004, 21:83-92.
25. Naegel A., Heisig M., Wittum G. A comparison of two- and three-dimensional models for the simulation of the permeability of human stratum corneum. Eur. J. Pharm. Biopharm. 2009, 72:332-338.
26. Riviere J.E., Brooks J.D. Predicting skin permeability from complex chemical mixtures: dependency of quantitative structure permeation relationships on biology of skin model used. Toxicol. Sci. 2011, 119:224-232.
27. Anissimov Y.G., Roberts M.S. Diffusion modeling of percutaneous absorption kinetics: 2. Finite vehicle volume and solvent deposited solids. J. Pharm. Sci. 2001, 90:504-520.
28. Anissimov Y.G., Roberts M.S. Diffusion modelling of percutaneous absorption kinetics: 4. Effects of a slow equilibration process within stratum corneum on absorption and desorption kinetics. J. Pharm. Sci. 2009, 98:772-781.
29. Hadgraft J., Lane M.E. Skin permeation: the years of enlightenment. Int. J. Pharm. 2005, 305:2-12.
30. Nitsche J.M., Kasting G.B. Biophysical Models for Skin Transport and Absorption 2008, Informa Healthcare, New York.
31. Barbero A.M., Frasch H.F. Transcellular route of diffusion through stratum corneum: results from finite element models. J. Pharm. Sci. 2006, 95:2186-2194.
32. Frasch H.F., Barbero A.M., Hettick J.M., Nitsche J.M. Tissue binding affects the kinetics of theophylline diffusion through the stratum corneum barrier layer of skin. J. Pharm. Sci. 2011, 100:2989-2995.
33. Nitsche J.M. Dynamics of diffusion with reversible binding in microscopically heterogeneous membranes: general theory and applications to dermal penetration. Chem. Eng. Sci. 2011, 66:2019-2041.
34. Frasch H.F., Barbero A.M. The transient dermal exposure: theory and experimental examples using skin and silicone membranes. J. Pharm. Sci. 2008, 97:1578-1592.
35. OECD Guideline 428 - Guideline for the Testing of Chemicals: Skin Absorption: in vitro Method 2004, Organization for Economic Cooperation and Development, Paris.
36. OECD ENV/JM/MONO(2007)2 - Guidance Document on the Validation of (Quantitative) Structure-Activity Relationships [(Q)SAR] Models 2007, Organization for Economic Cooperation and Development, Paris.
37. USEPA EPA/600/8-91/011B - Dermal Exposure Assessment: Principles and Applications 1992, United States Environmental Protection Agency, Washington, DC.
38. USEPA EPA540/R/99/005 - Risk Assessment Guidance for Superfund, Vol. I: Human health Evaluation Manual (Part E, Supplemental Guidance for Dermal Risk Assessment) 2004, United States Environmental Protection Agency, Washington, DC.
39. USEPA Dermal Exposure Assessment: A Summary of EPA Approaches 2007, United States Environmental Protection Agency, Washington, DC.
40. NIOSH Publication No. 2009-147 - Current Intelligence Bulletin 61 A Strategy for Assigning New NIOSH Skin Notations 2009, National Institute for Occupational Safety and Health, Atlanta.
41. EC Guidance Document on Dermal Absorption 2004, European Commission, Brussel.
42. Johanson G., Rauma M. Basis for Skin Notation. Part 1. Dermal Penetration Data for Substances on the Swedish OEL List 2008, Göteborg University, Göteborg.
43. Abraham M.H., Martins F. Human skin permeation and partition: general linear free-energy relationship analyses. J. Pharm. Sci. 2004, 93:1508-1523.
44. Chen L.J., Lian G.P., Han L.J. Modeling transdermal permeation. Part I. Predicting skin permeability of both hydrophobic and hydrophilic solutes. AIChE J. 2010, 56:1136-1146.
45. Degim I.T. New tools and approaches for predicting skin permeability. Drug Discov. Today 2006, 11:517-523.
46. Lian G.P., Chen L.J., Han L.J. An evaluation of mathematical models for predicting skin permeability. J. Pharm. Sci. 2008, 97:584-598.
47. Moss G.P., Dearden J.C., Patel H., Cronin M.T.D. Quantitative structure-permeability relationships (QSPRs) for percutaneous absorption. Toxicol. In Vitro 2002, 16:299-317.
48. Patel H., Ten B.W., Cronin M.T.D. Quantitative structure-activity relationships (QSARs) for the prediction of skin permeation of exogenous chemicals. Chemosphere 2002, 48:603-613.
49. Potts R.O., Guy R.H. Predicting skin permeability. Pharm. Res. 1992, 9:663-669.
50. Vecchia B.E., Bunge A.L. Skin absorption databases and predictive equations. Transdermal Drug Delivery Systems 2002, Marcel Dekker, New York. J. Hadgraft, R.H. Guy (Eds.).
51. Wang T.F., Kasting G.B., Nitsche J.M. A multiphase microscopic diffusion model for stratum corneum permeability. II. Estimation of physicochemical parameters and application to a large permeability database. J. Pharm. Sci. 2007, 96:3024-3051.
52. Kasting G.B., Miller M.A., Nitsche J.M. Absorption and evaporation of volatile compounds applied to skin. Dermatologic, Cosmoceutic and Cosmetic Development: Therapeutics and Novel Approaches 2008, Informa Healthcare, New York. K.A. Walters, M.S. Roberts (Eds.).
53. Mitragotri S., Blankschtein D., Langer R. Transdermal drug delivery using low-frequency sonophoresis. Pharm. Res. 1996, 13:411-420.
54. Michaels A.S., Chandrasekaran S.K., Shaw J.E. Drug permeation through human skin: theory and in-vitro experimental measurement. AIChE J. 1975, 21:985-996.
55. Southwell D., Barry B.W., Woodford R. Variations in permeability of human skin within and between specimens. Int. J. Pharm. 1984, 18:299-309.
56. Anderson B.D., Higuchi W.I., Raykar P.V. Heterogeneity effects on permeability-partition coefficient relationships in human stratum corneum. Pharm. Res. 1988, 5:566-573.
57. Clowes H.M. Skin absorption: flow-through or statistic diffusion cells. Toxicol. In Vitro 1994, 8:827-830.
58. Hansen S., Henning A., Naegel A., Heisig M., Wittum G., Neumann D., Kostka K.H., Zbytovska J., Lehr C.M., Schaefer U.F. In-silico model of skin penetration based on experimentally determined input parameters. Part I. Experimental determination of partition and diffusion coefficients. Eur. J. Pharm. Biopharm. 2008, 68:352-367.
59. Kushner J., Kim D., So P.T.C., Blankschtein D., Langer R. Dual-channel two-photon miscroscopy study of transdermal transport in skin treated with low-frequency ultrasound and a chemical enhancer. J. Invest. Dermatol. 2007, 127:2832-2846.
60. Wilschut A., Tenberge W.F., Robinson P.J., McKone T.E. Estimating skin permeation - the validation of 5 mathematical skin permeation models. Chemosphere 1995, 30:1275-1296.
61. Abraham M.H., Chandha H.S., Martins F., Mitchell R.C., Michael W., Gratton J. Hydrogen bonding-part 4: a review of the correlation and prediction of transport properties by an LFER method: physicochemical properties, brain penetration and skin permeability. Pestic. Sci. 1999, 55:78-88.
62. Morimoto Y., Hatanaka T., Sugibayashi K., Omiya H. Prediction of skin permeability of drugs: comparison of human and hairless rat skin. J. Pharm. Pharmacol. 1992, 44:634-639.
63. Peck K.D., Ghanem A.H., Higuchi W.I. Hindered diffusion of polar molecules through and effective pore radii estimates of intact and ethanol treated human epidermal membrane. Pharm. Res. 1994, 11:1306-1314.
64. Tang H., Mitragotri S., Blankschtein D., Langer R. Theoretical description of transdermal transport of hydrophilic permeants: application to low-frequency sonophoresis. J. Pharm. Sci. 2001, 90:545-568.
65. Tezel A., Sens A., Mitragotri S. A theoretical analysis of low-frequency sonophoresis: dependence of transdermal transport pathways on frequency and energy density. Pharm. Res. 2002, 19:1843-1848.
66. Chen L.J., Lian G.P., Han L.J. Use of "bricks and mortar" model to predict transdermal permeation: model development and initial validation. Ind. Eng. Chem. Res. 2008, 47:6465-6472.
67. Lian G.P., Chen L.J., Pudney P.D.A., Melot M., Han L.J. Modeling transdermal permeation. Part II. Predicting the dermatopharmacokinetics of percutaneous solute. AIChE J. 2010, 56:2551-2560.
68. Groen D., Poole D.S., Gooris G.S., Bouwstra J.A. Investigating the barrier function of skin lipid models with varying compositions. Eur. J. Pharm. Biopharm. 2011, 79:334-342.
69. Bouwstra J.A., Honeywell-Nguyen P.L., Gooris G.S., Ponec M. Structure of the skin barrier and its modulation by vesicular formulations. Prog. Lipid Res. 2003, 42:1-36.
70. Norlen L. Nanostructure of the stratum corneum extracellular lipid matrix as observed by cryo-electron microscopy of vitreous skin sections. Int. J. Cosmet. Sci. 2007, 29:335-352.
71. Talreja P.S., Kasting G.B., Kleene N.K., Pickens W.L., Wang T.F. Visualization of the lipid barrier and measurement of lipid pathlength in human stratum corneum. AAPS PharmSci 2001, 3:1-9.
72. Sznitowska M., Berner B. Polar pathway for percutaneous absorption. Exogenous Dermatology 1995, 164-170. Karger, Basel. C. Surber, P. Elsner, A.J. Bircher (Eds.).
73. Wester R.C., Quan D., Maibach H.I. In vitro percutaneous absorption of model compounds glyphosate and malathion from cotton fabric into and through human skin. Food Chem. Toxicol. 1996, 34:731-735.
74. Scott R.C., Corrigan M.A., Smith F., Mason H. The influence of skin structure on permeability: an intersite and interspecies comparison with hydrophilic penetrants. J. Invest. Dermatol. 1991, 96:921-925.
75. Peck K.D., Ghanem A.H., Higuchi W.I. The effect of temperature upon permeation of polar and ionic solutes through human epidermal membrane. J. Pharm. Sci. 1995, 84:975-982.
76. 14C-chloroform in humans. Hum. Exp. Toxicol. 1992, 14:260-265.
77. Barber E., Teetsel N., Kolberg K.F., Guest D. A comparative study of the rates of in vitro percutaneous absorption of eight chemicals using rat and human skin. Toxicol. Sci. 1992, 19:493-497.
78. Scheuplein R.J., Blank I.H. Mechanism of percutaneous absorption. iv. penetration of nonelectrolytes (alcohols) from aqueous solutions and from pure liquids. J. Invest. Dermatol. 1973, 60:286-296.
79. Bond J.R., Barry B.W. Limitations of hairless mouse skin as a model for in vitro permeation studies through human skin: hydration damage. J. Invest. Dermatol. 1988, 90:486-489.
80. Bronaugh R.L., Stewart R.F., Simon M. Methods for in vitro percutaneous absorption studies VII: use of excised human skin. J. Pharm. Sci. 1986, 75:1094-1097.
81. Galey W.R., Lonsdale H.K., Nacht S. The in vitro permeability of skin and buccal mucosa to selected drugs and tritiated water. J. Invest. Dermatol. 1976, 67:713-717.
82. Harrison S.M., Barry B.W., Dugard P.H. Effects of freezing on human skin permeability. J. Pharm. Pharmacol. 1984, 36:261-262.
83. Rigg C.C., Barry B.W. Shed snake skin and hairless mouse skin as model membranes for human skin during permeation studies. J. Invest. Dermatol. 1990, 94:235-240.
84. Bronaugh R.L., Congdon E.R., Scheuplein R.J. The effect of cosmetic vehicles on the penetration of N-nitrosodiethanolamine through excised human skin. J. Invest. Dermatol. 1981, 76:94-96.
85. Scheuplein R.J. Mechanisms of percutaneous absorption: transient diffusion and the relative importance of various routes of skin penetration. J. Invest. Dermatol. 1967, 48:78-89.
86. Cornwell P.A., Barry B.W. Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-flurouracil. J. Pharm. Pharmacol. 1994, 46:261-269.
87. Wilkinson S.C., Williams F.M. Effects of experimental conditions on absorption of glycol ethers through human skin in vitro. Int. Arch. Occup. Environ. Health 2002, 75:519-527.
88. Venier M., Adami G., Larese F., Maina G., Renzi N. Percutaneous absorption of 5 glycol ethers through human skin in vitro. Toxicol. In Vitro 2004, 18:665-671.
89. Blank I.H., Scheuplein R.J., Macfarlane D.J. Mechanism of percutaneous absorption III. The effect of temperature on the transport of non-electrolytes across the skin. J. Invest. Dermatol. 1967, 49:582-589.
90. Bronaugh R.L., Congdon E.R. Percutaneous absorption of hair dyes: correlation with partition coefficients. J. Invest. Dermatol. 1984, 83:124-127.
91. Wester R.C., Hui X., Hartway T., Maibach H.I., Bell K., Schell M.J., Northington D.J., Strong P., Culver B.D. In vivo percutaneous absorption of boric acid, borax, and disodium octaborate tetrahydrate in humans compared to in vitro absorption in human skin from infinite and finite doses. Toxicol. Sci. 1998, 45:42-51.
92. Kenyon S.H., Carmichael P.L., Khalaque S., Panchal S., Waring R., Harris R. The passage of trimethylamine across rat and human skin. Food Chem. Toxicol. 2004, 42:1619-1628.
93. Blank I.H. Penetration of low molecular weight alcohols into skin. 1. The effect of concentration of alcohol and type of vehicle. J. Invest. Dermatol. 1964, 43:415-420.
94. Anderson B.D., Raykar P.V. Solute structure-permeability relationships in human stratum corneum. J. Invest. Dermatol. 1989, 93:280-286.
95. Dal Pozzo A., Donzelli G., Liggeri E., Rodriguez L. Percutaneous absorption of nicotinic acid derivatives in vitro. J. Pharm. Sci. 1991, 80:54-56.
96. Sato K., Sugibayashi K., Morimoto Y. Species differences in percutaneous absorption of nicorandil. J. Pharm. Sci. 1991, 80:104-107.
97. Cronin M.T., Schultz T.W. Pitfalls in QSAR. J. Mol. Struct. Theochem 2003, 622:39-51.
98. Kasting G.B., Smith R.L., Cooper E.R. Effect of lipid solubility and molecular size on percutaneous absorption. Skin Pharmacokinetics 1987, 138-153. Karger, Basel, Switzerland. B. Shroot, H. Schaefer (Eds.).
99. Flynn G.L. Physiochemical determinants of skin absorption. Principles of Route-to-Route Extrapolation for Risk Assessment 1990, 93-127. Elsevier, Amsterdam. T.R. Gerity, C.J. Henry (Eds.).
100. Cronin M.T., Dearden J.C., Moss G.P., Murray-Dickson G. Investigation of the mechanism of flux across human skin in vitro by quantitative structure-permeability relationships. Eur. J. Pharm. Sci. 1999, 7:325-330.
101. Moss G.P., Sun Y., Prapopoulou M., Davey N., Adams R., Pugh W.J., Brown M.B. The application of Gaussian processes in the prediction of percutaneous absorption. J. Pharm. Pharmacol. 2009, 61:1147-1153.
102. Norlén L. Stratum corneum keratin structure, function and formation - a comprehensive review. Int. J. Cosmet. Sci. 2006, 28:397-425.
103. Norlén L. Nanostructure of the stratum corneum extracellular lipid matrix as observed by cryo-electron microscopy of vitreous skin sections. Int. J. Cosmet. Sci. 2007, 29:335-352.
104. Norlén L., Plasencia I., Bagatolli L. Stratum corneum lipid organization as observed by atomic force, confocal and two-photon excitation fluorescence microscopy. Int. J. Cosmet. Sci. 2008, 30:391-411.
105. Meidan V.M., Bonner M.C., Michniak B.B. Transfollicular drug delivery - is it a reality?. Int. J. Pharm. 2005, 306:1-14.
106. Masukawa Y., Narita H., Shimizu E., Kondo N., Sugai Y., Oba T., Homma R., Ishikawa J., Takagi Y., Kitahara T., Takema Y., Kita K. Characterization of overall ceramide species in human stratum corneum. J. Lipid Res. 2008, 49:1466-1476.
107. Ponec M., Weerheim A., Lankhorst P., Wertz P. New acylceramide in native and reconstructed epidermis. J. Invest. Dermatol. 2003, 120:581-588.
108. Weerheim A., Ponec M. Determination of stratum corneum lipid profile by tape stripping in combination with high-performance thin-layer chromatography. Arch. Dermatol. Res. 2001, 292.
109. Norlén L., Nicander I., Rozell B.L., Ollmar S., Forslind B. Inter- and intra-individual differences in human stratum corneum lipid content related to physical parameters of skin barrier function in vivo. J. Invest. Dermatol. 1999, 112:72-77.
110. Rawlings A.V. Recent advances in skin 'barrier' research. J. Pharm. Pharmacol. 2010, 62:671-677.
111. Nitsche J.M., Wang T.F., Kasting G.B. A two-phase analysis of solute partitioning into the stratum corneum. J. Pharm. Sci. 2006, 95:649-666.
112. Raykar P.V., Fung M.C., Anderson B.D. The role of protein and lipid domains in the uptake of solutes by human stratum corneum. Pharm. Res. 1988, 5:140-150.
113. Wang L.M., Chen L.J., Lian G.P., Han L.J. Determination of partition and binding properties of solutes to stratum corneum. Int. J. Pharm. 2010, 398:114-122.
114. Hatanaka T., Inuma M., Sugibayashi K., Morimoto Y. Prediction of skin permeability of drugs. I. Comparison with artificial membrane. Chem. Pharm. Bull. 1990, 38:3452-3459.
115. Phillips R.J., Deen W., Brady J.F. Hindered transport of spherical macromolecules in fibrous membranes and gels. AIChE J. 1989, 35:1761-1769.
116. Rawlings A.V., Harding C.R. Moisturization and skin barrier function. Dermatol. Ther. 2004, 17:43-48.
117. Walters K.A., Roberts M.S. The Structure and Function of Skin 2005, Marcel Dekker Inc., New York.
118. Nakagawa N., Sakai S., Matsumoto M., Yamada K., Nagano M., Yuki T., Sumida Y., Uchiwa H. Relationship between NMF (lactate and potassium) content and the physical properties of the stratum corneum in healthy subjects. J. Invest. Dermatol. 2004, 122:755-763.
119. Naegel A., Hansen S., Neumann D., Lehr C.M., Schaefer U.F., Wittum G., Heisig M. In-silico model of skin penetration based on experimentally determined input parameters. Part II. Mathematical modelling of in-vitro diffusion experiments. Identification of critical input parameters. Eur. J. Pharm. Biopharm. 2008, 68:368-379.
120. Kasting G.B., Barai N.D., Wang T.F., Nitsche J.M. Mobility of water in human stratum corneum. J. Pharm. Sci. 2003, 92:2326-2340.
121. Bodde H.E., Van D., Koerten H.K., De H. Visualization of in vitro percutaneous penetration of mercuric chloride transport through intercellular space versus cellular uptake through desmosomes. J. Control. Release 1991, 15:227-236.
122. Jacobi U., Tassopoulos T., Surber C., Lademann J. Cutaneous distribution and localization of dyes affected by vehicles all with different lipophilicity. Arch. Derm. Res. 2006, 297:303-310.
123. Yu B., Kim K.H., So P.T.C., Blankschtein D., Langer R. Evaluation of fluorescent probe surface intensities as an indicator of transdermal permeant distributions using wide-area two-photon fluorescence microscopy. J. Pharm. Sci. 2003, 92:2354-2365.
124. Hansen S., Naegel A., Heisig M., Wittum G., Neumann D., Kostka K.-H., Meiers P., Lehr C.-M., Schaefer U. The role of corneocytes in skin transport revised-a combined computational and experimental approach. Pharm. Res. 2009, 26:1379-1397.
125. Mitragotri S. A theoretical analysis of permeation of small hydrophobic solutes across the stratum corneum based on scaled particle theory. J. Pharm. Sci. 2002, 91:744-752.
126. Hansen S., Selzer D., Schaefer U.F., Kasting G.B. An extended database of keratin binding. J. Pharm. Sci. 2011, 100:1712-1726.
127. Johnson E.M., Berk D.A., Jain R.K., Deen W.M. Hindered diffusion in agarose gels: test of effective medium model. Biophys. J. 1996, 70:1017-1026.
128. Einstein A. Uber die von der molekular-kineticshen theorie der warme geforderte bewegung von in ruhenden flussigkeiten suspendierten teilchen. Ann. Phys. 1905, 17:549-560.
129. Jackson G.W., James D.G. The permeability of fibrous porous media. Can. J. Chem. Eng. 1986, 64:362-374.
130. Heisig M., Lieckfeldt R., Wittum G., Mazurkevich G., Lee G. Non steady-state descriptions of drug permeation through stratum corneum.1. The biphasic brick-and-mortar model. Pharm. Res. 1996, 13:421-426.
131. Surber C., Wilhelm K.P., Hori M., Maibach H.I., Guy R.H. Optimization of topical therapy: partitioning of drugs into stratum corneum. Pharm. Res. 1990, 7:1320-1324.
132. Surber C., Wilhelm K.P., Maibach H.I., Hall L.L., Guy R.H. Partitioning of chemicals into human stratum corneum: implications for risk assessment following dermal exposure. Fundam. Appl. Toxicol. 1990, 15:99-107.
133. Alvarez-Román R., Naik A., Kalia Y.N., Fessi H., Guy R.H. Visualization of skin penetration using confocal laser scanning microscopy. Eur. J. Pharm. Biopharm. 2004, 58:301-316.
134. Yu B., Kim K.H., So P.T.C., Blankschtein D., Langer R. Visualization of oleic acid-induced transdermal diffusion pathways using two-photon fluorescence microscopy. J. Invest. Dermatol. 2003, 120:448-455.
135. Saar B.G., Contreras-Rojas L.R., Xie X.S., Guy R.H. Imaging drug delivery to skin with stimulated Raman scattering microscopy. Mol. Pharm. 2011, 8:969-975.
136. Pirot F., Kalia Y.N., Stinchcomb A.L., Keating G., Bunge A., Guy R.H. Characterization of the permeability barrier of human skin in vivo. Proc. Natl. Acad. Sci. U. S. A. 1997, 94:1562-1567.
137. Romonchuk W.J., Bunge A.L. Permeation of 4-cyanophenol and methyl paraben from powder and saturated aqueous solution through silicone rubber membranes and human skin. J. Pharm. Sci. 2006, 95:2526-2533.
138. USEPA KOWWIN v1.67a 2008, United States Environmental Protection Agency, Washington, DC.
139. Hansch C., Leo A., Hoekman D. Exploring QSAR: Hydrophobic, Electronic, and Steric Constants 1995, American Chemical Society, Washington, DC.
140. Green P.G., Hinz R.S., Cullander C., Yamane G., Guy R.H. Iontophoretic delivery of amino acids and amino acid derivatives across the skin in vitro. Pharm. Res. 1991, 8:1113-1120.
141. Sangster J. LOGKOW - A Databank of Evaluated Octanol-Water Partition Coefficients (Log P) 2006, http://logkow.cisti.nrc.ca/logkow/index.jsp. 18 Jan 2012, Sangster Research Laboratories, Canada.
142. Fauchere J.L., Pliska V. Hydrophobic parameters of aminoacid side chains from the partitioning of N-acetylaminoacid amides. Eur. J. Med. Chem. 1983, 18:369-375.
143. Cohnen E., Flasch H., Heinz N., Hempelman F.W. Partition coefficients and Rm-values of cardenolides. Arzneim. Forsch. 1978, 28:2179-2182.