Ceramide analogue 14S24 selectively recovers perturbed human skin barrier

British Journal of Dermatology

Volumn 157, Issue 4, 2007, Pages 704-712

  Vavrova K ^a   Hrabalek A ^a   Mac Mary, S ^b   Humbert, P ^b   Muret, P ^b  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b UNIVERSITÉ DE FRANCHE COMTÉ   (France)

Author keywords

Atopic dermatitis; Ceramide analogue; Cutaneous microdialysis; Ex vivo in vitro model; Skin barrier recovery

Indexed keywords

CERAMIDE DERIVATIVE; DODECYL SULFATE SODIUM; N TETRACONASOYL LEVO SERINE TETRADECYL ESTER; THEOPHYLLINE; UNCLASSIFIED DRUG;

ARTICLE; DERMIS; ELECTRIC CAPACITANCE; EXTRACTION; HUMAN; HYDRATION; LIPOPHILICITY; MICRODIALYSIS; MOISTURE; PRIORITY JOURNAL; SKIN FUNCTION; SKIN WATER LOSS;

ADULT; BODY WATER; CERAMIDES; DETERGENTS; DRUG EVALUATION, PRECLINICAL; FEMALE; HUMANS; MICRODIALYSIS; MIDDLE AGED; SERINE; SKIN; SKIN ABSORPTION; SODIUM DODECYL SULFATE; SOLVENTS; THEOPHYLLINE; TISSUE CULTURE TECHNIQUES; WATER LOSS, INSENSIBLE;

EID: 34548564146     PISSN: 00070963     EISSN: 13652133     Source Type: Journal    
DOI: 10.1111/j.1365-2133.2007.08113.x     Document Type: Article

References (50)

1. Choi MJ, Maibach HI. Role of ceramides in barrier function of healthy and diseased skin. Am J Clin Dermatol 2005 6 : 215 23.
2. Bouwstra JA, Ponec M. The skin barrier in healthy and diseased state. Biochim Biophys Acta 2006 1758 : 2080 95.
3. Coderch L, Lopez O, de la Maza A et al. Ceramides and skin function. Am J Clin Dermatol 2003 4 : 107 29.
4. Imokawa G, Abe A, Jin K et al. Decreased level of ceramides in stratum corneum of atopic dermatitis: an etiologic factor in atopic dry skin? J Invest Dermatol 1991 96 : 523 6.
5. Motta S, Monti M, Sesana S et al. Abnormality of water barrier function in psoriasis. Role of ceramide fractions. Arch Dermatol 1994 130 : 452 6.
6. Rogers J, Harding C, Mayo A et al. Stratum corneum lipids: the effect of ageing and the seasons. Arch Dermatol Res 1996 288 : 765 70.
7. Altemus M, Rao B, Dhabhar FS et al. Stress-induced changes in skin barrier function in healthy women. J Invest Dermatol 2001 117 : 309 17.
8. Imokawa G. Lipid abnormalities in atopic dermatitis. J Am Acad Dermatol 2001 45 : S29 32.
9. Ogawa H, Yoshiike T. A speculative view of atopic dermatitis: barrier dysfunction in pathogenesis. J Dermatol Sci 1993 5 : 197 204.
10. Chamlin SL, Kao J, Frieden IJ et al. Ceramide-dominant barrier repair lipids alleviate childhood atopic dermatitis: changes in barrier function provide a sensitive indicator of disease activity. J Am Acad Dermatol 2002 47 : 198 208.
11. Fukunaga K, Yoshida M, Nakajima F et al. Design, synthesis, and evaluation of beta-galactosylceramide mimics promoting beta-glucocerebrosidase activity in keratinocytes. Bioorg Med Chem Lett 2003 13 : 813 15.
12. Imokawa G, Yada Y, Higuchi K et al. Pseudo-acylceramide with linoleic acid produces selective recovery of diminished cutaneous barrier function in essential fatty acid-deficient rats and has an inhibitory effect on epidermal hyperplasia. J Clin Invest 1994 94 : 89 96.
13. Vávrová K, Hrabálek A, Doležal P. Pseudoceramides and pharmaceutical and/or cosmetic compositions designed for administration to the skin containing the same. Czech Patient No. 298319 (23.6.2006), International patent application no. PCT/CZ2007/000057 (19.6.2007).
14. Vávrová K, Zbytovská J, Palát K et al. Ceramide analogue 14S24 ((S)-2-tetracosanoylamino-3-hydroxypropionic acid tetradecyl ester) is effective in skin barrier repair in vitro. Eur J Pharm Sci 2004 21 : 581 7.
15. Man MM, Feingold KR, Thornfeldt CR et al. Optimization of physiological lipid mixtures for barrier repair. J Invest Dermatol 1996 106 : 1096 101.
16. Man MQ, Feingold KR, Elias PM. Exogenous lipids influence permeability barrier recovery in acetone-treated murine skin. Arch Dermatol 1993 129 : 728 38.
17. Pinnagoda J, Tupker RA, Agner T et al. Guidelines for transepidermal water loss (TEWL) measurement. A report from the Standardization Group of the European Society of Contact Dermatitis. Contact Dermatitis 1990 22 : 164 78.
18. Petersen LJ, Brasso K, Pryds M et al. Histamine release in intact human skin by monocyte chemoattractant factor-1, RANTES, macrophage inflammatory protein-1 alpha, stem cell factor, anti-IgE, and codeine as determined by an ex vivo skin microdialysis technique. J Allergy Clin Immunol 1996 98 : 790 6.
19. Kuss O, Diepgen TL. Proper statistical analysis of transepidermal water loss (TEWL) measurements in bioengineering studies. Contact Dermatitis 1998 39 : 64 7.
20. Philippe M, Garson JC, Gilard P et al. Synthesis of 2-N-oleoylamino- octadecane-1,3-diol: a new ceramide highly effective for the treatment of skin and hair. Int J Cosmet Sci 1995 17 : 133 45.
21. zur Muhlen A, Klotz A, Weimans S et al. Using skin models to assess the effects of a protection cream on skin barrier function. Skin Pharmacol Physiol 2004 17 : 167 75.
22. Zhai H, Leow YH, Maibach HI. Human barrier recovery after acute acetone perturbation: an irritant dermatitis model. Clin Exp Dermatol 1998 23 : 11 13.
23. Abrams K, Harvell JD, Shriner D et al. Effect of organic solvents on in vitro human skin water barrier function. J Invest Dermatol 1993 101 : 609 13.
24. Barany E, Lindberg M, Loden M. Biophysical characterization of skin damage and recovery after exposure to different surfactants. Contact Dermatitis 1999 40 : 98 103.
25. Gloor M, Senger B, Langenauer M et al. On the course of the irritant reaction after irritation with sodium lauryl sulphate. Skin Res Technol 2004 10 : 144 8.
26. Froebe CL, Simion FA, Rhein LD et al. Stratum corneum lipid removal by surfactants: relation to in vivo irritation. Dermatologica 1990 181 : 277 83.
27. Fartasch M, Schnetz E, Diepgen TL. Characterization of detergent-induced barrier alterations - effect of barrier cream on irritation. J Investig Dermatol Symp Proc 1998 3 : 121 7.
28. Yoshiike T, Aikawa Y, Sindhvananda J et al. Skin barrier defect in atopic dermatitis: increased permeability of the stratum corneum using dimethyl sulfoxide and theophylline. J Dermatol Sci 1993 5 : 92 6.
29. Kreilgaard M. Assessment of cutaneous drug delivery using microdialysis. Adv Drug Deliv Rev 2002 54 (Suppl. 1 S99 121.
30. Schnetz E, Fartasch M. Microdialysis for the evaluation of penetration through the human skin barrier - a promising tool for future research? Eur J Pharm Sci 2001 12 : 165 74.
31. Benfeldt E. In vivo microdialysis for the investigation of drug levels in the dermis and the effect of barrier perturbation on cutaneous drug penetration. Studies in hairless rats and human subjects. Acta Derm Venereol Suppl (Stockh) 1999 206 : 1 59.
32. Benfeldt E, Serup J. Effect of barrier perturbation on cutaneous penetration of salicylic acid in hairless rats: in vivo pharmacokinetics using microdialysis and non-invasive quantification of barrier function. Arch Dermatol Res 1999 291 : 517 26.
33. Benfeldt E, Serup J, Menne T. Effect of barrier perturbation on cutaneous salicylic acid penetration in human skin: in vivo pharmacokinetics using microdialysis and non-invasive quantification of barrier function. Br J Dermatol 1999 140 : 739 48.
34. Benfeldt E, Hansen SH, Volund A et al. Bioequivalence of topical formulations in humans: evaluation by dermal microdialysis sampling and the dermatopharmacokinetic method. J Invest Dermatol 2007 127 : 170 8.
35. Held E, Lund H, Agner T. Effect of different moisturizers on SLS-irritated human skin. Contact Dermatitis 2001 44 : 229 34.
36. Kucharekova M, Schalkwijk J, van de Kerkhof PC et al. Effect of a lipid-rich emollient containing ceramide 3 in experimentally induced skin barrier dysfunction. Contact Dermatitis 2002 46 : 331 8.
37. Berardesca E, Barbareschi M, Veraldi S et al. Evaluation of efficacy of a skin lipid mixture in patients with irritant contact dermatitis, allergic contact dermatitis or atopic dermatitis: a multicenter study. Contact Dermatitis 2001 45 : 280 5.
38. Kucharekova M, van de Kerkhof PC, van der Valk PG. A randomized comparison of an emollient containing skin-related lipids with a petrolatum-based emollient as adjunct in the treatment of chronic hand dermatitis. Contact Dermatitis 2003 48 : 293 9.
39. Yang L, Mao-Qiang M, Taljebini M et al. Topical stratum corneum lipids accelerate barrier repair after tape stripping, solvent treatment and some but not all types of detergent treatment. Br J Dermatol 1995 133 : 679 85.
40. Lodén M, Bárány E. Skin-identical lipids versus petrolatum in the treatment of tape-stripped and detergent-perturbed human skin. Acta Derm Venereol 2000 80 : 412 15.
41. Imokawa G, Akasaki S, Hattori M et al. Selective recovery of deranged water-holding properties by stratum corneum lipids. J Invest Dermatol 1986 87 : 758 61.
42. Matsuki H, Kiyokane K, Matsuki T et al. Reevaluation of the importance of barrier dysfunction in the nonlesional dry skin of atopic dermatitis patients through the use of two barrier creams. Exog Dermatol 2004 3 : 293 302.
43. Takagi Y, Nakagawa H, Higuchi K et al. Characterization of surfactant-induced skin damage through barrier recovery induced by pseudoacylceramides. Dermatology 2005 211 : 128 34.
44. Wertz PW, Miethke MC, Long SA et al. The composition of the ceramides from human stratum corneum and from comedones. J Invest Dermatol 1985 84 : 410 12.
45. Farwanah H, Wohlrab J, Neubert RH et al. Profiling of human stratum corneum ceramides by means of normal phase LC/APCI-MS. Anal Bioanal Chem 2005 383 : 632 7.
46. Vávrová K, Hrabálek A, Doležal P et al. l-Serine and glycine based ceramide analogues as transdermal permeation enhancers: polar head size and hydrogen bonding. Bioorg Med Chem Lett 2003 13 : 2351 3.
47. Ongpipattanakul B, Burnette RR, Potts RO et al. Evidence that oleic acid exists in a separate phase within stratum corneum lipids. Pharm Res 1991 8 : 350 4.
48. Tsai JC, Sheu HM, Hung PL et al. Effect of barrier disruption by acetone treatment on the permeability of compounds with various lipophilicities: implications for the permeability of compromised skin. J Pharm Sci 2001 90 : 1242 54.
49. Chilcott RP, Dalton CH, Emmanuel AJ et al. Transepidermal water loss does not correlate with skin barrier function in vitro. J Invest Dermatol 2002 118 : 871 5.
50. Levin J, Maibach H. The correlation between transepidermal water loss and percutaneous absorption: an overview. J Control Release 2005 103 : 291 9.