The effects of transdermal permeation enhancers on thermotropic phase behaviour of a stratum corneum lipid model

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 351, Issue 1-3, 2009, Pages 30-37

  Zbytovska J ^a   Vavrova K ^a   Kiselev, M A ^b,c   Lessieur, P ^d   Wartewig, S ^e   Neubert, R H H ^b  

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

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^c JOINT INSTITUTE FOR NUCLEAR RESEARCH   (Russian Federation)

^d UNIVERSITÉ PARIS SACLAY   (France)

^e Institute of Applied Dermatopharmacy   (Germany)

Author keywords

Ceramide analogue; Oleic acid; Small angle X ray diffraction; Stratum corneum lipids; Thermotropic phase behaviour; Urea

Indexed keywords

ACIDS; AMIDES; DIFFRACTION; ESTERS; LIPIDS; METABOLISM; OLEIC ACID; PHASE SEPARATION; UREA; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

CERAMIDE ANALOGUE; CERAMIDES; COMPLEX SYSTEMS; CONCENTRATION-DEPENDENT; LIPID MEMBRANES; LIPID SYSTEMS; PERMEATION ENHANCERS; PHASE BEHAVIOUR; PHASE TRANSITION TEMPERATURES; PHYTOSPHINGOSINES; SIMPLE MODEL; SMALL ANGLE X-RAY DIFFRACTIONS; SMALL-ANGLE X-RAY DIFFRACTION; STRATUM CORNEUM; STRATUM CORNEUM LIPIDS; TEMPERATURE DEPENDENT; THERMOTROPIC PHASE; THERMOTROPIC PHASE BEHAVIOUR; TRANSDERMAL PERMEATION; TWO PHASE;

PHASE TRANSITIONS;

CERAMIDE DERIVATIVE; ESTER DERIVATIVE; N (2 HYDROXYSTEAROYL)PHYTOSPHINGOSINE; N LAUROYLGLYCINE LAURYL ESTER; OLEIC ACID; UNCLASSIFIED DRUG; UREA;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; LIPID COMPOSITION; LIPID MEMBRANE; MEMBRANE TRANSPORT; PHASE SEPARATION; PHASE TRANSITION; PRIORITY JOURNAL; SKIN PENETRATION; STRATUM CORNEUM; TEMPERATURE DEPENDENCE; THERMOSTABILITY; TRANSITION TEMPERATURE; X RAY DIFFRACTION;

EID: 70350131504     PISSN: 09277757     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2009.09.025     Document Type: Article

References (44)

1. Windsor T., and Burch G.E. Differential roles of layers of human epigastric skin on diffusion rate of water. Arch. Intern. Med. 74 (1944) 428-436
2. Masukawa Y., Narita H., Shimizu E., Kondo N., Sugai Y., Oba T., Homma R., Ishikawa J., Takagi Y., Kitahara T., Takema Y., and Kita K. Characterization of overall ceramide species in human stratum corneum. J. Lipid Res. 49 (2008) 1466-1476
3. Wertz P.W., and van den Bergh B. The physical, chemical and functional properties of lipids in the skin and other biological barriers. Chem. Phys. Lipids 91 (1998) 85-96
4. Coderch L., Lopez O., de la Maza A., and Parra J.L. Ceramides and skin function. Am. J. Clin. Dermatol. 4 (2003) 107-129
5. Williams A.C., and Barry B.W. Penetration enhancers. Adv. Drug Del. Rev. 56 (2004) 603-618
6. Asbill C.S., and Michniak B.B. Percutaneous penetration enhancers: local versus transdermal activity. Pharm. Sci. Technol. Today 3 (2000) 36-40
7. Vávrová K., Zbytovská J., and Hrabálek A. Amphiphilic transdermal permeation enhancers: structure-activity relationships. Curr. Med. Chem. 12 (2005) 2273-2291
8. R.H.H. Neubert, W.A. Wohlrab, W. Marsch, Dermatopharmazie, Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart, 2001, pp. 3-25, 105-134.
9. 2+ modulate the mixing properties of lipids in stratum corneum model mixtures. Biophys. J. 92 (2007) 99-114
10. Rerek M.E., Chen H., Markovic B., Van Wyck D., Garidel P., Mendelsohn R., and Moore D.J. Phytosphingosine and sphingosine ceramide headgroup hydrogen bonding: structural insights through thermotropic hydrogen/deuterium exchange. J. Phys. Chem. B 105 (2001) 9355-9362
11. Garidel P. Calorimetric and spectroscopic investigations of phytosphingosine ceramide membrane organization. Phys. Chem. Chem. Phys. 4 (2002) 1934-1942
12. Bouwstra J.A., Gooris G.S., Dubbelaar F.E.R., and Ponec M. Cholesterol sulfate and calcium affect stratum corneum lipid organization over a wide temperature range. J. Lipid Res. 40 (1999) 2303-2312
13. Wartewig S., Neubert R., Rettig W., and Hesse K. Structure of stratum corneum lipids characterized by FT-Raman spectroscopy and DSC. IV. Mixtures of ceramides and oleic acid. Chem. Phys. Lipids 91 (1998) 145-152
14. Zbytovská J., Raudenkolb S., Wartewig S., Hübner W., Rettig W., Pissis P., Hrabálek A., Doležal P., and Neubert R. Phase behaviour of transkarbam 12. Chem. Phys. Lipids 129 (2004) 97-109
15. Bonté F., Pinguet P., Saunois A., Meybeck A., Beugin S., Ollivon M., and Lesieur S. Thermotropic phase behavior of in vivo extracted human stratum corneum lipids. Lipids 32 (1997) 653-660
16. de Jager M., Groening W., van der Spek J., Janmaat C., Gooris G., Ponec M., and Bouwstra J. Preparation and characterization of a stratum corneum substitute for in vitro percutaneous penetration studies. Biochim. Biophys. Acta 1758 (2006) 636-644
17. de Jager M.W., Gooris G.S., Ponec M., and Bouwstra J.A. Lipid mixtures prepared wit well-defined synthetic ceramides closely mimic the unique stratum corneum lipid phase behavior. J. Lipid Res. 46 (2005) 2649-2656
18. Kiselev M.A., Ryabova N.Y., Balagurov A.M., Dante S., Hauss T., Zbytovská J., Wartewig S., and Neubert R. New insights into the structure and hydration of a stratum corneum lipid model membrane by neutron diffraction. Eur. Biophys. J. 34 (2005) 1030-1040
19. Zbytovská J., Kiselev M.A., Funari S.S., Garamus V.M., Wartewig S., Palát K., and Neubert R. Influence of cholesterol on the structure of stratum corneum lipid model membrane. Colloid Surf. A 328 (2008) 90-99
20. Vávrová K., Hrabálek A., Doležal P., Šámalová L., Palát K., Zbytovská J., Holas T., and Klimentová J. Synthetic ceramides analogues as skin permeation enhancers: structure-activity relationships. Bioorg. Med. Chem. 11 (2003) 5381-5390
21. Wertz P.W., Schwartzendruber D.C., Madison K.C., and Downing D.T. Composition and morphology of epidermal cyst lipids. J. Invest. Dermatol. 89 (1987) 419-425
22. Abraham W., and Downing D.T. Preparation of model membranes for skin permeability studies using stratum corneum lipids. J. Invest. Dermatol. 93 (1989) 809-813
23. Lafleur M. Phase behaviour of model stratum corneum lipid mixtures: an infrared spectroscopy investigation. Can. J. Chem. 76 (1998) 1501-1511
24. Bouwstra J.A., Thewalt J., Gooris G.S., and Kitson N. A model membrane approach to the epidermal permeability barrier: an X-ray diffraction study. Biochemistry 36 (1997) 7717-7725
25. Kitson N., Thewalt J., Lafleur M., and Bloom M. A model membrane approach to the epidermal permeability barrier. Biochemistry 33 (1994) 6707-6715
26. Velkova V., and Lafleur M. Influence of the lipid composition on the organization of skin lipid model mixtures: an infrared spectroscopy investigation. Chem. Phys. Lipids 117 (2002) 63-74
27. Moore D.J., Rerek M.E., and Mendelsohn R. Lipid domains and orthorhombic phases in model stratum corneum: evidence from Fourier transform infrared spectroscopy studies. Biochem. Biophys. Res. Commun. 231 (1997) 797-801
28. ten Grotenhuis E., Demel R.A., Ponec M., Boer D.R., van Miltenburg J.C., and Bouwstra J.A. Phase behavior of stratum corneum lipids in mixed Langmuir-Blodgett monolayers. Biophys. J. 71 (1996) 1389-1399
29. Ongpipattanakul B., Francoeur M.L., and Potts R.O. Polymorphism in stratum corneum lipids. Biochim. Biophys. Acta 1190 (1994) 115-122
30. Boncheva M., Damien F., and Normand V. Molecular organization of the lipid matrix in intact stratum corneum using ATR-FTIR spectroscopy. Biochim. Biophys. Acta 1778 (2008) 1344-1355
31. White S.H., Mirejovsky D., and King G.I. Structure of lamellar lipid domains and corneocyte envelopes of murine stratum corneum. An X-ray diffraction study. Biochemistry 27 (1988) 3725-3732
32. Bouwstra J.A., Gooris G.S., van der Spek J.A., and Bras W. Structural investigations of human stratum corneum by small-angle X-ray scattering. J. Invest. Dermatol. 97 (1991) 1005-1012
33. McIntosh T.J., Stewart M.E., and Downing D.T. X-ray diffraction analysis of isolated skin lipids: reconstruction of intercellular lipid domains. Biochemistry 35 (1996) 3649-3653
34. Bouwstra J.A., Gooris G.S., Dubbelaar F.E.R., Weerheim A.M., Ijzerman A.P., and Ponec M. The role of ceramide 1 in the molecular organisation of SC lipids. J. Lipid Res. 39 (1998) 186-196
35. Williams A.C. Urea and its derivatives as penetration enhancers. In: Smith E.W., and Maibach H.I. (Eds). Percutaneous Penetration Enhancers (1995), CRC Press 289-296
36. Kim C.K., Kim J.J., Chi S.C., and Shim C.K. Effect of fatty acids and urea on the penetration of ketoprofen through rat skin. Int. J. Pharm. 99 (1993) 109-118
37. Valenta C., and Wedenig S. Effects of penetration enhancers on the in-vitro percutaneous absorption of progesterone. J. Pharm. Pharmacol. 49 (1997) 955-959
38. Bouwstra J.A., Gooris G.S., Cheng K., Weerheim A., Bras W., and Ponec M. Phase behavior of isolated skin lipids. J. Lipid Res. 37 (1996) 999-1011
39. Zbytovská J., Kiselev M.A., Funari S.S., Garamus V.M., Wartewig S., and Neubert R. Influence of phytosphingosine-type ceramides on the structure of DMPC membrane. Chem. Phys. Lipids 138 (2005) 69-80
40. Moore D.J., and Rerek M.E. Insights into the molecular organization of lipids in the skin barrier from infrared spectroscopy studies of stratum corneum lipid models. Acta Derm. Venereol. Suppl. 208 (2000) 16-22
41. Ongpipattanakul B., Burnette R.R., Potts R.O., and Francoeur M.L. Evidence that oleic acid exists in a separate phase within stratum corneum lipids. Pharm. Res. 8 (1991) 350-354
42. Tanojo H., Bos-van Geest A., Bouwstra J.A., Junginger H.E., and Boddé H. In vitro human skin barrier perturbation by oleic acid: thermal analysis and freeze fracture electron microscopy studies. Thermochim. Acta 293 (1997) 77-85
43. 2H-NMR. Int. J. Pharm. 307 (2006) 225-231
44. Vávrová K., Hrabálek A., Doležal P., Holas T., and Zbytovská J. L-serine and glycine based ceramide analogues as transdermal permeation enhancers: polar head size and hydrogen bonding. Bioorg. Med. Chem. Lett. 13 (2003) 2351-2353