Penetration enhancing effect of phytoceramides

Abstract

Ceramides are essential components in the stratum corneum barrier function. Different classes of ceramides are present in human skin, differing in the nature of sphingosine and acyl moieties with respect to chain length, degree of saturation and the presence of an OH group [1]. Ceramides with a saturated sphingosine base containing a hydroxyl function at C4 are known as phytoceramides. A few studies demonstrated the penetration enhancing properties of ceramides [2-5], however, systematic studies using phytoceramides are lacking. This led us to assess the penetration enhancing effect of phytosphingosine and a series of nine phytoceramides via transdermal experiments using in vitro Franz diffusion cells. As transdermal model compounds, testosterone, caffeine and ibuprofen were tested in a 50:50 (V/V) EtOH:H2O dose formulation [6]. Results showed that the penetration enhancing effect of the phytoceramides depends on the used model compound. Selected phytoceramides exhibited a penetration enhancing ratio of more than two. References [1] Janůšová, B.; Zbytovská, J.; Lorenc, P.; Vavrysová, H.; Palát K.; Hrabálek, A.; Vávrová, K. (2011). Effect of ceramide acyl chain length on skin permeability and thermotropic phase behavior of model stratum corneum lipid membranes. Biochimica et Biophysica, 1811, 129–137. [2] Vávrová, K.; Hrabálek, A.; Dolezal, P.; Holas, T.; Zbytovská, J. (2003). L-serine and glycine based ceramide analogues as transdermal permeation enhancers: polar head size and hydrogen bonding. Bioorganic & medicinal chemistry letters, 13, 2351-2353. [3] Vávrová, K.; Zbytovská, J.; Hrabálek, A. (2005). Amphiphilic transdermal permeation enhancers: structure-activity relationships. Current Medicinal Chemistry, 12, 2273-2291. [4] Novotý, J.; Janůšová, B.; Novotý, M.; Hrabálek, A.; Vávrová, K. (2009). Short-chain ceramides decrease skin barrier properties. Skin pharmacology and Physiology, 22, 22-30. [5] Sinko, B.; Kökösi, J.; Avdeef, A.; Takács-Novák, K. (2009). A PAMPA study of the permeability-enhancing effect of new ceramide analogues. Chemistry & Biodiversity, 6, 1867-1874. [6] Baert, B.; Deconinck, E.; Van Gele, M.; Slodicka, M.; Stoppie, P.; Bode, S.; Slegers, G.; Vander Heyden, Y.; Lambert, J.; Beetens, J.; De Spiegeleer, B. (2007). Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds. Bioorganic & medicinal chemistry, 15(22), 6943-6955