Stratum corneum lipid structure investigated by EPR spin-probe method: application of terpenes

Lipids. 2010 Nov;45(11):1081-7. doi: 10.1007/s11745-010-3479-z. Epub 2010 Oct 6.

Abstract

Electron paramagnetic resonance (EPR) in conjunction with a slow-tumbling simulation was utilized for defining stratum corneum (SC) lipid structure. SC from the back of hairless mouse (HOS:HR-1) was stripped consecutively from one to three or four times using a glass plate coated with a cyanoacrylate resin. Aliphatic spin probes, 5-doxylstearic acid (5-DSA) and 3β-doxyl-5α-cholestane (CHL), were used to evaluate the SC ordering. EPR spectrum of 5-DSA incorporated in the SC demonstrated a characteristic peak for the first strip. A slow-tumbling simulation for 5-DSA showed clear differences in EPR intensities as well as ordering values (S(0)) of the SC for control and terpenes treated SC. The α-terpineol enhanced the permeation of the single chain 5-DSA about three times more than that of the control. However, EPR spectra of CHL in the SC did not show a clear difference for each strip, except for the signal intensity. The results imply that CHL permeates into SC lipid differently from 5-DSA. The enhancement of the 5-DSA is more significant than that of CHL. Therefore, the present results can be useful for various drug administrations via the skin.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chemical Fractionation / methods
  • Cholestanes / pharmacology
  • Computer Simulation
  • Cyclic N-Oxides / chemistry
  • Cyclic N-Oxides / pharmacology
  • Cyclohexane Monoterpenes
  • Cyclohexenes / pharmacology
  • Electron Spin Resonance Spectroscopy / methods
  • Lipids / analysis*
  • Lipids / chemistry
  • Mice
  • Models, Biological
  • Monoterpenes / pharmacology
  • Skin / chemistry*
  • Skin / drug effects
  • Skin / metabolism
  • Skin / ultrastructure*
  • Spin Labels*
  • Terpenes / chemistry
  • Terpenes / pharmacology*

Substances

  • Cholestanes
  • Cyclic N-Oxides
  • Cyclohexane Monoterpenes
  • Cyclohexenes
  • Lipids
  • Monoterpenes
  • Spin Labels
  • Terpenes
  • 3-doxylcholestane
  • alpha-terpineol
  • 5-doxylstearic acid