Effects of ethanol/l-menthol on the dynamics and partitioning of spin-labeled lipids in the stratum corneum

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 67, Issue 2, 2007, Pages 406-412

  dos Anjos, Jorge Luiz Vieira ^a   Neto, Diógenes de Sousa ^b   Alonso, Antonio ^a  

^a FEDERAL UNIVERSITY OF GOIÁS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

EPR; Ethanol; l Menthol; Spin label; Stratum corneum

Indexed keywords

5 DOXYL METHYLSTEARIC ACID; 5 DOXYLSTEARIC ACID; ALCOHOL; ANDROSTANE DERIVATIVE; LIPID; MEMBRANE LIPID; MENTHOL; STEARIC ACID DERIVATIVE; STEROID; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONCENTRATION (PARAMETERS); DYNAMICS; ELECTRON SPIN RESONANCE; EPIDERMIS; EXTRACTION; HYDROGEN BOND; HYDROPHOBICITY; MEMBRANE STABILIZATION; NONHUMAN; PARTITION COEFFICIENT; RAT; SPIN LABELING; STRATUM CORNEUM; SURFACE PROPERTY;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; ELECTRON SPIN RESONANCE SPECTROSCOPY; EPIDERMIS; ETHANOL; HYDROGEN BONDING; LIPID METABOLISM; LIPIDS; MEMBRANE LIPIDS; MENTHOL; MODELS, CHEMICAL; RATS; RATS, WISTAR; SPIN LABELS;

EID: 34547700406     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2007.02.004     Document Type: Article

References (28)

1. Wertz P.W., and Downing D.T. Covalently bound ω-hydroxyacylsphingosine in the stratum corneum. Biochim. Biophys. Acta 917 (1987) 108-111
2. Swartzendruber D.C., Wertz P.W., Kitko D.J., Madison K.C., and Downing D.T. Molecular models of the intercellular lipid lamellae in mammalian stratum corneum. J. Invest. Dermatol. 92 (1989) 251-257
3. Bouwstra J.A., Honeywell-Nguyen P.L., Gooris G.S., and Ponec M. Structure of the skin barrier and its modulation by vesicular formulations. Prog. Lipid Res. 42 (2003) 1-36
4. Gray G.M., White R.J., and Yardley H.J. Lipid composition of the superficial stratum corneum cells of the epidermis. Br. J. Dermatol. 106 (1982) 59-63
5. Williams A.C., and Barry B.W. Penetration enhancers. Adv. Drug Deliv. Rev. 56 (2004) 603-618
6. Yamane M.A., Williams A.C., and Barry B.W. Effects of terpenes and oleic acid as skin penetration enhancers towards 5-fluorouracil as assessed with time, permeation, partitioning and differential scanning calorimetry. Int. J. Pharm. 116 (1995) 237-251
7. Gao S., and Singh J. In vitro percutaneous absorption enhancement of a lipophilic drug tamoxifen by terpenes. J. Control. Release 51 (1998) 193-199
8. Thomas N.S., and Panchagnula R. Transdermal delivery of zidovudine: effect of vehicles on permeation across rat skin and their mechanism of action. Eur. J. Pharm. Sci. 18 (2003) 71-79
9. Narishetty S.T.K., and Panchagnula R. Effect of l-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine. J. Control. Release 102 (2005) 59-70
10. Narishetty S.T., and Panchagnula R. Transdermal delivery of zidovudine: effect of terpenes and their mechanism of action. J. Control. Release 95 (2004) 367-379
11. Vaddi H.K., Ho P.C., Chan Y.W., and Chan S.Y. Terpenes in ethanol: haloperidol permeation and partition through human skin and stratum corneum changes. J. Control. Release 81 (2002) 121-133
12. Queirós W.P., Neto D.S., and Alonso A. Dynamics and partitioning of spin-labeled stearates into the lipid domain of stratum corneum. J. Control. Release 106 (2005) 374-385
13. Couto S.G., Oliveira M.S., and Alonso A. Dynamics of proteins and lipids in the stratum corneum: effects of percutaneous permeation enhancers. Biophys. Chem. 116 (2005) 23-31
14. Alonso A., Meirelles N.C., and Tabak M. Effect of hydration upon the fluidity of intercellular membranes of stratum corneum: an EPR study. Biochim. Biophys. Acta 1237 (1995) 6-15
15. Alonso A., Meirelles N.C., and Tabak M. Lipid chain dynamics in stratum corneum studied by spin label electron paramagnetic resonance. Chem. Phys. Lipids 104 (2000) 101-111
16. Alonso A., Meirelles N.C., Yushmanov V.E., and Tabak M. Water increases the fluidity of intercellular membranes of stratum corneum: correlation with water permeability, elastic, and electrical properties. J. Invest. Dermatol. 106 (1996) 1058-1063
17. Schneider D.J., and Freed J.H. Spin labeling: Theory and application. In: Berliner L.J., and Reuben J. (Eds). Biological Magnetic Resonance vol. 8 (1989), Plenum Press, New York 1-76
18. Budil D.E., Lee S., Saxena S., and Freed J.H. Nonlinear-least-squares analysis of slow-motional EPR spectra in one and two dimensions using a modified Levenberg-Marquardt algorithm. J. Magn. Reson. A 120 (1996) 155-189
19. Alonso A., Santos W.P., Leonor S.J., Santos J.G., and Tabak M. Stratum corneum protein dynamics as evaluated by a spin label maleimide derivative. Effect of urea. Biophys. J. 81 (2001) 3566-3576
20. Alonso A., Silva J.V., and Tabak M. Hydration effects on the protein dynamics in stratum corneum as evaluated by EPR spectroscopy. Biochim. Biophys. Acta 1646 (2003) 32-41
21. Feller S.E., Brown C.A., Nizza D.T., and Gawrisch K. Nuclear overhauser enhancement spectroscopy cross-relaxation rates and ethanol distribution across membranes. Biophys. J. 82 (2002) 1396-1404
22. Ly H.V., and Longo M.L. The influence of short-chain alcohols on interfacial tension, mechanical properties, area/molecule, and permeability of fluid lipid bilayers. Biophys. J. 87 (2004) 1013-1033
23. Goates C.Y., and Knutson K. Enhanced permeation of polar compounds through human epidermis. I. Permeability and membrane structural changes in the presence of short chain alcohols. Biochim. Biophys. Acta 1195 (1994) 169-179
24. Krill S.L., Knutson K., and Higuchi W.I. Ethanol effects on the stratum corneum lipid phase behavior. Biochim. Biophys. Acta 112 (1992) 169-179
25. Kim Y.-H., Higuchi W.I., Herron J.N., and Abraham W. Fluorescence anisotropy studies on the interaction of the short chain n-alkanols with stratum corneum lipid liposomes (SCLL) and distearoylphosphatidylcholine (DSPC)/distearoylphosphatidic acid (DSPA) liposomes. Biochim. Biophys. Acta 1148 (1993) 139-151
26. Ahmed S.N., Brown D.A., and London E. On the origin of sphingolipid/cholesterol-rich detergent-insoluble cell membranes: physiological concentrations of cholesterol and sphingolipid induce formation of a detergent-insoluble, liquid-ordered lipid phase in model membranes. Biochemistry 36 (1997) 10944-10953
27. Xiang T.X., Chen J., and Anderson B.D. A quantitative model for the dependence of solute permeability on peptide and cholesterol content in biomembranes. J. Membr. Biol. 177 (2000) 137-148
28. Klymchenko A.S., Duportail G., Demchenko A.P., and Mély Y. Bimodal distribution and fluorescence response of environment-sensitive probes in lipid bilayers. Biophys. J. 86 (2004) 2929-2941