메뉴 건너뛰기




Volumn 350, Issue 1-2, 2008, Pages 103-112

Terpenes increase the partitioning and molecular dynamics of an amphipathic spin label in stratum corneum membranes

Author keywords

EPR; Lipid dynamics; Spin label; Stratum corneum; Terpene

Indexed keywords

CINEOLE; DIPALMITOYLPHOSPHATIDYLCHOLINE; LIMONENE; MENTHOL; TEMPOL; TERPENE DERIVATIVE; TERPINEOL;

EID: 38349088308     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2007.08.024     Document Type: Article
Times cited : (49)

References (45)
  • 1
    • 0029073932 scopus 로고
    • Effect of hydration upon the fluidity of intercellular membranes of stratum corneum: an EPR study
    • 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
    • (1995) Biochim. Biophys. Acta , vol.1237 , pp. 6-15
    • Alonso, A.1    Meirelles, N.C.2    Tabak, M.3
  • 2
    • 0030012304 scopus 로고    scopus 로고
    • Water increases the fluidity of intercellular membranes of stratum corneum: correlation with water permeability, elastic, and electrical properties
    • 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
    • (1996) J. Invest. Dermatol. , vol.106 , pp. 1058-1063
    • Alonso, A.1    Meirelles, N.C.2    Yushmanov, V.E.3    Tabak, M.4
  • 3
    • 0033988656 scopus 로고    scopus 로고
    • Lipid chain dynamics in stratum corneum studied by spin label electron paramagnetic resonance
    • 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
    • (2000) Chem. Phys. Lipids , vol.104 , pp. 101-111
    • Alonso, A.1    Meirelles, N.C.2    Tabak, M.3
  • 4
    • 8544253205 scopus 로고    scopus 로고
    • Transdermal self-permeation enhancement of ibuprofen
    • Al-Saidan S.M. Transdermal self-permeation enhancement of ibuprofen. J. Controlled Release 100 (2004) 199-209
    • (2004) J. Controlled Release , vol.100 , pp. 199-209
    • Al-Saidan, S.M.1
  • 5
    • 34547700406 scopus 로고    scopus 로고
    • Effects of ethanol/l-menthol on the dynamics and partitioning of spin-labeled lipids in the stratum corneum
    • Anjos J.L.V., Neto D.S., and Alonso A. Effects of ethanol/l-menthol on the dynamics and partitioning of spin-labeled lipids in the stratum corneum. Eur. J. Pharmaceut. Biopharmaceut. 67 (2007) 406-412
    • (2007) Eur. J. Pharmaceut. Biopharmaceut. , vol.67 , pp. 406-412
    • Anjos, J.L.V.1    Neto, D.S.2    Alonso, A.3
  • 6
    • 36049038516 scopus 로고    scopus 로고
    • Effects of 1,8-cineole on the dynamics of lipids and proteins of stratum corneum
    • Anjos J.L.V., Neto D.S., and Alonso A. Effects of 1,8-cineole on the dynamics of lipids and proteins of stratum corneum. Int. J. Pharm. 345 (2007) 81-87
    • (2007) Int. J. Pharm. , vol.345 , pp. 81-87
    • Anjos, J.L.V.1    Neto, D.S.2    Alonso, A.3
  • 7
    • 0025906898 scopus 로고
    • Lipid-protein-partitioning theory of skin penetration enhancement
    • Barry B.W. Lipid-protein-partitioning theory of skin penetration enhancement. J. Controlled Release 15 (1991) 237-248
    • (1991) J. Controlled Release , vol.15 , pp. 237-248
    • Barry, B.W.1
  • 9
    • 33845308573 scopus 로고    scopus 로고
    • The skin barrier in healthy and diseased state
    • Bouwstra J.A., and Ponec M. The skin barrier in healthy and diseased state. Biochim. Biophys. Acta 1758 (2006) 2080-2095
    • (2006) Biochim. Biophys. Acta , vol.1758 , pp. 2080-2095
    • Bouwstra, J.A.1    Ponec, M.2
  • 10
    • 0025955486 scopus 로고
    • Structural investigations on human stratum corneum by small-angle X-ray scattering
    • Bouwstra J.A., Gooris G.S., van der Spek J.A., and Bras W. Structural investigations on human stratum corneum by small-angle X-ray scattering. J. Invest. Dermatol. 97 (1991) 1005-1012
    • (1991) J. Invest. Dermatol. , vol.97 , pp. 1005-1012
    • Bouwstra, J.A.1    Gooris, G.S.2    van der Spek, J.A.3    Bras, W.4
  • 11
    • 0026669010 scopus 로고
    • Structure of human stratum corneum as function of temperature and hydration: a wide angle X-ray diffraction study
    • Bouwstra J.A., Gooris G.S., Salomons-de Vries M.A., van der Spek J.A., and Bras W. Structure of human stratum corneum as function of temperature and hydration: a wide angle X-ray diffraction study. Int. J. Pharm. 84 (1992) 205-216
    • (1992) Int. J. Pharm. , vol.84 , pp. 205-216
    • Bouwstra, J.A.1    Gooris, G.S.2    Salomons-de Vries, M.A.3    van der Spek, J.A.4    Bras, W.5
  • 12
    • 0023646683 scopus 로고
    • Temperature dependence of membrane ion conductance analyzed by using the amphiphilic anion 5/6-carboxyfluorescein
    • Bramhall J., Hofmann J., DeGuzman R., Montestruque S., and Schell R. Temperature dependence of membrane ion conductance analyzed by using the amphiphilic anion 5/6-carboxyfluorescein. Biochemistry 26 (1987) 6330-6340
    • (1987) Biochemistry , vol.26 , pp. 6330-6340
    • Bramhall, J.1    Hofmann, J.2    DeGuzman, R.3    Montestruque, S.4    Schell, R.5
  • 13
    • 0000326938 scopus 로고    scopus 로고
    • Nonlinear-least-squares analysis of slow-motional EPR spectra in one and two dimensions using a modified Levenberg-Marquardt algorithm
    • 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
    • (1996) J. Magn. Reson. A , vol.120 , pp. 155-189
    • Budil, D.E.1    Lee, S.2    Saxena, S.3    Freed, J.H.4
  • 14
    • 0029024469 scopus 로고
    • Permeability of dimyristoyl phosphatidylcholine/dipalmitoyl phosphatidylcholine bilayer membranes with coexisting gel and liquid-crystalline phases
    • Clerc S.G., and Thompson T.E. Permeability of dimyristoyl phosphatidylcholine/dipalmitoyl phosphatidylcholine bilayer membranes with coexisting gel and liquid-crystalline phases. Biophys. J. 68 (1995) 2333-2341
    • (1995) Biophys. J. , vol.68 , pp. 2333-2341
    • Clerc, S.G.1    Thompson, T.E.2
  • 15
    • 0028314174 scopus 로고
    • Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-fluorouracil
    • Cornwell P.A., and Barry B.W. Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-fluorouracil. J. Pharm. Pharmacol. 46 (1994) 261-269
    • (1994) J. Pharm. Pharmacol. , vol.46 , pp. 261-269
    • Cornwell, P.A.1    Barry, B.W.2
  • 16
    • 0030057728 scopus 로고    scopus 로고
    • Modes of action of terpene penetration enhancers in human skin; differential scanning calorimetry, small-angle X-ray diffraction and enhancer uptake studies
    • Cornwell P.A., Barry B.W., Bouwstra J.A., and Gooris G.S. Modes of action of terpene penetration enhancers in human skin; differential scanning calorimetry, small-angle X-ray diffraction and enhancer uptake studies. Int. J. Pharm. 127 (1996) 9-26
    • (1996) Int. J. Pharm. , vol.127 , pp. 9-26
    • Cornwell, P.A.1    Barry, B.W.2    Bouwstra, J.A.3    Gooris, G.S.4
  • 17
    • 0026662746 scopus 로고
    • Energy aspects of oil/water partition leading to the novel hydrophobic parameters for the analysis of quantitative structure activity relationships
    • Da Y.-Z., Ito K., and Fujiwara H. Energy aspects of oil/water partition leading to the novel hydrophobic parameters for the analysis of quantitative structure activity relationships. J. Med. Chem. 35 (1992) 3382-3387
    • (1992) J. Med. Chem. , vol.35 , pp. 3382-3387
    • Da, Y.-Z.1    Ito, K.2    Fujiwara, H.3
  • 18
    • 0034607386 scopus 로고    scopus 로고
    • The effect of terpene enhancer lipophilicity on the percutaneous permeation of hydrocortisone formulated in HPMC gel systems
    • El-Kattan A.F., Asbill C.S., and Michniak B.B. The effect of terpene enhancer lipophilicity on the percutaneous permeation of hydrocortisone formulated in HPMC gel systems. Int. J. Pharm. 198 (2000) 179-189
    • (2000) Int. J. Pharm. , vol.198 , pp. 179-189
    • El-Kattan, A.F.1    Asbill, C.S.2    Michniak, B.B.3
  • 19
    • 0017125226 scopus 로고
    • Water and nonelectrolyte permeability of lipid bilayer membranes
    • Finkelstein A. Water and nonelectrolyte permeability of lipid bilayer membranes. J. Gen. Physiol. 68 (1976) 127-135
    • (1976) J. Gen. Physiol. , vol.68 , pp. 127-135
    • Finkelstein, A.1
  • 20
    • 0032509925 scopus 로고    scopus 로고
    • In vitro percutaneous absorption enhancement of a lipophilic drug tamoxifen by terpenes
    • Gao S., and Singh J. In vitro percutaneous absorption enhancement of a lipophilic drug tamoxifen by terpenes. J. Controlled Release 51 (1998) 193-199
    • (1998) J. Controlled Release , vol.51 , pp. 193-199
    • Gao, S.1    Singh, J.2
  • 21
    • 0023216780 scopus 로고
    • Stratum corneum lipid phase transitions and water barrier properties
    • Golden G.M., Guzek D.B., Kennedy A.H., McKie J.E., and Potts R.O. Stratum corneum lipid phase transitions and water barrier properties. Biochemistry 26 (1987) 2382-2388
    • (1987) Biochemistry , vol.26 , pp. 2382-2388
    • Golden, G.M.1    Guzek, D.B.2    Kennedy, A.H.3    McKie, J.E.4    Potts, R.O.5
  • 22
    • 34147191465 scopus 로고    scopus 로고
    • Infrared spectroscopic study of stratum corneum model membranes prepared from human ceramides, cholesterol, and fatty acids
    • Gooris G.S., and Bouwstra J.A. Infrared spectroscopic study of stratum corneum model membranes prepared from human ceramides, cholesterol, and fatty acids. Biophys. J. 92 (2007) 2785-2795
    • (2007) Biophys. J. , vol.92 , pp. 2785-2795
    • Gooris, G.S.1    Bouwstra, J.A.2
  • 23
    • 0026033106 scopus 로고
    • Enhancement of propranolol hydrochloride and diazepam skin absorption in vitro: effect of enhancer lipophilicity
    • Hori M., Satoh S., Maibach H.I., and Guy R.H. Enhancement of propranolol hydrochloride and diazepam skin absorption in vitro: effect of enhancer lipophilicity. J. Pharm. Sci. 80 (1991) 32-35
    • (1991) J. Pharm. Sci. , vol.80 , pp. 32-35
    • Hori, M.1    Satoh, S.2    Maibach, H.I.3    Guy, R.H.4
  • 24
    • 0037133255 scopus 로고    scopus 로고
    • Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes
    • Jain A.K., Thomas N.S., and Panchagnula R. Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes. J. Controlled Release 79 (2002) 93-101
    • (2002) J. Controlled Release , vol.79 , pp. 93-101
    • Jain, A.K.1    Thomas, N.S.2    Panchagnula, R.3
  • 25
    • 0035479551 scopus 로고    scopus 로고
    • Effects of cholesterol and temperature on the permeability of dimyristoylphosphatidylcholine bilayers near the chain melting phase transition
    • Kraske W.V., and Mountcastle D.B. Effects of cholesterol and temperature on the permeability of dimyristoylphosphatidylcholine bilayers near the chain melting phase transition. Biochim. Biophys. Acta 1514 (2001) 159-164
    • (2001) Biochim. Biophys. Acta , vol.1514 , pp. 159-164
    • Kraske, W.V.1    Mountcastle, D.B.2
  • 26
    • 0042344818 scopus 로고    scopus 로고
    • Lipid membrane polarity profiles by high-field EPR
    • Kurad D., Jeschke G., and Marsh D. Lipid membrane polarity profiles by high-field EPR. Biophys. J. 85 (2003) 1025-1033
    • (2003) Biophys. J. , vol.85 , pp. 1025-1033
    • Kurad, D.1    Jeschke, G.2    Marsh, D.3
  • 27
    • 0036365893 scopus 로고    scopus 로고
    • In vitro skin permeation of morphine hydrochloride during the finite application of penetration-enhancing system containing water, ethanol and l-menthol
    • Morimoto H., Wada Y., Seki T., and Sugibayashi K. In vitro skin permeation of morphine hydrochloride during the finite application of penetration-enhancing system containing water, ethanol and l-menthol. Biol. Pharm. Bull. 25 (2002) 134-136
    • (2002) Biol. Pharm. Bull. , vol.25 , pp. 134-136
    • Morimoto, H.1    Wada, Y.2    Seki, T.3    Sugibayashi, K.4
  • 28
    • 1542719315 scopus 로고    scopus 로고
    • Transdermal delivery of zidovudine: effect of terpenes and their mechanism of action
    • Narishetty S.T.K., and Panchagnula R. Transdermal delivery of zidovudine: effect of terpenes and their mechanism of action. J. Controlled Release 95 (2004) 367-379
    • (2004) J. Controlled Release , vol.95 , pp. 367-379
    • Narishetty, S.T.K.1    Panchagnula, R.2
  • 29
    • 11844281473 scopus 로고    scopus 로고
    • Effect of l-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine
    • 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. Controlled Release 102 (2005) 59-70
    • (2005) J. Controlled Release , vol.102 , pp. 59-70
    • Narishetty, S.T.K.1    Panchagnula, R.2
  • 30
    • 0024473801 scopus 로고
    • Effect of limonene and related compounds on the percutaneous absorption of indomethacin
    • Okabe H., Takayama K., Ogura A., and Nagai T. Effect of limonene and related compounds on the percutaneous absorption of indomethacin. Drug Des. Deliv. 4 (1989) 313-321
    • (1989) Drug Des. Deliv. , vol.4 , pp. 313-321
    • Okabe, H.1    Takayama, K.2    Ogura, A.3    Nagai, T.4
  • 32
    • 0032833887 scopus 로고    scopus 로고
    • Electron diffraction provides new information on human stratum corneum lipid organization studied in relation to depth and temperature
    • Pilgram G.S.K., Pelt A.M.E., Bouwstra J.A., and Koerten H.K. Electron diffraction provides new information on human stratum corneum lipid organization studied in relation to depth and temperature. J. Invest. Dermatol. 113 (1999) 403-409
    • (1999) J. Invest. Dermatol. , vol.113 , pp. 403-409
    • Pilgram, G.S.K.1    Pelt, A.M.E.2    Bouwstra, J.A.3    Koerten, H.K.4
  • 33
    • 23944525626 scopus 로고    scopus 로고
    • Dynamics and partitioning of spin-labeled stearates into the lipid domain of stratum corneum
    • Queirós W.P., Neto D.S., and Alonso A. Dynamics and partitioning of spin-labeled stearates into the lipid domain of stratum corneum. J. Controlled Release 106 (2005) 374-385
    • (2005) J. Controlled Release , vol.106 , pp. 374-385
    • Queirós, W.P.1    Neto, D.S.2    Alonso, A.3
  • 34
    • 0005251117 scopus 로고
    • The temperature dependence and thermodynamics of partitioning of phenols in the n-octanol-water system
    • Rogers J.A., and Wong A. The temperature dependence and thermodynamics of partitioning of phenols in the n-octanol-water system. Int. J. Pharm. 6 (1980) 339-348
    • (1980) Int. J. Pharm. , vol.6 , pp. 339-348
    • Rogers, J.A.1    Wong, A.2
  • 35
    • 0001867405 scopus 로고
    • Spin labeling: theory and application
    • Berliner L.J., and Reuben J. (Eds), Plenum Press, New York
    • 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
    • (1989) Biological Magnetic Resonance , vol.8 , pp. 1-76
    • Schneider, D.J.1    Freed, J.H.2
  • 36
    • 0015793995 scopus 로고
    • Lateral phase separation in phospholipid membranes
    • Shimshick E.J., and McConnell H.M. Lateral phase separation in phospholipid membranes. Biochemistry 12 (1973) 2351-2360
    • (1973) Biochemistry , vol.12 , pp. 2351-2360
    • Shimshick, E.J.1    McConnell, H.M.2
  • 37
    • 0029054719 scopus 로고
    • Very high frequency electron paramagnetic resonance of 2,2,6,6-tetramethyl-1-piperidinyloxy in 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine liposomes: partitioning and molecular dynamics
    • Smirnov A., Smirnova T., and Morse P.D. Very high frequency electron paramagnetic resonance of 2,2,6,6-tetramethyl-1-piperidinyloxy in 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine liposomes: partitioning and molecular dynamics. Biophys. J. 68 (1995) 2350-2360
    • (1995) Biophys. J. , vol.68 , pp. 2350-2360
    • Smirnov, A.1    Smirnova, T.2    Morse, P.D.3
  • 38
    • 0034907851 scopus 로고    scopus 로고
    • Responding phospholipid membranes-interplay between hydration and permeability
    • Sparr E., and Wennerström H. Responding phospholipid membranes-interplay between hydration and permeability. Biophys. J. 81 (2001) 1014-1028
    • (2001) Biophys. J. , vol.81 , pp. 1014-1028
    • Sparr, E.1    Wennerström, H.2
  • 39
    • 0035998950 scopus 로고    scopus 로고
    • Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry
    • Vaddi H.K., Ho P.C., and Chan S.Y. Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry. J. Pharm. Sci. 91 (2002) 1639-1651
    • (2002) J. Pharm. Sci. , vol.91 , pp. 1639-1651
    • Vaddi, H.K.1    Ho, P.C.2    Chan, S.Y.3
  • 40
    • 0037123737 scopus 로고    scopus 로고
    • Terpenes in ethanol: haloperidol permeation and partition through human skin and stratum corneum changes
    • 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. Controlled Release 81 (2002) 121-133
    • (2002) J. Controlled Release , vol.81 , pp. 121-133
    • Vaddi, H.K.1    Ho, P.C.2    Chan, Y.W.3    Chan, S.Y.4
  • 41
    • 0027508689 scopus 로고
    • Configuration entropy is the driving force of ethanol action on membrane architecture
    • Wang D.-C., Taraschi T.F., Rubin E., and Janes N. Configuration entropy is the driving force of ethanol action on membrane architecture. Biochim. Biophys. Acta 1145 (1993) 141-148
    • (1993) Biochim. Biophys. Acta , vol.1145 , pp. 141-148
    • Wang, D.-C.1    Taraschi, T.F.2    Rubin, E.3    Janes, N.4
  • 42
    • 0023068117 scopus 로고
    • Covalently bound ω-hydroxyacylsphingosine in the stratum corneum
    • Wertz P.W., and Downing D.T. Covalently bound ω-hydroxyacylsphingosine in the stratum corneum. Biochim. Biophys. Acta 917 (1987) 108-111
    • (1987) Biochim. Biophys. Acta , vol.917 , pp. 108-111
    • Wertz, P.W.1    Downing, D.T.2
  • 43
    • 0024290394 scopus 로고
    • Structure of lamellar lipid domains and corneocyte envelopes of murine stratum corneum. An X-ray diffraction study
    • 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
    • (1988) Biochemistry , vol.27 , pp. 3725-3732
    • White, S.H.1    Mirejovsky, D.2    King, G.I.3
  • 45
    • 0028830178 scopus 로고
    • Effects of terpenes and oleic acid as skin penetration enhancers towards 5-fluorouracil as assessed with time, permeation, partitioning and differential scanning calorimetry
    • 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
    • (1995) Int. J. Pharm. , vol.116 , pp. 237-251
    • Yamane, M.A.1    Williams, A.C.2    Barry, B.W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.