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Volumn 1811, Issue 3, 2011, Pages 129-137

Effect of ceramide acyl chain length on skin permeability and thermotropic phase behavior of model stratum corneum lipid membranes

Author keywords

Differential scanning calorimetry; Infrared spectroscopy; Short chain ceramides; Skin barrier; Stratum corneum; Structure activity relationships

Indexed keywords

CARBENE; CERAMIDE; CERAMIDE ACYL CHAIN; CHOLESTEROL; CHOLESTEROL SULFATE; INDOMETACIN; LIGNOCERIC ACID; NONHYDROXYACYLSPHINGOSINE CERAMIDE; THEOPHYLLINE; UNCLASSIFIED DRUG;

EID: 78651233478     PISSN: 13881981     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbalip.2010.12.003     Document Type: Article
Times cited : (73)

References (43)
  • 2
    • 37249053783 scopus 로고    scopus 로고
    • Thematic review series: Skin lipids. The role of epidermal lipids in cutaneous permeability barrier homeostasis
    • K.R. Feingold Thematic review series: skin lipids. The role of epidermal lipids in cutaneous permeability barrier homeostasis J. Lipid Res. 48 2007 2531 2546
    • (2007) J. Lipid Res. , vol.48 , pp. 2531-2546
    • Feingold, K.R.1
  • 3
    • 33749049791 scopus 로고    scopus 로고
    • Epidermal sphingolipids: Metabolism, function, and roles in skin disorders
    • W.M. Holleran, Y. Takagi, and Y. Uchida Epidermal sphingolipids: metabolism, function, and roles in skin disorders FEBS Lett. 580 2006 5456 5466
    • (2006) FEBS Lett. , vol.580 , pp. 5456-5466
    • Holleran, W.M.1    Takagi, Y.2    Uchida, Y.3
  • 4
    • 23844476054 scopus 로고    scopus 로고
    • Role of ceramides in barrier function of healthy and diseased skin
    • M.J. Choi, and H.I. Maibach Role of ceramides in barrier function of healthy and diseased skin Am. J. Clin. Dermatol. 6 2005 215 223
    • (2005) Am. J. Clin. Dermatol. , vol.6 , pp. 215-223
    • Choi, M.J.1    Maibach, H.I.2
  • 5
    • 34548156506 scopus 로고    scopus 로고
    • Properties of ceramides and their impact on the stratum corneum structure: A review: Part 1. Ceramides
    • S. Wartewig, and R.H. Neubert Properties of ceramides and their impact on the stratum corneum structure: a review: Part 1. Ceramides Skin Pharmacol. Physiol. 20 2007 220 229
    • (2007) Skin Pharmacol. Physiol. , vol.20 , pp. 220-229
    • Wartewig, S.1    Neubert, R.H.2
  • 8
    • 77955617285 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of skin ceramides
    • J. Novotný, A. Hrabálek, and K. Vávrová Synthesis and structure-activity relationships of skin ceramides Curr. Med. Chem. 17 2010 2301 2324
    • (2010) Curr. Med. Chem. , vol.17 , pp. 2301-2324
    • Novotný, J.1    Hrabálek, A.2    Vávrová, K.3
  • 10
    • 33845346790 scopus 로고    scopus 로고
    • Biophysics of sphingolipids: I. Membrane properties of sphingosine, ceramides and other simple sphingolipids
    • F.M. Goni, and A. Alonso Biophysics of sphingolipids: I. Membrane properties of sphingosine, ceramides and other simple sphingolipids Biochim. Biophys. Acta 1758 2006 1902 1921
    • (2006) Biochim. Biophys. Acta , vol.1758 , pp. 1902-1921
    • Goni, F.M.1    Alonso, A.2
  • 12
    • 71849114210 scopus 로고    scopus 로고
    • Synthesis of fluorescent C24-ceramide: Evidence for acyl chain length dependent differences in penetration of exogenous NBD-ceramides into human skin
    • J. Novotný, K. Pospěchová, A. Hrabálek, R. Čáp, and K. Vávrová Synthesis of fluorescent C24-ceramide: evidence for acyl chain length dependent differences in penetration of exogenous NBD-ceramides into human skin Bioorg. Med. Chem. Lett. 19 2009 6975 6977
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 6975-6977
    • Novotný, J.1    Pospěchová, K.2    Hrabálek, A.3    Čáp, R.4    Vávrová, K.5
  • 13
    • 23844512530 scopus 로고    scopus 로고
    • Amphiphilic transdermal permeation enhancers: Structure-activity relationships
    • DOI 10.2174/0929867054864822
    • K. Vávrová, J. Zbytovská, and A. Hrabálek Amphiphilic transdermal permeation enhancers: structure-activity relationships Curr. Med. Chem. 12 2005 2273 2291 (Pubitemid 41179712)
    • (2005) Current Medicinal Chemistry , vol.12 , Issue.19 , pp. 2273-2291
    • Vavrova, K.1    Zbytovska, J.2    Hrabalek, A.3
  • 14
    • 34548564146 scopus 로고    scopus 로고
    • Ceramide analogue 14 S24 selectively recovers perturbed human skin barrier
    • K. Vávrová, A. Hrabálek, S. Mac-Mary, P. Humbert, and P. Muret Ceramide analogue 14 S24 selectively recovers perturbed human skin barrier Br. J. Dermatol. 157 2007 704 712
    • (2007) Br. J. Dermatol. , vol.157 , pp. 704-712
    • Vávrová, K.1    Hrabálek, A.2    Mac-Mary, S.3    Humbert, P.4    Muret, P.5
  • 15
    • 18344419439 scopus 로고    scopus 로고
    • Ceramide analogue 14 S24 ((S)-2-tetracosanoylamino-3-hydroxypropionic acid tetradecyl ester) is effective in skin barrier repair in vitro
    • K. Vávrová, J. Zbytovská, K. Palát, T. Holas, J. Klimentová, A. Hrabálek, and P. Doležal Ceramide analogue 14 S24 ((S)-2-tetracosanoylamino-3-hydroxypropionic acid tetradecyl ester) is effective in skin barrier repair in vitro Eur. J. Pharm. Sci. 21 2004 581 587
    • (2004) Eur. J. Pharm. Sci. , vol.21 , pp. 581-587
    • Vávrová, K.1    Zbytovská, J.2    Palát, K.3    Holas, T.4    Klimentová, J.5    Hrabálek, A.6    Doležal, P.7
  • 16
    • 0037666173 scopus 로고    scopus 로고
    • L-Serine and glycine based ceramide analogues as transdermal permeation enhancers: Polar head size and hydrogen bonding
    • K. Vávrová, A. Hrabálek, P. Doležal, T. Holas, and J. Zbytovská 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
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 2351-2353
    • Vávrová, K.1    Hrabálek, A.2    Doležal, P.3    Holas, T.4    Zbytovská, J.5
  • 17
    • 0037687903 scopus 로고    scopus 로고
    • Intracellular delivery of ceramide lipids via liposomes enhances apoptosis in vitro
    • J.A. Shabbits, and L.D. Mayer Intracellular delivery of ceramide lipids via liposomes enhances apoptosis in vitro Biochim. Biophys. Acta 1612 2003 98 106
    • (2003) Biochim. Biophys. Acta , vol.1612 , pp. 98-106
    • Shabbits, J.A.1    Mayer, L.D.2
  • 18
    • 3142538584 scopus 로고    scopus 로고
    • The Tinsley LCR Databridge Model 6401 and electrical impedance measurements to evaluate skin integrity in vitro
    • W.J. Fasano, and P.M. Hinderliter The Tinsley LCR Databridge Model 6401 and electrical impedance measurements to evaluate skin integrity in vitro Toxicol. In Vitro 18 2004 725 729
    • (2004) Toxicol. in Vitro , vol.18 , pp. 725-729
    • Fasano, W.J.1    Hinderliter, P.M.2
  • 19
    • 77953011322 scopus 로고    scopus 로고
    • Model membranes prepared with ceramide EOS, cholesterol and free fatty acids form a unique lamellar phase
    • D. Groen, G.S. Gooris, and J.A. Bouwstra Model membranes prepared with ceramide EOS, cholesterol and free fatty acids form a unique lamellar phase Langmuir 26 2010 4168 4175
    • (2010) Langmuir , vol.26 , pp. 4168-4175
    • Groen, D.1    Gooris, G.S.2    Bouwstra, J.A.3
  • 20
    • 0032213049 scopus 로고    scopus 로고
    • Vibrational spectroscopic studies of lipid domains in biomembranes and model systems
    • R. Mendelsohn, and D.J. Moore Vibrational spectroscopic studies of lipid domains in biomembranes and model systems Chem. Phys. Lipids 96 1998 141 157
    • (1998) Chem. Phys. Lipids , vol.96 , pp. 141-157
    • Mendelsohn, R.1    Moore, D.J.2
  • 22
    • 33744956909 scopus 로고    scopus 로고
    • Structural organisation and phase behaviour of a stratum corneum lipid analogue: Ceramide 3A
    • P. Garidel Structural organisation and phase behaviour of a stratum corneum lipid analogue: ceramide 3A Phys. Chem. Chem. Phys. 8 2006 2265 2275
    • (2006) Phys. Chem. Chem. Phys. , vol.8 , pp. 2265-2275
    • Garidel, P.1
  • 23
    • 43049147557 scopus 로고    scopus 로고
    • Molecular organization of the lipid matrix in intact Stratum corneum using ATR-FTIR spectroscopy
    • M. Boncheva, F. Damien, and V. Normand Molecular organization of the lipid matrix in intact Stratum corneum using ATR-FTIR spectroscopy Biochim. Biophys. Acta 1778 2008 1344 1355
    • (2008) Biochim. Biophys. Acta , vol.1778 , pp. 1344-1355
    • Boncheva, M.1    Damien, F.2    Normand, V.3
  • 24
    • 0000548084 scopus 로고
    • Vibrational analysis of the n-paraffins: I. Assignments of infrared bands in the spectra of C3H8 through n-C19H40 Spectrochim
    • R.G. Snyder, and J.H. Schachtschneider Vibrational analysis of the n-paraffins: I. Assignments of infrared bands in the spectra of C3H8 through n-C19H40 Spectrochim Acta 19 1963 85 116
    • (1963) Acta , vol.19 , pp. 85-116
    • Snyder, R.G.1    Schachtschneider, J.H.2
  • 25
    • 0001073950 scopus 로고
    • Vibrational spectroscopic study on polymorphism and order-disorder phase transition in oleic acid
    • M. Kobayashi, F. Kaneko, K. Sato, and M. Suzuki Vibrational spectroscopic study on polymorphism and order-disorder phase transition in oleic acid J. Phys. Chem. 90 1986 6371 6378
    • (1986) J. Phys. Chem. , vol.90 , pp. 6371-6378
    • Kobayashi, M.1    Kaneko, F.2    Sato, K.3    Suzuki, M.4
  • 26
    • 0035960199 scopus 로고    scopus 로고
    • Phytosphingosine and sphingosine ceramide headgroup hydrogen bonding: Structural insights through thermotropic hydrogen/deuterium exchange
    • M.E. Rerek, H. Chen, B. Markovic, D. Van Wyck, P. Patrick Garidel, R. Mendelsohn, and D.J. Moore Phytosphingosine and sphingosine ceramide headgroup hydrogen bonding: structural insights through thermotropic hydrogen/deuterium exchange J. Phys. Chem. B 105 2001 9355 9362
    • (2001) J. Phys. Chem. B , vol.105 , pp. 9355-9362
    • Rerek, M.E.1    Chen, H.2    Markovic, B.3    Van Wyck, D.4    Patrick Garidel, P.5    Mendelsohn, R.6    Moore, D.J.7
  • 27
    • 0031249751 scopus 로고    scopus 로고
    • FTIR spectroscopy studies of the conformational order and phase behavior of ceramides
    • D.J. Moore, M.E. Rerek, and R. Mendelsohn FTIR spectroscopy studies of the conformational order and phase behavior of ceramides J. Phys. Chem. B 101 1997 8933 8940
    • (1997) J. Phys. Chem. B , vol.101 , pp. 8933-8940
    • Moore, D.J.1    Rerek, M.E.2    Mendelsohn, R.3
  • 28
    • 77953693957 scopus 로고    scopus 로고
    • The microstructure of the stratum corneum lipid barrier: Mid-infrared spectroscopic studies of hydrated ceramide:palmitic acid:cholesterol model systems
    • P. Garidel, B. Folting, I. Schaller, and A. Kerth The microstructure of the stratum corneum lipid barrier: mid-infrared spectroscopic studies of hydrated ceramide:palmitic acid:cholesterol model systems Biophys. Chem. 150 2010 144 156
    • (2010) Biophys. Chem. , vol.150 , pp. 144-156
    • Garidel, P.1    Folting, B.2    Schaller, I.3    Kerth, A.4
  • 29
    • 0000050707 scopus 로고
    • Infrared study of the amide group isolated in an amorphous hydrocarbon matrix at low-temperature - Aggregation and rearrangement upon annealing
    • R.G. Snyder, L.X.Q. Chen, V.J.P. Srivatsavoy, H.L. Strauss, and S. Kubota Infrared study of the amide group isolated in an amorphous hydrocarbon matrix at low-temperature - aggregation and rearrangement upon annealing J. Phys. Chem. 99 1995 2214 2223
    • (1995) J. Phys. Chem. , vol.99 , pp. 2214-2223
    • Snyder, R.G.1    Chen, L.X.Q.2    Srivatsavoy, V.J.P.3    Strauss, H.L.4    Kubota, S.5
  • 30
    • 0345310076 scopus 로고    scopus 로고
    • Study of the structure and phase behavior of dipalmitoylphosphatidylcholine by infrared spectroscopy: Characterization of the pretransition and subtransition
    • T. Le Bihan, and M. Pezolet Study of the structure and phase behavior of dipalmitoylphosphatidylcholine by infrared spectroscopy: characterization of the pretransition and subtransition Chem. Phys. Lipids 94 1998 13 33
    • (1998) Chem. Phys. Lipids , vol.94 , pp. 13-33
    • Le Bihan, T.1    Pezolet, M.2
  • 31
    • 0036214899 scopus 로고    scopus 로고
    • Conformational characterization of ceramides by nuclear magnetic resonance spectroscopy
    • L. Li, X. Tang, K.G. Taylor, D.B. DuPre, and M.C. Yappert Conformational characterization of ceramides by nuclear magnetic resonance spectroscopy Biophys. J. 82 2002 2067 2080
    • (2002) Biophys. J. , vol.82 , pp. 2067-2080
    • Li, L.1    Tang, X.2    Taylor, K.G.3    Dupre, D.B.4    Yappert, M.C.5
  • 32
    • 0025905320 scopus 로고
    • Evidence that oleic acid exists in a separate phase within stratum corneum lipids
    • B. Ongpipattanakul, R.R. Burnette, R.O. Potts, and M.L. Francoeur Evidence that oleic acid exists in a separate phase within stratum corneum lipids Pharm. Res. 8 1991 350 354
    • (1991) Pharm. Res. , vol.8 , pp. 350-354
    • Ongpipattanakul, B.1    Burnette, R.R.2    Potts, R.O.3    Francoeur, M.L.4
  • 33
    • 0028893173 scopus 로고
    • Organization of the intercellular spaces of porcine epidermal and palatal stratum corneum: A quantitative study employing ruthenium tetroxide
    • D.C. Swartzendruber, A. Manganaro, K.C. Madison, M. Kremer, P.W. Wertz, and C.A. Squier Organization of the intercellular spaces of porcine epidermal and palatal stratum corneum: a quantitative study employing ruthenium tetroxide Cell Tissue Res. 279 1995 271 276
    • (1995) Cell Tissue Res. , vol.279 , pp. 271-276
    • Swartzendruber, D.C.1    Manganaro, A.2    Madison, K.C.3    Kremer, M.4    Wertz, P.W.5    Squier, C.A.6
  • 34
    • 58149188064 scopus 로고    scopus 로고
    • Effects of ceramide and other simple sphingolipids on membrane lateral structure
    • F.M. Goni, and A. Alonso Effects of ceramide and other simple sphingolipids on membrane lateral structure Biochim. Biophys. Acta 1788 2009 169 177
    • (2009) Biochim. Biophys. Acta , vol.1788 , pp. 169-177
    • Goni, F.M.1    Alonso, A.2
  • 35
    • 0041384271 scopus 로고    scopus 로고
    • Disruption of lipid order by short-chain ceramides correlates with inhibition of phospholipase D and downstream signaling by FcepsilonRI
    • A. Gidwani, H.A. Brown, D. Holowka, and B. Baird Disruption of lipid order by short-chain ceramides correlates with inhibition of phospholipase D and downstream signaling by FcepsilonRI J. Cell Sci. 116 2003 3177 3187
    • (2003) J. Cell Sci. , vol.116 , pp. 3177-3187
    • Gidwani, A.1    Brown, H.A.2    Holowka, D.3    Baird, B.4
  • 36
    • 34547181885 scopus 로고    scopus 로고
    • Raft domain reorganization driven by short- and long-chain ceramide: A combined AFM and FCS study
    • S. Chiantia, N. Kahya, and P. Schwille Raft domain reorganization driven by short- and long-chain ceramide: a combined AFM and FCS study Langmuir 23 2007 7659 7665
    • (2007) Langmuir , vol.23 , pp. 7659-7665
    • Chiantia, S.1    Kahya, N.2    Schwille, P.3
  • 37
    • 34548486456 scopus 로고    scopus 로고
    • Effect of ceramide N-acyl chain and polar headgroup structure on the properties of ordered lipid domains (lipid rafts)
    • P. Sawatzki Megha, T. Kolter, R. Bittman, and E. London Effect of ceramide N-acyl chain and polar headgroup structure on the properties of ordered lipid domains (lipid rafts) Biochim. Biophys. Acta 1768 2007 2205 2212
    • (2007) Biochim. Biophys. Acta , vol.1768 , pp. 2205-2212
    • Sawatzki, M.P.1    Kolter, T.2    Bittman, R.3    London, E.4
  • 38
    • 28144431972 scopus 로고    scopus 로고
    • Acyl chain length affects ceramide action on sterol/sphingomyelin-rich domains
    • S. Nybond, Y.J. Bjorkqvist, B. Ramstedt, and J.P. Slotte Acyl chain length affects ceramide action on sterol/sphingomyelin-rich domains Biochim. Biophys. Acta 1718 2005 61 66
    • (2005) Biochim. Biophys. Acta , vol.1718 , pp. 61-66
    • Nybond, S.1    Bjorkqvist, Y.J.2    Ramstedt, B.3    Slotte, J.P.4
  • 39
    • 47349115203 scopus 로고    scopus 로고
    • Physicochemical and biological characterization of ceramide-containing liposomes: Paving the way to ceramide therapeutic application
    • E. Khazanov, A. Priev, J.P. Shillemans, and Y. Barenholz Physicochemical and biological characterization of ceramide-containing liposomes: paving the way to ceramide therapeutic application Langmuir 24 2008 6965 6980
    • (2008) Langmuir , vol.24 , pp. 6965-6980
    • Khazanov, E.1    Priev, A.2    Shillemans, J.P.3    Barenholz, Y.4
  • 40
    • 0032799361 scopus 로고    scopus 로고
    • In vivo human skin permeability enhancement by oleic acid: A laser Doppler velocimetry study
    • H. Tanojo, E. Boelsma, H.E. Junginger, M. Ponec, and H.E. Bodde In vivo human skin permeability enhancement by oleic acid: a laser Doppler velocimetry study J. Control. Release 58 1999 97 104
    • (1999) J. Control. Release , vol.58 , pp. 97-104
    • Tanojo, H.1    Boelsma, E.2    Junginger, H.E.3    Ponec, M.4    Bodde, H.E.5
  • 41
    • 0021085875 scopus 로고
    • Effect of essential fatty acid deficiency on the epidermal sphingolipids of the rat
    • P.W. Wertz, E.S. Cho, and D.T. Downing Effect of essential fatty acid deficiency on the epidermal sphingolipids of the rat Biochim. Biophys. Acta 753 1983 350 355
    • (1983) Biochim. Biophys. Acta , vol.753 , pp. 350-355
    • Wertz, P.W.1    Cho, E.S.2    Downing, D.T.3
  • 42
    • 43649107128 scopus 로고    scopus 로고
    • FTIR studies show lipophilic moisturizers to interact with stratum corneum lipids, rendering the more densely packed
    • J. Caussin, G.S. Gooris, and J.A. Bouwstra FTIR studies show lipophilic moisturizers to interact with stratum corneum lipids, rendering the more densely packed Biochim. Biophys. Acta 1778 2008 1517 1524
    • (2008) Biochim. Biophys. Acta , vol.1778 , pp. 1517-1524
    • Caussin, J.1    Gooris, G.S.2    Bouwstra, J.A.3
  • 43
    • 60549106497 scopus 로고    scopus 로고
    • Infrared spectroscopy studies of mixtures prepared with synthetic ceramides varying in head group architecture: Coexistence of liquid and crystalline phases
    • M. Janssens, G.S. Gooris, and J.A. Bouwstra Infrared spectroscopy studies of mixtures prepared with synthetic ceramides varying in head group architecture: coexistence of liquid and crystalline phases Biochim. Biophys. Acta 1788 2009 732 742
    • (2009) Biochim. Biophys. Acta , vol.1788 , pp. 732-742
    • Janssens, M.1    Gooris, G.S.2    Bouwstra, J.A.3


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