Thermal dependence of Raman descriptors of ceramides. Part I: Effect of double bonds in hydrocarbon chains

Analytical and Bioanalytical Chemistry

Volumn 397, Issue 3, 2010, Pages 1281-1296

  Tfayli, Ali ^a   Guillard, Emmanuelle ^a,b   Manfait, Michel ^b   Baillet Guffroy, Arlette ^a  

^a University Paris Saclay   (France)

^b UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Ceramide III; Conformational disorder; Lipid lateral packing; Raman spectroscopy; Stratum corneum; Thermotropic behavior

Indexed keywords

CERAMIDES; CONFORMATIONAL DISORDER; CONFORMATIONAL DISORDERS; STRATUM CORNEUM; THERMOTROPIC BEHAVIOR;

CONFORMATIONS; HYDROCARBONS; RAMAN SCATTERING; RAMAN SPECTROSCOPY;

AMIDES;

CERAMIDE;

ARTICLE; CHEMISTRY; CONFORMATION; RAMAN SPECTROMETRY; TEMPERATURE;

CERAMIDES; MOLECULAR CONFORMATION; SPECTRUM ANALYSIS, RAMAN; TEMPERATURE;

EID: 77953479897     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-010-3614-y     Document Type: Article

References (54)

1. Elias PM (2005) Interactions among stratum corneum defensive functions. J Invest Dermatol 125:183-200
2. Wertz PW (1996) The nature of the epidermal barrier: biochemical aspects. Adv Drug Deliv Rev 18:283-294
3. Wertz PW, van den Bergh B (1998) The physical, chemical and functional properties of lipids in the skin and other biological barriers. Chem Phys Lipids 91(2):85-96
4. Jungersted JM et al (2008) Lipids and skin barrier function - a clinical perspective. Contact Dermat 58(5):255-262
5. Stewart ME, Downing DT (1999) A new 6-hydroxy-4-sphinge-nine-containing ceramide in human skin. J Lipid Res 40(8):1434-1439
6. Wertz PW et al (1987) Essential fatty acids and epidermal integrity. Arch Dermatol 123(10):1381-1384
7. Wertz PW et al (1987) Composition and morphology of epidermal cyst lipids. J Invest Dermatol 89(4):419-425
8. Raudenkolb S et al (2003) Polymorphism of ceramide 3. Part 1: an investigation focused on the head group of N-octadecanoyl phytosphingosine. Chem Phys Lipids 123(1):9-17
9. Raudenkolb S, Wartewig S, Neubert RH (2003) Polymorphism of ceramide 3. Part 2: a vibrational spectroscopic and X-ray powder diffraction investigation of N-octadecanoyl phytosphingosine and the analogous specifically deuterated d(35) derivative. Chem Phys Lipids 124(2):89-101
10. Gniadecka M et al (1998) Structure of water, proteins, and lipids in intact human skin, hair, and nail. J Invest Dermatol 110:393-398
11. Goni FM, Alonso A (2006) Biophysics of sphingolipids I membrane properties of sphingosine ceramides and other simple sphingolipids. Biochim Biophys Acta 1758(12):1902-1921
12. Holtje M et al (2001) Molecular dynamics simulations of stratum corneum lipid models: fatty acids and cholesterol. Biochim Biophys Acta 1511(1):156-167
13. Onken HD, Moyer CA (1963) The water barrierinhuman epidermis. Physical and chemical nature. Arch Dermatol 87:584-590
14. Bouwstra JA, Ponec M (2006) The skin barrier in healthy and diseased state. Biochim Biophys Acta 1758(12):2080-2095
15. Chen H et al (2000) Fourier transform infrared spectroscopy and differential scanning calorimetry studies of fatty acid homogeneous ceramide 2. Biochim Biophys Acta 1468(1-2):293-303
16. Moore DJ, Rerek ME, Mendelsohn R (1997) FTIR spectroscopy studies of the conformational order and phase behavior of ceramides. J Phys Chem 101(44):8933-8940
17. Neubert R et al (1997) Structure of stratum corneum lipids characterized by FT-Raman spectroscopy and DSC II. Mixtures of ceramides and saturated fatty acids. Chem Phys Lipids 89(1):3-14 (Pubitemid 27458222)
18. Wegener M et al (1996) Structure of stratum corneum lipids characterized by FT-Raman spectroscopy and DSC I. Ceramides. Int J Pharm 128:203-213
19. Bouwstra JA et al (1998) Role of ceramide 1 in the molecular organization of the stratum corneum lipids. J Lipid Res 39 (1):186-196
20. Wegener M et al (1997) Structure of stratum corneum lipids characterized by FT-Raman spectroscopy and DSC III. Mixtures of ceramides and cholesterol. Chem Phys Lipids 88(1):73-82 (Pubitemid 27395415)
21. Raudenkolb S, Wartewig S, Neubert RH (2005) Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(alpha-hydroxyoctadecanoyl)-phytosphingosine. Chem Phys Lipids 133(1):89-102
22. Garidel P (2005) Structural organisation and phase behaviour of a stratum corneum lipid analogue: ceramide 3A. ChemPhysChem 8 (19):2265-2275
23. Lambers H et al (1999) Ceramides. C.R. 1 (ed)
24. Product data sheet of ceramide III IIIB, D G P C A, reference B 04/02
25. Product data sheet of ceramide IIIA, D G P C A, reference B 03/01
26. Caussin J et al (2008) Lipid organization in human and porcine stratum corneum differs widely, while lipid mixtures with porcine ceramides model human stratum corneum lipid organization very closely. Biochim Biophys Acta 1778(6):1472-1482
27. Gaber BP, Peticolas WL (1977) On the quantitative interpretation of biomembrane structure by Raman spectroscopy. Biochim Biophys Acta 465(2):260-274
28. Gaber BP, Yager P, Peticolas WL (1978) Interpretation of biomembrane structure by Raman difference spectroscopy. Nature of the endothermic transitions in phosphatidylcholines. Biophys J 21(2):161-176
29. Bouwstra JA et al (1996) Phase behavior of isolated skin lipids. J Lipid Res 37(5):999-1011
30. Bouwstra JA et al (2002) Phase behavior of stratum corneum lipid mixtures based on human ceramides: the role of natural and synthetic ceramide 1. J Invest Dermatol 118(4):606-617
31. Caussin J, Gooris GS, Bouwstra JA (2008) FTIR studies show lipophilic moisturizers to interact with stratum corneum lipids, rendering the more densely packed. Biochim Biophys Acta 1778 (6):1517-1524
32. Lafleur M (1998) Phase behaviour of model stratum corneum lipid mixtures: an infrared spectroscopy investigation. Can J Chem 76(11):1501-1511
33. Laugel C, Yagoubi N, Baillet A (2005) ATR-FTIR spectroscopy: a chemometric approach for studying the lipid organisation of the stratum corneum. Chem Phys Lipids 135(1):55-68
34. Mimeault M, Bonenfant D (2002) FTIR spectroscopic analyses of the temperature and pH influences on stratum corneum lipid phase behaviors and interactions. Talanta 56(3):395-405
35. Rerek ME et al (2005) FTIR spectroscopic studies of lipid dynamics in phytosphingosine ceramide models of the stratum corneum lipid matrix. Chem Phys Lipids 134(1):51-58
36. Snyder RG, Hsu SL, Krimm S (1978) Vibrational spectra in the C-H stretching region and the structure of the polymethylene chain. Spectrochim Acta 34A:395-406
37. Snyder RG et al (1996) IR spectroscopic study of the structure and phase behavior of long-chain diacyl phosphatidylcholines in the gel state. Biophys J 71(6):3186-3198
38. Gaber BP, Yager P, Peticolas WL (1978) Conformational nonequivalence of chains 1 and 2 of dipalmitoyl phosphatidylcholine as observed by Raman spectroscopy. Biophys J 24 (3):677-688
39. Yellin N, Levin IW (1977) Hydrocarbon chain disorder in lipid bilayers. Temperature dependent Raman spectra of 1,2-diacyl phosphatidylcholine-water gels. Biochim Biophys Acta 489 (2):177-190
40. O'Leary TJ, Levin IW (1984) Raman spectroscopic study of an interdigitated lipid bilayer. Dipalmitoylphosphatidylcholine dispersed in glycerol. Biochim Biophys Acta 776(2):185-189
41. Bunow MR, Levin IW (1980) Molecular conformations of cerebrosides in bilayers determined by Raman spectroscopy. Biophys J 32(3):1007-1021
42. Csiszar A et al (2006) The phase transition behavior of 1, 2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) model membrane influenced by 2, 4-dichlorophenol - an FT-Raman spectroscopy study. Chem Phys Lipids 139(2):115-124
43. Onogi C, Motoyama M, Hamaguchi H (2008) High concentration trans form unsaturated lipids detected in a HeLa cell by Raman microspectroscopy. J Raman Spectrosc 39(5):555-556
44. Wartewig S, Neubert RH (2007) Properties of ceramides and their impact on the stratum corneum structure: a review Part 1: ceramides. Skin Pharmacol Physiol 20(5):220-229
45. Moore DJ, Rerek ME, Mendelsohn R (1997) Lipid domains and orthorhombic phases in model stratum corneum: evidence from Fourier transform infrared spectroscopy studies. Biochem Biophys Res Commun 231(3):797-801
46. Moore DJ, Rerek ME, Mendelsohn R (1999) Role of ceramides 2 and 5 in the structure of the stratum corneum lipid barrier. Int J Cosmet Sci 21(5):353-368
47. Sprunt JC, Jayasooriya UA, Wilson RH (2000) A simultaneous FT-Raman-DSC (SRD) study of polymorphism in sn-1,3-distearoyl-2-oleoylglycerol (SOS). ChemPhysChem 2(19):4299-4305
48. Wartewig S et al (1998) Structure of stratum corneum lipids characterized by FT-Raman spectroscopy and DSC IV. Mixtures of ceramides and oleic acid. Chem Phys Lipids 91:145-152
49. Lawson EE et al (1998) Thermally induced molecular disorder in human stratum corneum lipids compared with a model phospho-lipid system; FT-Raman spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc 54A(3):543-558
50. Koningsten JA (1971) In: Koningsten JA (ed) Introduction of the theory of the Raman effect. D. Reidel, Dordrecht
51. Gobinet C et al (2005) Independent component analysis and Raman spectroscopy on paraffinised non dewaxed cutaneous biopsies: a promising methodology for melanoma early diagnosis. In: International Workshop on Biosignal Processing and Classification BPC. Barcelona, Spain
52. Gobinet C et al (2005) A method of digital deparaffining based on Raman spectroscopy and independent component analysis: application to melanoma early diagnosis. In: European Medical & Biological Engineering Conference EMBEC 05. Prague, Czech Republic
53. Pare C, Lafleur M (1998) Polymorphism of POPE/cholesterol system: a 2H nuclear magnetic resonance and infrared spectroscopic investigation. Biophys J 74(2 Pt 1):899-909
54. Percot A, Lafleur M (2001) Direct observation of domains in model stratum corneum lipid mixtures by Raman microspectroscopy. Biophys J 81(4):2144-2153