Novel sphingolipid derivatives promote keratinocyte differentiation

Experimental Dermatology

Volumn 17, Issue 12, 2008, Pages 1004-1016

  Paragh, György ^a,b   Schling, Petra ^a   Ugocsai, Peter ^a   Kel, Alexander E ^c   Liebisch, Gerhard ^a   Heimerl, Susanne ^a   Moehle, Christoph ^a   Schiemann, Yvonne ^d   Wegmann, Michael ^d   Farwick, Mike ^d   Wikonkál, Norbert M ^b   Mandl, József ^b   Langmann, Thomas ^a   Schmitz, Gerd ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b SEMMELWEIS UNIVERSITY   (Hungary)

^c BIOBASE GMBH   (Germany)

^d EVONIK INDUSTRIES AG   (Germany)

Author keywords

Ceramides; Microarray; NHEK; Promoter analysis; Salicylic acid

Indexed keywords

ACID; ALKYLAMINE SALICYLATE; COLECALCIFEROL; PHYTOSPHINGOSINE; RETINOL; SALICYLIC ACID; SPHINGANINE; SPHINGOLIPID; SPHINGOSINE; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CELL DIFFERENTIATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; COVALENT BOND; CYTOTOXICITY; DNA MICROARRAY; FEMALE; GENE EXPRESSION; GENETIC REGULATION; HUMAN; HUMAN CELL; KERATINOCYTE; STRUCTURE ACTIVITY RELATION; TRANSCRIPTION REGULATION;

ADULT; ANTIGENS, DIFFERENTIATION; BASE SEQUENCE; BINDING SITES; CELL DIFFERENTIATION; CELL SURVIVAL; CELLS, CULTURED; CHOLECALCIFEROL; FEMALE; GENE EXPRESSION PROFILING; GENE EXPRESSION REGULATION; GLYCOPROTEINS; HUMANS; INTERMEDIATE FILAMENT PROTEINS; KERATIN-10; KERATINOCYTES; MIDDLE AGED; MODELS, GENETIC; MOLECULAR SEQUENCE DATA; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; PROMOTER REGIONS, GENETIC; SALICYLATES; SPHINGOLIPIDS; TRANSGLUTAMINASES; VITAMIN A;

EID: 56349151842     PISSN: 09066705     EISSN: 16000625     Source Type: Journal    
DOI: 10.1111/j.1600-0625.2008.00736.x     Document Type: Article

References (61)

1. Lippens S, Denecker G, Ovaere P, Vandenabeele P, Declercq W. Death penalty for keratinocytes: Apoptosis versus cornification. Cell Death Differ 2005: 12 (Suppl 2): 1497-1508.
2. Elias P M. Epidermal lipids, barrier function, and desquamation. J Invest Dermatol 1983: 80(Suppl): 44s-49s.
3. Wertz P W. Lipids and barrier function of the skin. Acta Derm Venereol Suppl (Stockh) 2000: 208: 7-11.
4. Schurer N Y, Plewig G, Elias P M. Stratum corneum lipid function. Dermatologica 1991: 183: 77-94.
5. Schurer N Y, Elias P M. The biochemistry and function of stratum corneum lipids. Adv Lipid Res 1991: 24: 27-56.
6. Wertz P W, van den B B. The physical, chemical and functional properties of lipids in the skin and other biological barriers. Chem Phys Lipids 1998: 91: 85-96.
7. Elias P M. Epidermal barrier function: Intercellular lamellar lipid structures, origin, composition and metabolism. J Control Release 1991: 15: 199-208.
8. Tachi M, Iwamori M. Mass spectrometric characterization of cholesterol esters and wax esters in epidermis of fetal, adult and keloidal human skin. Exp Dermatol 2008: 17: 318-323.
9. Robson K J, Stewart M E, Michelsen S, Lazo N D, Downing D T. 6-hydroxy-4-sphingenine in human epidermal ceramides. J Lipid Res 1994: 35: 2060-2068.
10. Chopart A. A new type of covalently bound ceramide in human epithelia. In: Marks R, Leveque JL, Voegeli R eds. The Essential Stratum Corneum. London: Martin Dunitz, 2002: 331-334.
11. Swartzendruber D C, Wertz P W, Madison K C, Downing D T. Evidence that the corneocyte has a chemically bound lipid envelope. J Invest Dermatol 1987: 88: 709-713.
12. Behne M, Uchida Y, Seki T, de Montellano P O, Elias P M, Holleran W M. Omega-hydroxyceramides are required for corneocyte lipid envelope (CLE) formation and normal epidermal permeability barrier function. J Invest Dermatol 2000: 114: 185-192.
13. Watson A L, Fray T R, Bailey J, Baker C B, Beyer S A, Markwell P J. Dietary constituents are able to play a beneficial role in canine epidermal barrier function. Exp Dermatol 2006: 15: 74-81.
14. Wakita H, Matsushita K, Nishimura K, Tokura Y, Furukawa F, Takigawa M. Sphingosylphosphorylcholine stimulates proliferation and upregulates cell surface-associated plasminogen activator activity in cultured human keratinocytes. J Invest Dermatol 1998: 110: 253-258.
15. Geilen C C, Wieder T, Orfanos C E. Ceramide signalling: Regulatory role in cell proliferation, differentiation and apoptosis in human epidermis. Arch Dermatol Res 1997: 289: 559-566.
16. Geilen C C, Barz S, Bektas M. Sphingolipid signaling in epidermal homeostasis. Current knowledge and new therapeutic approaches in dermatology. Skin Pharmacol Appl Skin Physiol 2001: 14: 261-271.
17. Jung E M, Griner R D, Mann-Blakeney R, Bollag W B. A potential role for ceramide in the regulation of mouse epidermal keratinocyte proliferation and differentiation. J Invest Dermatol 1998: 110: 318-323.
18. Kim S, Hong I, Hwang J S et al. Phytosphingosine stimulates the differentiation of human keratinocytes and inhibits TPA-induced inflammatory epidermal hyperplasia in hairless mouse skin. Mol Med 2006: 12: 17-24.
19. Pillai S, Bikle D D, Hincenbergs M, Elias P M. Biochemical and morphological characterization of growth and differentiation of normal human neonatal keratinocytes in a serum-free medium. J Cell Physiol 1988: 134: 229-237.
20. Hennings H, Michael D, Cheng C, Steinert P, Holbrook K, Yuspa S H. Calcium regulation of growth and differentiation of mouse epidermal cells in culture. Cell 1980: 19: 245-254.
21. Smith E L, Walworth N C, Holick M F. Effect of 1 alpha,25-dihydroxyvitamin D3 on the morphologic and biochemical differentiation of cultured human epidermal keratinocytes grown in serum-free conditions. J Invest Dermatol 1986: 86: 709-714.
22. Poumay Y, Pittelkow M R. Cell density and culture factors regulate keratinocyte commitment to differentiation and expression of suprabasal K1/K10 keratins. J Invest Dermatol 1995: 104: 271-276.
23. Doucet O, Robert C, Zastrow L. Use of a serum-free reconstituted epidermis as a skin pharmacological model. Toxicology in Vitro 1996: 10: 305-313.
24. de Brugerolle D F, Picarles V, Chibout S et al. Predictivity of an in vitro model for acute and chronic skin irritation (SkinEthic) applied to the testing of topical vehicles. Cell Biol Toxicol 1999: 15: 121-135.
25. Gysler A, Kleuser B, Sippl W et al. Skin penetration and metabolism of topical glucocorticoids in reconstructed epidermis and in excised human skin. Pharm Res 1999: 16: 1386-1391.
26. Lehmann B, Querings K, Reichrath J. Vitamin D and skin: New aspects for dermatology. Exp Dermatol 2004: 13(Suppl 4): 11-15.
27. Hanifin J M, Stevens V, Sheth P, Breneman D. Novel treatment of chronic severe hand dermatitis with bexarotene gel. Br J Dermatol 2004: 150: 545-553.
28. Thiers B H. The use of topical calcipotriene/calcipotriol in conditions other than plaque-type psoriasis. J Am Acad Dermatol 1997: 37: S69-S71.
29. Katayama I, Miyazaki Y, Nishioka K. Topical vitamin D3 (tacalcitol) for steroid-resistant prurigo. Br J Dermatol 1996: 135: 237-240.
30. Sabat R, Philipp S, Hoflich C et al. Immunopathogenesis of psoriasis. Exp Dermatol 2007: 16: 779-798.
31. Holleran W M, Takagi Y, Uchida Y. Epidermal sphingolipids: Metabolism, function, and roles in skin disorders. FEBS Lett 2006: 580: 5456-5466.
32. Imokawa G, Abe A, Jin K, Higaki Y, Kawashima M, Hidano A. Decreased level of ceramides in stratum corneum of atopic dermatitis: An etiologic factor in atopic dry skin? J Invest Dermatol 1991: 96: 523-526.
33. Attar P S, Wertz P W, McArthur M, Imakado S, Bickenbach J R, Roop D R. Inhibition of retinoid signaling in transgenic mice alters lipid processing and disrupts epidermal barrier function. Mol Endocrinol 1997: 11: 792-800.
34. Brod J, Bavelier E, Justine P, Weerheim A, Ponec M. Acylceramides and lanosterol-lipid markers of terminal differentiation in cultured human keratinocytes: Modulating effect of retinoic acid. In Vitro Cell Dev Biol 1991: 27A: 163-168.
35. Manggau M, Kim DS, Ruwisch L et al. 1alpha,25-dihydroxyvitamin D3 protects human keratinocytes from apoptosis by the formation of sphingosine-1-phosphate. J Invest Dermatol 2001: 117: 1241-1249.
36. Geilen C C, Bektas M, Wieder T, Kodelja V, Goerdt S, Orfanos CE 1alpha,25-dihydroxyvitamin D3 induces sphingomyelin hydrolysis in HaCaT cells via tumor necrosis factor alpha. J Biol Chem 1997: 272: 8997-9001.
37. Sun W, Xu R, Hu W et al. Upregulation of the human alkaline ceramidase 1 and acid ceramidase mediates calcium-induced differentiation of epidermal keratinocytes. J Invest Dermatol 2008: 128: 389-397.
38. Man M Q, Feingold K R, Elias P M. Exogenous lipids influence permeability barrier recovery in acetone-treated murine skin. Arch Dermatol 1993: 129: 728-738.
39. Spiegel S, Milstien S. Sphingolipid metabolites: Members of a new class of lipid second messengers. J Membr Biol 1995: 146: 225-237.
40. Gomez-Munoz A, Frago L M, Alvarez L, Varela-Nieto I. Stimulation of DNA synthesis by natural ceramide 1-phosphate. Biochem J 1997: 325 (Pt 2): 435-440.
41. Xu J, Zhang Q X, Pilquil C, Berthiaume L G, Waggoner D W, Brindley D N. Lipid phosphate phosphatase-1 in the regulation of lysophosphatidate signaling. Ann N Y Acad Sci 2000: 905: 81-90.
42. Wakita H, Tokura Y, Yagi H, Nishimura K, Furukawa F, Takigawa M. Keratinocyte differentiation is induced by cell-permeant ceramides and its proliferation is promoted by sphingosine. Arch Dermatol Res 1994: 286: 350-354.
43. Di Nardo A, Benassi L, Magnoni C, Cossarizza A, Seidenari S, Giannetti A. Ceramide 2 (N-acetyl sphingosine) is associated with reduction in Bcl-2 protein levels by Western blotting and with apoptosis in cultured human keratinocytes. Br J Dermatol 2000: 143: 491-497.
44. Takeda S, Mitsutake S, Tsuji K, Igarashi Y. Apoptosis occurs via the ceramide recycling pathway in human HaCaT keratinocytes. J Biochem (Tokyo) 2006: 139: 255-262.
45. Bektas M, Dullin Y, Wieder T et al. Induction of apoptosis by synthetic ceramide analogues in the human keratinocyte cell line HaCaT. Exp Dermatol 1998: 7: 342-349.
46. Babson A L, Phillips G E. A rapid colorimetric assay for serum lactic dehydrogenase. Clin Chim Acta 1965: 12: 210-215.
47. Bradford M M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976: 72: 248-254.
48. Langmann T, Moehle C, Mauerer R et al. Loss of detoxification in inflammatory bowel disease: Dysregulation of pregnane X receptor target genes. Gastroenterology 2004: 127: 26-40.
49. Chen X, Wu J M, Hornischer K, Kel A, Wingender E. TiProD: The Tissue-specific Promoter Database. Nucleic Acids Res 2006: 34: D104-D107.
50. Matys V, Kel-Margoulis O V, Fricke E et al. TRANSFAC and its module TRANSCompel: Transcriptional gene regulation in eukaryotes. Nucleic Acids Res 2006: 34: D108-D110.
51. Kel O V, Romaschenko A G, Kel A E, Wingender E, Kolchanov N A. A compilation of composite regulatory elements affecting gene transcription in vertebrates. Nucleic Acids Res 1995: 23: 4097-4103.
52. Kel-Margoulis O V, Kel A E, Reuter I, Deineko I V, Wingender E. TRANSCompel: A database on composite regulatory elements in eukaryotic genes. Nucleic Acids Res 2002: 30: 332-334.
53. Kel A E, Gossling E, Reuter I, Cheremushkin E, Kel-Margoulis O V, Wingender E. MATCH: A tool for searching transcription factor binding sites in DNA sequences. Nucleic Acids Res 2003: 31: 3576-3579.
54. Kel A, Konovalova T, Waleev T, Cheremushkin E, Kel-Margoulis O, Wingender E. Composite Module Analyst: A fitness-based tool for identification of transcription factor binding site combinations. Bioinformatics 2006: 22: 1190-1197.
55. Waleev T, Shtokalo D, Konovalova T et al. Composite Module Analyst: identification of transcription factor binding site combinations using genetic algorithm. Nucleic Acids Res 2006: 34: W541-W545.
56. Kel A E, Kel-Margoulis O V, Farnham P J, Bartley S M, Wingender E, Zhang M Q. Computer-assisted identification of cell cycle-related genes: New targets for E2F transcription factors. J Mol Biol 2001: 309: 99-120.
57. Kel A, Reymann S, Matys V, Nettesheim P, Wingender E, Borlak J. A novel computational approach for the prediction of networked transcription factors of aryl hydrocarbon-receptor-regulated genes. Mol Pharmacol 2004: 66: 1557-1572.
58. Honma M, Stubbs M, Collins I, Workman P, Aherne W, Watt F M. Identification of novel keratinocyte differentiation modulating compounds by high-throughput screening. J Biomol Screen 2006: 11: 977-984.
59. Seo E Y, Lee W H, Piao Y J et al. Identification of calcium-inducible genes in primary keratinocytes using suppression-subtractive hybridization. Exp Dermatol 2004: 13: 163-169.
60. Allombert-Blaise C, Tamiji S, Mortier L et al. Terminal differentiation of human epidermal keratinocytes involves mitochondria- and caspase-dependent cell death pathway. Cell Death Differ 2003: 10: 850-852.
61. Farwick M, Watson R E B, Rawlings A V et al. Salicyloyl-phytosphingosine: A novel agent for the repair of photoaged skin. Int J Cosmet Sci 2007: 29: 319-329.