Sphingolipids as therapeutics

Pharmacological Research

Volumn 47, Issue 5, 2003, Pages 365-371

  Kester, Mark ^a   Kolesnick, Richard ^b  

^a PENN STATE COLLEGE OF MEDICINE   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

Cancer; Cardiovascular; Ceramide; Sphingolipids; Sphingosine; Therapeutics

Indexed keywords

2 DECANOYLAMINO 3 MORPHOLINO 1 PHENYL 1 PROPANOL; ANTHRACYCLINE; ANTIESTROGEN; ANTIFUNGAL AGENT; CERAMIDASE INHIBITOR; CERAMIDE; CERAMIDE GLUCOSYLTRANSFERASE; COMPLEMENTARY DNA; DOXORUBICIN; FENRETINIDE; FINGOLIMOD; HYDROLASE INHIBITOR; INOSITOLPHOSPHORYLCERAMIDE INHIBITOR; OLIGONUCLEOTIDE; PACLITAXEL; PHOSPHOTRANSFERASE INHIBITOR; RETINOID; SAFINGOL; SPHINGOLIPID; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE DERIVATIVE; SPHINGOSINE KINASE; SPHINGOSINE KINASE INHIBITOR; TAMOXIFEN; TAXANE DERIVATIVE; TRIMETHYLSPHINGOSINE; UNCLASSIFIED DRUG; VINCA ALKALOID;

ANGIOGENESIS; APOPTOSIS; AUTOIMMUNE DISEASE; BIOAVAILABILITY; BRAIN ISCHEMIA; CANCER CELL; CANCER CELL CULTURE; CANCER CHEMOTHERAPY; CANCER RADIOTHERAPY; CANCER RESISTANCE; CELL MEMBRANE PERMEABILITY; CHEMICAL ANALYSIS; CHINESE MEDICINE; CLINICAL TRIAL; DRUG DELIVERY SYSTEM; DRUG EFFECT; DRUG MECHANISM; DRUG TARGETING; ENZYME REGULATION; ETHNOPHARMACOLOGY; FERTILITY; HUMAN; LIPID METABOLISM; LYMPHOCYTOPENIA; METABOLITE; MOLECULAR CLONING; MOLECULAR MECHANICS; MULTIPLE SCLEROSIS; MYCOSIS; NONHUMAN; PRIORITY JOURNAL; RADIOSENSITIVITY; REPERFUSION INJURY; REVIEW; SIGNAL TRANSDUCTION; STENOSIS;

EID: 0037401646     PISSN: 10436618     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1043-6618(03)00048-3     Document Type: Review

References (83)

1. Hannun Y.A., Luberto C., Argraves K.M. Enzymes of sphingolipid metabolism: from modular to integrative signaling. Biochemistry. 40(16):2001;4893-4903.
2. Merrill A.H. Jr., Sullards M.C., Wang E., Voss K.A., Riley R.T. Sphingolipid metabolism: roles in signal transduction and disruption by fumonisins. Environ. Health Perspect. 109(Suppl 2):2001;283-289.
3. Kolesnick R.N., Goni F.M., Alonso A. Compartmentalization of ceramide signaling: physical foundations and biological effects. J. Cell Physiol. 184(3):2000;285-300.
4. Venkataraman K., Futerman A.H. Ceramide as a second messenger: sticky solutions to sticky problems. Trends Cell Biol. 10(10):2000;408-412.
5. Dickson R.C., Lester R.L. Yeast sphingolipids. Biochim. Biophys. Acta. 1426(2):1999;347-357.
6. Spiegel S., Milstien S. Sphingosine 1-phosphate, a key cell signaling molecule. J. Biol. Chem. 277(29):2002;25851-25854.
7. Hannun Y.A., Obeid L.M. The Ceramide-centric universe of lipid-mediated cell regulation: stress encounters of the lipid kind. J. Biol. Chem. 277(29):2002;25847-25850.
8. Spiegel S., Milstien S. Sphingosine-1-phosphate: signaling inside and out. FEBS Lett. 476(1/2):2000;55-57.
9. Senchenkov A., Litvak D.A., Cabot M.C. Targeting ceramide metabolism - a strategy for overcoming drug resistance. J. Natl. Cancer Inst. 93(5):2001;347-357.
10. Ogretmen B., Hannun Y.A. Updates on functions of ceramide in chemotherapy-induced cell death and in multidrug resistance. Drug Resist. Updat. 4(6):2001;368-377.
11. Lucci A., Han T.Y., Liu Y.Y., Giuliano A.E., Cabot M.C. Modification of ceramide metabolism increases cancer cell sensitivity to cytotoxics. Int. J. Oncol. 15(3):1999;541-546.
12. Cabot M.C., Giuliano A.E., Han T.Y., Liu Y.Y. SDZ PSC 833, the cyclosporine A analogue and multidrug resistance modulator, activates ceramide synthesis and increases vinblastine sensitivity in drug-sensitive and drug-resistant cancer cells. Cancer Res. 59(4):1999;880-885.
13. Cabot M.C., Giuliano A.E., Volner A., Han T.Y. Tamoxifen retards glycosphingolipid metabolism in human cancer cells. FEBS Lett. 394(2):1996;129-131.
14. Lavie Y., Cao H., Volner A.et al. Agents that reverse multidrug resistance, tamoxifen, verapamil, and cyclosporin A, block glycosphingolipid metabolism by inhibiting ceramide glycosylation in human cancer cells. J. Biol. Chem. 272(3):1997;1682-1687.
15. Maurer B.J., Metelitsa L.S., Seeger R.C., Cabot M.C., Reynolds C.P. Increase of ceramide and induction of mixed apoptosis/necrosis by N-(4-hydroxyphenyl)-retinamide in neuroblastoma cell lines. J. Natl. Cancer Inst. 91(13):1999;1138-1146.
16. Charles A.G., Han T.Y., Liu Y.Y., Hansen N., Giuliano A.E., Cabot M.C. Taxol-induced ceramide generation and apoptosis in human breast cancer cells. Cancer Chemother. Pharmacol. 47(5):2001;444-450.
17. Mehta S., Blackinton D., Omar I.et al. Combined cytotoxic action of paclitaxel and ceramide against the human Tu138 head and neck squamous carcinoma cell line. Cancer Chemother. Pharmacol. 46(2):2000;85-92.
18. Haimovitz-Friedman A., Kan C.C., Ehleiter D.et al. Ionizing radiation acts on cellular membranes to generate ceramide and initiate apoptosis. J. Exp. Med. 180(2):1994;525-535.
19. Michael J.M., Lavin M.F., Watters D.J. Resistance to radiation-induced apoptosis in Burkitt's lymphoma cells is associated with defective ceramide signaling. Cancer Res. 57(16):1997;3600-3605.
20. Lavie Y., Cao H., Bursten S.L., Giuliano A.E., Cabot M.C. Accumulation of glucosylceramides in multidrug-resistant cancer cells. J. Biol. Chem. 271(32):1996;19530-19536.
21. Lucci A., Cho W.I., Han T.Y., Giuliano A.E., Morton D.L., Cabot M.C. Glucosylceramide: a marker for multiple-drug resistant cancers. Anticancer Res. 18(1B):1998;475-480.
22. Spinedi A., Bartolomeo S.D., Piacentini M. Apoptosis induced by N-hexanoylsphingosine in CHP-100 cells associates with accumulation of endogenous ceramide and is potentiated by inhibition of glucocerebroside synthesis. Cell Death Differ. 5(9):1998;785-791.
23. Liu Y.Y., Han T.Y., Giuliano A.E., Cabot M.C. Ceramide glycosylation potentiates cellular multidrug resistance. Faseb J. 15(3):2001;719-730.
24. Selzner M., Bielawska A., Morse M.A.et al. Induction of apoptotic cell death and prevention of tumor growth by ceramide analogues in metastatic human colon cancer. Cancer Res. 61(3):2001;1233-1240.
25. Liu Y.Y., Han T.Y., Giuliano A.E., Ichikawa S., Hirabayashi Y., Cabot M.C. Glycosylation of ceramide potentiates cellular resistance to tumor necrosis factor-alpha-induced apoptosis. Exp. Cell Res. 252(2):1999;464-470.
26. Liu Y.Y., Han T.Y., Giuliano A.E., Cabot M.C. Expression of glucosylceramide synthase, converting ceramide to glucosylceramide, confers adriamycin resistance in human breast cancer cells. J Biol Chem. 274(2):1999;1140-1146.
27. Laethem R.M., Hannun Y.A., Jayadev S.et al. Increases in neutral, Mg2+-dependent and acidic, Mg2+-independent sphingomyelinase activities precede commitment to apoptosis and are not a consequence of caspase 3-like activity in Molt-4 cells in response to thymidylate synthase inhibition by GW1843. Blood. 91(11):1998;4350-4360.
28. Turnbull K.J., Brown B.L., Dobson P.R. Caspase-3-like activity is necessary but not sufficient for daunorubicin-induced apoptosis in Jurkat human lymphoblastic leukemia cells. Leukemia. 13(7):1999;1056-1061.
29. Mathias S., Pena L.A., Kolesnick R.N. Signal transduction of stress via ceramide. Biochem J. 335(Pt 3):1998;465-480.
30. Hong S.B., Li C.M., Rhee H.J.et al. Molecular cloning and characterization of a human cDNA and gene encoding a novel acid ceramidase-like protein. Genomics. 62(2):1999;232-241.
31. Liu H., Chakravarty D., Maceyka M., Milstien S., Spiegel S. Sphingosine kinases: a novel family of lipid kinases. Prog. Nucleic Acid Res. Mol. Biol. 71:2002;493-511.
32. El Bawab S., Roddy P., Qian T., Bielawska A., Lemasters J.J., Hannun Y.A. Molecular cloning and characterization of a human mitochondrial ceramidase. J. Biol. Chem. 275(28):2000;21508-21513.
33. Muramatsu T. Essential roles of carbohydrate signals in development, immune response and tissue functions, as revealed by gene targeting. J. Biochem. (Tokyo). 127(2):2000;171-176.
34. Horinouchi K., Erlich S., Perl D.P.et al. Acid sphingomyelinase deficient mice: a model of types A and B Niemann-Pick disease. Nat. Genet. 10(3):1995;288-293.
35. Morita Y., Perez G.I., Paris F.et al. Oocyte apoptosis is suppressed by disruption of the acid sphingomyelinase gene or by sphingosine-1-phosphate therapy. Nat. Med. 6(10):2000;1109-1114.
36. Paris F., Fuks Z., Kang A.et al. Endothelial apoptosis as the primary lesion initiating intestinal radiation damage in mice. Science. 293(5528):2001;293-297.
37. Dickson R.C., Lester R.L. Sphingolipid functions in Saccharomyces cerevisiae. Biochim. Biophys. Acta. 1583(1):2002;13-25.
38. Hla T., Lee M.J., Ancellin N., Paik J.H., Kluk M.J. Lysophospholipids-receptor revelations. Science. 294(5548):2001;1875-1878.
39. Allende M.L., Proia R.L. Sphingosine-1-phosphate receptors and the development of the vascular system. Biochim. Biophys. Acta. 1582(1-3):2002;222-227.
40. Bourbon N.A., Yun J., Kester M. Ceramide directly activates protein kinase C zeta to regulate a stress-activated protein kinase signaling complex. J. Biol. Chem. 275(45):2000;35617-35623.
41. Bourbon N.A., Yun J., Berkey D., Wang Y., Kester M. Inhibitory actions of ceramide upon PKC-epsilon/ERK interactions. Am. J. Physiol. Cell Physiol. 280(6):2001;C1403-C1411.
42. Kolesnick R. The therapeutic potential of modulating the ceramide/sphingomyelin pathway. J. Clin. Invest. 110(1):2002;3-8.
43. Prinetti A., Chigorno V., Prioni S.et al. Changes in the lipid turnover, composition, and organization, as sphingolipid-enriched membrane domains, in rat cerebellar granule cells developing in vitro. J. Biol. Chem. 276(24):2001;21136-21145.
44. Chalfant C.E., Rathman K., Pinkerman R.L.et al. De novo ceramide regulates the alternative splicing of caspase 9 and Bcl-x in A549 lung adenocarcinoma cells. Dependence on protein phosphatase-1. J. Biol. Chem. 277(15):2002;12587-12595.
45. Zhang Y., Yao B., Delikat S.et al. Kinase suppressor of ras is ceramide-activated protein kinase. Cell. 89(1):1997;63-72.
46. Huwiler A., Johansen B., Skarstad A., Pfeilschifter J. Ceramide binds to the CaLB domain of cytosolic phospholipase A2 and facilitates its membrane docking and arachidonic acid release. Faseb J. 15(1):2001;7-9.
47. Heinrich M., Wickel M., Winoto-Morbach S.et al. Ceramide as an activator lipid of cathepsin D. Adv. Exp. Med. Biol. 477:2000;305-315.
48. Muller G., Ayoub M., Storz P., Rennecke J., Fabbro D., Pfizenmaier K. PKC zeta is a molecular switch in signal transduction of TNF-alpha, bifunctionally regulated by ceramide and arachidonic acid. Embo J. 14(9):1995;1961-1969.
49. Bourbon N.A., Sandirasegarane L., Kester M. Ceramide-induced inhibition of Akt is mediated through protein kinase Czeta: implications for growth arrest. J. Biol. Chem. 277(5):2002;3286-3292.
50. Zhou M., Horita D.A., Waugh D.S., Byrd R.A., Morrison D.K. Solution structure and functional analysis of the cysteine-rich C1 domain of kinase suppressor of ras (KSR). J. Mol. Biol. 315(3):2002;435-446.
51. Kashiwagi K., Shirai Y., Kuriyama M., Sakai N., Saito N. Importance of C1B domain for lipid messenger-induced targeting of protein kinase C. J. Biol. Chem. 277(20):2002;18037-18045.
52. Charles R., Sandirasegarane L., Yun J.et al. Ceramide-coated balloon catheters limit neointimal hyperplasia after stretch injury in carotid arteries. Circ. Res. 87(4):2000;282-288.
53. Furuya K., Ginis I., Takeda H., Chen Y., Hallenbeck J.M. Cell permeable exogenous ceramide reduces infarct size in spontaneously hypertensive rats supporting in vitro studies that have implicated ceramide in induction of tolerance to ischemia. J. Cereb. Blood Flow Metab. 21(3):2001;226-232.
54. Johns D.G., Webb R.C., Charpie J.R. Impaired ceramide signalling in spontaneously hypertensive rat vascular smooth muscle: a possible mechanism for augmented cell proliferation. J. Hypertens. 19(1):2001;63-70.
55. Murohara T., Buerke M., Margiotta J.et al. Myocardial and endothelial protection by TMS in ischemia-reperfusion injury. Am. J. Physiol. 269(2 Pt 2):1995;H504-H514.
56. Liu J., Ginis I., Spatz M., Hallenbeck J.M. Hypoxic preconditioning protects cultured neurons against hypoxic stress via TNF-alpha and ceramide. Am. J. Physiol. Cell Physiol. 278(1):2000;C144-C153.
57. Yan F., Polk D.B. Kinase suppressor of ras is necessary for tumor necrosis factor alpha activation of extracellular signal-regulated kinase/mitogen-activated protein kinase in intestinal epithelial cells. Cancer Res. 61(3):2001;963-969.
58. Ginis I., Jaiswal R., Klimanis D., Liu J., Greenspon J., Hallenbeck J.M. TNF-alpha-induced tolerance to ischemic injury involves differential control of NF-kappaB transactivation: the role of NF-kappaB association with p300 adaptor. J. Cereb. Blood Flow Metab. 22(2):2002;142-152.
59. Schmelz E.M., Sullards M.C., Dillehay D.L., Merrill A.H. Jr. Colonic cell proliferation and aberrant crypt foci formation are inhibited by dairy glycosphingolipids in 1,2-dimethylhydrazine-treated CF1 mice. J. Nutr. 130(3):2000;522-527.
60. Schmelz E.M., Roberts P.C., Kustin E.M.et al. Modulation of intracellular beta-catenin localization and intestinal tumorigenesis in vivo and in vitro by sphingolipids. Cancer Res. 61(18):2001;6723-6729.
61. Vesper H., Schmelz E.M., Nikolova-Karakashian M.N., Dillehay D.L., Lynch D.V., Merrill A.H. Jr. Sphingolipids in food and the emerging importance of sphingolipids to nutrition. J. Nutr. 129(7):1999;1239-1250.
62. Heidler S.A., Radding J.A. Inositol phosphoryl transferases from human pathogenic fungi. Biochim. Biophys. Acta. 1500(1):2000;147-152.
63. Fantini J., Hammache D., Pieroni G., Yahi N. Role of glycosphingolipid microdomains in CD4-dependent HIV-1 fusion. Glycoconj. J. 17(3/4):2000;199-204.
64. Paris F., Perez G.I., Fuks Z.et al. Sphingosine 1-phosphate preserves fertility in irradiated female mice without propagating genomic damage in offspring. Nat. Med. 8(9):2002;901-902.
65. Lin X., Fuks Z., Kolesnick R. Ceramide mediates radiation-induced death of endothelium. Crit. Care Med. 28(4 Suppl):2000;N87-N93.
66. Liu Y., Wada R., Yamashita T.et al. Edg-1, the G protein-coupled receptor for sphingosine-1-phosphate, is essential for vascular maturation. J. Clin. Invest. 106(8):2000;951-961.
67. Eiden P. Ceramide-containing cream. Skin barrier is repaired. MMW Fortschr Med. 141(43):1999;56-57.
68. Wertz P.W. Lipids and barrier function of the skin. Acta Derm. Venereol. Suppl. 208:2000;7-11.
69. Uchida Y., Hara M., Nishio H.et al. Epidermal sphingomyelins are precursors for selected stratum corneum ceramides. J. Lipid Res. 41(12):2000;2071-2082.
70. Farrell A.M., Uchida Y., Nagiec M.M.et al. UVB irradiation up-regulates serine palmitoyltransferase in cultured human keratinocytes. J. Lipid Res. 39(10):1998;2031-2038.
71. De Souza PL. Sphingosine kinase. Available at: http://www.novogen.com/pharma/pharma0401.cfm?mainsection=04&subsection= 03#04 .
72. Schwartz G.K., Ward D., Saltz L.et al. A pilot clinical/pharmacological study of the protein kinase C-specific inhibitor safingol alone and in combination with doxorubicin. Clin. Cancer Res. 3(4):1997;537-543.
73. Maurer B.J., Melton L., Billups C., Cabot M.C., Reynolds C.P. Synergistic cytotoxicity in solid tumor cell lines between N-(4-hydroxyphenyl)retinamide and modulators of ceramide metabolism. J. Natl. Cancer Inst. 92(23):2000;1897-1909.
74. Wang H., Maurer B.J., Reynolds C.P., Cabot M.C. N-(4-hydroxyphenyl)retinamide elevates ceramide in neuroblastoma cell lines by coordinate activation of serine palmitoyltransferase and ceramide synthase. Cancer Res. 61(13):2001;5102-5105.
75. Mandala S., Hajdu R., Bergstrom J.et al. Alteration of lymphocyte trafficking by sphingosine-1-phosphate receptor agonists. Science. 296(5566):2002;346-349.
76. Brinkmann V., Davis M.D., Heise C.E.et al. The immune modulator FTY720 targets sphingosine 1-phosphate receptors. J. Biol. Chem. 277(24):2002;21453-21457.
77. Fujita T., Inoue K., Yamamoto S.et al. Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite. J. Antibiot. (Tokyo). 47(2):1994;208-215.
78. Brinkmann V., Pinschewer D.D., Feng L., Chen S. FTY720: altered lymphocyte traffic results in allograft protection. Transplantation. 72(5):2001;764-769.
79. Yanagawa Y., Masubuchi Y., Chiba K. FTY720, a novel immunosuppressant induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats, III. Increase in frequency of CD62L-positive T cells in Peyer's patches by FTY720-induced lymphocyte homing. Immunology. 95(4):1998;591-594.
80. Pinschewer D.D., Ochsenbein A.F., Odermatt B., Brinkmann V., Hengartner H., Zinkernagel R.M. FTY720 immunosuppression impairs effector T cell peripheral homing without affecting induction, expansion, and memory. J. Immunol. 164(11):2000;5761-5770.
81. Rios Candelore M., Wright M., Tota L.et al. Phytosphingosine 1-phosphate: a high affinity ligand for the S1P(4)/Edg-6 receptor. Biochem. Biophys. Res. Commun. 297(3):2002;600.
82. Brinkmann V., Lynch K. FTY720: targeting G-protein-coupled receptors for sphingosine 1- phosphate in transplantation and autoimmunity. Curr. Opin. Immunol. 14(5):2002;569.
83. Budde K., Schmouder R.L., Brunkhorst R.et al. First human trial of FTY720, a novel immunomodulator, in stable renal transplant patients. J. Am. Soc. Nephrol. 13(4):2002;1073-1083.