Development of small-molecule inhibitors of sphingosine-1-phosphate signaling

Pharmacology and Therapeutics

Volumn 132, Issue 3, 2011, Pages 352-360

  Edmonds, Yvette ^a   Milstien, Sheldon ^a   Spiegel, Sarah ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Antagonists; Asthma; Cancer; Inflammatory bowel disease; Inhibitors; Multiple sclerosis; Rheumatoid arthritis; Sepsis; Sphingosine kinase; Sphingosine 1 phosphate

Indexed keywords

1 [4 (1,2,3,4 TETRAHYDROXYBUTYL) 1H IMIDAZOL 2 YL]ETHANONE OXIME; 2 (4 HYDROXYANILINO) 4 (4 CHLOROPHENYL)THIAZOLE; 2,2 DIMETHYL(1 OXO 2 HEXADECYN 1 YL) 1,1 DIMETHYLETHYL ESTER 3 OXAZOLIDINECARBOXYLIC ACID; 3 (4 CHLOROPHENYL)ADAMANTANE 1 CARBOXYLIC ACID(PYRIDIN 4 YLMETHYL)AMIDE; 4 [4 (4 CHLOROPHENYL)THIAZOL 2 YLAMINO]PHENOL; ABC 294640; CERAMIDE; CISPLATIN; FINGOLIMOD; GEMCITABINE; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE 2; IMATINIB; LX 2931; METHOTREXATE; N METHYL 5 (4' PENTYLPHENYL) 2 AMINOPENT 4 ENE 1,3 DIOL; N,N DIMETHYLSPHINGOSINE; PHOSPHOTRANSFERASE INHIBITOR; RESVERATROL; SAFINGOL; SK1 I; SORAFENIB; SPHINGOSINE; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE KINASE 1; SPHINGOSINE KINASE 2; TUMOR NECROSIS FACTOR RECEPTOR ASSOCIATED FACTOR 2; UBIQUITIN PROTEIN LIGASE E3; UNCLASSIFIED DRUG;

ADJUVANT THERAPY; APOPTOSIS; ARTICLE; ASTHMA; ASTROCYTOSIS; AUTOCRINE EFFECT; BINDING AFFINITY; BREAST CANCER; CANCER CELL; CANCER GROWTH; CANCER INVASION; CANCER SURVIVAL; CELL GROWTH; CELL PROLIFERATION; CELL SURVIVAL; CHRONIC MYELOID LEUKEMIA; COLON CANCER; CYTOTOXICITY; DRUG EFFICACY; DRUG POTENTIATION; DRUG TARGETING; ENTERITIS; GLIOBLASTOMA; GROWTH DISORDER; HEAD AND NECK CANCER; HUMAN; KIDNEY CANCER; LEUKEMIA; LIVER CANCER; METASTASIS; MULTIPLE SCLEROSIS; NONHUMAN; OVARY CANCER; PANCREAS CANCER; PARACRINE SIGNALING; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN DEGRADATION; PROTEIN EXPRESSION; PROTEIN METABOLISM; RHEUMATOID ARTHRITIS; SEPSIS; SIGNAL TRANSDUCTION; SKIN CANCER; SMOOTH MUSCLE CONTRACTION; SOLID TUMOR; TRANSCRIPTION REGULATION; UPREGULATION; VASCULARIZATION;

ANIMALS; CLINICAL TRIALS, PHASE I AS TOPIC; CLINICAL TRIALS, PHASE II AS TOPIC; DRUG EVALUATION, PRECLINICAL; HUMANS; LYSOPHOSPHOLIPIDS; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); PROTEIN KINASE INHIBITORS; RECEPTORS, LYSOSPHINGOLIPID; SIGNAL TRANSDUCTION; SPHINGOSINE;

EID: 80054999107     PISSN: 01637258     EISSN: 1879016X     Source Type: Journal    
DOI: 10.1016/j.pharmthera.2011.08.004     Document Type: Article

References (56)

1. S.E. Alvarez, K.B. Harikumar, N.C. Hait, J. Allegood, G.M. Strub, E.Y. Kim, M. Maceyka, H. Jiang, C. Luo, T. Kordula, S. Milstien, and S. Spiegel Sphingosine-1-phosphate is a missing cofactor for the E3 ubiquitin ligase TRAF2 Nature 465 2010 1084 1088
2. S.E. Alvarez, S. Milstien, and S. Spiegel Autocrine and paracrine roles of sphingosine-1-phosphate Trends Endocrinol Metab 18 2007 300 307 (Pubitemid 47531961)
3. J.W. Antoon, M.D. White, W.D. Meacham, E.M. Slaughter, S.E. Muir, S. Elliott, L.V. Rhodes, H.B. Ashe, T.E. Wiese, C.D. Smith, M.E. Burow, and B.S. Beckman Antiestrogenic effects of the novel sphingosine kinase-2 inhibitor ABC294640 Endocrinology 151 2010 5124 5135
4. J.T. Bagdanoff, M.S. Donoviel, A. Nouraldeen, M. Carlsen, T.C. Jessop, J. Tarver, S. Aleem, L. Dong, H. Zhang, L. Boteju, J. Hazelwood, J. Yan, M. Bednarz, S. Layek, I.B. Owusu, S. Gopinathan, L. Moran, Z. Lai, J. Kramer, and S.D. Kimball Inhibition of sphingosine 1-phosphate lyase for the treatment of rheumatoid arthritis: discovery of (E)-1-(4-((1R,2S,3R)-1,2,3,4- tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone oxime (LX2931) and (1R,2S,3R)-1-(2-(isoxazol-3-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol (LX2932) J Med Chem 53 2010 8650 8662
5. T.H. Beckham, S. Elojeimy, J.C. Cheng, L.S. Turner, S.R. Hoffman, J.S. Norris, and X. Liu Targeting sphingolipid metabolism in head and neck cancer: rational therapeutic potentials Expert Opin Ther Targets 14 2010 529 539
6. V. Beljanski, C. Knaak, Y. Zhuang, and C.D. Smith Combined anticancer effects of sphingosine kinase inhibitors and sorafenib Invest New Drugs 29 2011 132 142
7. E.V. Berdyshev, I. Gorshkova, A. Skobeleva, R. Bittman, X. Lu, S.M. Dudek, T. Mirzapoiazova, J.G. Garcia, and V. Natarajan FTY720 inhibits ceramide synthases and up-regulates dihydrosphingosine 1-phosphate formation in human lung endothelial cells J Biol Chem 284 2009 5467 5477
8. V. Brinkmann FTY720 (fingolimod) in multiple sclerosis: therapeutic effects in the immune and the central nervous system Br J Pharmacol 158 2009 1173 1182
9. Y. Chiba, H. Takeuchi, H. Sakai, and M. Misawa SKI-II, an inhibitor of sphingosine kinase, ameliorates antigen-induced bronchial smooth muscle hyperresponsiveness, but not airway inflammation, in mice J Pharmacol Sci 114 2010 304 310
10. Y. Chiba, H. Takeuchi, H. Sakai, and M. Misawa Sphingosine-1-phosphate augments agonist-mediated contraction in the bronchial smooth muscles of mice Pharmacol Rep 63 2011 544 547
11. J.W. Choi, S.E. Gardell, D.R. Herr, R. Rivera, C.W. Lee, K. Noguchi, S.T. Teo, Y.C. Yung, M. Lu, G. Kennedy, and J. Chun FTY720 (fingolimod) efficacy in an animal model of multiple sclerosis requires astrocyte sphingosine 1-phosphate receptor 1 (S1P1) modulation Proc Natl Acad Sci USA 108 2011 751 756
12. A.A. Chumanevich, D. Poudyal, X. Cui, T. Davis, P.A. Wood, C.D. Smith, and L.J. Hofseth Suppression of colitis-driven colon cancer in mice by a novel small molecule inhibitor of sphingosine kinase Carcinogenesis 31 2010 1787 1793
13. S. Das, and D.K. Das Anti-inflammatory responses of resveratrol Inflamm Allergy Drug Targets 6 2007 168 173 (Pubitemid 47455785)
14. M.A. Dickson, R.D. Carvajal, A.H. Merrill Jr., M. Gonen, L.M. Cane, and G.K. Schwartz A phase I clinical trial of safingol in combination with cisplatin in advanced solid tumors Clin Cancer Res 17 2011 2484 2492
15. L.R. Fitzpatrick, C. Green, E.E. Frauenhoffer, K.J. French, Y. Zhuang, L.W. Maines, J.J. Upson, E. Paul, H. Donahue, T.J. Mosher, and C.D. Smith Attenuation of arthritis in rodents by a novel orally-available inhibitor of sphingosine kinase Inflammopharmacology 19 2011 75 87
16. K.J. French, Y. Zhuang, L.W. Maines, P. Gao, W. Wang, V. Beljanski, J.J. Upson, C.L. Green, S.N. Keller, and C.D. Smith Pharmacology and antitumor activity of ABC294640, a selective inhibitor of sphingosine kinase-2 J Pharmacol Exp Ther 333 2010 129 139
17. H. Fyrst, and J.D. Saba An update on sphingosine-1-phosphate and other sphingolipid mediators Nat Chem Biol 6 2010 489 497
18. M.H. Graler Targeting sphingosine 1-phosphate (S1P) levels and S1P receptor functions for therapeutic immune interventions Cell Physiol Biochem 26 2010 79 86
19. J. Guillermet-Guibert, L. Davenne, D. Pchejetski, N. Saint-Laurent, L. Brizuela, C. Guilbeau-Frugier, M.B. Delisle, O. Cuvillier, C. Susini, and C. Bousquet Targeting the sphingolipid metabolism to defeat pancreatic cancer cell resistance to the chemotherapeutic gemcitabine drug Mol Cancer Ther 8 2009 809 820
20. N.C. Hait, J. Allegood, M. Maceyka, G.M. Strub, K.B. Harikumar, S.K. Singh, C. Luo, R. Marmorstein, T. Kordula, S. Milstien, and S. Spiegel Regulation of histone acetylation in the nucleus by sphingosine-1-phosphate Science 325 2009 1254 1257
21. M. Idzko, H. Hammad, M. van Nimwegen, M. Kool, T. Muller, T. Soullie, M.A. Willart, D. Hijdra, H.C. Hoogsteden, and B.N. Lambrecht Local application of FTY720 to the lung abrogates experimental asthma by altering dendritic cell function J Clin Invest 116 2006 2935 2944 (Pubitemid 44684478)
22. P.D. Issuree, P.N. Pushparaj, S. Pervaiz, and A.J. Melendez Resveratrol attenuates C5a-induced inflammatory responses in vitro and in vivo by inhibiting phospholipase D and sphingosine kinase activities FASEB J 23 2009 2412 2424
23. P.S. Jolly, M. Bektas, A. Olivera, C. Gonzalez-Espinosa, R.L. Proia, J. Rivera, S. Milstien, and S. Spiegel Transactivation of sphingosine-1-phosphate receptors by Fc{epsilon}RI triggering is required for normal mast cell degranulation and chemotaxis J Exp Med 199 2004 959 970 (Pubitemid 38481087)
24. K. Kamada, N. Arita, T. Tsubaki, N. Takubo, T. Fujino, Y. Soga, T. Miyazaki, H. Yamamoto, and M. Nose Expression of sphingosine kinase 2 in synovial fibroblasts of rheumatoid arthritis contributing to apoptosis by a sphingosine analogue, FTY720 Pathol Int 59 2009 382 389
25. T. Kanno, T. Nishizaki, R.L. Proia, T. Kajimoto, S. Jahangeer, T. Okada, and S. Nakamura Regulation of synaptic strength by sphingosine 1-phosphate in the hippocampus Neuroscience 171 2010 973 980
26. D. Kapitonov, J.C. Allegood, C. Mitchell, N.C. Hait, J.A. Almenara, J.K. Adams, R.E. Zipkin, P. Dent, T. Kordula, S. Milstien, and S. Spiegel Targeting sphingosine kinase 1 inhibits Akt signaling, induces apoptosis, and suppresses growth of human glioblastoma cells and xenografts Cancer Res 69 2009 6915 6923
27. M. Karin The IkappaB kinase-a bridge between inflammation and cancer Cell Res 18 2008 334 342 (Pubitemid 351333897)
28. M. Kim, S.W. Park, V.D. D'Agati, and H.T. Lee Isoflurane activates intestinal sphingosine kinase to protect against bilateral nephrectomy-induced liver and intestine dysfunction Am J Physiol Renal Physiol 300 2011 F167 F176
29. M. Kitano, T. Hla, M. Sekiguchi, Y. Kawahito, R. Yoshimura, K. Miyazawa, T. Iwasaki, and H. Sano Sphingosine 1-phosphate/sphingosine 1-phosphate receptor 1 signaling in rheumatoid synovium: regulation of synovial proliferation and inflammatory gene expression Arthritis Rheum 54 2006 742 753
30. M. Kitano, T. Hla, M. Sekiguchi, Y. Kawahito, R. Yoshimura, K. Miyazawa, T. Iwasaki, H. Sano, J.D. Saba, and Y.Y. Tam Sphingosine 1-phosphate/sphingosine 1-phosphate receptor 1 signaling in rheumatoid synovium: regulation of synovial proliferation and inflammatory gene expression Arthritis Rheum 54 2006 742 753
31. W.Q. Lai, A.W. Irwan, H.H. Goh, H.S. Howe, D.T. Yu, R. Valle-Onate, I.B. McInnes, A.J. Melendez, and B.P. Leung Anti-inflammatory effects of sphingosine kinase modulation in inflammatory arthritis J Immunol 181 2008 8010 8017
32. E. Langholz, P. Munkholm, M. Davidsen, and V. Binder Colorectal cancer risk and mortality in patients with ulcerative colitis Gastroenterology 103 1992 1444 1451
33. C. Loveridge, F. Tonelli, T. Leclercq, K.G. Lim, J.S. Long, E. Berdyshev, R.J. Tate, V. Natarajan, S.M. Pitson, N.J. Pyne, and S. Pyne The sphingosine kinase 1 inhibitor 2-(p-hydroxyanilino)-4-(p-chlorophenyl)thiazole induces proteasomal degradation of sphingosine kinase 1 in mammalian cells J Biol Chem 285 2010 38841 38852
34. L.W. Maines, L.R. Fitzpatrick, C.L. Green, Y. Zhuang, and C.D. Smith Efficacy of a novel sphingosine kinase inhibitor in experimental Crohn's disease Inflammopharmacology 18 2010 73 85
35. E. Masini, L. Giannini, S. Nistri, L. Cinci, R. Mastroianni, W. Xu, S.A. Comhair, D. Li, S. Cuzzocrea, G.M. Matuschak, and D. Salvemini Ceramide: a key signaling molecule in a guinea pig model of allergic asthmatic response and airway inflammation J Pharmacol Exp Ther 324 2008 548 557 (Pubitemid 351185855)
36. M. Mehling, V. Brinkmann, J. Antel, A. Bar-Or, N. Goebels, C. Vedrine, C. Kristofic, J. Kuhle, R.L. Lindberg, and L. Kappos FTY720 therapy exerts differential effects on T cell subsets in multiple sclerosis Neurology 71 2008 1261 1267
37. T. Nishiuma, Y. Nishimura, T. Okada, E. Kuramoto, Y. Kotani, S. Jahangeer, and S. Nakamura Inhalation of sphingosine kinase inhibitor attenuates airway inflammation in asthmatic mouse model Am J Physiol Lung Cell Mol Physiol 294 2008 L1085 L1093
38. S.W. Paugh, B.S. Paugh, M. Rahmani, D. Kapitonov, J.A. Almenara, T. Kordula, S. Milstien, J.K. Adams, R.E. Zipkin, S. Grant, and S. Spiegel A selective sphingosine kinase 1 inhibitor integrates multiple molecular therapeutic targets in human leukemia Blood 112 2008 1382 1391
39. D. Pchejetski, T. Bohler, L. Brizuela, L. Sauer, N. Doumerc, M. Golzio, V. Salunkhe, J. Teissie, B. Malavaud, J. Waxman, and O. Cuvillier FTY720 (fingolimod) sensitizes prostate cancer cells to radiotherapy by inhibition of sphingosine kinase-1 Cancer Res 70 2010 8651 8661
40. P. Puneet, C.T. Yap, L. Wong, Y. Lam, D.R. Koh, S. Moochhala, J. Pfeilschifter, A. Huwiler, and A.J. Melendez SphK1 regulates proinflammatory responses associated with endotoxin and polymicrobial sepsis Science 328 2010 1290 1294
41. N.J. Pyne, and S. Pyne Sphingosine 1-phosphate and cancer Nat Rev Cancer 10 2010 489 503
42. S. Ren, C. Xin, J. Pfeilschifter, and A. Huwiler A novel mode of action of the putative sphingosine kinase inhibitor 2-(p-hydroxyanilino)-4-(p- chlorophenyl) thiazole (SKI II): induction of lysosomal sphingosine kinase 1 degradation Cell Physiol Biochem 26 2010 97 104
43. C. Ricci, F. Onida, F. Servida, F. Radaelli, G. Saporiti, K. Todoerti, G.L. Deliliers, and R. Ghidoni In vitro anti-leukaemia activity of sphingosine kinase inhibitor Br J Haematol 144 2009 350 357
44. S.R. Schwab, J.P. Pereira, M. Matloubian, Y. Xu, Y. Huang, and J.G. Cyster Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients Science 309 2005 1735 1739 (Pubitemid 41285945)
45. D. Shida, K. Takabe, D. Kapitonov, S. Milstien, and S. Spiegel Targeting SphK1 as a new strategy against cancer Curr Drug Targets 9 2008 662 673
46. A.J. Snider, K.A. Orr Gandy, and L.M. Obeid Sphingosine kinase: role in regulation of bioactive sphingolipid mediators in inflammation Biochimie 92 2010 707 715
47. S. Sobue, T. Iwasaki, C. Sugisaki, K. Nagata, R. Kikuchi, M. Murakami, A. Takagi, T. Kojima, Y. Banno, Y. Akao, Y. Nozawa, R. Kannagi, M. Suzuki, A. Abe, T. Naoe, and T. Murate Quantitative RT-PCR analysis of sphingolipid metabolic enzymes in acute leukemia and myelodysplastic syndromes Leukemia 20 2006 2042 2046 (Pubitemid 44614898)
48. S. Spiegel, and S. Milstien Sphingosine-1-phosphate: an enigmatic signalling lipid Nat Rev Mol Cell Biol 4 2003 397 407 (Pubitemid 36565571)
49. S. Spiegel, and S. Milstien The outs and the ins of sphingosine-1- phosphate in immunity Nat Rev Immunol 11 2011 403 415
50. Stevenson C. E., Takabe K., Nagahashi M., Milstien S., & Spiegel S. (in press). Targeting sphingosine-1-phosphate in hematologic malignancies. Anticancer Agents Med Chem.
51. G.M. Strub, M. Paillard, J. Liang, L. Gomez, J.C. Allegood, N.C. Hait, M. Maceyka, M.M. Price, Q. Chen, D.C. Simpson, T. Kordula, S. Milstien, E.J. Lesnefsky, and S. Spiegel Sphingosine-1-phosphate produced by sphingosine kinase 2 in mitochondria interacts with prohibitin 2 to regulate complex IV assembly and respiration FASEB J 25 2011 600 612
52. N. Takasugi, T. Sasaki, K. Suzuki, S. Osawa, H. Isshiki, Y. Hori, N. Shimada, T. Higo, S. Yokoshima, T. Fukuyama, V.M. Lee, J.Q. Trojanowski, T. Tomita, and T. Iwatsubo BACE1 activity is modulated by cell-associated sphingosine-1-phosphate J Neurosci 31 2011 6850 6857
53. S. Tsunemi, T. Iwasaki, S. Kitano, T. Imado, K. Miyazawa, and H. Sano Effects of the novel immunosuppressant FTY720 in a murine rheumatoid arthritis model Clin Immunol 136 2010 197 204
54. J.R. Van Brocklyn, C.A. Jackson, D.K. Pearl, M.S. Kotur, P.J. Snyder, and T.W. Prior Sphingosine kinase-1 expression correlates with poor survival of patients with glioblastoma multiforme: roles of sphingosine kinase isoforms in growth of glioblastoma cell lines J Neuropathol Exp Neurol 64 2005 695 705 (Pubitemid 41177111)
55. i-coupled orphan receptor edg-1 and intracellular to regulate proliferation and survival J Cell Biol 142 1998 229 240 (Pubitemid 28341153)
56. H. Zhang, N.N. Desai, A. Olivera, T. Seki, G. Brooker, and S. Spiegel Sphingosine-1-phosphate, a novel lipid, involved in cellular proliferation J Cell Biol 114 1991 155 167 (Pubitemid 21909788)