Synthesis and evaluation of sphingosine analogues as inhibitors of sphingosine kinases

Journal of Medicinal Chemistry

Volumn 52, Issue 12, 2009, Pages 3618-3626

  Wong, Lingkai ^a   Tan, Sheryl S L ^b   Lam, Yulin ^a   Melendez, Alirio J ^b,c  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^c UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CERAMIDE; N,N DIMETHYLSPHINGOSINE; PHOSPHOTRANSFERASE INHIBITOR; PROTEIN KINASE C; PROTEIN KINASE C ALPHA; SPHINGANINE; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE DERIVATIVE; SPHINGOSINE KINASE 1; SPHINGOSINE KINASE 2; TERT BUTYL 4 HEXADEC 2 YNOYL 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL PROLIFERATION; CELL STRAIN HL 60; CELL STRAIN U937; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HUMAN; HUMAN CELL; NONHUMAN; STRUCTURE ACTIVITY RELATION;

CELL LINE; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; HL-60 CELLS; HUMANS; MOLECULAR CONFORMATION; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); PROTEIN KINASE INHIBITORS; SPHINGOSINE; STEREOISOMERISM;

EID: 67549106796     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900121d     Document Type: Article

References (32)

1. Kee, T. H.; Vit, P.; Melendez, A. J. Sphingosine kinase signalling in immune cells. Clin. Exp. Pharmacol. Physiol. 2005, 32, 153-161. (Pubitemid 40387111)
2. Hannun, Y. A. The sphingomyelin cycle and the second messenger function of ceramide. J. Biol. Chem. 1994, 269, 3125-3318.
3. Spiegel, S.; Milstien, S. Sphingosine 1-phosphate, a key cell signaling molecule. J. Biol. Chem. 2002, 277, 25851-25854. (Pubitemid 34967061)
4. Haimovitz-Friedman, A.; Kolesnick, R. N.; Fuks, Z. Ceramide signaling in apoptosis. Br. Med. Bull. 1997, 53, 539-553. (Pubitemid 27397309)
5. Kondo, T.; Matsuda, T.; Kitano, T.; Takahashi, A.; Tashima, M.; Ishikura, H.; Umehara, H.; Domae, N.; Uchiyama, T.; Okazaki, T. Role of c-jun expression increased by heat shock- and ceramide-activated caspase-3 in HL-60 cell apoptosis. Possible involvement of ceramide in heat shock-induced apoptosis. J. Biol. Chem. 2000, 275, 7668-7676. (Pubitemid 30159669)
6. Takabe, K.; Paugh, S. W.; Milstien, S.; Spiegel, S. "Inside- out" signaling of sphingosine-1-phosphate: therapeutic targets. Pharmacol. Rev. 2008, 60, 181-195. (Pubitemid 351962008)
7. Kohama, T.; Olivera, A.; Edsall, L.; Nagiec, M. M.; Dickson, R.; Spiegel, S. Molecular cloning and functional characterization of murine sphingosine kinase. J. Biol. Chem. 1998, 273, 23722-23728. (Pubitemid 28435703)
8. Melendez, A. J.; Carlos-Dias, E.; Gosink, M.; Allen, J. M.; Takacs, L. Human sphingosine kinase: molecular cloning, functional characterization and tissue distribution. Gene 2000, 251, 19-26. (Pubitemid 30339413)
9. Pitson, S. M.; D'Andrea, R. J.; Vandeleur, L.; Moretti, P. A. B.; Xia, P.; Gamble, J. R.; Vadas, M. A.; Wattenberg, B. W. Human sphingosine kinase: purification, molecular cloning and characterization of the native and recombinant enzymes. Biochem. J. 2000, 350, 429-441. (Pubitemid 30708411)
10. Liu, H.; Sugiura, M.; Nava, V. E.; Edsall, L. C.; Kono, K.; Poulton, S.; Milstien, S.; Kohama, T.; Spiegel, S. Molecular cloning and functional characterization of a novel mammalian sphingosine kinase type 2 isoform. J. Biol. Chem. 2000, 275, 19513-19520. (Pubitemid 30441543)
11. Buehrer, B. M.; Bell, R. M. Sphingosine kinase: properties and cellular functions. Adv. Lipid Res. 1993, 26, 59-67.
12. Edsall, L. C.; Van Brocklyn, J. R.; Cuvillier, O.; Kleuser, B.; Spiegel, S. N,N-Dimethylsphingosine is a potent competitive inhibitor of sphingosine kinase but not of protein kinase C: modulation of cellular levels of sphingosine 1-phosphate and ceramide. Biochemistry 1998, 37, 12892-12898. (Pubitemid 28433522)
13. Kono, K.; Tanaka, M.; Mizuno, T.; Kodama, K.; Ogita, T.; Kohama, T. B-535a, b and c, new sphingosine kinase inhibitors, produced by a marine bacterium; taxonomy, fermentation, isolation, physico-chemical properties and structure determination. J. Antibiot. (Tokyo) 2000, 53, 753-758. (Pubitemid 30682304)
14. Igarashi, Y.; Hakomori, S.; Toyokuni, T.; Dean, B.; Fujita, S.; Sugimoto, M.; Ogawa, T.; El-Ghendy, K.; Racker, E. Effect of chemically well-defined sphingosine and its N-methyl derivatives on protein kinase C and src kinase activities. Biochemistry 1989, 28, 6796-6800. (Pubitemid 19219864)
15. Megidish, T.; White, T.; Takio, K.; Titani, K.; Igarashi, Y.; Hakomori, S.-i. The signal modulator protein 14-3-3 is a target of sphingosineor N,N-dimethylsphingosine-dependent kinase in 3T3(A31) cells. Biochem. Biophys. Res. Commun. 1995, 216, 739-747.
16. Kim, J.-W.; Kim, Y.-W.; Inagaki, Y.; Hwang, Y.-A.; Mitsutake, S.; Ryu, Y.-W.; Lee, W. K.; Ha, H.-J.; Park, C.-S.; Igarashi, Y. Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases. Bioorg. Med. Chem. 2005, 13, 3475-3485. (Pubitemid 40545803)
17. De Jonghe, S.; Van Overmeire, I.; Poulton, S.; Hendrix, C.; Busson, R.; Van Calenbergh, S.; De Keukeleire, D.; Spiegel, S.; Herdewijn, P. Structure-activity relationship of short-chain sphingoid bases as inhibitors of sphingosine kinase. Bioorg. Med. Chem. Lett. 1999, 9, 3175-3180. (Pubitemid 29515403)
18. Van Overmeire, I.; Boldin, S. A.; Dumont, F.; Van Calenbergh, S.; Slegers, G.; De Keukeleire, D.; Futerman, A. H.; Herdewijn, P. Effect of aromatic short-chain analogues of ceramide on axonal growth in hippocampal neurons. J. Med. Chem. 1999, 42, 2697-2705. (Pubitemid 29344310)
19. Garner, P.; Park, J. M.; Malecki, E. A stereodivergent synthesis of D-erythro-sphingosine and D-threo-sphingosine from L-serine. J. Org. Chem. 1988, 53, 4395-4398. (Pubitemid 18222438)
20. Williams, L.; Zhang, Z.; Shao, F.; Carroll, P. J.; Joullie, M. M. Grignard reactions to chiral oxazolidine aldehydes. Tetrahedron 1996, 52, 11673-11694. (Pubitemid 26280041)
21. Bielawska, A.; Hannun, Y. A. Preparation of radiolabeled ceramides and phosphosphingolipids. Methods Enzymol. 2000, 311, 499-518. (Pubitemid 29512786)
22. Cherest, M.; Felkin, H.; Prudent, N. Torsional strain involving partial bonds. The stereochemistry of the lithium aluminum hydride reduction of some simple open-chain ketones. Tetrahedron Lett. 1968, 9, 2199-2204.
23. Herold, P. Synthesis of D-erythro- and D-threo-sphingosine derivatives from L-serine. Helv. Chim. Acta 1988, 71, 354-362. (Pubitemid 18065129)
24. Kaiser, E.; Tam, J. P.; Kubiak, T. M.; Merrifield, R. B. Chlorotrimethylsilane- phenol as a mild deprotection reagent for the tert-butyl based protecting groups in peptide synthesis. Tetrahedron Lett. 1988, 29, 303-306.
25. Mori, A.; Miyakawa, Y.; Ohashi, E.; Haga, T.; Maegawa, T.; Sajiki, H. Pd/C-catalyzed chemoselective hydrogenation in the presence of diphenylsulfide. Org. Lett. 2006, 8, 3279-3281. (Pubitemid 44187434)
26. Meyer zu Heringdorf, D.; Lass, H.; Kuchar, I.; Lipinski, M.; Alemany, R.; Rumenapp, U.; Jakobs, K. H. Stimulation of intracellular sphingosine- 1-phosphate production by G-protein-coupled sphingosine-1-phosphate receptors. Eur. J. Pharmacol. 2001, 414, 145-154.
27. Zhi, L.; Leung, B. P.; Melendez, A. J. Sphingosine kinase 1 regulates pro-inflammatory responses triggered by TNFalpha in primary human monocytes. J. Cell. Physiol. 2006, 208, 109-115. (Pubitemid 43848994)
28. Shida, D.; Takabe, K.; Kapitonov, D.; Milstien, S.; Spiegel, S. Targeting SphK1 as a new strategy against cancer. Curr. Drug Targets 2008, 8, 662-673.
29. Lai, W. Q.; Irwan, A. W.; Goh, H. H.; Howe, H. S.; Yu, D. T.; Valle- Oñate, R.; McInnes, I. B.; Melendez, A. J.; Leung, B. P. Antiinflammatory effects of sphingosine kinase modulation in inflammatory arthritis. J. Immunol. 2008, 181, 8010-8017.
30. Lai, W. Q.; Goh, H. H.; Bao, Z.; Wong,W. S.; Melendez, A. J.; Leung, B. P. The role of sphingosine kinase in a murine model of allergic asthma. J. Immunol. 2008, 180, 4323-4329.
31. Melendez, A. J. Allergy therapy: the therapeutic potential of targeting sphingosine kinase signalling in mast cells. Eur. J. Immunol. 2008, 38, 2969-2974.
32. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of proteindye binding. Anal. Biochem. 1976, 72, 248-254.