Sphingosine 1-phosphate lyase inhibition by 2-acetyl-4-(tetrahydroxybutyl)imidazole (THI) under conditions of vitamin B6 deficiency

Molecular and Cellular Biochemistry

Volumn 400, Issue 1-2, 2015, Pages 125-133

  Ohtoyo, Mamoru ^a   Tamura, Masakazu ^a   Machinaga, Nobuo ^a   Muro, Fumihito ^a   Hashimoto, Ryuji ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

2 Acetyl 4 (tetrahydroxybutyl)imidazole; 4 Deoxypyridoxine; S1P lyase; Sphingosine 1 phosphate; Vitamin B6

Indexed keywords

2 ACETYL 4 (TETRAHYDROXYBUTYL)IMIDAZOLE; DEOXYPYRIDOXINE; FOOD DYE; LYASE; PHOSPHATIDYLCHOLINE; SPHINGOLIPID; SPHINGOSINE 1 PHOSPHATE LYASE; UNCLASSIFIED DRUG; 2-ACETYL-4(5)-TETRAHYDROXYBUTYLIMIDAZOLE; CARAMEL COLORING; CARBOHYDRATE; IMIDAZOLE DERIVATIVE; PYRIDOXAL 5 PHOSPHATE; SPHINGOSINE 1-PHOSPHATE LYASE (ALDOLASE);

ANIMAL CELL; ARTICLE; AUTORADIOGRAPHY; CELL VIABILITY; CONTROLLED STUDY; EFFECTIVE CONCENTRATION; ENZYMATIC ASSAY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME PHOSPHORYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; MOUSE; NONHUMAN; PYRIDOXINE DEFICIENCY; TANDEM MASS SPECTROMETRY; ANIMAL; ANTAGONISTS AND INHIBITORS; ENZYMOLOGY; METABOLISM; PATHOLOGY;

ALDEHYDE-LYASES; ANIMALS; CARBOHYDRATES; IMIDAZOLES; MICE; PYRIDOXAL PHOSPHATE; VITAMIN B 6 DEFICIENCY;

EID: 84922073657     PISSN: 03008177     EISSN: 15734919     Source Type: Journal    
DOI: 10.1007/s11010-014-2268-z     Document Type: Article

References (36)

1. Sinkeldam EJ, de Groot AP, van den Berg H, Chappel CI (1988) The effect of pyridoxine on the number of lymphocytes in the blood of rats fed caramel colour (III). Food Chem Toxicol 26:195–203
2. Gobin SJ, Paine AJ (1989) Effect of oral and parenteral administration of B6 vitamers on the lymphopenia produced by feeding ammonia caramel or 2-acetyl-4(5)-(1,2,3,4-tetrahydroxy)butylimidazole to rats. Food Chem Toxicol 27:627–630
3. Iscaro A, Mackay IR, O’Brien C (1988) Lymphopenic effects on mice of a component of ammonia caramel, 2-acetyl-4(5)-tetrahydroxybutylimidazole (THI). Immunol Cell Biol 66:395–402
4. Gobin SJ, Phillips JA (1991) Immunosuppressive effects of 2-acetyl-4-tetrahydroxybutyl imidazole (THI) in the rat. Clin Exp Immunol 85:335–340
5. Gugasyan R, Coward A, O’Connor L, Shortman K, Scollay R (1998) Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole. Immunology 93:398–404
6. Schwab SR, Pereira JP, Matloubian M, Xu Y, Huang Y, Cyster JG (2005) Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients. Science 309:1735–1739
7. Schwab SR, Cyster JG (2007) Finding a way out: lymphocyte egress from lymphoid organs. Nat Immunol 8:1295–1301
8. Bagdanoff JT, Donoviel MS, Nouraldeen A et al (2010) 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 53:8650–8662
9. Bagdanoff JT, Donoviel MS, Nouraldeen A et al (2009) Inhibition of sphingosine-1-phosphate lyase for the treatment of autoimmune disorders. J Med Chem 52:3941–3953
10. Reina E, Camacho L, Casas J, Van Veldhoven PP, Fabrias G (2012) Determination of sphingosine-1-phosphate lyase activity by gas chromatography coupled to electron impact mass spectrometry. Chem Phys Lipids 165:225–231
11. Bassi R, Anelli V, Giussani P, Tettamanti G, Viani P, Riboni L (2006) Sphingosine-1-phosphate is released by cerebellar astrocytes in response to bFGF and induces astrocyte proliferation through Gi-protein-coupled receptors. Glia 53:621–630
12. Sensken SC, Bode C, Nagarajan M, Peest U, Pabst O, Gräler MH (2010) Redistribution of sphingosine 1-phosphate by sphingosine kinase 2 contributes to lymphopenia. J Immunol 184:4133–4142
13. Berdyshev EV, Gorshkova I, Usatyuk P, Kalari S, Zhao Y, Pyne NJ, Pyne S, Sabbadini RA, Garcia JG, Natarajan V (2011) Intracellular S1P generation is essential for S1P-induced motility of human lung endothelial cells: role of sphingosine kinase 1 and S1P lyase. PLoS ONE 6:e16571
14. Billich A, Beerli C, Bergmann R, Bruns C, Loetscher E (2013) Cellular assay for the characterization of sphingosine-1-phosphate lyase inhibitors. Anal Biochem 434:247–253
15. Loetscher E, Schneider K, Beerli C, Billich A (2013) Assay to measure the secretion of sphingosine-1-phosphate from cells induced by S1P lyase inhibitors. Biochem Biophys Res Commun 433:345–348
16. Mukhopadhyay D, Howell KS, Riezman H, Capitani G (2008) Identifying key residues of sphinganine-1-phosphate lyase for function in vivo and in vitro. J Biol Chem 283:20159–20169
17. Nussbaumer P (2008) Medicinal chemistry aspects of drug targets in sphingolipid metabolism. ChemMedChem 3:543–551
18. Serra M, Saba JD (2010) Sphingosine 1-phosphate lyase, a key regulator of sphingosine 1-phosphate signaling and function. Adv Enzyme Regul 50:349–362
19. van de Kamp JL, Westrick JA, Smolen A (1995) B-6 vitamer concentrations in mouse plasma, erythrocytes and tissues. Nutr Res 15:415–422
20. Wei IL (1999) The influence of dietary restriction on vitamin B-6 vitamer distribution and on vitamin B-6 metabolizing enzymes in rats. J Am Coll Nutr 18:144–151
21. Leklem JE (1990) Vitamin B-6: a status report. J Nutr 120:1503–1507
22. Itoh T, Doi H, Chin S, Nishimura T, Kasahara S (1988) Establishment of mouse thymic nurse cell clones from a spontaneous BALB/c thymic tumor. Eur J Immunol 18:821–824
23. Long RF, Morrison AL (1954) The synthesis of 4-deoxypyridoxine phosphates. J Chem Soc 3854–3856. doi:10.1039/JR9540003854
24. Cliff MD, Pyne SG (1997) Asymmetric synthesis of 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles. J Org Chem 62:1023–1032
25. Berdyshev EV, Gorshkova IA, Garcia JG, Natarajan V, Hubbard WC (2005) Quantitative analysis of sphingoid base-1-phosphates as bisacetylated derivatives by liquid chromatography–tandem mass spectrometry. Anal Biochem 339:129–136
26. Ikeda M, Kihara A, Kariya Y, Lee YM, Igarashi Y (2005) Sphingolipid-to-glycerophospholipid conversion in SPL-null cells implies the existence of an alternative isozyme. Biochem Biophys Res Commun 329:474–479
27. Hanna MC, Turner AJ, Kirkness EF (1997) Human pyridoxal kinase. cDNA cloning, expression, and modulation by ligands of the benzodiazepine receptor. J Biol Chem 272:10756–10760
28. Soga T, Heiger DN (2000) Amino acid analysis by capillary electrophoresis electrospray ionization mass spectrometry. Anal Chem 72:1236–1241
29. Soga T, Ueno Y, Naraoka H, Ohashi Y, Tomita M, Nishioka T (2002) Simultaneous determination of anionic intermediates for Bacillus subtilis metabolic pathways by capillary electrophoresis electrospray ionization mass spectrometry. Anal Chem 74:2233–2239
30. Soga T, Ohashi Y, Ueno Y, Naraoka H, Tomita M, Nishioka T (2003) Quantitative metabolome analysis using capillary electrophoresis mass spectrometry. J Proteome Res 2:488–494
31. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M (2009) Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics 6:78–95
32. Meister A, Sober HA, Peterson EA (1954) Studies on the coenzyme activation of glutamic-aspartic apotransaminase. J Biol Chem 206:89–100
33. Trakatellis A, Dimitriadou A, Trakatelli M (1997) Pyridoxine deficiency: new approaches in immunosuppression and chemotherapy. Postgrad Med J 73:617–622
34. Said HM, Ortiz A, Ma TY (2003) A carrier-mediated mechanism for pyridoxine uptake by human intestinal epithelial Caco-2 cells: regulation by a PKA-mediated pathway. Am J Physiol Cell Physiol 285:C1219–C1225
35. Shane B, Snell EE (1976) Transport and metabolism of vitamin B6 in the yeast Saccharomyces carlsbergensis 4228. J Biol Chem 251:1042–1051
36. Yu XQ, Kramer J, Moran L, O’Neill E, Nouraldeen A, Oravecz T, Wilson AG (2010) Pharmacokinetic/pharmacodynamic modelling of 2-acetyl-4(5)-tetrahydroxybutyl imidazole-induced peripheral lymphocyte sequestration through increasing lymphoid sphingosine 1-phosphate. Xenobiotica 40:350–356