Structure-Activity relationships and molecular modeling of sphingosine kinase inhibitors

Journal of Medicinal Chemistry

Volumn 56, Issue 22, 2013, Pages 9310-9327

  Baek, Dong Jae ^a   MacRitchie, Neil ^b   Anthony, Nahoum G ^b   MacKay, Simon P ^b   Pyne, Susan ^b   Pyne, Nigel J ^b   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

(1 (4 DODECYLPHENETHYL)PYRROLIDIN 2 YL)METHANOL; (1 (4 METHYLPHENETHYL)PYRROLIDIN 2 YL)METHANOL; (1 (4 OCTYLPHENETHYL)PYRROLIDIN 2 YL)METHANOL; (4 (2 HYDROXYETHYL)PHENYL) 4 OCTYLBENZAMIDE; (4 DODECYLPHENYL) (2 (HYDROXYMETHYL)PYRROLIDIN 1 YL)METHANONE; (4 DODECYLPHENYL)(2 (HYDROXYMETHYL)PYRROLIDIN 1 YL)METHANONE; (4 DODECYLPHENYL)(4 HYDROXYPIPERIDIN 1 YL)METHANONE; (4 HYDROXYPIPERIDIN 1 YL)(4 OCTYLPHENYL)METHANONE; 1 (3 (4 OCTYLPHENYL)PROPYL)PIPERIDIN 4 OL; 1 (4 (4 OCTYLPHENYL)BUTYL)PIPERIDIN 4 OL; 1 (4 DODECYLPHENETHYL)PIPERIDIN 4 AMINE; 1 (4 DODECYLPHENETHYL)PIPERIDIN 4 OL; 1 (4 HEXYLPHENETHYL)PIPERIDIN 4 OL; 1 (4 METHYLPHENETHYL)PIPERIDIN 4 AMINE; 1 (4 METHYLPHENETHYL)PIPERIDIN 4 OL; 1 (4 OCTYLBENZYL)PIPERIDIN 4 OL; 1 (4 OCTYLPHENETHYL)PIPERIDIN 4 AMINE; 1 (4 OCTYLPHENETHYL)PIPERIDIN 4 OL; 1 (4 OCTYLPHENETHYL)PIPERIDIN 4 ONE; 1 (4 OCTYLPHENETHYL)PYRROLIDIN 3 OL; 1 METHYL 4 (4 OCTYLPHENETHYL)PYRIDINIUM IODIDE; 4 (4 OCTYLPHENETHYL)PYRIDINE; 4 AZIDO 1 (4 METHYLPHENETHYL)PIPERIDINE; 4 AZIDO 1 (4 OCTYLPHENETHYL)PIPERIDINE; 4 FLUORO 1 (4 OCTYLPHENETHYL)PIPERIDINE; 4 METHOXY 1 (4 OCTYLPHENETHYL)PIPERIDINE; 4 OCTYL N (PYRIDIN 4 YLMETHYL)BENZAMIDE; N (4 HYDROXYPHENYL) 4 OCTYLBENZAMIDE; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; MOLECULAR MODEL; PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION;

BENZAMIDES; ENZYME INHIBITORS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, MOLECULAR; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); PIPERIDINES; PROTEIN CONFORMATION; QUATERNARY AMMONIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 84889261997     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401399c     Document Type: Article

References (28)

1. Hait, N. C.; Allegood, J.; Maceyka, M.; Strub, G. M.; Harikumar, K. B.; Singh, S. K.; Luo, C.; Marmorstein, R.; Kordula, T.; Milstien, S.; Spiegel, S. Regulation of histone acetylation in the nucleus by sphingosine-1-phosphate Science 2009, 325, 1254-1257
2. Mizugishi, K.; Yamashita, T.; Olivera, A.; Miller, G. F.; Spiegel, S.; Proia, R. L. Essential role for sphingosine kinases in neural and vascular development Mol. Cell. Biol. 2005, 25, 11113-11121 (Pubitemid 41747151)
3. Pyne, S.; Pyne, N. J. Translational aspects of sphingosine 1-phosphate biology Trends Mol. Med. 2011, 17, 463-472
4. Xia, P.; Gamble, J. R.; Wang, L.; Pitson, S. M.; Moretti, P. A.; Wattenberg, B. W.; D'Andrea, R. J.; Vadas, M. A. An oncogenic role of sphingosine kinase Curr. Biol. 2000, 10, 1527-1530 (Pubitemid 32003646)
5. Paugh, S. W.; Paugh, B. S.; Rahmani, M.; Kapitonov, D.; Almenara, J. A.; Kordula, T.; Milstien, S.; Adams, J. K.; Zipkin, R. E.; Grant, S.; Spiegel, S. A selective sphingosine kinase 1 inhibitor integrates multiple molecular therapeutic targets in human leukemia Blood 2008, 112, 1382-1391
6. Schnute, M. E.; McReynolds, M. D.; Kasten, T.; Yates, M.; Jerome, G.; Rains, J. W.; Hall, T.; Chrencik, J.; Kraus, M.; Cronin, C. N.; Saabye, M.; Highkin, M. K.; Broadus, R.; Ogawa, S.; Cukyne, K.; Zawadzke, L. E.; Peterkin, V.; Iyanar, K.; Scholten, J. A.; Wendling, J.; Fujiwara, H.; Nemirovskiy, O.; Wittwer, A. J.; Nagiec, M. M. Modulation of cellular S1P levels with a novel, potent and specific inhibitor of sphingosine kinase-1 Biochem. J. 2012, 444, 79-88
7. Baek, D. J.; MacRitchie, N.; Pyne, N. J.; Pyne, S.; Bittman, R. Synthesis of selective inhibitors of sphingosine kinase 1 Chem. Commun. 2013, 49, 2136-2138
8. Tonelli, F.; Lim, K. G.; Loveridge, C.; Long, J.; Pitson, S. M.; Tigyi, G.; Bittman, R.; Pyne, S.; Pyne, N. J. FTY720 and (S)-FTY720 vinylphosphonate inhibit sphingosine kinase 1 and promote its proteasomal degradation in human pulmonary artery smooth muscle, breast cancer and androgen-independent prostate cancer cells Cell. Signalling 2010, 22, 1536-1542
9. Lahiri, S.; Park, H.; Laviad, E. L.; Lu, X.; Bittman, R.; Futerman, A. H. Ceramide synthesis is modulated by the sphingosine analog FTY720 via a mixture of uncompetitive and noncompetitive inhibition in an acyl-CoA chain length-dependent manner J. Biol. Chem. 2009, 284, 16090-16098
10. Bandhuvula, P.; Tam, Y. Y.; Oskouian, B.; Saba, J. D. The immune modulator FTY720 inhibits sphingosine-1-phosphate lyase activity J. Biol. Chem. 2005, 280, 33697-33700 (Pubitemid 41443086)
11. Lim, K. G.; Tonelli, F.; Li, Z.; Lu, X.; Bittman, R.; Pyne, S.; Pyne, N. J. FTY720 analogues as sphingosine kinase 1 inhibitors: enzyme inhibition kinetics, allosterism, proteasomal degradation and actin rearrangement in MCF-7 breast cancer cells J. Biol. Chem. 2011, 286, 18633-18640
12. Liu, Z.; MacRitchie, N.; Pyne, S.; Pyne, N. J.; Bittman, R. Synthesis of (S)-FTY720 vinylphosphonate analogues and evaluation of their potential as sphingosine kinase 1 inhibitors and activators Bioorg. Med. Chem. 2013, 21, 2503-2510
13. French, K. J.; Zhuang, Y.; Maines, L. W.; Gao, P.; Wang, W.; Beljanski, V.; Upson, J. J.; Green, C. L.; Keller, S. N.; Smith, C. D. Pharmacology and anti-tumor activity of ABC294640, a selective inhibitor of sphingosine kinase-2 J. Pharmacol. Exp. Ther. 2010, 333, 129-139
14. Lim, K. G.; Sun, C.; Bittman, R.; Pyne, N. J.; Pyne, S. (R)-FTY720 methyl ether is a specific sphingosine kinase 2 inhibitor: effect on sphingosine kinase 2 expression in HEK 293 cells and actin rearrangement and survival of MCF-7 breast cancer cells Cell. Signalling 2011, 23, 1590-1595
15. Liu, K.; Guo, T. L.; Hait, N. C.; Allegood, J.; Parikh, H. I.; Xu, W.; Kellogg, G. E.; Grant, S.; Spiegel, S.; Zhang, S. Biological characterization of 3-(2-amino-ethyl)-5-[3-(4-butoxyl-phenyl)-propylidene]-thiazolidine-2,4-dione (K145) as a selective sphingosine kinase-2 inhibitor and anticancer agent PLoS One 2013, 8, e56471
16. Kharel, Y.; Raje, M.; Gao, M.; Gellett, A. M.; Tomsig, J. L.; Lynch, K. R.; Santos, W. L. Sphingosine kinase type 2 inhibition elevates circulating sphingosine 1-phosphate Biochem. J. 2012, 447, 149-157
17. French, K. J.; Schrecengost, R. S.; Lee, B. D.; Zhuang, Y.; Smith, S. N.; Eberly, J. L.; Yun, J. K.; Smith, C. D. Discovery and evaluation of inhibitors of human sphingosine kinase Cancer Res. 2003, 63, 5962-5969 (Pubitemid 37187498)
18. Mathews, T. P.; Kennedy, A. J.; Kharel, Y.; Kennedy, P. C.; Nicoara, O.; Sunkara, M.; Morris, A. J.; Wamhoff, B. R.; Lynch, K. R.; Macdonald, T. L. Discovery, biological evaluation, and structure-activity relationship of amidine based sphingosine kinase inhibitors J. Med. Chem. 2010, 53, 2766-2778
19. Kennedy, A. J.; Mathews, T. P.; Kharel, Y.; Field, S. D.; Moyer, M. L.; East, J. E.; Houck, J. D.; Lynch, K. R.; Macdonald, T. L. Development of amidine-based sphingosine kinase 1 nanomolar inhibitors and reduction of sphingosine 1-phosphate in human leukemia cells J. Med. Chem. 2011, 54, 3524-3548
20. Gustin, D. J.; Li, Y.; Brown, M. L.; Min, X.; Schmitt, M. J.; Wanska, M.; Wang, X.; Connors, R.; Johnstone, S.; Cardozo, M.; Cheng, A. C.; Jeffries, S.; Franks, B.; Li, S.; Shen, S.; Wong, M.; Wesche, H.; Xu, G.; Carlson, T. J.; Plant, M.; Morgenstern, K.; Rex, K.; Schmitt, J.; Coxon, A.; Walker, N.; Kayser, F.; Wang, Z. Structure guided design of a series of sphingosine kinase (SphK) inhibitors Bioorg. Med. Chem. Lett. 2013, 23, 4608-4616
21. Gao, P.; Peterson, Y. K.; Smith, R. A.; Smith, C. D. Characterization of isoenzyme-selective inhibitors of human sphingosine kinases PLoS One 2012, 7, e44543
22. Lu, X.; Sun, C.; Valentine, W. J.; E, S.; Liu, J.; Tigyi, G.; Bittman, R. Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720 J. Org. Chem. 2009, 74, 3192-3195
23. Kiuchi, M.; Adachi, K.; Kohara, T.; Minoguchi, M.; Hanano, T.; Aoki, Y.; Mishina, T.; Arita, M.; Nakao, N.; Ohtsuki, M.; Hoshino, Y.; Teshima, K.; Chiba, K.; Sasaki, S.; Fujita, T. Synthesis and immunosuppressive activity of 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols J. Med. Chem. 2000, 43, 2946-2961 (Pubitemid 30599653)
24. Knott, K.; Kharel, Y.; Raje, M. R.; Lynch, K. R.; Santos, W. L. Effect of alkyl chain length on sphingosine kinase 2 selectivity Bioorg. Med. Chem. Lett. 2012, 22, 6817-6820
25. Raje, M. R.; Knott, K.; Kharel, Y.; Bissel, P.; Lynch, K. R.; Santos, W. L. Design, synthesis and biological activity of sphingosine kinase selective inhibitors Bioorg. Med. Chem. 2012, 20, 183-194
26. Wang, Z.; Min, X.; Xiao, S. H.; Johnstone, S.; Romanow, W.; Meininger, D.; Xu, H.; Liu, J.; Dai, J.; An, S.; Thibault, S.; Walker, N. Molecular basis of sphingosine kinase 1 substrate recognition and catalysis Structure 2013, 21, 798-809
27. Conejo-García, A.; Pisani, L.; Núñez, M. D. C.; Catto, M.; Nicolotti, O.; Leonetti, F.; Campos, J. M.; Gallo, M.; Espinosa, A.; Carotti, A. Homodimeric bis-quaternary heterocyclic ammonium salts as potent acetyl- and butyrylcholinesterase inhibitors: a systematic investigation of the influence of linker and cationic heads over affinity and selectivity J. Med. Chem. 2011, 54, 2627-2645
28. Chen, Y.; Kamlet, A. S.; Steinman, J. B.; Liu, D. R. A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system Nat. Chem. 2011, 3, 146-153