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Crystal Structure of Sphingosine Kinase 1 with PF-543.

Wang J, Knapp S, Pyne NJ, Pyne S, Elkins JM
ACS Med Chem Lett 5 1329-33 (2014)
Cited: 55 times
EuropePMC logo PMID: 25516793

Abstract

The most potent inhibitor of Sphingosine Kinase 1 (SPHK1) so far identified is PF-543. The crystal structure of SPHK1 in complex with inhibitor PF-543 to 1.8 Å resolution reveals the inhibitor bound in a bent conformation analogous to that expected of a bound sphingosine substrate but with a rotated head group. The structural data presented will aid in the design of SPHK1 and SPHK2 inhibitors with improved properties.

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  5. Structure-Activity Relationship Studies and Molecular Modeling of Naphthalene-Based Sphingosine Kinase 2 Inhibitors. Congdon MD, Kharel Y, Brown AM, Lewis SN, Bevan DR, Lynch KR, Santos WL. ACS Med Chem Lett 7 229-234 (2016)
  6. Design of new quinolin-2-one-pyrimidine hybrids as sphingosine kinases inhibitors. Vettorazzi M, Insuasty D, Lima S, Gutiérrez L, Nogueras M, Marchal A, Abonia R, Andújar S, Spiegel S, Cobo J, Enriz RD. Bioorg Chem 94 103414 (2020)
  7. Structure-activity relationship studies of the lipophilic tail region of sphingosine kinase 2 inhibitors. Congdon MD, Childress ES, Patwardhan NN, Gumkowski J, Morris EA, Kharel Y, Lynch KR, Santos WL. Bioorg Med Chem Lett 25 4956-4960 (2015)
  8. Discovery of a Small Side Cavity in Sphingosine Kinase 2 that Enhances Inhibitor Potency and Selectivity. Sibley CD, Morris EA, Kharel Y, Brown AM, Huang T, Bevan DR, Lynch KR, Santos WL. J Med Chem 63 1178-1198 (2020)
  9. Discovery of Harmaline as a Potent Inhibitor of Sphingosine Kinase-1: A Chemopreventive Role in Lung Cancer. Roy S, Mohammad T, Gupta P, Dahiya R, Parveen S, Luqman S, Hasan GM, Hassan MI. ACS Omega 5 21550-21560 (2020)
  10. Lipophilic tail modifications of 2-(hydroxymethyl)pyrrolidine scaffold reveal dual sphingosine kinase 1 and 2 inhibitors. Li H, Sibley CD, Kharel Y, Huang T, Brown AM, Wonilowicz LG, Bevan DR, Lynch KR, Santos WL. Bioorg Med Chem 30 115941 (2021)
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  17. Development of 1,2,3-Triazole-Based Sphingosine Kinase Inhibitors and Their Evaluation as Antiproliferative Agents. Corvino A, Rosa R, Incisivo GM, Fiorino F, Frecentese F, Magli E, Perissutti E, Saccone I, Santagada V, Cirino G, Riemma MA, Temussi PA, Ciciola P, Bianco R, Caliendo G, Roviezzo F, Severino B. Int J Mol Sci 18 E2332 (2017)
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  19. Probing the substitution pattern of indole-based scaffold reveals potent and selective sphingosine kinase 2 inhibitors. Congdon M, Fritzemeier RG, Kharel Y, Brown AM, Serbulea V, Bevan DR, Lynch KR, Santos WL. Eur J Med Chem 212 113121 (2021)
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  21. Theoretical models to predict the inhibitory effect of ligands of sphingosine kinase 1 using QTAIM calculations and hydrogen bond dynamic propensity analysis. Vettorazzi M, Menéndez C, Gutiérrez L, Andujar S, Appignanesi G, Enriz RD. J Comput Aided Mol Des 32 781-791 (2018)
  22. A Dansyl-Modified Sphingosine Kinase Inhibitor DPF-543 Enhanced De Novo Ceramide Generation. Shamshiddinova M, Gulyamov S, Kim HJ, Jung SH, Baek DJ, Lee YM. Int J Mol Sci 22 9190 (2021)
  23. Identification of selective inhibitors of sphingosine kinases 1 and 2 through a structure-activity relationship study of 4-epi-jaspine B. Ohno H, Honda M, Hamada N, Miyagaki J, Iwata A, Otsuki K, Maruyama T, Nakamura S, Nakanishi I, Inuki S, Fujii N, Oishi S. Bioorg Med Chem 25 3046-3052 (2017)
  24. Design, synthesis and analysis of novel sphingosine kinase-1 inhibitors to improve oral bioavailability. Butler KJ, Castro AA, Dwyer TS, Hardwick LM, Iacino MC, Manore SG, Mays KM, McGlade CA, Hair LN, Parker EW, Smith MR, Turnow MT, Wilson MR, Woodson SR, Cotham WE, Walla MD, Hurlbert JC, Christian Grattan T. Bioorg Med Chem Lett 50 128329 (2021)
  25. Host-Erythrocytic Sphingosine-1-Phosphate Regulates Plasmodium Histone Deacetylase Activity and Exhibits Epigenetic Control over Cell Death and Differentiation. Sah RK, Anand S, Dar W, Jain R, Kumari G, Madan E, Saini M, Gupta A, Joshi N, Hada RS, Gupta N, Pati S, Singh S. Microbiol Spectr e0276622 (2023)
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