User menu

The trypanocidal drug suramin and other trypan blue mimetics are inhibitors of pyruvate kinases and bind to the adenosine site

Bibliographic reference Morgan, Hugh P. ; McNae, Iain W. ; Nowicki, Matthew W. ; Zhong, Wenhe ; Michels, Paul ; et. al. The trypanocidal drug suramin and other trypan blue mimetics are inhibitors of pyruvate kinases and bind to the adenosine site. In: Journal of Biological Chemistry, Vol. 286, no. 36, p. 31232-31240 (2011)
Permanent URL
  1. Ehrlich, Berlin Klin. Wochenschrift, 20, 329 (1904)
  2. Klinger, Mol. Pharmacol., 55, 462 (1999)
  3. Braga-Silva Lys Adriana, Souza dos Santos André Luis, Portela Maristela Barbosa, Souto-Padrón Thaïs, Soares Rosangela Maria de Araújo, Effect of suramin on the human pathogenCandida albicans: implications on the fungal development and virulence, 10.1111/j.1574-695x.2007.00321.x
  4. De Clercq Erik, Antiviral drug discovery: Ten more compounds, and ten more stories (part B), 10.1002/med.20149
  5. Baghdiguian, Cancer J., 10, 31 (1997)
  6. MISSET Onno, OPPERDOES Fred R., The phosphoglycerate kinases from Trypanosoma brucei. A comparison of the glycosomal and the cytosolic isoenzymes and their sensitivity towards Suramin, 10.1111/j.1432-1033.1987.tb10667.x
  7. Willson Michèle, Callens Mia, Kuntz Douglas A., Perié Jacques, Opperdoes Fred R., Synthesis and activity of inhibitors highly specific for the glycolytic enzymes from Trypanosoma brucei, 10.1016/0166-6851(93)90218-m
  8. Jagielski Adam K., Kryśkiewicz Edyta, Bryła Jadwiga, Suramin-induced reciprocal changes in glucose and lactate synthesis in renal tubules contribute to its hyperglycaemic action, 10.1016/j.ejphar.2006.03.029
  9. Opperdoes F R, Compartmentation of Carbohydrate Metabolism in Trypanosomes, 10.1146/annurev.mi.41.100187.001015
  10. Drew Mark E., Morris James C., Wang Zefeng, Wells Lance, Sanchez Marco, Landfear Scott M., Englund Paul T., The Adenosine Analog Tubercidin Inhibits Glycolysis inTrypanosoma bruceias Revealed by an RNA Interference Library, 10.1074/jbc.m309320200
  11. Albert Marie-Astrid, Haanstra Jurgen R., Hannaert Véronique, Van Roy Joris, Opperdoes Fred R., Bakker Barbara M., Michels Paul A. M., Experimental andin SilicoAnalyses of Glycolytic Flux Control in Bloodstream FormTrypanosoma brucei, 10.1074/jbc.m502403200
  12. Morgan Hugh P., McNae Iain W., Nowicki Matthew W., Hannaert Véronique, Michels Paul A. M., Fothergill-Gilmore Linda A., Walkinshaw Malcolm D., Allosteric Mechanism of Pyruvate Kinase fromLeishmania mexicanaUses a Rock and Lock Model, 10.1074/jbc.m109.079905
  13. Hawking F., Suramin: With Special Reference to Onchocerciasis, Advances in Pharmacology (1978) ISBN:9780120329151 p.289-322, 10.1016/s1054-3589(08)60486-x
  14. Potterton Elizabeth, Briggs Peter, Turkenburg Maria, Dodson Eleanor, A graphical user interface to theCCP4 program suite, 10.1107/s0907444903008126
  15. Evans Philip, Scaling and assessment of data quality, 10.1107/s0907444905036693
  16. McCoy Airlie J., Grosse-Kunstleve Ralf W., Adams Paul D., Winn Martyn D., Storoni Laurent C., Read Randy J., Phasercrystallographic software, 10.1107/s0021889807021206
  17. Rigden Daniel J, Phillips Simon E.V, Michels Paul A.M, Fothergill-Gilmore Linda A, The structure of pyruvate kinase from Leishmania mexicana reveals details of the allosteric transition and unusual effector specificity 1 1Edited by I. A. Wilson, 10.1006/jmbi.1999.2918
  18. Murshudov G. N., Vagin A. A., Dodson E. J., Refinement of Macromolecular Structures by the Maximum-Likelihood Method, 10.1107/s0907444996012255
  19. Emsley Paul, Cowtan Kevin, Coot: model-building tools for molecular graphics, 10.1107/s0907444904019158
  20. DeLano W. L. (2010) The PyMOL Molecular Graphics System, version 1.3r1, Schrödinger, LLC, New York
  21. Potterton Elizabeth, McNicholas Stuart, Krissinel Eugene, Cowtan Kevin, Noble Martin, TheCCP4 molecular-graphics project, 10.1107/s0907444902015391
  22. Jiang Jian-kang, Boxer Matthew B., Vander Heiden Matthew G., Shen Min, Skoumbourdis Amanda P., Southall Noel, Veith Henrike, Leister William, Austin Christopher P., Park Hee Won, Inglese James, Cantley Lewis C., Auld Douglas S., Thomas Craig J., Evaluation of thieno[3,2-b]pyrrole[3,2-d]pyridazinones as activators of the tumor cell specific M2 isoform of pyruvate kinase, 10.1016/j.bmcl.2010.04.015
  23. Hannaert Véronique, Yernaux Cédric, Rigden Daniel J, Fothergill-Gilmore Linda A, Opperdoes Fred R, Michels Paul A.M, The putative effector-binding site ofLeishmania mexicanapyruvate kinase studied by site-directed mutagenesis, 10.1016/s0014-5793(02)02374-8
  24. La Rocca Renato V., Stein Cy A., Danesi Romano, Myers Charles E., Suramin, a novel antitumor compound, 10.1016/0960-0760(90)90439-r
  25. Cer R. Z., Mudunuri U., Stephens R., Lebeda F. J., IC50-to-Ki: a web-based tool for converting IC50 to Ki values for inhibitors of enzyme activity and ligand binding, 10.1093/nar/gkp253
  26. Tulloch Lindsay B., Morgan Hugh P., Hannaert Véronique, Michels Paul A.M., Fothergill-Gilmore Linda A., Walkinshaw Malcolm D., Sulphate Removal Induces a Major Conformational Change in Leishmania mexicana Pyruvate Kinase in the Crystalline State, 10.1016/j.jmb.2008.08.037
  27. Hsin Kun-Yi, Morgan Hugh P., Shave Steven R., Hinton Andrew C., Taylor Paul, Walkinshaw Malcolm D., EDULISS: a small-molecule database with data-mining and pharmacophore searching capabilities, 10.1093/nar/gkq878
  28. Subramanian S., Ross Philip D., Dye-Ligand Affinity Chromatography: The Interaction of Cibacron Blue F3GA® with Proteins and Enzyme, 10.3109/10409238409102302
  29. Morgan Hugh P., McNae Iain W., Hsin Kun-Yi, Michels Paul A. M., Fothergill-Gilmore Linda A., Walkinshaw Malcolm D., An improved strategy for the crystallization ofLeishmania mexicanapyruvate kinase, 10.1107/s1744309109053494
  30. Valentini Giovanna, Chiarelli Laurent R., Fortin Riccardo, Dolzan Manuela, Galizzi Alessandro, Abraham Donald J., Wang Changqing, Bianchi Paola, Zanella Alberto, Mattevi Andrea, Structure and Function of Human Erythrocyte Pyruvate Kinase : MOLECULAR BASIS OF NONSPHEROCYTIC HEMOLYTIC ANEMIA, 10.1074/jbc.m202107200
  31. Dombrauckas Jill D., Santarsiero Bernard D., Mesecar Andrew D., Structural Basis for Tumor Pyruvate Kinase M2 Allosteric Regulation and Catalysis†,‡, 10.1021/bi0474923
  32. Ernest Isabelle, Callens Mia, Opperdoes Fred R., Michels Paul A.M., Pyruvate kinase of Leishmania mexicana mexicana Cloning and analysis of the gene, overexpression in Escherichia coli and characterization of the enzyme, 10.1016/0166-6851(94)90133-3
  33. Larsen Todd M., Benning Matthew M., Rayment Ivan, Reed George H., Structure of the Bis(Mg2+)−ATP−Oxalate Complex of the Rabbit Muscle Pyruvate Kinase at 2.1 Å Resolution:  ATP Binding over a Barrel†,‡, 10.1021/bi980243s
  34. Boxer Matthew B., Jiang Jian-kang, Vander Heiden Matthew G., Shen Min, Skoumbourdis Amanda P., Southall Noel, Veith Henrike, Leister William, Austin Christopher P., Park Hee Won, Inglese James, Cantley Lewis C., Auld Douglas S., Thomas Craig J., Evaluation of SubstitutedN,N′-Diarylsulfonamides as Activators of the Tumor Cell Specific M2 Isoform of Pyruvate Kinase, 10.1021/jm901577g
  35. Mahoney, J. Biol. Chem., 265, 5424 (1990)
  36. Veech, J. Biol. Chem., 254, 6538 (1979)
  37. AKERBOOM Theodorus P. M., BOOKELMAN Hans, ZUURENDONK Peter F., MEER Roelof, TAGER Joseph M., Intramitochondrial and Extramitochondrial Concentrations of Adenine Nucleotides and Inorganic Phosphate in Isolated Hepatocytes from Fasted Rats, 10.1111/j.1432-1033.1978.tb12182.x
  38. La Rocca R. V., Cooper M. R., Stein C. A., Kohler D., Uhrich M., Weinberger E., Myers C. E., Short report: A pilot study of suramin in the treatment of progressive refractory follicular lymphomas*, 10.1093/oxfordjournals.annonc.a058264
  39. Huang Shuan Shian, Koh Han A., Huang Jung San, Suramin enters and accumulates in low pH intracellular compartments of v-sis-transformed NIH 3T3 cells, 10.1016/s0014-5793(97)01213-1
  40. SCHAFTINGEN Emile, OPPERDOES Fred R., HERS Henry-Gery, Effects of various metabolic conditions and of the trivalent arsenical melarsen oxide on the intracellular levels of fructose 2,6-bisphosphate and of glycolytic intermediates in Trypanosoma brucei, 10.1111/j.1432-1033.1987.tb13563.x
  41. Eigenbrodt, Crit. Rev. Oncog., 3, 91 (1992)
  42. Avliyakulov Nuraly K., Lukeš Julius, Kajava Andrey V., Liedberg Bo, Lundström Ingemar, Svensson Samuel P. S., Suramin blocks nucleotide triphosphate binding to ribosomal protein L3 from Trypanoplasma borreli : Suramin binding to ribosomal protein L3, 10.1046/j.1432-1327.2000.01169.x
  43. Fairlamb A.H., Bowman I.B.R., Uptake of the trypanocidal drug suramin by bloodstream forms of Trypanosoma brucei and its effect on respiration and growth rate in vivo, 10.1016/0166-6851(80)90050-x
  44. Ashizawa, J. Biol. Chem., 266, 16842 (1991)
  45. Mitsuya H, Popovic M, Yarchoan R, Matsushita S, Gallo R., Broder S, Suramin protection of T cells in vitro against infectivity and cytopathic effect of HTLV-III, 10.1126/science.6091268
  46. Pal Arun, Hall Belinda S, Field Mark C, Evidence for a non-LDL-mediated entry route for the trypanocidal drug suramin in Trypanosoma brucei, 10.1016/s0166-6851(02)00096-8
  47. Kleine F., Fischer W., Bericht über die Prüfung von „Bayer 205” in Afrika1), 10.1055/s-0028-1136308
  48. Voogd, Pharmacol. Rev., 45, 177 (1993)
  49. McGeary Ross, Bennett Andrew, Tran Quoc, Cosgrove Kelly, Ross Benjamin, Suramin: Clinical Uses and Structure-Activity Relationships, 10.2174/138955708786369573
  50. Lipinski Christopher A., Lombardo Franco, Dominy Beryl W., Feeney Paul J., Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, 10.1016/s0169-409x(96)00423-1
  51. Freissmuth, Mol. Pharmacol., 49, 602 (1996)