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Elucidation of human choline kinase crystal structures in complex with the products ADP or phosphocholine.

Malito E, Sekulic N, Too WC, Konrad M, Lavie A
J Mol Biol 364 136-51 (2006)
Related entries: 2cko, 2ckq

Cited: 52 times
EuropePMC logo PMID: 17007874

Abstract

Choline kinase, responsible for the phosphorylation of choline to phosphocholine as the first step of the CDP-choline pathway for the biosynthesis of phosphatidylcholine, has been recognized as a new target for anticancer therapy. Crystal structures of human choline kinase in its apo, ADP and phosphocholine-bound complexes, respectively, reveal the molecular details of the substrate binding sites. ATP binds in a cavity where residues from both the N and C-terminal lobes contribute to form a cleft, while the choline-binding site constitutes a deep hydrophobic groove in the C-terminal domain with a rim composed of negatively charged residues. Upon binding of choline, the enzyme undergoes conformational changes independently affecting the N-terminal domain and the ATP-binding loop. From this structural analysis and comparison with other kinases, and from mutagenesis data on the homologous Caenorhabditis elegans choline kinase, a model of the ternary ADP.phosphocholine complex was built that reveals the molecular basis for the phosphoryl transfer activity of this enzyme.

Articles - 2ckp mentioned but not cited (2)

  1. Elucidation of human choline kinase crystal structures in complex with the products ADP or phosphocholine. Malito E, Sekulic N, Too WC, Konrad M, Lavie A. J Mol Biol 364 136-151 (2006)
  2. Structural and enzymatic characterization of the choline kinase LicA from Streptococcus pneumoniae. Wang L, Jiang YL, Zhang JR, Zhou CZ, Chen Y. PLoS One 10 e0120467 (2015)


Reviews citing this publication (6)

  1. The genomic enzymology of antibiotic resistance. Morar M, Wright GD. Annu Rev Genet 44 25-51 (2010)
  2. Choline kinase alpha-Putting the ChoK-hold on tumor metabolism. Arlauckas SP, Popov AV, Delikatny EJ. Prog Lipid Res 63 28-40 (2016)
  3. Involvement of human choline kinase alpha and beta in carcinogenesis: a different role in lipid metabolism and biological functions. Gallego-Ortega D, Gómez del Pulgar T, Valdés-Mora F, Cebrián A, Lacal JC. Adv Enzyme Regul 51 183-194 (2011)
  4. Choline Kinase: An Unexpected Journey for a Precision Medicine Strategy in Human Diseases. Lacal JC, Zimmerman T, Campos JM. Pharmaceutics 13 788 (2021)
  5. Phosphoconjugation and dephosphorylation reactions of steroid hormone in insects. Sonobe H, Ito Y. Mol Cell Endocrinol 307 25-35 (2009)
  6. ChoK-ing the Pathogenic Bacteria: Potential of Human Choline Kinase Inhibitors as Antimicrobial Agents. Khalifa M, Few LL, See Too WC. Biomed Res Int 2020 1823485 (2020)

Articles citing this publication (44)

  1. Differential role of human choline kinase alpha and beta enzymes in lipid metabolism: implications in cancer onset and treatment. Gallego-Ortega D, Ramirez de Molina A, Ramos MA, Valdes-Mora F, Barderas MG, Sarmentero-Estrada J, Lacal JC. PLoS One 4 e7819 (2009)
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  4. Functional interactions between Choline kinase α, epidermal growth factor receptor and c-Src in breast cancer cell proliferation. Miyake T, Parsons SJ. Oncogene 31 1431-1441 (2012)
  5. Crystal structure of a mammalian CTP: phosphocholine cytidylyltransferase catalytic domain reveals novel active site residues within a highly conserved nucleotidyltransferase fold. Lee J, Johnson J, Ding Z, Paetzel M, Cornell RB. J Biol Chem 284 33535-33548 (2009)
  6. Crystal structures of human choline kinase isoforms in complex with hemicholinium-3: single amino acid near the active site influences inhibitor sensitivity. Hong BS, Allali-Hassani A, Tempel W, Finerty PJ, Mackenzie F, Dimov S, Vedadi M, Park HW. J Biol Chem 285 16330-16340 (2010)
  7. Structure of the antibiotic resistance factor spectinomycin phosphotransferase from Legionella pneumophila. Fong DH, Lemke CT, Hwang J, Xiong B, Berghuis AM. J Biol Chem 285 9545-9555 (2010)
  8. Balance of human choline kinase isoforms is critical for cell cycle regulation: implications for the development of choline kinase-targeted cancer therapy. Gruber J, Gruber J, See Too WC, Wong MT, Lavie A, McSorley T, Konrad M. FEBS J 279 1915-1928 (2012)
  9. Biochemical characterization of the initial steps of the Kennedy pathway in Trypanosoma brucei: the ethanolamine and choline kinases. Gibellini F, Hunter WN, Smith TK. Biochem J 415 135-144 (2008)
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  11. New splicing mutation in the choline kinase beta (CHKB) gene causing a muscular dystrophy detected by whole-exome sequencing. Oliveira J, Negrão L, Fineza I, Taipa R, Melo-Pires M, Fortuna AM, Gonçalves AR, Froufe H, Egas C, Santos R, Sousa M. J Hum Genet 60 305-312 (2015)
  12. Plasmodium falciparum Choline Kinase Inhibition Leads to a Major Decrease in Phosphatidylethanolamine Causing Parasite Death. Serrán-Aguilera L, Denton H, Rubio-Ruiz B, López-Gutiérrez B, Entrena A, Izquierdo L, Smith TK, Conejo-García A, Hurtado-Guerrero R. Sci Rep 6 33189 (2016)
  13. The mechanism of allosteric coupling in choline kinase α1 revealed by the action of a rationally designed inhibitor. Sahún-Roncero M, Rubio-Ruiz B, Saladino G, Conejo-García A, Espinosa A, Velázquez-Campoy A, Gervasio FL, Entrena A, Hurtado-Guerrero R. Angew Chem Int Ed Engl 52 4582-4586 (2013)
  14. The novel choline kinase inhibitor ICL-CCIC-0019 reprograms cellular metabolism and inhibits cancer cell growth. Trousil S, Kaliszczak M, Schug Z, Nguyen QD, Tomasi G, Favicchio R, Brickute D, Fortt R, Twyman FJ, Carroll L, Kalusa A, Navaratnam N, Adejumo T, Carling D, Gottlieb E, Aboagye EO. Oncotarget 7 37103-37120 (2016)
  15. Design, synthesis, crystallization and biological evaluation of new symmetrical biscationic compounds as selective inhibitors of human Choline Kinase α1 (ChoKα1). Schiaffino-Ortega S, Baglioni E, Mariotto E, Bortolozzi R, Serrán-Aguilera L, Ríos-Marco P, Carrasco-Jimenez MP, Gallo MA, Hurtado-Guerrero R, Marco C, Basso G, Viola G, Entrena A, López-Cara LC. Sci Rep 6 23793 (2016)
  16. Modulation of choline kinase activity in human cancer cells observed by dynamic 31P NMR. Gabellieri C, Beloueche-Babari M, Jamin Y, Payne GS, Leach MO, Eykyn TR. NMR Biomed 22 456-461 (2009)
  17. Structures of 5-methylthioribose kinase reveal substrate specificity and unusual mode of nucleotide binding. Ku SY, Yip P, Cornell KA, Riscoe MK, Behr JB, Guillerm G, Howell PL. J Biol Chem 282 22195-22206 (2007)
  18. Antiplasmodial activity and mechanism of action of RSM-932A, a promising synergistic inhibitor of Plasmodium falciparum choline kinase. Zimmerman T, Moneriz C, Diez A, Bautista JM, Gómez Del Pulgar T, Cebrián A, Lacal JC. Antimicrob Agents Chemother 57 5878-5888 (2013)
  19. Genomic Analysis of Genes Involved in the Biosynthesis of Very Long Chain Polyunsaturated Fatty Acids in Thraustochytrium sp. 26185. Zhao X, Dauenpen M, Qu C, Qiu X. Lipids 51 1065-1075 (2016)
  20. Novel 4-amino bis-pyridinium and bis-quinolinium derivatives as choline kinase inhibitors with antiproliferative activity against the human breast cancer SKBR-3 cell line. Gómez-Pérez V, McSorley T, See Too WC, Konrad M, Campos JM. ChemMedChem 7 663-669 (2012)
  21. A kinase bioscavenger provides antibiotic resistance by extremely tight substrate binding. Terekhov SS, Mokrushina YA, Nazarov AS, Zlobin A, Zalevsky A, Bourenkov G, Golovin A, Golovin A, Belogurov A, Osterman IA, Kulikova AA, Mitkevich VA, Lou HJ, Turk BE, Wilmanns M, Smirnov IV, Altman S, Gabibov AG. Sci Adv 6 eaaz9861 (2020)
  22. The hepatic circadian clock regulates the choline kinase α gene through the BMAL1-REV-ERBα axis. Gréchez-Cassiau A, Feillet C, Guérin S, Delaunay F. Chronobiol Int 32 774-784 (2015)
  23. Potential choline kinase inhibitors: a molecular modeling study of bis-quinolinium compounds. Srivani P, Sastry GN. J Mol Graph Model 27 676-688 (2009)
  24. Kinetic and mechanistic characterisation of Choline Kinase-α. Hudson CS, Knegtel RM, Brown K, Charlton PA, Pollard JR. Biochim Biophys Acta 1834 1107-1116 (2013)
  25. Highly specific antibodies for co-detection of human choline kinase α1 and α2 isoforms. Too WC, Wong MT, Few LL, Konrad M. PLoS One 5 e12999 (2010)
  26. Human Choline Kinase-α Promotes Hepatitis C Virus RNA Replication through Modulation of Membranous Viral Replication Complex Formation. Wong MT, Chen SS. J Virol 90 9075-9095 (2016)
  27. Phosphorylation of Human Choline Kinase Beta by Protein Kinase A: Its Impact on Activity and Inhibition. Chang CC, Few LL, Konrad M, See Too WC. PLoS One 11 e0154702 (2016)
  28. Design of symmetrical and nonsymmetrical N,N-dimethylaminopyridine derivatives as highly potent choline kinase alpha inhibitors. Trousil S, Carroll L, Kalusa A, Aberg O, Kaliszczak M, Aboagye EO. Medchemcomm 2013 693-696 (2013)
  29. Genomics, evolution, and crystal structure of a new family of bacterial spore kinases. Scheeff ED, Axelrod HL, Miller MD, Chiu HJ, Deacon AM, Wilson IA, Manning G. Proteins 78 1470-1482 (2010)
  30. Structural modeling and biochemical characterization of recombinant KPN_02809, a zinc-dependent metalloprotease from Klebsiella pneumoniae MGH 78578. Wong MT, Choi SB, Kuan CS, Chua SL, Chang CH, Normi YM, See Too WC, Wahab HA, Few LL. Int J Mol Sci 13 901-917 (2012)
  31. Importance of Skin Changes in the Differential Diagnosis of Congenital Muscular Dystrophies. Yis U, Baydan F, Karakaya M, Hız Kurul S, Cirak S. Biomed Res Int 2016 3128735 (2016)
  32. Insights into the binding specificity and catalytic mechanism of N-acetylhexosamine 1-phosphate kinases through multiple reaction complexes. Wang KC, Lyu SY, Liu YC, Chang CY, Wu CJ, Li TL. Acta Crystallogr D Biol Crystallogr 70 1401-1410 (2014)
  33. Molecular basis for the interaction between human choline kinase alpha and the SH3 domain of the c-Src tyrosine kinase. Kall SL, Whitlatch K, Smithgall TE, Lavie A. Sci Rep 9 17121 (2019)
  34. Letter 1H and 13C NMR spectral assignments of pyridinium salts linked to a N-9 or N-3 adenine moiety. Rubio-Ruiz B, Conejo-García A, Gallo MA, Espinosa A, Entrena A. Magn Reson Chem 50 466-469 (2012)
  35. [99mTc]Tc-DTPA-Bis(cholineethylamine) as an Oncologic Tracer for the Detection of Choline Transporter (ChT) and Choline Kinase (ChK) Expression in Cancer. Jaswal AP, Hazari PP, Prakash S, Sethi P, Kaushik A, Roy BG, Kathait S, Singh B, Mishra AK, Mishra AK. ACS Omega 7 12509-12523 (2022)
  36. BUMPY STEM Is an Arabidopsis Choline/Ethanolamine Kinase Required for Normal Development and Chilling Responses. Rabeler C, Chen M, Kaplinsky N. Front Plant Sci 13 851960 (2022)
  37. Bi-allelic variants in CHKA cause a neurodevelopmental disorder with epilepsy and microcephaly. Klöckner C, Fernández-Murray JP, Tavasoli M, Sticht H, Stoltenburg-Didinger G, Scholle LM, Bakhtiari S, Kruer MC, Darvish H, Firouzabadi SG, Pagnozzi A, Shukla A, Girisha KM, Narayanan DL, Kaur P, Maroofian R, Zaki MS, Noureldeen MM, Merkenschlager A, Gburek-Augustat J, Cali E, Banu S, Nahar K, Efthymiou S, Houlden H, Jamra RA, Williams J, McMaster CR, Platzer K. Brain 145 1916-1923 (2022)
  38. Choline Kinase Alpha2 Promotes Lipid Droplet Lipolysis in Non-Small-Cell Lung Carcinoma. Zhu R, Yang Y, Shao F, Wang J, Gao Y, He J, Lu Z. Front Oncol 12 848483 (2022)
  39. Novel Non-Congeneric Derivatives of the Choline Kinase Alpha Inhibitor ICL-CCIC-0019. Wang N, Brickute D, Braga M, Barnes C, Lu H, Allott L, Aboagye EO. Pharmaceutics 13 1078 (2021)
  40. The moonlighting function of glycolytic enzyme enolase-1 promotes choline phospholipid metabolism and tumor cell proliferation. Ma Q, Jiang H, Ma L, Zhao G, Xu Q, Guo D, He N, Liu H, Meng Z, Liu J, Zhu L, Lin Q, Wu X, Li M, Luo S, Fang J, Lu Z. Proc Natl Acad Sci U S A 120 e2209435120 (2023)
  41. Letter 1H, 13C NMR studies of new 3-aminophenol isomers linked to pyridinium salts. Schiaffino-Ortega S, Espinosa A, Gallo MA, López-Cara LC, Entrena A. Magn Reson Chem 52 40-46 (2014)
  42. Letter 1 H and 13 C NMR spectral assignments of 1,1'-(((ethane-1,2-diylbis(oxy))bis(4,1-phenylene))bis(methylene))-bispyridinium and -bisquinolinium bromide derivatives. Schiaffino-Ortega S, Kimatrai-Salvador M, Baglioni E, Gallo MA, Entrena Guadix A, Lopez-Cara LC. Magn Reson Chem 54 905-911 (2016)
  43. Digital Cascade Assays for ADP- or ATP-Producing Enzymes Using a Femtoliter Reactor Array Device. Ueno H, Sano M, Hara M, Noji H. ACS Sens 8 3400-3407 (2023)
  44. Unusual metal ion cofactor requirement of Entamoeba histolytica choline and ethanolamine kinase isoforms. Chang CH, Few LL, Lim BH, Yvonne-Tee GB, Chew AL, See Too WC. Parasitol Res 122 1651-1661 (2023)


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