Structure-activity relationships of β-hydroxyphosphonate nucleoside analogues as cytosolic 5′-nucleotidase II potential inhibitors: Synthesis, in vitro evaluation and molecular modeling studies

European Journal of Medicinal Chemistry

Volumn 77, Issue , 2014, Pages 18-37

  Meurillon, Maïa ^a   Marton, Zsuzsanna ^a   Hospital, Audrey ^a   Jordheim, Lars Petter ^b   Béjaud, Jérôme ^a   Lionne, Corinne ^a   Dumontet, Charles ^b   Périgaud, Christian ^a   Chaloin, Laurent ^a   Peyrottes, Suzanne ^a  

^a UNIV MONTPELLIER   (France)

^b CENTRE DE RECHERCHE EN CANCÉROLOGIE DE LYON   (France)

Author keywords

Enzyme inhibitors; Leukemia; Nucleotides; Phosphonate

Indexed keywords

1 (2 O ACETYL 5 O BENZOYL 3 O BENZYL 6 DEOXY 6 DIETHYLPHOSPHONO BETA DEXTRO GLUCOFURANOSYL)URACIL; 1 (2,2' ANHYDRO 6 DEOXY 6 DIETHYLPHOSPHONO BETA DEXTRO ALTROFURANOSYL)URACIL; 1 (5) (6 DEOXY 6 DIETHYLPHOSPHONO 2,3 SECO BETA DEXTRO RIBOHEXOFURANOSYL)CYTOSINE; 1 (5) (6 DEOXY 6 DIETHYLPHOSPHONO 2,3 SECO BETA DEXTRO RIBOHEXOFURANOSYL)URACIL; 1 (5) (6 DEOXY 6 PHOSPHONO 2,3 SECO BETA DEXTRO RIBOHEXOFURASONYL)CYTOSINE (DISODIUM SALT); 1 (5) (6 DEOXY 6 PHOSPHONO 2,3 SECO BETA DEXTRO RIBOHEXOFURASONYL)URACIL (DISODIUM SALT); 1 (6 DEOXY 6 DIETHYLPHOSPHONO BETA DEXTRO ALTROFURANOSYL)CYTOSINE; 1 (6 DEOXY 6 DIETHYLPHOSPHONO BETA DEXTRO ALTROFURANOSYL)URACIL; 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 (2 PHENYLVINYL)CYTOSINE (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 (2 PHENYLVINYL)URACIL (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 (3,3 DIMETHYL 1 BUTYN 1 YL)CYTOSINE (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 (3,3 DIMETHYL 1 BUTYN 1 YL)URACIL (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 HEXYN 1 YL CYTOSINE (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 HEXYN 1 YL URACIL (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 PHENYL CYTOSINE (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 PHENYL URACIL (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 PHENYLETHYNYL CYTOSINE (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALLOFURANOSYL) 5 PHENYLETHYNYL URACIL (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO ALTROFURANOSYL)CYTOSINE (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO GLUCOFURANOSYL)CYTOSINE (MONOSODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO GLUCOFURANOSYL)URACIL (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO MANNOFURANOSYL)CYTOSINE (DISODIUM SALT); 1 (6 DEOXY 6 PHOSPHONO BETA DEXTRO MANNOFURANOSYL)URACIL (DISODIUM SALT); 3 O BENZYL 1,2 5,6 O DIISOPROPYLIDENE ALPHA DEXTRO GLUCOFURANOSE; 3 O BENZYL 1,2 O ISOPROPYLIDENE ALPHA DEXTRO GLUCOFURANOSE; 3 O BENZYL 6 DEOXY 6 IODO 1,2 O ISOPROPYLIDENE ALPHA DEXTRO GLUCOFURANOSE; 5 O BENZOYL 3 O BENZYL 6 DEOXY 1,2 O DIACETYL 6 DIETHYLPHOSPHONO ALPHA DEXTRO GLUCOFURANOSE; 5 O BENZOYL 3 O BENZYL 6 DEOXY 6 DIETHYLPHOSPHONO 1,2 O ISOPROPYLIDENE ALPHA DEXTRO GLUCOFURANOSE; NUCLEOSIDE ANALOG; UNCLASSIFIED DRUG; UNINDEXED DRUG; 5' NUCLEOTIDASE; ENZYME INHIBITOR; NT5C2 PROTEIN, HUMAN; NUCLEOSIDE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL ANALYSIS; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME PURIFICATION; IN VITRO STUDY; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DOSE RESPONSE; HUMAN; METABOLISM; SYNTHESIS;

5'-NUCLEOTIDASE; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NUCLEOSIDES; ORGANOPHOSPHONATES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84895790804     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.02.055     Document Type: Article

References (45)

1. A.J. Berdis DNA polymerases as therapeutic targets† Biochemistry 47 2008 8253 8260
2. M.O. Akanbi, K. Scarci, B. Taiwo, and R.L. Murphy Combination nucleoside/nucleotide reverse transcriptase inhibitors for treatment of HIV infection Expert Opinion on Pharmacotherapy 13 2012 65 79
3. K.L. Bogan, and C. Brenner 5 '-nucleotidases and their new roles in NAD(+) and phosphate metabolism New Journal of Chemistry 34 2010 845 853
4. A. Fyrberg, F. Albertioni, and K. Lotfi Cell cycle effect on the activity of deoxynucleoside analogue metabolising enzymes Biochemical and Biophysical Research 357 2007 847 853 (Pubitemid 46693649)
5. V. Bianchi, and J. Spychala Mammalian 5'-nucleotidases Journal of Biological Chemistry 278 2003 46195 46198
6. C. Rampazzo, C. Miazzi, E. Franzolin, G. Pontarin, P. Ferraro, M. Frangini, P. Reichard, and V. Bianchi Regulation by degradation, a cellular defense against deoxyribonucleotide pool imbalances Mutation Research - Genetic Toxicology and Environmental Mutagenesis 703 2010 2 10
7. C.M. Galmarini, X. Thomas, F. Calvo, P. Rousselot, M. Rabilloud, A. El Jaffari, E. Cros, and C. Dumontet In vivo mechanisms of resistance to cytarabine in acute myeloid leukaemia British Journal of Pharmacology 117 2002 860 868 (Pubitemid 34639247)
8. L.P. Jordheim, and L. Chaloin Therapeutic perspectives for cN-II in Cancer Current Medicinal Chemistry 20 2013 4292 4303
9. C.M. Galmarini, K. Graham, X. Thomas, F. Calvo, P. Rousselot, A. El Jafaari, E. Cros, J.R. Mackey, and C. Dumontet Expression of high Km 5'-nucleotidase in leukemic blasts is an independent prognostic factor in adults with acute myeloid leukemia Blood 98 2001 1922 1926
10. C.M. Galmarini, X. Thomas, K. Graham, A. El Jafaari, E. Cros, L. Jordheim, J.R. Mackey, and C. Dumontet Deoxycytidine kinase and cN-II nucleotidase expression in blast cells predict survival in acute myeloid leukaemia patients treated with cytarabine British Journal of Pharmacology 122 2003 53 60 (Pubitemid 36819338)
11. M.G. Careddu, S. Allegrini, R. Pesi, M. Camici, M. Garcia Gil, and M.G. Tozzi Knockdown of cytosolic 5'-nucleotidase II (cN-II) reveals that its activity is essential for survival in astrocytoma cells Biochimica Biophysica Acta - Molecular Cell Research 1783 2008 1529 1535
12. J.A. Meyer, J. Wang, L.E. Hogan, J.J. Yang, S. Dandekar, J.P. Patel, Z. Tang, P. Zumbo, S. Li, J. Zavadil, R.L. Levine, T. Cardozo, S.P. Hunger, E.A. Raetz, W.E. Evans, D.J. Morrison, C.E. Mason, and W.L. Carroll Relapse-specific mutations in NT5C2 in childhood acute lymphoblastic leukemia Nature Genetics 45 2013 290 294
13. G. Tzoneva, A. Perez-Garcia, Z. Carpenter, H. Khiabanian, V. Tosello, M. Allegretta, E. Paietta, J. Racevskis, J.M. Rowe, M.S. Tallman, M. Paganin, G. Basso, J. Hof, R. Kirschner-Schwabe, T. Palomero, R. Rabadan, and A. Ferrando Activating mutations in the NT5C2 nucleotidase gene drive chemotherapy resistance in relapsed ALL Natural Medicines 19 2013 368 371
14. D.N. Filoni, R. Pesi, M.G. Careddu, M. Camici, S. Allegrini, A. Collavoli, I. Scarfone, F. Zucchi, A. Galli, and M.G. Tozzi Initial studies to define the physiologic role of cN-II, Nucleosides Nucleotides Nucleic Acids 30 2011 1155 1160
15. F. Gallier, P. Lallemand, M. Meurillon, L.P. Jordheim, C. Dumontet, C. Périgaud, C. Lionne, S. Peyrottes, and L. Chaloin Structural insights into the inhibition of cytosolic 5′-Nucleotidase ii (cN-II) by ribonucleoside 5′-Monophosphate analogues PLoS Computational Biology 7 2011 e1002295
16. J. Spychala, V. Madridmarina, and I.H. Fox High Km soluble 5'-nucleotidase from human-placenta - properties and allosteric regulation by IMP and ATP Journal of Biological Chemistry 263 1988 18759 18765 (Pubitemid 19016333)
17. F. Gallier, S. Peyrottes, and C. Perigaud Ex-chiral-pool synthesis of beta-hydroxyphosphonate nucleoside analogues European Journal of Organic Chemistry 2007 925 933
18. S.K. Roy, and J.Y. Tang Efficient large scale synthesis of 2'-O-alkyl pyrimidine ribonucleosides Organic Process Research and Development 4 2000 170 171
19. U. Legorburu, C.B. Reese, and Q.L. Song Conversion of uridine into 2'-O-(2-methoxyethyl)uridine and 2'-O-(2-methoxyethyl)cytidine Tetrahedron 55 1999 5635 5640
20. A. Miah, C.B. Reese, Q.L. Song, Z. Sturdy, S. Neidle, I.J. Simpson, M. Read, and E. Rayner 2',3 '-anhydrouridine. A useful synthetic intermediate Journal of the Chemical Society, Perkin Transactions 1 1998 3277 3283 (Pubitemid 128765284)
21. J.X. Khym, and W.E. Cohen Characterizations and some chemical reactions of periodate-oxidized nucleosides Journal of the American Chemical Society 82 1960 6380 6386
22. Y. Ishido, N. Nakazaki, and N. Sakairi Partial protection of carbohydrate-derivatives. 3. Regioselective 2'-O-deacylation of fully acylated purine and pyrimidine ribonucleosides with hydrazine hydrate Journal of the Chemical Society, Perkin Transactions 1 1979 2088 2098
23. D. Rai, M. Johar, T. Manning, B. Agrawal, D.Y. Kunimoto, and R. Kumar Design and studies of novel 5-substituted alkynylpyrimidine nucleosides as potent inhibitors of mycobacteria Journal of Medicinal Chemistry 48 2005 7012 7017 (Pubitemid 41533123)
24. G. Sartori, G. Enderlin, G. Herve, and C. Len Highly effective synthesis of C-5-substituted 2'-Deoxyuridine using Suzuki-Miyaura cross-coupling in water Synthesis 44 2012 767 772
25. M.J. Robins, and P.J. Barr Nucleic-acid related-compounds 39. Efficient conversion of 5-iodo to 5-alkynyl and derived 5-substituted uracil bases and nucleosides Journal of Organic Chemistry 48 1983 1854 1862
26. M. Bobek, I. Kavai, R.A. Sharma, S. Grill, G. Dutschman, and Y.C. Cheng Acetylenic nucleosides. 4.1-beta-D-arabinofuranosyl-5-ethynylcytosine - improved synthesis and evaluation of biochemical and antiviral properties Journal of Medicinal Chemistry 30 1987 2154 2157 (Pubitemid 18046081)
27. S. Ghilagaber, W.N. Hunter, and R. Marquez Efficient coupling of low boiling point alkynes and 5-iodonucleosides Tetrahedron Letters 48 2007 483 486 (Pubitemid 44895615)
28. L.P. Jordheim, Z. Marton, M. Rhimi, E. Cros-Perrial, C. Lionne, S. Peyrottes, C. Dumontet, N. Aghajari, and L. Chaloin Identification and characterization of inhibitors of cytoplasmic 5'-nucleotidase cN-II issued from virtual screening Biochemical Pharmacology 85 2013 497 506
29. A. Hospital, M. Meurillon, S. Peyrottes, and C. Périgaud An alternative pathway to ribonucleoside β-hydroxyphosphonate analogues and related prodrugs Organic Letters 15 2013 4778 4781
30. A. Pedretti, L. Villa, and G. Vistoli VEGA - an open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming Journal of Computer-Aided Molecular Design 18 2004 167 173 (Pubitemid 39069412)
31. J. Gasteiger, and M. Marsili Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges Tetrahedron 36 1980 3219 3228
32. J. Zhang, T. Kleinoeder, and J. Gasteiger Prediction of pK(a) values for aliphatic carboxylic acids and alcohols with empirical atomic charge descriptors Journal of Chemical Information and Modelling 46 2006 2256 2266 (Pubitemid 46008099)
33. K. Wallden, and P. Nordlund Structural basis for the allosteric regulation and substrate recognition of human cytosolic 5'-Nucleotidase ii Journal of Molecular Biology 408 2011 684 696
34. W.L. DeLano The PyMOL Molecular Graphics System 2008 DeLano Scientific LLC Palo Alto, CA http://www.pymol.org
35. R.A. Laskowski, and M.B. Swindells LigPlot+: multiple ligand-protein interaction diagrams for drug discovery Journal of Chemical Information and Modelling 51 2011 2778 2786
36. J.C. Phillips, R. Braun, W. Wang, J. Gumbart, E. Tajkhorshid, E. Villa, C. Chipot, R.D. Skeel, L. Kale, and K. Schulten Scalable molecular dynamics with NAMD Journal of Computational Chemistry 26 2005 1781 1802 (Pubitemid 43078511)
37. S.E. Feller, Y.H. Zhang, R.W. Pastor, and B.R. Brooks Constant-pressure molecular-dynamics simulation - the Langevin piston method Journal of Chemical Physics 103 1995 4613 4621
38. G.J. Martyna, D.J. Tobias, and M.L. Klein Constant-pressure molecular-dynamics algorithms Journal of Chemical Physics 101 1994 4177 4189
39. U. Essmann, L. Perera, M.L. Berkowitz, T. Darden, H. Lee, and L.G. Pedersen A smooth particle mesh Ewald method Journal of Chemical Physics 103 1995 8577 8593
40. A.D. MacKerell Jr., N. Banavali, and N. Foloppe Development and current status of the CHARMM force field for nucleic acids Biopolymers 56 2000 257 265 (Pubitemid 34105873)
41. W. Humphrey, A. Dalke, and K. Schulten VMD: visual molecular dynamics Journal of Molecular Graphics and Modelling 14 1996 33 38 (Pubitemid 26152973)
42. K. Tadano, Y. Idogaki, H. Yamada, and T. Suami Introduction of gem-dialkyl group to hexofuranose by ortho Ester Claisen rearrangement Chemistry Letters 1985 1925 1928
43. K.I. Tadano, Y. Idogaki, H. Yamada, and T. Suami Ortho Ester Claisen rearrangements of 3 3-C-(Hydroxymethyl)methylene derivatives of hexofuranose - stereoselective introduction of a quaternary center on C-3 of d-ribo-hexofuranose, l-lyxo-Hexofuranose, and d-arabino-hexofuranose Journal of Organic Chemistry 52 1987 1201 1210
44. K. Seo Synthesis of 1,2,4-tri-O-acetyl-6-deoxy-6-C-(isopropylphosphinyl)- 3,5-di-O-methyl-D-glucoseptanose and 1,2,4-tri-O-acetyl-3-O-benzyl-6-C- (butylphosphinyl)-6-deoxy-5-O-methyl-D-glucoseptanose Carbohydrate Research 123 1983 201 207
45. S. Peyrottes, F. Gallier, J. Bejaud, and C. Perigaud Use of microwave irradiation for sugar and nucleoside phosphonates synthesis Tetrahedron Letters 47 2006 7719 7721 (Pubitemid 44472529)