Therapeutic perspectives for cN-II in cancer

Current Medicinal Chemistry

Volumn 20, Issue 34, 2013, Pages 4292-4303

  Jordheim, Lars Petter ^a,b,c,d   Chaloin, Laurent ^e  

^a UNIVERSITÉ DE LYON   (France)

^b UNIVERSITÉ LYON 1   (France)

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

^d CENTRE LÉON BÉRARD   (France)

^e University of Montpellier I and II   (France)

Author keywords

Cell models; Clinical trials; CN II; Crystallography; Enzymatic assay; Inhibitor; Virtual screening

Indexed keywords

5' NUCLEOTIDASE; CYTOPLASMIC 5' NUCLEOTIDASE CN II; NUCLEOSIDE ANALOG; PHOSPHOTRANSFERASE; UNCLASSIFIED DRUG;

ALLOSTERISM; ARTICLE; CANCER CELL; CYTOTOXICITY; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; IN VITRO STUDY; NONHUMAN; SITE DIRECTED MUTAGENESIS; STRUCTURE ACTIVITY RELATION;

5'-NUCLEOTIDASE; ANIMALS; CYTOPLASM; HUMANS; MOLECULAR TARGETED THERAPY; NEOPLASMS; PHOSPHOTRANSFERASES;

EID: 84887887553     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/0929867311320340008     Document Type: Article

References (82)

1. Weinberg, G.; Ullman, B.; Martin, D.W., Jr. Mutator phenotypes in mammalian cell mutants with distinct biochemical defects and abnormal deoxyribonucleoside triphosphate pools. Proc. Natl. Acad. Sci. U S A, 1981, 78(4), 2447-2451.
2. Bester, A.C.; Roniger, M.; Oren, Y.S.; Im, M.M.; Sarni, D.; Chaoat, M.; Bensimon, A.; Zamir, G.; Shewach, D.S.; Kerem, B. Nucleotide deficiency promotes genomic instability in early stages of cancer development. Cell, 2011, 145(3), 435-446.
3. Hunsucker, S.A.; Mitchell, B.S.; Spychala, J. The 5'-nucleotidases as regulators of nucleotide and drug metabolism. Pharmacol. Ther., 2005, 107(1), 1-30.
4. Rampazzo, C.; Miazzi, C.; Franzolin, E.; Pontarin, G.; Ferraro, P.; Frangini, M.; Reichard, P.; Bianchi, V. Regulation by degradation, a cellular defense against deoxyribonucleotide pool imbalances. Mutat. Res., 2010, 703(1), 2-10.
5. Bianchi, V.; Spychala, J. Mammalian 5'-nucleotidases. J. Biol. Chem., 2003, 278(47), 46195-46198.
6. Buschmann, J.; Moritz, B.; Jeske, M.; Lilie, H.; Schierhorn, A.; Wahle, E. Identification of Drosophila and Human 7-Methyl GMPspecific Nucleotidases. J. Biol. Chem., 2013, 288(4), 2441-2451.
7. Stagg, J. The double-edge sword effect of anti-CD73 cancer therapy. Oncoimmunology, 2012, 1(2), 217-218.
8. Carson, D.A.; Wasson, D.B. Characterization of an adenosine 5'-triphosphate-and deoxyadenosine 5'-triphosphate-activated nucleotidase from human malignant lymphocytes. Cancer Res., 1982, 42(11), 4321-4324.
9. Spychala, J.; Madrid-Marina, V.; Fox, I.H. High Km soluble 5'-nucleotidase from human placenta. Properties and allosteric regulation by IMP and ATP. J. Biol. Chem., 1988, 263(35), 18759-18765.
10. Oka, J.; Matsumoto, A.; Hosokawa, Y.; Inoue, S. Molecular cloning of human cytosolic purine 5'-nucleotidase. Biochem. Biophys. Res. Commun., 1994, 205(1), 917-922.
11. Gazziola, C.; Moras, M.; Ferraro, P.; Gallinaro, L.; Verin, R.; Rampazzo, C.; Reichard, P.; Bianchi, V. Induction of human high K(M) 5'-nucleotidase in cultured 293 cells. Exp. Cell. Res., 1999, 253(2), 474-482.
12. Gazziola, C.; Ferraro, P.; Moras, M.; Reichard, P.; Bianchi, V. Cytosolic high K(m) 5'-nucleotidase and 5'(3')-deoxyribonucleotidase in substrate cycles involved in nucleotide metabolism. J. Biol. Chem., 2001, 276(9), 6185-6190.
13. Rampazzo, C.; Gazziola, C.; Ferraro, P.; Gallinaro, L.; Johansson, M.; Reichard, P.; Bianchi, V. Human high-Km 5'-nucleotidase effects of overexpression of the cloned cDNA in cultured human cells. Eur. J. Biochem., 1999, 261(3), 689-697.
14. Itoh, R. IMP-GMP 5'-nucleotidase. Comp. Biochem. Physiol. B., 1993, 105(1), 13-19.
15. Itoh, R.; Mitsui, A.; Tsushima, K. 5'-nucleotidase of chicken liver. Biochim. Biophys. Acta, 1967, 146(1), 151-159.
16. Tozzi, M.G.; Camici, M.; Allegrini, S.; Pesi, R.; Turriani, M.; Del Corso, A.; Ipata, P.L. Cytosolic 5'-nucleotidase/phosphotransferase of human colon carcinoma. Adv. Exp. Med. Biol., 1991, 309B, 173-176.
17. Pesi, R.; Turriani, M.; Allegrini, S.; Scolozzi, C.; Camici, M.; Ipata, P.L.; Tozzi, M.G. The bifunctional cytosolic 5'-nucleotidase: regulation of the phosphotransferase and nucleotidase activities. Arch. Biochem. Biophys., 1994, 312(1), 75-80.
18. Banditelli, S.; Baiocchi, C.; Pesi, R.; Allegrini, S.; Turriani, M.; Ipata, P.L.; Camici, M.; Tozzi, M.G. The phosphotransferase activity of cytosolic 5'-nucleotidase; a purine analog phosphorylating enzyme. Int. J. Biochem. Cell. Biol., 1996, 28(6), 711-720.
19. Allegrini, S.; Pesi, R.; Tozzi, M.G.; Fiol, C.J.; Johnson, R.B.; Eriksson, S. Bovine cytosolic IMP/GMP-specific 5'-nucleotidase: cloning and expression of active enzyme in Escherichia coli. Biochem. J., 1997, 328( Pt 2), 483-487.
20. Mazzon, C.; Rampazzo, C.; Scaini, M.C.; Gallinaro, L.; Karlsson, A.; Meier, C.; Balzarini, J.; Reichard, P.; Bianchi, V. Cytosolic and mitochondrial deoxyribonucleotidases: activity with substrate analogs, inhibitors and implications for therapy. Biochem. Pharmacol., 2003, 66(3), 471-479.
21. Jordheim, L.P.; Cros, E.; Galmarini, C.M.; Dumontet, C.; Bretonnet, A.S.; Krimm, I.; Lancelin, J.M.; Gagnieu, M.C. F-ara-AMP is a substrate of cytoplasmic 5'-nucleotidase II (cN-II): HPLC and NMR studies of enzymatic dephosphorylation. Nucleosides Nucleotides Nucleic Acids, 2006, 25(3), 289-297.
22. Brouwer, C.; Vogels-Mentink, T.M.; Keizer-Garritsen, J.J.; Trijbels, F.J.; Bokkerink, J.P.; Hoogerbrugge, P.M.; van Wering, E.R.; Veerman, A.J.; De Abreu, R.A. Role of 5'-nucleotidase in thiopurine metabolism: enzyme kinetic profile and association with thio-GMP levels in patients with acute lymphoblastic leukemia during 6-mercaptopurine treatment. Clin. Chim. Acta, 2005, 361(1-2), 95-103.
23. Spychala, J.; Chen, V.; Oka, J.; Mitchell, B.S. ATP and phosphate reciprocally affect subunit association of human recombinant High Km 5'-nucleotidase. Role for the C-terminal polyglutamic acid tract in subunit association and catalytic activity. Eur. J. Biochem., 1999, 259(3), 851-858.
24. Pesi, R.; Allegrini, S.; Careddu, M.G.; Filoni, D.N.; Camici, M.; Tozzi, M.G. Active and regulatory sites of cytosolic 5'-nucleotidase. FEBSJ., 2010, 277(23), 4863-4872.
25. Wallden, K.; Stenmark, P.; Nyman, T.; Flodin, S.; Graslund, S.; Loppnau, P.; Bianchi, V.; Nordlund, P. Crystal structure of human cytosolic 5'-nucleotidase II: insights into allosteric regulation and substrate recognition. J. Biol. Chem., 2007, 282(24), 17828-17836.
26. Jordheim, L.P.; Marton, Z.; Rhimi, M.; Cros-Perrial, E.; Lionne, C.; Peyrottes, S.; Dumontet, C.; Aghajari, N.; Chaloin, L. Identification and characterization of inhibitors of cytoplasmic 5'-nucleotidase cN-II issued from virtual screening. Biochem. Pharmacol., 2013, 85(4), 497-506.
27. Ipata, P.L.; Tozzi, M.G. Recent advances in structure and function of cytosolic IMP-GMP specific 5'-nucleotidase II (cN-II). Purinergic. Signal., 2006, 2(4), 669-675.
28. Allegrini, S.; Scaloni, A.; Careddu, M.G.; Cuccu, G.; D'Ambrosio, C.; Pesi, R.; Camici, M.; Ferrara, L.; Tozzi, M.G. Mechanistic studies on bovine cytosolic 5'-nucleotidase II, an enzyme belonging to the HAD superfamily. Eur. J. Biochem., 2004, 271(23-24), 4881-4891.
29. Skladanowski, A.C.; Sala, G.B.; Newby, A.C. Inhibition of IMPspecific cytosolic 5'-nucleotidase and adenosine formation in rat polymorphonuclear leucocytes by 5'-deoxy-5'-isobutylthio derivatives of adenosine and inosine. Biochem. J., 1989, 262(1), 203-208.
30. Marques, A.F.; Teixeira, N.A.; Gambaretto, C.; Sillero, A.; Sillero, M.A. IMP-GMP 5'-nucleotidase from rat brain: activation by polyphosphates. J. Neurochem., 1998, 71(3), 1241-1250.
31. Pinto, R.M.; Canales, J.; Gunther Sillero, M.A.; Sillero, A. Diadenosine tetraphosphate activates cytosol 5'-nucleotidase. Biochem. Biophys. Res. Commun., 1986, 138(1), 261-267.
32. van den Berghe, G.; van Pottelsberghe, C.; Hers, H.G. A kinetic study of the soluble 5'-nucleotidase of rat liver. Biochem. J., 1977, 162(3), 611-616.
33. Turriani, M.; Pesi, R.; Nardone, A.; Turchi, G.; Sgarrella, F.; Ipata, P.L.; Tozzi, M.G. Cytosolic 5'-nucleotidase/nucleoside phosphotransferase: a nucleoside analog activating enzyme? J. Biochem. Toxicol., 1994, 9(1), 51-57.
34. Baiocchi, C.; Pesi, R.; Camici, M.; Itoh, R.; Grazi Tozzi, M. Mechanism of the reaction catalysed by cytosolic 5'-nucleotidase/phosphotransferase: formation of a phosphorylated intermediate. Biochem. J., 1996, 317( Pt 3), 797-801.
35. Worku, Y.; Newby, A.C. Nucleoside exchange catalysed by the cytoplasmic 5'-nucleotidase. Biochem. J., 1982, 205(3), 503-510.
36. Johnson, M.A.; Fridland, A. Phosphorylation of 2',3'-dideoxyinosine by cytosolic 5'-nucleotidase of human lymphoid cells. Mol. Pharmacol., 1989, 36(2), 291-295.
37. Allegrini, S.; Pesi, R.; Tozzi, M.G.; Ipata, P.L.; Camici, M. Cytosolic 5'-nucleotidase/nucleoside phosphotransferase: a single assay for a bifunctional enzyme. J. Biochem. Biophys. Methods, 1993, 27(4), 293-299.
38. Keller, P.M.; McKee, S.A.; Fyfe, J.A. Cytoplasmic 5'-nucleotidase catalyzes acyclovir phosphorylation. J. Biol. Chem., 1985, 260(15), 8664-8647.
39. Tozzi, M.G.; Camici, M.; Pesi, R.; Allegrini, S.; Sgarrella, F.; Ipata, P.L. Nucleoside phosphotransferase activity of human colon carcinoma cytosolic 5'-nucleotidase. Arch. Biochem. Biophys., 1991, 291(2), 212-217.
40. Wu, J.Z.; Larson, G.; Walker, H.; Shim, J.H.; Hong, Z. Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5'-nucleotidase II: Implications for ribavirin metabolism in erythrocytes. Antimicrob. Agents Chemother., 2005, 49(6), 2164-2171.
41. Allegrini, S.; Scaloni, A.; Ferrara, L.; Pesi, R.; Pinna, P.; Sgarrella, F.; Camici, M.; Eriksson, S.; Tozzi, M.G. Bovine cytosolic 5'-nucleotidase acts through the formation of an aspartate 52-phosphoenzyme intermediate. J. Biol. Chem., 2001, 276(36), 33526-33532.
42. Wallden, K.; Nordlund, P. Structural basis for the allosteric regulation and substrate recognition of human cytosolic 5'-nucleotidase II. J. Mol. Biol., 2011, 408(4), 684-696.
43. Pesi, R.; Baiocchi, C.; Allegrini, S.; Moretti, E.; Sgarrella, F.; Camici, M.; Tozzi, M.G. Identification, separation and characterisation of two forms of cytosolic 5'-nucleotidase/nucleoside phosphotransferase in calf thymus. Biol. Chem., 1998, 379(6), 699-704.
44. Burroughs, A.M.; Allen, K.N.; Dunaway-Mariano, D.; Aravind, L. Evolutionary genomics of the HAD superfamily: understanding the structural adaptations and catalytic diversity in a superfamily of phosphoesterases and allied enzymes. J. Mol. Biol., 2006, 361(5), 1003-1034.
45. Collet, J.F.; Stroobant, V.; Pirard, M.; Delpierre, G.; Van Schaftingen, E. A new class of phosphotransferases phosphorylated on an aspartate residue in an amino-terminal DXDX(T/V) motif. J. Biol. Chem., 1998, 273(23), 14107-14112.
46. Carson, D.A.; Carrera, C.J.; Wasson, D.B.; Iizasa, T. Deoxyadenosine-resistant human T lymphoblasts with elevated 5'-nucleotidase activity. BBA-Mol. Cell. Res., 1991, 1091(1), 22-28.
47. Schirmer, M.; Stegmann, A.P.; Geisen, F.; Konwalinka, G. Lack of cross-resistance with gemcitabine and cytarabine in cladribineresistant HL60 cells with elevated 5'-nucleotidase activity. Exp Hematol, 1998, 26(13), 1223-1228.
48. Jordheim, L.P.; Dumontet, C. Review of recent studies on resistance to cytotoxic deoxynucleoside analogues. Biochim. Biophys. Acta, 2007, 1776(2), 138-159.
49. Dumontet, C.; Fabianowska-Majewska, K.; Mantincic, D.; Callet Bauchu, E.; Tigaud, I.; Gandhi, V.; Lepoivre, M.; Peters, G.J.; Rolland, M.O.; Wyczechowska, D.; Fang, X.; Gazzo, S.; Voorn, D.A.; Vanier-Viornery, A.; MacKey, J. Common resistance mechanisms to deoxynucleoside analogues in variants of the human erythroleukaemic line K562. Br. J. Haematol., 1999, 106(1), 78-85.
50. Lotfi, K.; Mansson, E.; Chandra, J.; Wang, Y.; Xu, D.; Knaust, E.; Spasokoukotskaja, T.; Liliemark, E.; Eriksson, S.; Albertioni, F. Pharmacological basis for cladribine resistance in a human acute T lymphoblastic leukaemia cell line selected for resistance to etoposide. Br. J. Haematol., 2001, 113(2), 339-346.
51. Mansson, E.; Flordal, E.; Liliemark, J.; Spasokoukotskaja, T.; Elford, H.; Lagercrantz, S.; Eriksson, S.; Albertioni, F. Downregulation of deoxycytidine kinase in human leukemic cell lines resistant to cladribine and clofarabine and increased ribonucleotide reductase activity contributes to fludarabine resistance. Biochem. Pharmacol., 2003, 65(2), 237-247.
52. Wrabel, A.; Mirzaee, S.; Eriksson, S.; Lotfi, K.; Albertioni, F. In: Inhibition of 5-nucleotidases enhance nucleoside analogues cytotoxicity in leukemic cells, 97th Annual Meeting of the American Association for Cancer Research, Washington, DC, USA, April 1-5, 2006.
53. Careddu, M.G.; Allegrini, S.; Pesi, R.; Camici, M.; Garcia-Gil, M.; Tozzi, M.G. Knockdown of cytosolic 5'-nucleotidase II (cN-II) reveals that its activity is essential for survival in astrocytoma cells. Biochim. Biophys. Acta, 2008, 1783(8), 1529-1535.
54. Li, L.; Fridley, B.; Kalari, K.; Jenkins, G.; Batzler, A.; Safgren, S.; Hildebrandt, M.; Ames, M.; Schaid, D.; Wang, L. Gemcitabine and cytosine arabinoside cytotoxicity: association with lymphoblastoid cell expression. Cancer Res., 2008, 68(17), 7050-7058.
55. Li, L.; Schaid, D.J.; Fridley, B.L.; Kalari, K.R.; Jenkins, G.D.; Abo, R.P.; Batzler, A.; Moon, I.; Pelleymounter, L.; Eckloff, B.W.; Wieben, E.D.; Sun, Z.; Yang, P.; Wang, L. Gemcitabine metabolic pathway genetic polymorphisms and response in patients with nonsmall cell lung cancer. Pharmacogenet. Genomics, 2012, 22(2), 105-116.
56. Meyer, J.A.; Wang, J.; Hogan, L.E.; Yang, J.J.; Dandekar, S.; Patel, J.P.; Tang, Z.; Zumbo, P.; Li, S.; Zavadil, J.; Levine, R.L.; Cardozo, T.; Hunger, S.P.; Raetz, E.A.; Evans, W.E.; Morrison, D.J.; Mason, C.E.; Carroll, W.L. Relapse-specific mutations in NT5C2 in childhood acute lymphoblastic leukemia. Nat. Genet., 2013, 45(3), 290-294.
57. Tzoneva, G.; Perez-Garcia, A.; Carpenter, Z.; Khiabanian, H.; Tosello, V.; Allegretta, M.; Paietta, E.; Racevskis, J.; Rowe, J.M.; Tallman, M.S.; Paganin, M.; Basso, G.; Hof, J.; Kirschner-Schwabe, R.; Palomero, T.; Rabadan, R.; Ferrando, A. Activating mutations in the NT5C2 nucleotidase gene drive chemotherapy resistance in relapsed ALL. Nat. Med., 2013, 19(3), 368-371.
58. Albertioni, F.; Bayat, N.; Karlsson, K.; Juliusson, G.; Peterson, C.; Eriksson, S.; Lotfi, K. In: Activity profiles of 5'-nucleotidases in peripheral blood cells from patients with untreated B-cell chronic lymphocytic leukemia: correlation to anti-cancer nucleoside-monophosphate degrading activity, 96th Annual Meeting of the American Association for Cancer Research, Anaheim, CA, USA, April 16-20, 2005.
59. Albertioni, F.; Karlsson, K.; Juliusson, G.; Lotfi, K. In: Relationship of 5'-nuclotidase and deoxynucleoside kinase activity to the clinical activity of cladribine and fludarabine, 98th Annual Meeting of the American Association for Cancer Research, Los Angeles, CA, USA, April 14-18, 2007.
60. Yamauchi, T.; Negoro, E.; Kishi, S.; Takagi, K.; Yoshida, A.; Urasaki, Y.; Iwasaki, H.; Ueda, T. Intracellular cytarabine triphosphate production correlates to deoxycytidine kinase/cytosolic 5'-nucleotidase II expression ratio in primary acute myeloid leukemia cells. Biochem. Pharmacol., 2009, 77(12), 1780-1786.
61. Kawasaki, H.; Carrera, C.J.; Piro, L.D.; Saven, A.; Kipps, T.J.; Carson, D.A. Relationship of deoxycytidine kinase and cytoplasmic 5'-nucleotidase to the chemotherapeutic efficacy of 2-chlorodeoxyadenosine. Blood, 1993, 81(3), 597-601.
62. Woodahl, E.L.; Wang, J.; Heimfeld, S.; Sandmaier, B.M.; O'Donnell, P.V.; Phillips, B.; Risler, L.; Blough, D.K.; McCune, J.S. A novel phenotypic method to determine fludarabine triphosphate accumulation in T-lymphocytes from hematopoietic cell transplanta tion patients. Cancer Chemother. Pharmacol., 2009, 63(3), 391-401.
63. Woodahl, E.L.; Wang, J.; Heimfeld, S.; Sandmaier, B.M.; McCune, J.S. Intracellular disposition of fludarabine triphosphate in human natural killer cells. Cancer Chemother. Pharmacol., 2009, 63(5), 959-964.
64. Mitra, A.K.; Crews, K.R.; Pounds, S.; Cao, X.; Feldberg, T.; Ghodke, Y.; Gandhi, V.; Plunkett, W.; Dolan, M.E.; Hartford, C.; Raimondi, S.; Campana, D.; Downing, J.; Rubnitz, J.E.; Ribeiro, R.C.; Lamba, J.K. Genetic variants in cytosolic 5'-nucleotidase II are associated with its expression and cytarabine sensitivity in HapMap cell lines and in patients with acute myeloid leukemia. J. Pharmacol. Exp. Ther., 2011, 339(1), 9-23.
65. Mackey, J.R.; Galmarini, C.M.; Graham, K.A.; Joy, A.A.; Delmer, A.; Dabbagh, L.; Glubrecht, D.; Jewell, L.D.; Lai, R.; Lang, T.; Hanson, J.; Young, J.D.; Merle-Beral, H.; Binet, J.L.; Cass, C.E.; Dumontet, C. Quantitative analysis of nucleoside transporter and metabolism gene expression in chronic lymphocytic leukemia (CLL): identification of fludarabine-sensitive and-insensitive populations. Blood, 2005, 105(2), 767-774.
66. Suzuki, K.; Sugawara, T.; Oyake, T.; Uchiyama, T.; Aoki, Y.; Tsukushi, Y.; Onodera, S.; Ito, S.; Murai, K.; Ishida, Y. Clinical significance of high-Km 5'-nucleotidase (cN-II) mRNA expression in high-risk myelodysplastic syndrome. Leuk. Res., 2007, 31(10), 1343-1349.
67. Galmarini, C.M.; Graham, K.; Thomas, X.; Calvo, F.; Rousselot, P.; El Jafaari, A.; Cros, E.; Mackey, J.R.; Dumontet, C. Expression of high Km 5'-nucleotidase in leukemic blasts is an independent prognostic factor in adults with acute myeloid leukemia. Blood, 2001, 98(6), 1922-1926.
68. Galmarini, C.M.; Thomas, X.; Calvo, F.; Rousselot, P.; Rabilloud, M.; El Jaffari, A.; Cros, E.; Dumontet, C. In vivo mechanisms of resistance to cytarabine in acute myeloid leukaemia. Br. J. Haematol., 2002, 117(4), 860-868.
69. Galmarini, C.M.; Thomas, X.; Graham, K.; El Jafaari, A.; Cros, E.; Jordheim, L.; Mackey, J.R.; Dumontet, C. Deoxycytidine kinase and cN-II nucleotidase expression in blast cells predict survival in acute myeloid leukaemia patients treated with cytarabine. Br. J. Haematol., 2003, 122(1), 53-60.
70. Galmarini, C.M.; Cros, E.; Thomas, X.; Jordheim, L.; Dumontet, C. The prognostic value of cN-II and cN-III enzymes in adult acute myeloid leukemia. Haematologica, 2005, 90(12), 1699-1701.
71. Seve, P.; Mackey, J.R.; Isaac, S.; Tredan, O.; Souquet, P.J.; Perol, M.; Cass, C.; Dumontet, C. cN-II expression predicts survival in patients receiving gemcitabine for advanced non-small cell lung cancer. Lung Cancer, 2005, 49(3), 363-370.
72. Mitra, A.K.; Kirstein, M.N.; Khatri, A.; Skubitz, K.M.; Dudek, A.Z.; Greeno, E.W.; Kratzke, R.A.; Lamba, J.K. Pathway-based pharmacogenomics of gemcitabine pharmacokinetics in patients with solid tumors. Pharmacogenomics, 2012, 13(9), 1009-1021.
73. Pieters, R.; Huismans, D.R.; Loonen, A.H.; Peters, G.J.; Hahlen, K.; van der Does-van den Berg, A.; van Wering, E.R.; Veerman, A.J. Relation of 5'-nucleotidase and phosphatase activities with immunophenotype, drug resistance and clinical prognosis in childhood leukemia. Leuk. Res., 1992, 16(9), 873-880.
74. Rinaldo-Matthis, A.; Rampazzo, C.; Balzarini, J.; Reichard, P.; Bianchi, V.; Nordlund, P. Crystal structures of the mitochondrial deoxyribonucleotidase in complex with two specific inhibitors. Mol. Pharmacol., 2004, 65(4), 860-867.
75. Rampazzo, C.; Mazzon, C.; Reichard, P.; Bianchi, V. 5'-Nucleotidases: specific assays for five different enzymes in cell extracts. Biochem. Biophys. Res. Commun., 2002, 293(1), 258-263.
76. Ripphausen, P.; Freundlieb, M.; Brunschweiger, A.; Zimmermann, H.; Muller, C.E.; Bajorath, J. Virtual screening identifies novel sulfonamide inhibitors of ecto-5'-nucleotidase. J. Med. Chem., 2012, 55(14), 6576-6581.
77. Baqi, Y.; Lee, S.Y.; Iqbal, J.; Ripphausen, P.; Lehr, A.; Scheiff, A.B.; Zimmermann, H.; Bajorath, J.; Muller, C.E. Development of potent and selective inhibitors of ecto-5'-nucleotidase based on an anthraquinone scaffold. J. Med. Chem., 2010, 53(5), 2076-2086.
78. Giovannetti, E.; Mey, V.; Nannizzi, S.; Pasqualetti, G.; Marini, L.; Del Tacca, M.; Danesi, R. Cellular and pharmacogenetics foundation of synergistic interaction of pemetrexed and gemcitabine in human non-small-cell lung cancer cells. Mol. Pharmacol., 2005, 68(1), 110-118.
79. Giovannetti, E.; Mey, V.; Loni, L.; Nannizzi, S.; Barsanti, G.; Savarino, G.; Ricciardi, S.; Del Tacca, M.; Danesi, R. Cytotoxic activity of gemcitabine and correlation with expression profile of drug-related genes in human lymphoid cells. Pharmacol. Res., 2007, 55(4), 343-349.
80. Gallier, F.; Lallemand, P.; Meurillon, M.; Jordheim, L.P.; Dumontet, C.; Perigaud, C.; Lionne, C.; Peyrottes, S.; Chaloin, L. Structural insights into the inhibition of cytosolic 5'-nucleotidase II (cNII) by ribonucleoside 5'-monophosphate analogues. PLoS Comput. Biol., 2011, 7(12), e1002295.
81. Jordheim, L.P.; Cros, E.; Gouy, M.H.; Galmarini, C.M.; Peyrottes, S.; Mackey, J.; Perigaud, C.; Dumontet, C. Characterization of a gemcitabine-resistant murine leukemic cell line: reversion of in vitro resistance by a mononucleotide prodrug. Clin. Cancer Res., 2004, 10(16), 5614-5621.
82. Gouy, M.H.; Jordheim, L.P.; Lefebvre, I.; Cros, E.; Dumontet, C.; Peyrottes, S.; Perigaud, C. Special feature of mixed phosphotriester derivatives of cytarabine. Bioorg. Med. Chem., 2009, 17(17), 6340-6347.