P. Nmr-1h and H. , 6 -Phenylethyladenosine 5'-monophosphate (12) White powder (38 mg); R t = 1038 min (10-50% of CH 3 CN in 10 mM TEAA buffer), H NMR (DMSO-d 6 ) ? 2.95 (bs, 2H, CH 2 -Ph), 3.72 (bs, 2H, CH 2 -NH), 3.84-3.89 (m, 2H (d, J 1 ' ,2' = 5.4, 1H, H-1'), 7.16-7.21 (m, 1H, H-4 Arom C NMR (DMSO-d 6 ) ? 35.6 (CH 2 -Ph), 41.8 (CH 2 -NH), p.71, 1993.

R. 1. Sampath, D. Rao, V. Plunkett, and W. , Mechanisms of apoptosis induction by nucleoside analogs, Oncogene, vol.22, issue.56, pp.9063-9074, 2003.
DOI : 10.1038/sj.onc.1207229

W. Parker, Enzymology of Purine and Pyrimidine Antimetabolites Used in the Treatment of Cancer, Chemical Reviews, vol.109, issue.7, pp.2880-2893, 2009.
DOI : 10.1021/cr900028p

C. Cabello, W. Bair, S. Ley, S. Lamore, and S. Azimian, The experimental chemotherapeutic N6-furfuryladenosine (kinetinriboside ) induces rapid ATP depletion, genotoxic stress, and CDKN1A(p21) upregulation in human cancer cell lines, Biochem Pharmacol, vol.77, 2009.

B. Choi, W. Kim, Q. Wang, D. Kim, and S. Tan, Kinetin riboside preferentially induces apoptosis by modulating Bcl-2 family proteins and caspase-3 in cancer cells, Cancer Letters, vol.261, issue.1, pp.37-45, 2008.
DOI : 10.1016/j.canlet.2007.11.014

C. Laezza, M. Caruso, T. Gentile, M. Notarnicola, and A. Malfitano, -isopentenyladenosine inhibits cell proliferation and induces apoptosis in a human colon cancer cell line DLD1, International Journal of Cancer, vol.60, issue.6, pp.1322-1329, 2009.
DOI : 10.1002/ijc.24056
URL : https://hal.archives-ouvertes.fr/pasteur-00167016

C. Laezza, A. Malfitano, D. Matola, T. Ricchi, P. Bifulco et al., Involvement of Akt/NF-??B pathway in N6-isopentenyladenosine-induced apoptosis in human breast cancer cells, Molecular Carcinogenesis, vol.9, issue.10, pp.892-901, 2010.
DOI : 10.1002/mc.20666

M. Spinola, F. Colombo, F. Falvella, and T. Dragani, N6-isopentenyladenosine: A potential therapeutic agent for a variety of epithelial cancers, International Journal of Cancer, vol.260, issue.12, p.17304507, 2007.
DOI : 10.1002/ijc.22601

K. Dolezal, I. Popa, E. Hauserová, L. Spíchal, and K. Chakrabarty, Preparation, biological activity and endogenous occurrence of N6-benzyladenosines, Bioorganic & Medicinal Chemistry, vol.15, issue.11, pp.3737-3747, 2007.
DOI : 10.1016/j.bmc.2007.03.038

J. Cheong, D. Goh, J. Yong, S. Tan, and E. Ong, Inhibitory effect of kinetin riboside in human heptamoa, HepG2, Mol. BioSyst., vol.35, issue.9, 2009.
DOI : 10.1039/B712807J

P. Dudzik, J. Duli?ska-litewka, E. Wyszko, P. J?drychowska, and M. Opa?ka, Effects of kinetin riboside on proliferation and proapoptotic activities in human normal and cancer cell lines, Journal of Cellular Biochemistry, vol.95, issue.11, pp.2115-2124, 2011.
DOI : 10.1002/jcb.23132

R. Ottria, S. Casati, E. Baldoli, J. Maier, and P. Ciuffreda, N6-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity, Bioorganic & Medicinal Chemistry, vol.18, issue.23, pp.8396-8402, 2010.
DOI : 10.1016/j.bmc.2010.09.030

R. Tiedemann, X. Mao, C. Shi, Y. Zhu, and S. Palmer, Identification of kinetin riboside as a repressor of CCND1 and CCND2 with preclinical antimyeloma activity, Journal of Clinical Investigation, vol.118, pp.1750-1764, 2008.
DOI : 10.1172/JCI34149

P. Mlejnek, Caspase inhibition and N6-benzyladenosine-induced apoptosis in HL-60 cells, Journal of Cellular Biochemistry, vol.6, issue.4, pp.678-689, 2001.
DOI : 10.1002/jcb.1262

P. Mlejnek and P. Dolezel, Apoptosis induced by N6-substituted derivatives of adenosine is related to intracellular accumulation of corresponding mononucleotides in HL-60 cells, Toxicology in Vitro, vol.19, issue.7, pp.985-990, 2005.
DOI : 10.1016/j.tiv.2005.06.023

L. Bennett, . Jr, D. Smithers, D. Hill, L. Rose et al., Biochemical properties of the nucleoside of 3-amino-1, 5-dihydro-5-methyl-1,4,5,6,8-pentaazaacenaphthylene (NSC-154020), Biochemical Pharmacology, vol.27, issue.2, pp.233-241, 1978.
DOI : 10.1016/0006-2952(78)90306-4

P. Plagemann, Transport, Phosphorylation, and Toxicity of a Tricyclic Nucleoside in Cultured Novikoff Rat Hepatoma Cells and Other Cell Lines and Release of Its Monophosphate by the Cells 2, JNCI: Journal of the National Cancer Institute, vol.57, issue.6, pp.1283-1295, 1976.
DOI : 10.1093/jnci/57.6.1283

C. Garrett, D. Coppola, R. Wenham, C. Cubitt, and A. Neuger, Phase I pharmacokinetic and pharmacodynamic study of triciribine phosphate monohydrate, a small-molecule inhibitor of AKT phosphorylation, in adult subjects with solid tumors containing activated AKT, Investigational New Drugs, vol.20, issue.6, pp.1381-1389, 2011.
DOI : 10.1007/s10637-010-9479-2

A. Padilla, C. Amiable, S. Pochet, P. Kaminski, and G. Labesse, Structure of the oncoprotein Rcl bound to three nucleotide analogues, Acta Crystallographica Section D Biological Crystallography, vol.32, issue.2, pp.247-255, 2013.
DOI : 10.1107/S0907444912045039
URL : https://hal.archives-ouvertes.fr/pasteur-00796442

B. Lewis, J. Prescott, S. Campbell, H. Shim, and R. Orlowski, Tumor induction by the c-Myc target genes rcl and lactate dehydrogenase A, Cancer Res, vol.60, pp.6178-6183, 2000.

B. Lewis, H. Shim, Q. Li, C. Wu, and L. Lee, Identification of putative c-Myc-responsive genes: characterization of rcl, a novel growth-related gene., Molecular and Cellular Biology, vol.17, issue.9, pp.4967-4978, 1997.
DOI : 10.1128/MCB.17.9.4967

D. Rhodes, T. Barrette, M. Rubin, D. Ghosh, and A. Chinnaiyan, Meta-analysis of microarrays: interstudy validation of gene expression profiles reveals pathway dysregulation in prostate cancer, Cancer Res, vol.62, pp.4427-4433, 2002.

S. Shin, D. Bosc, J. Ingle, T. Spelsberg, and R. Janknecht, Rcl is a novel ETV1/ER81 target gene upregulated in breast tumors, Journal of Cellular Biochemistry, vol.4, issue.3, 2008.
DOI : 10.1002/jcb.21884

G. Gorgun, A. Ramsay, T. Holderried, D. Zahrieh, L. Dieu et al., E??-TCL1 mice represent a model for immunotherapeutic reversal of chronic lymphocytic leukemia-induced T-cell dysfunction, Proceedings of the National Academy of Sciences, vol.106, issue.15, pp.6250-6255, 2009.
DOI : 10.1073/pnas.0901166106

Y. Ghiorghi, K. Zeller, C. Dang, and P. Kaminski, The c-Myc Target Gene Rcl (C6orf108) Encodes a Novel Enzyme, Deoxynucleoside 5'-monophosphate N-Glycosidase, Journal of Biological Chemistry, vol.282, issue.11, pp.8150-8156, 2007.
DOI : 10.1074/jbc.M610648200
URL : https://hal.archives-ouvertes.fr/pasteur-00166562

C. Dupouy, C. Zhang, A. Padilla, S. Pochet, and P. Kaminski, Probing the Active Site of the Deoxynucleotide N-Hydrolase Rcl Encoded by the Rat Gene c6orf108, Journal of Biological Chemistry, vol.285, issue.53, pp.41806-41814, 2010.
DOI : 10.1074/jbc.M110.181594
URL : https://hal.archives-ouvertes.fr/pasteur-00550450

K. Doddapaneni, B. Mahler, R. Pavlovicz, A. Haushalter, and C. Yuan, Solution Structure of RCL, a Novel 2???-Deoxyribonucleoside 5???-Monophosphate N-glycosidase, Journal of Molecular Biology, vol.394, issue.3, 2009.
DOI : 10.1016/j.jmb.2009.08.054

Y. Yang, A. Padilla, C. Zhang, G. Labesse, and P. Kaminski, Structural Characterization of the Mammalian Deoxynucleotide N-Hydrolase Rcl and Its Stabilizing Interactions with Two Inhibitors, Journal of Molecular Biology, vol.394, issue.3, pp.435-447, 2009.
DOI : 10.1016/j.jmb.2009.10.004
URL : https://hal.archives-ouvertes.fr/pasteur-00432797

M. Fleysher, R. Bernacki, and G. Bullard, Some Short-Chain N6- Substituted Adenosine-Analogs with Anti-Tumor Properties, J Med Chem, vol.23, p.7452700, 1980.
DOI : 10.1021/jm00186a031

H. Jiang, J. Kim, K. Frizzell, W. Kraus, and H. Lin, Clickable NAD Analogues for Labeling Substrate Proteins of Poly(ADP-ribose) Polymerases, Journal of the American Chemical Society, vol.132, issue.27, pp.9363-9372, 2010.
DOI : 10.1021/ja101588r

G. Murshudov, A. Vagin, and E. Dodson, Refinement of Macromolecular Structures by the Maximum-Likelihood Method, Acta Crystallographica Section D Biological Crystallography, vol.53, issue.3, pp.240-255, 1997.
DOI : 10.1107/S0907444996012255

P. Emsley and K. Cowtan, : model-building tools for molecular graphics, Acta Crystallographica Section D Biological Crystallography, vol.60, issue.12, pp.2126-2132, 2004.
DOI : 10.1107/S0907444904019158

A. Schüttelkopf and D. Van-aalten, : a tool for high-throughput crystallography of protein???ligand complexes, Acta Crystallographica Section D Biological Crystallography, vol.60, issue.8, pp.1355-1363, 2004.
DOI : 10.1107/S0907444904011679

T. Olsson, J. Ladbury, W. Pitt, and M. Williams, Extent of enthalpy-entropy compensation in protein-ligand interactions, Protein Science, vol.84, issue.9, 2011.
DOI : 10.1002/pro.692

S. Mcdermott, K. Eppert, F. Notta, M. Isaac, and A. Datti, A small molecule screening strategy with validation on human leukemia stem cells uncovers the therapeutic efficacy of kinetin riboside, Blood, vol.119, issue.5, pp.1200-120710, 2012.
DOI : 10.1182/blood-2011-01-330019

J. Voller, M. Zatloukal, R. Lenobel, K. Dolezal, and T. Béres, Anticancer activity of natural cytokinins: A structure???activity relationship study, Phytochemistry, vol.71, issue.11-12, pp.1350-1359, 2010.
DOI : 10.1016/j.phytochem.2010.04.018

M. Rajabi, P. Signorelli, E. Gorincioi, R. Ghidoni, and E. Santaniello, -Isopentenyladenosine on MCF-7 Breast Cancer Cells: Cell Cycle Analysis and DNA-Binding Study, DNA and Cell Biology, vol.29, issue.11, p.20818975, 2010.
DOI : 10.1089/dna.2010.1073
URL : https://hal.archives-ouvertes.fr/hal-00488634

E. Murakami, H. Bao, R. Mosley, J. Du, and M. Sofia, -Substituted Purine or 2-Aminopurine Nucleoside Monophosphates, Journal of Medicinal Chemistry, vol.54, issue.16, pp.5902-591410, 2011.
DOI : 10.1021/jm200650j
URL : https://hal.archives-ouvertes.fr/in2p3-01108823

N. Kaplan, J. Everse, J. Dixon, and F. Stolzenb, Purification and Separation of Pyridine Nucleotide-Linked Dehydrogenases by Affinity Chromatography Techniques, Techniques - Proceedings of the National Academy of Sciences of the United States of America, pp.3450-3454, 1974.
DOI : 10.1073/pnas.71.9.3450

A. Le, C. Cooper, A. Gouw, R. Dinavahi, and A. Maitra, Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression, Proceedings of the National Academy of Sciences, vol.107, issue.5, pp.2037-2042, 2010.
DOI : 10.1073/pnas.0914433107

B. Lewis, J. Prescott, S. Campbell, H. Shim, and R. Orlowski, Tumor induction by the c-Myc target genes rcl and lactate dehydrogenase A, Cancer Res, vol.60, pp.6178-6183, 2000.

B. Lomenick, R. Olsen, and J. Huang, Identification of Direct Protein Targets of Small Molecules, ACS Chemical Biology, vol.6, issue.1, pp.34-46, 2011.
DOI : 10.1021/cb100294v