Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates

Journal of Medicinal Chemistry

Volumn 54, Issue 1, 2011, Pages 222-232

  Topalis, Dimitri ^a   Pradère, Ugo ^b   Roy, Vincent ^b   Caillat, Christophe ^c   Azzouzi, Ahmed ^b   Broggi, Julie ^b   Snoeck, Robert ^d   Andrei, Graciela ^d   Lin, Jay ^e   Eriksson, Staffan ^e   Alexandre, Julie A C ^a   El Amri, Chahrazade ^a   Deville Bonne, Dominique ^a   Meyer, Philippe ^c   Balzarini, Jan ^d   Agrofoglio, Luigi A ^b  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITÉ D'ORLÉANS   (France)

^c CNRS   (France)

^d REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^e SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

(4 DIHYDROXYPHOSPHONYL BUT 2 ENYL) THYMINE; 4 DIHYDROXYPHOSPHONYL BUT 2 ENYL] 5 BROMOURACIL; ACYCLIC NUCLEOSIDE PHOSPHONATE; ANTIVIRUS AGENT; CIDOFOVIR; PYRIMIDINE; THYMIDINE PHOSPHATE; UNCLASSIFIED DRUG; URACIL;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTALLIZATION; DNA VIRUS; ENZYME SUBSTRATE; HERPES VIRUS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; NONHUMAN; SYNTHESIS; VIROTHERAPY;

ANTIVIRAL AGENTS; CATALYTIC DOMAIN; CELLS, CULTURED; CRYSTALLOGRAPHY, X-RAY; HERPESVIRIDAE; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEOSIDE-PHOSPHATE KINASE; PHOSPHONIC ACIDS; PRODRUGS; PYRIMIDINE NUCLEOSIDES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; THYMIDINE; THYMIDINE KINASE;

EID: 78651091005     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1011462     Document Type: Article

References (34)

1. De Clercq, E. Acyclic nucleoside phosphonates: past, present and future. Bridging chemistry to HIV, HBV, HCV, HPV, adeno-, herpes-, and poxvirus infections: the phosphonate bridge Biochem. Pharmacol. 2007, 73, 911-922
2. Balzarini, J.; Pannecouque, C.; De Clercq, E.; Aquaro, S.; Perno, C. F.; Egberink, H.; Holy, A. Antiretrovirus activity of a novel class of acyclic pyrimidine nucleoside phosphonates Antimicrob. Agents Chemother. 2002, 46, 2185-2193
3. Votruba, I.; Bernaerts, R.; Sakuma, T.; De Clercq, E.; Merta, A.; Rosenberg, I.; Holy, A. Intracellular phosphorylation of broad-spectrum anti-DNA virus agent (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine and inhibition of viral DNA synthesis Mol. Pharmacol. 1987, 32, 524-529
4. Cihlar, T.; Chen, M. S. Identification of enzymes catalyzing two-step phosphorylation of cidofovir and the effect of cytomegalovirus infection on their activities in host cells Mol. Pharmacol. 1996, 50, 1502-1510
5. Robbins, B. L.; Greenhaw, J.; Connelly, M. C.; Fridland, A. Metabolic pathways for activation of the antiviral agent 9-(2-phosphonylmethoxyethyl) adenine in human lymphoid cells Antimicrob. Agents Chemother. 1995, 39, 2304-2308
6. Koch, K.; Chen, Y.; Feng, J. Y.; Borroto-Esoda, K.; Deville-Bonne, D.; Gallois-Montbrun, S.; Janin, J.; Morera, S. Nucleosides Nucleotides Nucleic Acids 2009, 28, 776-792
7. Tuske, S.; Sarafianos, S. G.; Clark, A. D., Jr.; Ding, J.; Naeger, L. K.; White, K. L.; Miller, M. D.; Gibbs, C. S.; Boyer, P. L.; Clark, P.; Wang, G.; Gaffney, B. L.; Jones, R. A.; Jerina, D. M.; Hughes, S. H.; Arnold, E. Structures of HIV-1 RT-DNA complexes before and after incorporation of the anti-AIDS drug tenofovir Nat. Struct. Mol. Biol. 2004, 11, 469-474
8. Magee, W. C.; Hostetler, K. Y.; Evans, D. H. Mechanism of inhibition of vaccinia virus DNA polymerase by cidofovir diphosphate Antimicrob. Agents Chemother. 2005, 49, 3153-3162
9. Magee, W. C.; Aldern, K. A.; Hostetler, K. Y.; Evans, D. H. Cidofovir and (S)-9-[3-hydroxy-(2-phosphonomethoxy)propyl]adenine are highly effective inhibitors of vaccinia virus DNA polymerase when incorporated into the template strand Antimicrob. Agents Chemother. 2008, 52, 586-597
10. Topalis, D.; Alvarez, K.; Barral, K.; Munier-Lehmann, H.; Schneider, B.; Véron, M.; Guerreiro, C.; Mulard, L.; El-Amri, C.; Canard, B.; Deville-Bonne, D. Acyclic phosphonate nucleotides and human adenylate kinases: impact of a borano group on alpha-P position Nucleosides Nucleotides Nucleic Acids 2008, 27, 319-331
11. Topalis, D.; Kumamoto, H.; Amaya Velasco, M. F.; Dugue, L.; Haouz, A.; Alexandre, J. A.; Gallois-Montbrun, S.; Alzari, P. M.; Pochet, S.; Agrofoglio, L. A.; Deville-Bonne, D. Nucleotide binding to human UMP-CMP kinase using fluorescent derivatives a screening based on affinity for the UMP-CMP binding site FEBS J. 2007, 274, 3704-3714
12. Topalis, D.; Broggi, J.; Alexandre, J. A.; Pradere, U.; Roy, V.; Berteina-Raboin, S.; Agrofoglio, L. A.; Deville-Bonne, D. Evaluation of C-5 Substituted uracil acyclic phosphonates as substrates or inhibitors for dTMP and UMP-CMP kinases and potential antipox derivatives Antivir. Res. 2008, 78, A65
13. Kumamoto, H.; Broggi, J.; Topalis, D.; Pradere, U.; Roy, V.; Berteina-Raboin, S.; Nolan, S. P.; Deville-Bonne, D.; Snoeck, R.; Garin, D.; Agrofoglio, L. Preparation of acyclo nucleoside phosphonate analogues based-on cross-metathesis Tetrahedron 2008, 64, 3517-3526
14. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. A general model for selectivity in olefin cross metathesis J. Am. Chem. Soc. 2003, 125, 11360-11370
15. Cruickshank, K. A.; Jiricny, J.; Reese, C. B. The benzoylation of uracil and thymine Tetrahedron Lett. 1984, 25, 681-684
16. Vepsalainen, J. J. Bisphosphonate prodrugs: a new synthetic strategy to tetraacyloxymethyl esters of methylenebisphosphonates Tetrahedron Lett. 1999, 40, 8491-8493
17. Alexandre, J. A.; Roy, B.; Topalis, D.; Pochet, S.; Perigaud, C.; Deville-Bonne, D. Enantioselectivity of human AMP, dTMP and UMP-CMP kinases Nucleic Acid Res. 2007, 35 (14) 4895-4904
18. Huang, S. H.; Tang, A.; Drisco, B.; Zhang, S. Q.; Seeger, R.; Li, C.; Jong, A. Human dTMP kinase: gene expression and enzymatic activity coinciding with cell cycle progression and cell growth DNA Cell Biol. 1994, 13, 461-471
19. Pochet, S.; Dugué, L.; Labesse, G.; Delepierre, M.; Munier-Lehmann, H. Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans ChemBioChem 2003, 4, 742-747
20. Ostermann, N.; Schlichting, I.; Brundiers, R.; Konrad, M.; Reinstein, J.; Veit, T.; Goody, R. S.; Lavie, A. Insights into the phosphoryltransfer mechanism of human thymidylate kinase gained from crystal structures of enzyme complexes along the reaction coordinate Structure 2000, 8, 629-642
21. Deville-Bonne, D.; El-Amri, C.; Meyer, P.; Chen, Y.; Agrofoglio, L. A.; Janin, J. Human and viral nucleoside/nucleotide kinases involved in antiviral drug activation: Structural and catalytic properties Antivir. Res. 2010, 86, 101-120
22. Chen, Y. L.; Lin, D. W.; Chang, Z. F. Identification of a putative human mitochondrial thymidine monophosphate kinase associated with monocytic/macrophage terminal differentiation Genes Cells 2008, 13, 679-689
23. Hiratsuka, T. J. Affinity labeling of the myosin ATPase with ribose-modified fluorescent nucleotides and vanadate Biochemistry 1984, 96, 147-154
24. Hernandez, A.-I.; Balzarini, J.; Karlsson, A.; Camarasa, M.-J.; Pérez-Pérez, M.-J. Acyclic nucleotide analogues as novel inhibitors of human mitochondrial thymidine kinase J. Med. Chem. 2002, 45, 4254-4263
25. Choo, H.; Beadle, J.; Chong, Y.; Trahan, J.; Hostetler, K. Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: A new class of antiviral acyclic nucleoside phosphonates Bioorg. Med. Chem. 2007, 15, 1771-1779
26. Choo, H.; Beadle, J.; Kern, E.; Prichard, M.; KA., K.; Hartline, C.; Trahan, J.; Aldern, K.; Korba, B.; Hostetler, K. Antiviral activities of novel 5-phosphono-pent-2-en-1-yl nucleosides and their alkoxyalkyl phosphonoesters Antimicrob. Agents Chemother. 2007, 51, 611-615
27. Topalis, D.; Collinet, B.; Gasse, C.; Dugue, L.; Balzarini, J.; Pochet, S.; Deville-Bonne, D. Substrate specificity of vaccinia virus thymidylate kinase FEBS J. 2005, 272, 6254-6265
28. Pasti, C.; Gallois-Montbrun, S.; Munier-Lehmann, H.; Veron, M.; Gilles, A.-M.; Deville-Bonne, D. Reaction of human UMP-CMP kinase with natural and analog substrates Eur. J. Biochem. 2003, 270, 1784-1790
29. Kosinska, U.; Carnrot, C.; Eriksson, S.; Wang, L.; Eklund, H. Structure of the substrate complex of thymidine kinase from Ureaplasma urealyticum and investigations of possible drug targets for the enzyme FEBS J. 2005, 272, 6365-6372
30. Wang, L.; Munch-Petersen, B.; Herrstrom Sjoberg, A.; Hellman, U.; Bergman, T.; Jornvall, H.; Eriksson, S. Human thymidine kinase 2: molecular cloning and characterisation of the enzyme activity with antiviral and cytostatic nucleoside substrates FEBS Lett. 1999, 443, 170-174
31. Kabsch, B. Automatic processing of rotation diffraction data from crystals of initially unknown symmetry and cell constants J. Appl. Crystallogr. 1993, 26, 795-800
32. Storoni, L. C.; McCoy, A. J.; Read, R. J. Likelihood-enhanced fast rotation functions Acta Crystallogr., Sect. D 2004, 60, 432-438
33. Emsley, P.; Cowtan, K. Coot: model-building tools for molecular graphics Acta Crystallogr., Sect. D 2004, 60, 2126-2132
34. Adams, P. D.; Grosse-Kunstleve, R. W.; Hung, L.-W.; Ioerger, T. R.; McCoy, A. J.; Moriarty, N. W.; Read, R. J.; Sacchettini, J. C.; Sauter, N. K.; Terwilliger, T. C. PHENIX: building new software for automated crystallographic structure determination Acta Crystallogr., Sect. D 2002, 58, 1948-1954