Charge dependent substrate activity of C3 and N3 functionalized, organometallic technetium and rhenium-labeled thymidine derivatives toward human thymidine kinase 1

Bioconjugate Chemistry

Volumn 21, Issue 4, 2010, Pages 622-634

  Struthers, Harriet ^a   Viertl, David ^b   Kosinski, Marek ^b   Spingler, Bernhard ^c   Buchegger, Franz ^b   Schibli, Roger ^a  

^a ETH ZURICH   (Switzerland)

^b LAUSANNE UNIVERSITY HOSPITAL   (Switzerland)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

FLOXURIDINE; RHENIUM COMPLEX; TECHNETIUM 99M; THYMIDINE DERIVATIVE; THYMIDINE KINASE 1;

ARTICLE; CANCER CELL CULTURE; CATALYSIS; CELL PROLIFERATION; CHELATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLOADDITION; DRUG SYNTHESIS; DRUG UPTAKE; ENZYME SUBSTRATE COMPLEX; GLIOBLASTOMA; HUMAN; HUMAN CELL; INTERNALIZATION; ISOTOPE LABELING; MOLECULAR IMAGING; PHOSPHORYLATION; REACTION ANALYSIS; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STRUCTURE ACTIVITY RELATION;

EID: 77951281328     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc900380n     Document Type: Article

References (41)

1. Eriksson, S., Kierdaszuk, B., Munch-Petersen, B., Oberg, B., and Johansson, N. G. (1991) Comparison of the substrate specificities of human thymidine kinase-1 and kinase-2 and deoxycytidine kinase toward antiviral and cytostatic nucleoside analogs Biochem. Biophys. Res. Commun. 176, 586-592
2. Schinazi, R. F., Mead, J. R., and Feorino, P. M. (1992) Insights into HIV chemotherapy AIDS Res. Hum. Retrov. 8, 963-990
3. Eriksson, S., Munch-Petersen, B., Johansson, K., and Eklund, H. (2002) Structure and function of cellular deoxyribonucleoside kinases Cell. Mol. Life Sci. 59, 1327-1346
4. Eriksson, S. and Wang, J. H. (1995) Substrate specificities of mitochondrial thymidine kinase and cytosolic deoxycytidine kinase against 5-aryl substituted pyrimidine-2-deoxyribose analogs Nucleosides Nucleotides 14, 507-510
5. Al-Madhoun, A. S., Johnsamuel, J., Yan, J. H., Ji, W. H., Wang, J. H., Zhuo, J. C., Lunato, A. J., Woollard, J. E., Hawk, A. E., Cosquer, G. Y., Blue, T. E., Eriksson, S., and Tjarks, W. (2002) Synthesis of a small library of 3-(carboranylalkyl)thymidines and their biological evaluation as substrates for human thymidine kinases 1 and 2 J. Med. Chem. 45, 4018-4028
6. Byun, Y., Thirumamagal, B. T. S., Yang, W., Eriksson, S., Barth, R. F., and Tjarks, W. (2006) Preparation and biological evaluation of 10B-enriched 3-[5-{2-(2,3-dihydroxyprop-1-yl)-o-carboran-1-yl}pentan-1-yl]thymidine (N5-2OH), a new boron delivery agent for boron neutron capture therapy of brain tumors J. Med. Chem. 49, 5513-5523
7. Welin, M., Kosinska, U., Mikkelsen, N. E., Carnrot, C., Zhu, C. Y., Wang, L. Y., Eriksson, S., Munch-Petersen, B., and Eklund, H. (2004) Structures of thymidine kinase 1 of human and mycoplasmic origin Proc. Natl. Acad. Sci. U.S.A. 101, 17970-17975
8. Lunato, A. J., Wang, J. H., Woollard, J. E., Anisuzzaman, A. K. M., Ji, W. H., Rong, F. G., Ikeda, S., Soloway, A. H., Eriksson, S., Ives, D. H., Blue, T. E., and Tjarks, W. (1999) Synthesis of 5-(carboranylalkylmercapto)-2- deoxyuridines and 3-(carboranylalkyl)thymidines and their evaluation as substrates for human thymidine kinases 1 and 2 J. Med. Chem. 42, 3378-3389
9. Johnsamuel, J., Lakhi, N., Al-Madhoun, A. S., Byun, Y., Yan, J. H., Eriksson, S., and Tjarks, W. (2004) Synthesis of ethyleneoxide modified 3-carboranyl thymidine analogues and evaluation of their biochemical, physicochemical, and structural properties Bioorg. Med. Chem. 12, 4769-4781
10. Conti, P. S., Alauddin, M. M., Fissekis, J. R., Schmall, B., and Watanabe, K. A. (1995) Synthesis of 2-fluoro-5-[C-11]-methyl-1-b-D- arabinofuranosyluracil ([C-11]-Fmau)-a potential nucleoside analog for in-vivo study of cellular proliferation with PET Nucl. Med. Biol. 22, 783-789
11. Shields, A. F., Grierson, J. R., Dohmen, B. M., Machulla, H. J., Stayanoff, J. C., Lawhorn-Crews, J. M., Obradovich, J. E., Muzik, O., and Mangner, T. J. (1998) Imaging proliferation in vivo with [F-18]FLT and positron emission tomography Nat. Med. 4, 1334-1336
12. 76Br]Bromodeoxyuridine PET in tumor-bearing animals Nucl. Med. Biol. 28, 51-57
13. Desbouis, D., Struthers, H., Spiwok, V., Küster, T., and Schibli, R. (2008) Synthesis, in vitro, and in silico evaluation of organometallic technetium and rhenium thymidine complexes with retained substrate activity toward human thymidine kinase type 1 J. Med. Chem. 51, 6689-6698
14. Struthers, H., Spingler, B., Mindt, T. L., and Schibli, R. (2008) Click-to-Chelate: Design and incorporation of triazole-containing metal-chelating systems into biomolecules of diagnostic and therapeutic interest Chem.-Eur. J. 14, 6173-6183
15. Yan, J. H., Naeslund, C., Al-Madhoun, A. S., Wang, J. H., Ji, W. H., Cosquer, G. Y., Johnsamuel, J., Sjoberg, S., Eriksson, S., and Tjarks, W. (2002) Synthesis and biological evaluation of 3-carboranyl thymidine analogues Bioorg. Med. Chem. Lett. 12, 2209-2212
16. Mindt, T. L., Struthers, H., Brans, L., Anguelov, T., Schweinsberg, C., Maes, V., Tourwe, D., and Schibli, R. (2006) Click to Chelate: Synthesis and installation of metal chelates into biomolecules in a single step J. Am. Chem. Soc. 128, 15096-15097
17. Tornøe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67, 3057-3064
18. Kolb, H. C. and Sharpless, K. B. (2003) The growing impact of click chemistry on drug discovery Drug Discovery Today 8, 1128-1137
19. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes Angew. Chem., Int. Ed. 41, 2596-2599
20. 2)}] Inorg. Chem. 41, 6417-6425
21. + core (M = Tc, Re) Inorg. Chem. 44, 6763-6770
22. Schibli, R., La Bella, R., Alberto, R., Garcia-Garayoa, E., Ortner, K., Abram, U., and Schubiger, P. A. (2000) Influence of the denticity of ligand systems on the in vitro and in vivo behavior of 99mTc(I)-tricarbonyl complexes: a hint for the future functionalization of biomolecules Bioconjugate Chem. 11, 345-351
23. Farrugia, L. J. (1997) ORTEP-3 for Windows-a version of ORTEP-III with a Graphical User Interface (GUI) J. Appl. Crystallogr. 30, 565
24. + J. Am. Chem. Soc. 123, 3135-3136
25. Kornberg, A. and Pricer, W. E. (1951) Enzymatic phosphorylation of adenosine and 2,6-diaminopurine riboside J. Biol. Chem. 193, 481-495
26. Byun, Y., Yan, J. H., Al-Madhoun, A. S., Johnsamuel, J., Yang, W. L., Barth, R. F., Eriksson, S., and Tjarks, W. (2005) Synthesis and biological evaluation of neutral and zwitterionic 3-carboranyl thymidine analogues for boron neutron capture therapy J. Med. Chem. 48, 1188-1198
27. Zhang, J., Visser, F., King, K. M., Baldwin, S. A., Young, J. D., and Cass, C. E. (2007) The role of nucleoside transporters in cancer chemotherapy with nucleoside drugs Cancer Metastasis Rev. 26, 85-110
28. Yao, S. Y. M., Ng, A. M. L., Sundaram, M., Cass, C. E., Baldwin, S. A., and Young, J. D. (2001) Transport of antiviral 3-deoxy-nucleoside drugs by recombinant human and rat equilibrative, nitrobenzylthioinosine (NBMPR)-insensitive (ENT2) nucleoside transporter proteins produced in Xenopus oocytes Mol. Membr. Biol. 18, 161-167
29. Dupertuis, Y. M., Vazquez, M., Mach, J. P., De Tribolet, N., Pichard, C., Slosman, D. O., and Buchegger, F. (2001) Fluorodeoxyuridine improves imaging of human glioblastoma xenografts with radiolabeled iododeoxyuridine Cancer Res. 61, 7971-7977
30. Perillo-Adamer, F., Delaloye, A. B., Genton, C. S., Schaffland, A. O., Dupertuis, Y. M., and Buchegger, F. (2006) Short fluorodeoxyuridine exposure of different human glioblastoma lines induces high-level accumulation of S-phase cells that avidly incorporate I-125-iododeoxyuridine Eur. J. Nucl. Med. Mol. Imaging 33, 613-620
31. Perumal, M., Pillai, R. G., Barthel, H., Leyton, J., Latigo, J. R., Forster, M., Mitchell, F., Jackman, A. L., and Aboagye, E. O. (2006) Redistribution of nucleoside transporters to the cell membrane provides a novel approach for imaging thymidylate synthase inhibition by positron emission tomography Cancer Res. 66, 8558-8564
32. Pressacco, J., Mitrovski, B., Erlichman, C., and Hedley, D. W. (1995) Effects of thymidylate synthase inhibition on thymidine kinase activity and nucleoside transporter expression Cancer Res. 55, 1505-1508
33. Armstrong, R. D. and Diasio, R. B. (1980) Metabolism and biological activity of 5-deoxy-5-fluorouridine, a novel fluoropyrimidine Cancer Res. 40, 3333-3338
34. Tjarks, W., Tiwari, R., Byun, Y., Narayanasamy, S., and Barth, R. F. (2007) Carboranyl thymidine analogues for neutron capture therapy Chem. Commun. 4978-4991
35. + and recognized by the L-type amino acid transporter LAT1 J. Am. Chem. Soc. 128, 15996-15997
36. 6] by alkaline titration J. Chem. Soc., Dalton Trans. 2815-2820
37. Foulon, C. F., Adelstein, S. J., and Kassis, A. I. (1996) Kit formulation for the preparation of radiolabeled iododeoxyuridine by demetallation J. Nucl. Med. 37, S1-S3
38. Schaffland, A. O., Delaloye, A. B., Kosinski, M., Dupertuis, Y. M., and Buchegger, F. (2004) The prearation of clinical grade 5-[I-123]iodo-2- deoxyuridine and 5-[I-125]iodo-2-deoxyuridine with high in vitro stability and the potential for early proliferation scintigraphy Nucl. Med. Commun. 25, 461-468
39. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., and Spagna, R. (1999) SIR97: a new tool for crystal structure determination and refinement J. Appl. Crystallogr. 32, 115-119
40. Sheldrick, G. M. (2008) A short history of SHELX Acta Crystallogr., Sect. A: Found. Crystallogr. 64, 112-122
41. Spek, A. L. (2003) Single-crystal structure validation with the program PLATON J. Appl. Crystallogr. 36, 7-13