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

Journal of Medicinal Chemistry

Volumn 49, Issue 18, 2006, Pages 5513-5523

  Byun, Youngjoo ^a   Thirumamagal, B T S ^a   Yang, Weilian ^a   Eriksson, Staffan ^b   Barth, Rolf F ^a   Tjarks, Werner ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

3 [5 [2 (2,3 DIHYDROXYPROP 1 YL) O CARBORAN 1 YL]PENTAN 1 YL]THYMIDINE B 10; BORON 10; BORON DERIVATIVE; CARBORANE DERIVATIVE; THYMIDINE DERIVATIVE; THYMIDINE KINASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BRAIN TUMOR; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; GLIOMA; HYDROPHOBICITY; ISOMER; MATHEMATICAL COMPUTING; NEUTRON CAPTURE THERAPY; NEUTRON RADIATION; NONHUMAN; RAT; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SURVIVAL TIME; X RAY CRYSTALLOGRAPHY;

ANIMALS; BINDING SITES; BORON COMPOUNDS; BORON NEUTRON CAPTURE THERAPY; BRAIN NEOPLASMS; CALCIUM; GLIOMA; HUMANS; HYDROPHOBICITY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEOPLASM TRANSPLANTATION; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS; THYMIDINE; THYMIDINE KINASE;

EID: 33748563161     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060413w     Document Type: Article

References (50)

1. Grossman, S. A.; Batara, J. F. Current management of glioblastoma multiforme. Semin. Oncol. 2004, 31, 635-644.
2. Behin, A.; Hoang-Xuan, K.; Carpentier Antoine, F.; Delattre, J.-Y. Primary brain tumours in adults. Lancet 2003, 361, 323-331.
3. Nieder, C.; Grosu, A. L.; Mehta, M. P.; Andratschke, N.; Molls, M. Treatment of malignant gliomas: Radiotherapy, chemotherapy and integration of new targeted agents. Expert Rev. Neurother. 2004, 4, 691-703.
4. Demuth, T.; Berens Michael, E. Molecular mechanisms of glioma cell migration and invasion. J. Neuro-Oncol. 2004, 70, 217-228.
5. Giese, A.; Bjerkvig, R.; Berens, M. E.; Westphal, M. Cost of migration: invasion of malignant gliomas and implications for treatment. J. Clin. Oncol. 2003, 21, 1624-1636.
6. Barth, R. F.; Coderre, J. A.; Vicente, M. G. H.; Blue, T. E. Boron neutron capture therapy of cancer. Current status and future prospects. Clin. Cancer Res. 2005, 11, 3987-4002.
7. Soloway, A. H.; Tjarks, W.; Barnum, B. A.; Rong, F.-G.; Barth, R. F.; Codogni, I. M.; Wilson, J. G. The chemistry of neutron capture therapy. Chem. Rev. 1998, 98, 1515-1562.
8. Lunato, A. J.; Wang, J.; Woollard, J. E.; Anisuzzaman, A. K. M.; Ji, W.; Rong, F.-G.; Ikeda, S.; Soloway, A. H.; Eriksson, S.; Ives, D. H.; Blue, T. E.; Tjarks, W. 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. 1999, 42, 3378-3389.
9. Johnsamuel, J.; Lakhi, N.; Al-Madhoun, A. S.; Byun, Y.; Yan, J.; Eriksson, S.; Tjarks, W. Synthesis of ethyleneoxide modified 3-carboranyl thymidine analogues and evaluation of their biochemical, physicochemical, and structural properties. Bioorg. Med. Chem. 2004, 12, 4769-4781.
10. Byun, Y.; Yan, J.; Al-Madhoun, A. S.; Johnsamuel, J.; Yang, W.; Barth, R. F.; Eriksson, S.; Tjarks, W. Synthesis and biological evaluation of neutral and zwitterionic 3-carboranyl thymidine analogues for boron neutron capture therapy. J. Med. Chem. 2005, 48, 1188-1198.
11. Byun, Y.; Yan, J.; Al-Madhoun, A. S.; Johnsamuel, J.; Yang, W.; Barth, R. F.; Eriksson, S.; Tjarks, W. The synthesis and biochemical evaluation of thymidine analogs substituted with nido carborane at the N-3 position. Appl. Radiat. Isot. 2004, 61, 1125-1130.
12. Al-Madhoun, A. S.; Johnsamuel, J.; Yan, J.; Ji, W.; Wang, J.; Zhuo, J.-C.; Lunato, A. J.; Woollard, J. E.; Hawk, A. E.; Cosquer, G. Y.; Blue, T. E.; Eriksson, S.; Tjarks, W. 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. 2002, 45, 4018-4028.
13. Barth, R. F.; Yang, W.; Al-Madhoun, A. S.; Johnsamuel, J.; Byun, Y.; Chandra, S.; Smith, D. R.; Tjarks, W.; Eriksson, S. Boron-containing nucleosides as potential delivery agents for neutron capture therapy of brain tumors. Cancer Res. 2004, 64, 6287-6295.
14. Al-Madhoun, A. S.; Johnsamuel, J.; Barth, R. F.; Tjarks, W.; Eriksson, S. Evaluation of human thymidine kinase 1 substrates as new candidates for boron neutron capture therapy. Cancer Res. 2004, 64, 6280-6286.
15. Arner, E. S.; Eriksson, S. Mammalian deoxyribonuclease kinases. Pharmacol. Ther. 1995, 67, 155-186.
16. Eriksson, S.; Arner, E.; Spasokoukoskaja, T.; Wang, L.; Karlsson, A.; Brosjoe, O.; Gunven, P.; Julusson, G.; Liliemark, J. Properties and levels of deoxynucleoside kinases in normal and tumor cells; implications for chemotherapy. Adv. Enzyme Regul. 1994, 34, 13-25.
17. Eriksson, S.; Munch-Petersen, B.; Kierdaszuk, B.; Arner, E. Expression and substrate specificities of human thymidine kinase 1, thymidine kinase 2 and deoxycytidine kinase. Adv. Exp. Med. Biol. 1991, B309, 239-243.
18. Al-Nabulsi, I.; Takamiya, Y.; Voloshin, Y.; Drischilo, A.; Martuza, R. L.; Jorgensen, T. J. Expression of thymidine kinase is essential to low dose radiation resistance of rat glioma cells. Cancer Res. 1994, 54, 5614-5617.
19. Persson, L.; Gronowitz, S. J.; Källander, C. F. R. Thymidine kinase in extracts of human brain tumors. Acta Neurochir. 1986, 80, 123-127.
20. Hawthorne, M. F.; Lee Mark, W. A critical assessment of boron target compounds for boron neutron capture therapy. J. Neuro-Oncol. 2003, 62, 33-45.
21. Kabalka, G. W.; Hondrogiannis, G. Directive effects in the hydroboration of 1-alkenyl derivatives of o-carborane with representative hydroborating agents. J. Organomet. Chem. 1997, 536/537, 327-337.
22. Plesek, J.; Stibr, B.; Drdakova, E.; Plzak, Z.; Hermanek, S. Preparation of 1-allyl and 1-propenyl-1,2-dicarba-closo-dodecaborane(12). Chem. Ind. (London). 1982, 778-779.
23. Kusari, U.; Li, Y.; Bradley, M. G.; Sneddon, L. G. Polyborane reactions in ionic liquids: new efficient routes to functionalized decaborane and o-carborane clusters. J. Am. Chem. Soc. 2004, 126, 8662-8663.
24. Grimes, R. N. Carboranes; Academic Press: New York, 1970.
25. Gomez, F. A.; Johnson, S. E.; Hawthorne, M. F. Versatile protecting group for 1,2-dicarba-closo-dodecaborane(12) and the structure of a silylcarborane derivative. J. Am. Chem. Soc. 1991, 113, 5915-5917.
26. Olejniczak, A. B.; Plesek, J.; Kriz, O.; Lesnikowski, Z. J. A nucleoside conjugate containing a metallacarborane group and its incorporation into a DNA oligonucleotide. Angew. Chem., Int. Ed. 2003, 42, 5740-5743.
27. Pirkle, W. H.; Beare, S. D. Optically active solvents in nuclear magnetic resonance spectroscopy. IX. Direct determinations of optical purities and correlations of absolute configurations of alpha-amino acids. J. Am. Chem. Soc. 1969, 91, 5150-5155.
28. Fox, M. A.; Hughes, A. K. Cage C-H-X interactions in solid-state structures of icosahedral carboranes. Coord. Chem. Rev. 2004, 248, 457-476.
29. Yamamoto, K.; Endo, Y. Utility of boron clusters for drug design. Hansch-Fujita hydrophobic parameters π of dicarba-closo-dodecaboranyl groups. Bioorg. Med. Chem. Lett. 2001, 11, 2389-2392.
30. Pedretti, A.; Villa, L.; Vistoli, G. VEGA. An open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming. J. Comput.-Aided Mol. Des. 2004, 18, 167-173.
31. Oehrvik, A.; Lindh, M.; Einarsson, R.; Grassi, J.; Eriksson, S. Sensitive nonradiometric method for determining thymidine kinase I activity. Clin. Chem. 2004, 50, 1597-1606.
32. Clendenon, N. R.; Barth, R. F.; Gordon, W. A.; Goodman, J. H.; Alam, F.; Staubus, A. E.; Boesel, C. P.; Yates, A. J.; Moeschberger, M. L.; Fairchild, R. G. Boron neutron capture therapy of a rat glioma. Neurosurgery 1990, 26, 47-55.
33. Tzeng, J. J.; Barth, R. F.; Orosz, C. G.; James, S. M. Phenotype and functional activity of tumor-infiltrating lymphocytes isolated from immunogenic and nonimmunogenic rat brain tumors. Cancer Res. 1991, 51, 2373-2378.
34. Barth, R. F. Rat brain tumor models in experimental neurooncology: the 9L, C6, T9, F98, RG2 (D74), RT-2 and CNS-1 gliomas. J. Neuro-Oncol. 1998, 36, 91-102.
35. Hampton, A.; Chawla, R. R.; Francis, K. Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes. J. Med. Chem. 1982, 25, 644-649.
36. Barth, R. F.; Adams, D. M.; Soloway, A. H.; Mechetner, E. B.; Alam, F.; Anisuzzaman, A. K. M. Determination of boron in tissues and cells using direct-current plasma atomic emission spectroscopy. Anal. Chem. 1991, 63, 890-893.
37. Nottebrock, H.; Then, R. Thymidine concentrations in serum and urine of different animal species and man. Biochem. Pharmacol. 1977, 26, 2175-2179.
38. Birringer, M. S.; Claus, M. T.; Folkers, G.; Kloer, D. P.; Schulz, G. E.; Scapozza, L. Structure of a type II thymidine kinase with bound dTTP. FEBS Lett. 2005, 579, 1376-1382.
39. Welin, M.; Kosinska, U.; Mikkelsen, N.-E.; Carnrot, C.; Zhu, C.; Wang, L.; Eriksson, S.; Munch-Petersen, B.; Eklund, H. Structures of thymidine kinase 1 of human and mycoplasmic origin. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 17970-17975.
40. Kosinska, U.; Carnrot, C.; Eriksson, S.; Wang, L.; Eklund, H. Structure of the substrate complex of thymidine kinase from Urea-plasma urealyticum and investigations of possible drug targets for the enzyme. FEBS J. 2005, 272, 6365-6372.
41. Fioravanti, E.; Adam, V.; Munier-Lehmann, H.; Bourgeois, D. The crystal structure of mycobacterium tuberculosis thymidylate kinase in complex with 3′-azidodeoxythymidine monophosphate suggests a mechanism for competitive inhibition. Biochemistry. 2005, 44, 130-137.
42. Lavie, A.; Konrad, M. Structural requirements for efficient phosphorylation of nucleotide analogs by human thymidylate kinase. Mini-Rev. Med. Chem. 2004, 4, 351-359.
43. Ostermann, N.; Segura-Pena, D.; Meier, C.; Veit, T.; Monnerjahn, C.; Konrad, M.; Lavie, A. Structures of human thymidylate kinase in complex with prodrugs: Implications for the structure-based design of novel compounds. Biochemistry 2003, 42, 2568-2577.
44. Suzuki, N. N.; Koizumi, K.; Fukushima, M.; Matsuda, A.; Inagaki, F. Structural basis for the specificity, catalysis, and regulation of human uridine-cytidine kinase. Structure 2004, 12, 751-764.
45. Wurth, C.; Kessler, U.; Vogt, J.; Schulz, G. E.; Folkers, G.; Scapozza, L. The effect of substrate binding on the conformation and structural stability of Herpes simplex virus type 1 thymidine kinase. Protein Sci. 2001, 10, 63-73.
46. Johnsamuel, J.; Byun, Y.; Jones, T. P.; Endo, Y.; Tjarks, W. A new strategy for molecular modeling and receptor-based design of carborane containing compounds. J. Organomet. Chem. 2003, 680, 223-231.
47. Johnsamuel, J.; Byun, Y.; Jones, T. P.; Endo, Y.; Tjarks, W. A convenient method for the computer-aided molecular design of carborane containing compounds. Bioorg. Med. Chem. Lett. 2003, 13, 3213-3216.
48. McGovern, S. L.; Shoichet, B. K. Information decay in molecular docking screens against holo, apo, and modeled conformations of enzymes. J. Med. Chem. 2003, 46, 2895-2907.
49. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2004.
50. Spadola, L.; Novellino, E.; Folkers, G.; Scapozza, L. Homology modeling and docking studies on varicella zoster virus thymidine kinase. Eur. J. Med. Chem. 2003, 38, 413-419.