Boron-containing nucleosides as potential delivery agents for neutron capture therapy of brain tumors

Cancer Research

Volumn 64, Issue 17, 2004, Pages 6287-6295

  Barth, Rolf F ^a   Yang, Weilian ^a   Al Madhoun, Ashraf S ^c   Johnsamuel, Jayaseharan ^a   Byun, Youngjoo ^a   Chandra, Subhash ^b   Smith, Duane R ^b   Tjarks, Werner ^a   Eriksson, Staffan ^c  

^a OHIO STATE UNIVERSITY   (United States)

^b Department of Obstetrics Gynecology   (United States)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

3 (CARBORANYL)THYMIDINE DERIVATIVE; 3 (DIHYDROXYPROPYLCARBORANYL)THYMIDINE DERIVATIVE; 3 CARBORANYLTHYMIDINE DERIVATIVE; 3 HYDROXYPROPYL DERIVATIVE; 4 (DIHYDROOXYBORYL)PHENYLALANINE; 4 BORONOPHENYLALANINE; 5 (DIHYDROXYBORYL) 2' DEOXYURIDINE; BOROCAPTATE; BORON 10; BORON DERIVATIVE; BROXURIDINE; DIHYDROXYPROPYL DERIVATIVE; IDOXURIDINE; NUCLEIC ACID; NUCLEOSIDE; RECOMBINANT HUMAN THYMIDINE KINASE 1; SODIUM UNDEHYDROMERCAPTODODECABORATE; THYMIDINE DERIVATIVE; THYMIDINE KINASE; THYMIDINE KINASE 1 SUBSTRATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BRAIN TUMOR; CELLULAR DISTRIBUTION; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; GLIOMA; IN VITRO STUDY; IN VIVO STUDY; MASS SPECTROMETRY; MELANOMA; NEUTRON CAPTURE THERAPY; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; RAT; TUMOR LOCALIZATION;

ANIMALS; BORON COMPOUNDS; BORON NEUTRON CAPTURE THERAPY; BRAIN NEOPLASMS; CELL DIVISION; GLIOMA; HUMANS; MALE; MICE; MICE, INBRED C3H; MICE, NUDE; MIDDLE AGED; PHENYLALANINE; PHOSPHORYLATION; RATS; RATS, INBRED F344; SPECTROMETRY, MASS, SECONDARY ION; SUBCELLULAR FRACTIONS; THYMIDINE; THYMIDINE KINASE;

EID: 4344582408     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-04-0437     Document Type: Article

References (77)

1. Davis FG, Freeks S, Grutsch J, Barlas S, Brem S. Survival rates in patients with primary malignant brain tumors stratified by patient age and tumor histological type: and analysis based on surveillance, epidemiology and end results (SEER) data 1973-1991. J Neurosurg 1998;88:1-10.
2. Halperin EC, Burger PC, Bullard DE. The fallacy of the localized supratentorial malignant glioma. Int J Radiat Oncol Biol Phys 1988;15:505-9.
3. Loeffler JS, Alexander E III, Hochberg FH, et al. Clinical patterns of failure following stereotactic interstitial irradiation for malignant gliomas. Int J Radiat Oncol Biol Phys 1990;19:1455-62.
4. Mischel PS, Cloughesy TG. Targeted molecular therapy of GBM. Brain Pathology 2003;13:52-61.
5. Soloway AH, Tjarks W, Barnum BA, et al. The chemistry of neutron capture therapy. Chemical Rev 1998;98:1515-62.
6. Barth RF, Soloway AH, Goodman JH, et al. Boron neutron capture therapy of brain tumors: an emerging therapeutic modality. Neurosurgery (Baltim) 1999;44:433-51.
7. Coderre JA, Turcotte JC, Riley KJ, et al. Boron neutron capture therapy: cellular targeting of high linear energy transfer radiation. Technol Cancer Res Treat 2003;2: 1-21.
8. Barth RF. A critical assessment of boron neutron capture therapy. An overview. J Neuro-Oncol 2003;62:1-5.
9. Sauerwein W, Moss R, Wittig A, editors. Research and development in neutron capture therapy. Bologna, Italy: Monduzzi Ediotre S.p.A., International Proceedings Division; 2002.
10. Nakagawa Y, Hatanaka H. Boron neutron capture therapy: clinical brain tumor studies. J Neuro-Oncol 1997;33:105-15.
11. Nakagawa Y, Pooh K, Kobayashi T, et al. Clinical review of the Japanese experience with boron neutron capture therapy and a proposed strategy using epithermal neutron beams. J Neuro-Oncol 2003;62:87-99.
12. Diaz AZ. Assessment of the results from the Phase I/II boron neutron capture therapy trials at the Brookhaven National Laboratory from a clinician's point of view. J Neuro-Oncol 2003;62:101-9.
13. Busse PM, Harling OK, Palmer MR, et al. A critical examination of the results from the Harvard-MIT neutron capture therapy program phase I clinical trial of neutron capture therapy for intracranial disease. J Neuro-Oncol 2003;62:111-21.
14. Joensuu H, Kankaanranta L, Seppälä T, et al. Boron neutron capture therapy of brain tumors: clinical trials at the Finnish facility using boronophenylalanine. J Neuro-Oncol 2003;62:123-34.
15. Capala J, H-Stensam B, Sköld K, et al. Boron neutron capture therapy for glioblastoma multiforme: clinical studies in Sweden. J Neuro-Oncol 2003;62:135-44.
16. Vicente MG. Porphyrin-based sensitizers in the detection and treatment of cancer: recent progress. Curr Med Chem-Anti-Cancer Agents 2001;1:175-94.
17. Dewar MJS, Maitlis PM. A boron-containing purine analog. J Am Chem Soc 1959;81:6329-30.
18. Liao TK, Pondrebaroc EG, Cheng CC. Boron-substituted pyrimidines. J Am Chem Soc 1964;86:1869-70.
19. Schinazi RF, Prusoff WH. Synthesis of 5-(dihydroxyboryl)-2′- deoxyuridine and related boron-containing pyrimidines. J Org Chem 1985;50:841-7.
20. Lee LS, Chang Y. Human deoxythymidine kinase. II: Substrate specificity and kinetic behavior of the cytoplasmic and mitochondrial isozymes derived from blast cells of acute myelocytic leukemia. Biochemistry 1976;15:3686-90.
21. Hoshino T, Ahn D, Prados MD, Lamborn K, Wilson CB. Prognostic significance of the proliferative potential of intracranial gliomas measured by bromodeoxyuridine labeling. Int J Cancer 1993;53:550-5.
22. Lamborn KR, Prados MD, Kaplan SB, Davis RL. Final report on the University of California-San Francisco experience with bromodeoxyuridine labeling index as a prognostic factor for the survival of glioma patients. Cancer (Phila) 1999;85:925-35.
23. Soloway AH, Zhuo JC, Rong FG, et al. Identification, development, synthesis and evaluation of boron-containing nucleosides for neutron capture therapy. J Organo-Metallic Chemistry 1999;581:150-5.
24. Tjarks W. The use of boron clusters in the rational design of boronated nucleosides for neutron capture therapy of cancer. J Organomet Chem 2000;614-15, 37-47.
25. Lesnikowski ZJ, Schinazi RF. Boron containing oligonucleotides. Nucleosides Nucleotides 1998;17:635-47.
26. Lesnikowski ZJ, Shi J, Schinazi RF. Nucleic acids and nucleosides containing carboranes. J Organo-Metallic Chemistry 1999;581:156-69.
27. Nemoto H, Rong F-G, Yamamoto Y. The first alkylation of o-carboranes under essentially neutral conditions. Application to the synthesis of boron-10 carriers. J Org Chem 1990;55:6065-6.
28. Nemoto H, Cai J, Yamamoto Y. Synthesis of a water-soluble o-carbaborane bearing a uracil moiety via a palladium-catalyzed reaction under essentially neutral conditions, J Chem Soc Chem Commun 1994;5:577-8.
29. Sood A, Spielvogel BF, Powell WJ, et al. Cytotoxicity of ribo- and arabinoside boron nucleosides in tissue culture cells. Anticancer Res 1994;14:1483.
30. Burnham BS, Chen SY, Sood A, et al. The cytotoxicity of 3′-aminocyanaborane-2′, 3′-dideoxypyrimidines in murine and human tissue cultured cell lines. Anticancer Res 1995;15:951.
31. Eriksson S, Munch-Petersen B, Johansson K, Eklund H. Structure and function of cellular deoxyribonucleoside kinases. Cell Mol Life Sci 2002;59:1327-46.
32. Eriksson S, Wang L. The role of the cellular deoxynucleoside kinases in activation of nucleoside analogs used in chemotherapy. Recent Adv Nucleosides 2002;455-75.
33. Arner ES, Eriksson S. Mammalian deoxyribonuclease kinases. Pharmacol Ther 1995;67:155-86.
34. Persson L, Boethius J, Goronowitz JS, Källander C, Lindgren L. Thymidine kinase in brain tumour cysts. J Neurosurg 1985;63:568-72.
35. Arnér ESJ, Flygar M, Bohman C, Wallström B, Eriksson S. Deoxycytidine kinase is constitually expressed in human lymphocytes: consequences for compartmentation effects, unscheduled DNA synthesis and viral replication in resting cells. Exp Cell Res 1988;178:335-42.
36. Durham JP, Ives DH. Deoxycitine kinase. I. Distribution in normal and neoplastic tissues and interrelationships of deoxycitidine and 1-beta-D-arabinofuranosylcytosine phosphorylation. Mol Pharmacol 1969;5:358-75.
37. Mitchell BS, Song JJ, Johnson II EE, Chen E, Dayton JS. Regulation of human deoxycytidine kinase expression. Adv Enzyme Regul 1993;33:61-8.
38. Spasokoukotskaja T, Arnér ESJ, Brosjö O, et al. Expression of deoxycytidine kinase and phosphorylation of 2-chlorodeoxyadenosine in human normal and tumor cells and tissues. Eur J Cancer 1995;31A:202-8.
39. Arnér ESJ, Spasokoukotskaja T, Eriksson S. Selective assays for thymidine kinase 1 and 2 and deoxycytidine kinase and their activities in extracts from human cells and tissues. Biochem Biophys Res Commun 1992;188:712-8.
40. Kawasaki H, Carrera CJ, Carson DA. Quantitative immunoassay of human deoxycytidine kinase in malignant cells. Anal Biochem 1992;207:193-6.
41. Shimamoto Y, Koizume K, Okabe H, et al. Sensitivity of human cancer cells to the new anticancer ribonucleoside TAS-106 is correlated with expression of uridine-cytidine kinase 2. Jpn J Cancer Res 2002;93:825-33.
42. Itoh R, Yamada K. Determination of cytoplasmic 5′-nucleotidase which preferentially hydrolysis 6-hydroxypurine nucleotides in pig, rat, and human tissues by immunotitration. Int J Biochem Biophys 1991;23:461-5.
43. Lunato AJ, Wang J, Woollard JE, et al. 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;42:3378-89.
44. Al-Madhoun AS, Johnsamuel J, Yan J, et al. 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;45:4018-28.
45. Al-Madhoun AS, Johnsamuel J, Barth RF, Tjarks W, Eriksson S. Evaluation of human thymidine kinase 1 substrates as new candidates for boron neutron capture therapy. Cancer Res 2004;64:6280-6.
46. Barth RF. Rat brain tumor models in experimental neuro-oncology: the 9L, C6, T9, F98, RG2 (D74), RT-2, and CNS-1 gliomas. J Neuro-Oncol 1998;36:91-102.
47. Barth RF, Matalka KZ, Bailey MQ, et al. A nude rat model for neutron capture therapy of human intracerebral melanoma. Int J Radiat Oncol Biol Phys 1994;28: 1079-88.
48. Wang L, Saada A, Eriksson S. Kinetic properties of mutant human thymidine kinase 2 suggest a mechanism for mitochondrial DNA depletion myopathy. J Biol Chem 2003;278:6963-8.
49. Adams DM, Ji W, Barth RF, Tjarks W. Comparative in vitro evaluation of dequalinium B, a new boron carrier for neutron capture therapy (NCT). Anticancer Res 2000;20:3395-402.
50. Barth RF, Adams DM, Soloway AH, et al. Determination of boron in tissues and cells using direct-current plasma atomic emission spectroscopy. Anal Chem 1991;63: 890-3.
51. Barth RF, Yang W, Rotaru JH, et al. Boron neutron capture therapy of brain tumors: enhanced survival following intracarotid injection of either sodium borocaptate or boronophenylalanine with or without blood-brain barrier disruption. Cancer Res 1997;57:1129-36.
52. Yang W, Barth RF, Adams DM, et al. Convection enhanced delivery of boronated epidermal growth factor for molecular targeting of EGFR positive gliomas. Cancer Res 2002;62:6552-8.
53. Nowakowski RS, Lewin SB, Miller MW. Bromodeoxyuridine immunohistochemical determination of the lengths of the cell cycle and the DNA-synthetic phase for an anatomically defined population. J Neurocytol 1989;18:311-8.
54. 10B from p-boronophenylalanine in a brain tumor model for boron neutron capture therapy. Cancer Res 1996;56:4302-6.
55. Smith DR, Chandra S, Barth RF, et al. Quantitative imaging and microlocalization of boron-10 in brain tumors and infiltrating tumor cells by SIMS ion microscopy: relevance to neutron capture therapy. Cancer Res 2001;61:8179-87.
56. Chandra S, Kabalka GW, Lorey DR II, Smith DR, Coderre JA. Imaging of fluorine and boron from fluorinated boronophenylalanine in the same cell at organelle resolution by correlative ion microscopy and confocal laser scanning microscopy. Clin Cancer Res 2002;8:2675-83.
57. Ausserer WA, Ling Y-C, Chandra S, Morrison GH. Quantitative imaging of boron, calcium, magnesium potassium, and sodium distributions in cultured cells with ion microscopy. Anal Chem 1989;61:2690-5.
58. Tjarks W, Wang J, Chandra S, et al. Synthesis and biological evaluation of boronated nucleosides for boron neutron capture therapy (BNCT) of cancer. Nucleosides Nucleotides Nucleic Acids 2001;20:695-8.
59. Cai J, Soloway AH, Barth RF, et al. Boron-containing polyamines as DNA targeting agents for neutron capture therapy of brain tumors: synthesis and biological evaluation. J Med Chem 1997;40:3887-96.
60. Zhuo J-C, Cai J, Soloway AH, et al. W. Synthesis and biological evaluation of boron-containing polyamines as potential Agents for neutron capture therapy of brain tumors. J Med Chem 1999;42:1282-92.
61. Greig NH. Drug delivery to the brain by blood-brain barrier circumvention and drug modification, In: Neuwelt EA, editor. Implications of the blood-brain barrier and its manipulation. vol I. Basic Science Aspects. New York: Plenum; 1989. pp. 311-67.
62. Betz AL, Goldstein GW, Katzman R. Blood-brain-cerebrospinal fluid barriers. In: Siegel GJ, Agranoff R, Albers RW, Molinoff PB, editors. Basic neurochemistry, molecular, cellular and medical aspects. New York: Raven Press; 1994. p. 681-99.
63. Atkinson F, Cole S, Green C, van de Weterbeemd H. Liphophilicity and other parameters affecting brain penetration. Curr Med Chem 2002;2:229.
64. Hansch C, Bjorkroth JP, Leo AJ. Hydrophobicity and central nervous system agents: on the principal of minimal hydrophobicity in drug design. J Pharm Sci 1987;76:663.
65. Barth RF, Yang W, Rotaru JH, et al. Boron neutron capture therapy of brain tumors: enhanced survival and cure following blood-brain barrier disruption and intracarotid injection of sodium borocaptate and boronophenylalanine. Int J Radiat Oncol Biol Phys 2000;47:209-18.
66. Kassis AI, Adelstein J, Mariani G. Radiolabeled nucleoside analogs in cancer diagnosis and therapy. Q J Nucl Med 1996;40:301-19.
67. 123I]iodo-2′ deoxyuridine in a patient with a brain tumor. J Nucl Med 1996;37:19S-22S.
68. 123I]iodo- 2′ deoxyuridine in the radiotherapy of brain tumors in rats. J Nucl Med 1998;39:1148-54.
69. 123I]iodo- 2′ deoxyuridine in a rat model of leptomeningeal metastases. J Nucl Med 1997;38:386-90.
70. 123I]iodo-2′ deoxyuridine. Acta Oncol 2000;39:731-7.
71. Bobo RH, Laske DW, Akbasak A, et al. Convection-enhanced delivery of macromolecules in the brain. Proc Natl Acad Sci USA 1994;91:2076-80.
72. Viola JJ, Agbaria R, Walbridge S, et al. In situ cyclopentenyl cytosine infusion for the treatment of experimental brain tumors. Cancer Res 1995;55:1306-09.
73. Laske DW, Youle RJ, Oldfield EH. Tumor regression with regional distribution of the targeted toxin TF-CRM107 in patients with malignant brain tumors. Nat Med 1997; 3:1362-8.
74. 14C-sucrose in RG-2 rat gliomas after intravenous and convection-enhanced delivery. Neuro-Oncol 2004;6:104-12.
75. Degen JW, Walbridge S, Vortmeyer AO, Oldfield EH, Lonser RR. Safety and efficacy of convection-enhanced delivery of gemcitabine or carboplatin in a malignant glioma model in rats. J Neurosurg 2003;99:893-8.
76. Benjamin RK, Hochbert FH, Fox E, et al. Review of microdialysis in brain tumors, from concept to application: first annual Carolyn Frye-Halloran symposium. Neuro-Oncol 2004;6:65-74.
77. Eriksson S, Arner E, Spasokoukotskaja T, et al. Properties and levels of deoxynucleoside kinases in normal and tumor cells; implications for chemotherapy. Adv Enzyme Regul 1994;34:13-25.