Studies on the synthesis and biological properties of non-carrier-added [125I and 131I]-labeled arylalkylidenebisphosphonates: Potent bone-seekers for diagnosis and therapy of malignant osseous lesions

Journal of Medicinal Chemistry

Volumn 46, Issue 14, 2003, Pages 3021-3032

  Årstad, Erik ^a   Hoff, Per ^a   Skattebøl, Lars ^a   Skretting, Arne ^b   Breistøl, Knut ^b  

^a UNIVERSITY OF OSLO   (Norway)

^b OSLO UNIVERSITY HOSPITAL   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY(3 IODOPHENYLETHYLIDENE) 1,1 BISPHOSPHONIC ACID 1 131; 1 HYDROXY(3 IODOPHENYLETHYLIDENE) 1,1 BISPHOSPHONIC ACID I 125; BISPHOSPHONIC ACID DERIVATIVE; HYDROXYBISPHOSPHONATE; IODINE 125; IODINE 131; UNCLASSIFIED DRUG;

ADOLESCENT; ANIMAL CELL; ARTICLE; BINDING AFFINITY; BONE CANCER; BONE METASTASIS; CANCER DIAGNOSIS; CANCER THERAPY; CONTROLLED STUDY; DEIODINATION; DOSIMETRY; DRUG ACCUMULATION; DRUG ACTIVITY; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG EXCRETION; DRUG HALF LIFE; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; FEMALE; FEMUR; HUMAN; HUMAN CELL; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; OSTEOSARCOMA; RAT; RAT STRAIN; SCINTIGRAPHY; SURVIVAL TIME; TISSUE SPECIFICITY; TUMOR MODEL;

ANIMALS; ANTINEOPLASTIC AGENTS; BONE NEOPLASMS; DIPHOSPHONATES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; IODINE RADIOISOTOPES; MICE; MICE, INBRED BALB C; NEOPLASM TRANSPLANTATION; OSTEOSARCOMA; RADIOPHARMACEUTICALS; RATS; RATS, NUDE; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; TUMOR CELLS, CULTURED;

EID: 0037805683     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm021107v     Document Type: Article

References (37)

1. Rubens, R. D. Bone involvement in solid tumours. In Bisphosphonates on Bones; Bijvoet, O. L. M., Fleisch, H. A., Canfield, R. E., Russell, R. G. G., Eds.; Elsevier Sciences B. V.: Amsterdam, 1995; pp 337-345.
2. Coleman, R. E. The treatment of metastatic bone disease. In Bisphosphonates on Bones; Bijvoet, O. L. M., Fleisch, H. A., Canfield, R. E., Russell, R. G. G., Eds.; Elsevier Sciences B. V.: Amsterdam, 1995; pp 337-345.
3. Volkert, W. A.; Hoffman, T. J. Therapeutic radiopharmaceuticals. Chem Rev. 1999, 99, 2269-2292.
4. Bouchet, L. G.; Bolch, W. E.; Goddu, S. M.; Howell, R. W.; Rao, D. V. Considerations in the selection of radiopharmaceuticals for palliation of bone pain from metastatic osseous lesions. J. Nucl. Med. 2000, 41, 682-687.
5. Atkins, H. L. Overview of nuclides for bone pain palliation. Appl. Radiat. Isot. 1998, 49, 277-283.
6. Robinson, R. G.; Spicer, J. A.; Preston, D. F.; Wegst, A. V.; Martin, N. L. Treatment of metastatic bone pain with strontium-89. Nucl. Med. Biol. 1987, 14, 219-22.
7. Lewington, V. J.; McEvan, A. J.; Ackery, D. M.; Bayly, R. J.; Keeling, D. H.; Macleod, P. M.; Porter, A. T.; Zivanoic, M. A. A prospective, randomised double-blind crossover study to examine the efficacy of strontium-89 in pain palliation in patients with advanced prostate cancer metastatic to bone. Eur. J. Cancer 1991, 27, 954-958.
8. Anderson, P. M.; Wiseman, G. A.; Dispenzieri, A.; Arndt, C. A. S.; Hartmann, L. C.; Smithson, W. A.; Mullan, B. P.; Bruland, O. S. High-dose samarium-153 ethylenediamine tetramethylene phosphonate: Low toxicity of skeletal irradiation in patients with osteosarcoma and bone metastases. J. Clin. Oncol. 2002, 20, 189-196.
9. Aas, M.; Moe, L.; Gamlem, H.; Skretting, A.; Ottesen, N.; Bruland, O. S. Internal radionuclide therapy of primary osteosarcoma in dogs, using 153Sm-ethylene-diamino-tetramethylenephosphate (EDTMP). Clin. Cancer Res. 1999, 5 (10 Suppl), 3148s-3152s.
10. Goeckeler, W. F.; Edwards, B.; Volkert, W. A.; Holmes, R. A.; Simson, J.; Wilson, D. Skeletal localization of samarium-153 chelates: potential therapeutic bone agents. J. Nucl. Med. 1987, 28, 495-504.
11. Srivastava, S. C.; Meinken, G, E.; Richards, P.; Som, P.; Oster, Z. H.; Atkins, H. L.; Brill, A. B.; Knapp, F. F., Jr.; Butler, T. A. The development of in-vivo behavior of tin containing radiopharmaceuticals-I. Int. J. Nucl. Med. Biol. 1985, 12, 167-174.
12. Maxon, H. R. 3rd; Schroder, L. E.; Hertzberg, V. S.; Thomas, S. R.; Englaro E. E.; Samaratunga, R.; Smith, H.; Moulton, J. S.; Williams, C. C.; Ehrhardt, G. J.; Schneider, H. J. Rhenium-186-(Sn)HEDP for treatment of painful osseous metastases: results of a double-blind crossover comparison with placebo. J. Nucl. Med. 1991, 32, 1877-1881.
13. Hoefnagel, C. A.; Clarke, S. E.; Fischer, M.; Chatal, J. F.; Lewington, V. J.; Nilsson, S.; Troncone, L.; Vieira, M. R. Radionuclide therapy practice and facilities in Europe. EANM Radionuclide therapy Committee. Eur. J. Nucl. Med. 1999, 26, 277-282.
14. Press, O. W. Radiolabeled antibody therapy of B-cell lymphomas. Seminars in Oncology 1999, 26 (5 suppl. 14) 58-65.
15. Eisenhut, M. Iodine-131-labeled diphosphonates for the palliative treatment of bone metastases. J. Nucl. Med. 1984, 25, 1356-1361.
16. Eisenhut, M.; Berberich, R.; Kimmig, B.; Oberhausen, E. Iodine-131-labeled diphosphonates for the palliative treatment of bone metastases: II. J. Nucl. Med. 1986, 27, 1255-1261.
17. Larsen, R. H.; Bruland, Ø. Preliminary evaluation of a new radiolabeled bisphosphonate. J. Labeled Cpd. Radiopharm. 1998, 41, 823-830.
18. Larsen, R. H.; Murud, K. M.; Akabani, G.; Hoff, P.; Bruland, Ø. S.; Zalutsky, M. R. At-211- and I-131-labeled bisphosphonates with high in vivo stability and bone accumulation. J. Nucl. Med. 1999, 40, 1197-1203.
19. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M. C. The facile dealkylation of phosphonic acid dialkyl esters by bromotrimethylsilane. Tetrahedron Lett. 1977, 2, 155-158.
20. 131I]iodobenzylguanidine. Appl. Radiat. Isot. 1993, 44, 621-628.
21. Reeves, W. P.; White, M. R. Phase transfer catalysis: Preparation of alkyl cyanides. Synth. Commun. 1976, 6, 193-197.
22. Tam, C. C.; Mattocks, K. L.; Tishler, M. Enol-keto tautomerism of α-ketophosphonates. Proc. Natl. Acad. Sci., U.S.A. 1981, 78, 3301-3304.
23. Pudovik, A. N.; Zimin, M. G. Addition reactions of partially esterified phosphorous acids. Rearrangements of α-hydroxyalkyl phosphorous esters and their α-mercapto and α-amino-analogues. Pure Appl. Chem. 1980, 52, 989-1011, and references therein.
24. Nicholson, D. A.; Vaughn, H. A general method of preparation of tetramethyl alkyl-1-hydroxy-1,1-diphosphonates. J. Org. Chem. 1971, 36, 3843-3845.
25. Itsuno, S.; Sakurai, Y.; Ito, K. Reduction of some functional groups with zirconium tetrachloride/sodium borohydride. Synthesis 1988, 995-996.
26. Dedrick, R. L.; Bischoff, K. B.; Zaharko, D. S. Interspecies correlation of plasma concentration history of methotrexate. Cancer Chemother. Rep. Part 1 1970, 54, 95-101.
27. Lin, J. H. Bisphosphonates: A Review of Their Pharmacokinetic Properties. Bone 1996, 18, 75-85.
28. McAfee, J. G.; Subramanian, G. Interpretation of interspecies differences in the biodistribution of radioactive agents. In Third International Radiopharmaceutical Dosimetry Symposium; Watson, E. E., Schlafke, A. T; Coffey, J. L.; Cloutier, R. J., Eds., HHS Publication FDA 81-8166, Bureau of Radiological Health, Rockville, MD 20857, 1981; pp 292-307.
29. Engebraaten, O.; Fodstad, Ø. Site-specific experimental metastasis patterns of two human breast cancer cell lines in nude rats. Int. J. Cancer 1999, 82, 219-225.
30. 223Ra Demonstrated in an Experimental Skeletal Metastases Model. Cancer Res. 2002, 62, 3120-3125.
31. Kjønniksen, I.; Winderen, M.; Bruland, Ø.; Fodstad, Ø. Validity and usefulness of human tumor-models established by intratibial cell inoculation in nude rats. Cancer Res. 1994, 54, 1715-1719.
32. Fodstad, Ø.; Brøgger, A.; Bruland, Ø.; Solheim, Ø. P.; Nesland, J. M.; Pihl, A. Characteristics of a cell line established from a patient with multiple osteosarcoma, appearing 13 years after treatment for bilateral retinoblastoma. Int. J. Cancer 1986, 38, 33-40.
33. 153SM in rats. Appl. Radiat. Isot. 1994, 45, 949-953.
34. Castronovo, F. P.; Strauss, H. W.; Potsaid, M. S. Labeled phosphonic acid compositions for investigations of in vivo deposits of calcium. US Patent 4,515,766, May 7, 1985.
35. Winderen, M.; Kjønniksen, I.; Fodstad, Ø. Pronounced therapeutic effect of samarium 153-ethylenediaminetetramethylene phosphonate in an orthotopic human osteosarcoma tibial tumor model. J. Natl. Cancer Inst. 1995, 87, 221-222.
36. Clark, H. A.; Gordon, A. F.; Young, C. W.; Hunter, M. J. Position isomers of substituted aryltrimethylsilanes. J. Am. Chem. Soc. 1951, 73, 3798-3803.
37. Severson, R. G.; Rosscup, R. J.; Lindberg, D. R.; Engberg, R. D. Substituted phenylsilanes. II. The Bromination of the tolyltrimethylsilanes. J. Am. Chem. Soc. 1957, 79, 6540-6542.