A promising approach for treatment of tumor-induced bone diseases: Utilizing bisphosphonate derivatives of nucleoside antimetabolites

Bone

Volumn 47, Issue 1, 2010, Pages 12-22

  Reinholz, Monica M ^a   Zinnen, Shawn P ^c   Dueck, Amylou C ^d   Dingli, David ^a   Reinholz, Gregory G ^a   Jonart, Leslie A ^a   Kitzmann, Kathleen A ^a   Bruzek, Amy K ^a   Negron, Vivian ^a   Abdalla, Abdalla K ^a   Arendt, Bonnie K ^b   Croatt, Anthony J ^a   Sanchez Perez, Luis ^a   Sebesta, David P ^c   Lönnberg, Harri ^e   Yoneda, Toshiyuki ^f,g   Nath, Karl A ^a   Jelinek, Diane F ^b   Russell, Stephen J ^a   Ingle, James N ^a   Spelsberg, Thomas C ^b   Dixon, Henry B F ^c   Karpeisky, Alexander ^c   Lingle, Wilma L ^a   more..

^a MAYO CLINIC   (United States)

^b MAYO GRADUATE SCHOOL   (United States)

^c MBC Pharma Inc   (United States)

^d MAYO CLINIC   (United States)

^e UNIVERSITY OF TURKU   (Finland)

^f UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

^g OSAKA UNIVERSITY   (Japan)

Author keywords

Bisphosphonates; Bone cancer; Chemotherapeutics; Drug conjugation; Targeting

Indexed keywords

BISPHOSPHONIC ACID DERIVATIVE; CYTARABINE; ETIDRONIC ACID; FLUOROURACIL; FLUOROURIDINE; MBC 1; MBC 11; MBC 29; MBC 9; UNCLASSIFIED DRUG; ZOLEDRONIC ACID;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BONE DENSITY; BONE METASTASIS; BONE STRUCTURE; BREAST CANCER; CANCER SURVIVAL; CONTROLLED STUDY; DRUG EFFICACY; DRUG SYNTHESIS; DRUG TOLERABILITY; FEMALE; FEMUR; HUMAN; HUMAN CELL; METASTASIS INHIBITION; MOUSE; MULTIPLE MYELOMA; NONHUMAN; OVERALL SURVIVAL;

ANIMALS; ANTIMETABOLITES; BONE AND BONES; BONE DENSITY; BONE DISEASES; CELL LINE, TUMOR; CELL PROLIFERATION; DIPHOSPHONATES; HUMANS; KAPLAN-MEIERS ESTIMATE; MICE; MICE, INBRED BALB C; MICE, SCID; MULTIPLE MYELOMA; NEOPLASM TRANSPLANTATION; NEOPLASMS; NUCLEOSIDES; ORGAN SIZE; TUMOR BURDEN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 77954757272     PISSN: 87563282     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bone.2010.03.006     Document Type: Article

References (51)

1. Coleman R.E. Clinical features of metastatic bone disease and risk of skeletal morbidity. Clin Cancer Res 2006, 12(20 Pt 2):6243s-6249s.
2. Lipton A., Berenson J.R., Body J.J., Boyce B.F., Bruland O.S., Carducci M.A., et al. Advances in treating metastatic bone cancer: summary statement for the First Cambridge Conference. Clin Cancer Res 2006, 12(20 Pt 2):6209s-6212s.
3. Aapro M., Abrahamsson P.A., Body J.J., Coleman R.E., Colomer R., Costa L., et al. Guidance on the use of bisphosphonates in solid tumours: recommendations of an international expert panel. Ann Oncol 2008, 19(3):420-432.
4. Body J.-J. Bisphosphonates for malignancy-related bone disease: current status, future developments. Support Care Cancer 2006, V14(5):408-418.
5. Costa L. Bisphosphonates: reducing the risk of skeletal complications from bone metastasis. Breast 2007, 16(Suppl 3):S16-S20.
6. Hortobagyi G.N. Unmet needs in metastatic bone disease and its complications: is progress possible?. Semin Oncol 2001, 28(2 Suppl 6):1-3.
7. Karpeisky MY, Padyukova NS, Mikhailov SN, Dixon HBF, Tzeitline G 2001 Bisphosphonate conjugates and methods of making and using the same. United States patent US 6, 214, 812 B1. MBC Research, Inc., Boulder, CO, US.
8. Karpeisky MY, Padyukova NS, Mikhailov SN, Dixon HBF, Tzeitline G 2004 Bisphosphonate conjugates and methods of making and using the same. United States patent US 6, 750, 340 B2. MBC Research, Inc., Boulder, CO, US.
9. Ora M., Lonnberg T., Florea-Wang D., Zinnen S., Karpeisky A., Lonnberg H. Bisphosphonate derivatives of nucleoside antimetabolites: hydrolytic stability and hydroxyapatite adsorption of 5'-beta, gamma-methylene and 5'-beta, gamma-(1-hydroxyethylidene) triphosphates of 5-fluorouridine and ara-cytidine. J Org Chem 2008, 73(11):4123-4130.
10. Coleman R.E. Emerging strategies in bone health management for the adjuvant patient. Semin Oncol 2007, 34(6 Suppl 4):S11-S16.
11. Daubine F., Le Gall C., Gasser J., Green J., Clezardin P. Antitumor effects of clinical dosing regimens of bisphosphonates in experimental breast cancer bone metastasis. J Natl Cancer Inst 2007, 99(4):322-330.
12. Zheng Y., Zhou H., Brennan K., Blair J.M., Modzelewski J.R., Seibel M.J., et al. Inhibition of bone resorption, rather than direct cytotoxicity, mediates the anti-tumour actions of ibandronate and osteoprotegerin in a murine model of breast cancer bone metastasis. Bone 2007, 40(2):471-478.
13. Clezardin P., Ebetino F.H., Fournier P.G. Bisphosphonates and cancer-induced bone disease: beyond their antiresorptive activity. Cancer Res 2005, 65(12):4971-4974.
14. Green J.R. Bisphosphonates: preclinical review. Oncologist 2004, 9(Suppl 4):3-13.
15. Senaratne S.G., Colston K.W. Direct effects of bisphosphonates on breast cancer cells. Breast Cancer Res 2002, 4(1):18-23.
16. Senaratne S.G., Pirianov G., Mansi J.L., Arnett T.R., Colston K.W. Bisphosphonates induce apoptosis in human breast cancer cell lines. Br J Cancer 2000, 82(8):1459-1468.
17. Clezardin P., Fournier P., Boissier S., Peyruchaud O. In vitro and in vivo antitumor effects of bisphosphonates. Curr Med Chem 2003, 10(2):173-180.
18. Reinholz G.G., Getz B., Sanders E.S., Karpeisky M.Y., Padyukova N., Mikhailov S.N., et al. Distinct mechanisms of bisphosphonate action between osteoblasts and breast cancer cells: identity of a potent new bisphosphonate analogue. Breast Cancer Res Treat 2002, 71(3):257-268.
19. Clezardin P. The antitumor potential of bisphosphonates. Semin Oncol 2002, 29(6 Suppl 21):33-42.
20. Green J.R., Muller K., Jaeggi K.A. Preclinical pharmacology of CGP 42'446, a new, potent, heterocyclic bisphosphonate compound. J Bone Miner Res 1994, 9(5):745-751.
21. Pittock S.T., Norby S.M., Grande J.P., Croatt A.J., Bren G.D., Badley A.D., et al. MCP-1 is up-regulated in unstressed and stressed HO-1 knockout mice: pathophysiologic correlates. Kidney Int 2005, 68(2):611-622.
22. Lelekakis M., Moseley J.M., Martin T.J., Hards D., Williams E., Ho P., et al. A novel orthotopic model of breast cancer metastasis to bone. Clin Exp Metastasis 1999, 17(2):163-170.
23. Hiraga T., Williams P.J., Ueda A., Tamura D., Yoneda T. Zoledronic acid inhibits visceral metastases in the 4T1/luc mouse breast cancer model. Clin Cancer Res 2004, 10(13):4559-4567.
24. Mundy G. Preclinical models of bone metastases. Semin Oncol 2001, 28(4 Suppl 11):2-8.
25. Yoneda T., Michigami T., Yi B., Williams P.J., Niewolna M., Hiraga T. Actions of bisphosphonate on bone metastasis in animal models of breast carcinoma. Cancer 2000, 88(12 Suppl):2979-2988.
26. Westendorf J.J., Ahmann G.J., Greipp P.R., Witzig T.E., Lust J.A., Jelinek D.F. Establishment and characterization of three myeloma cell lines that demonstrate variable cytokine responses and abilities to produce autocrine interleukin-6. Leukemia 1996, 10(5):866-876.
27. Jelinek D.F., Witzig T.E., Arendt B.K. A role for insulin-like growth factor in the regulation of IL-6-responsive human myeloma cell line growth. J Immunol 1997, 159(1):487-496.
28. Abe M., Hiura K., Wilde J., Moriyama K., Hashimoto T., Ozaki S., et al. Role for macrophage inflammatory protein (MIP)-1alpha and MIP-1beta in the development of osteolytic lesions in multiple myeloma. Blood 2002, 100(6):2195-2202.
29. Brown S.A., Clines G.A., Guise T.A. Local effects of malignancy on bone. Curr Opin Endocrinol Diabetes Obes 2007, 14(6):436-441.
30. Yoneda T., Hiraga T. Crosstalk between cancer cells and bone microenvironment in bone metastasis. Biochem Biophys Res Commun 2005, 328(3):679-687.
31. Uludag H. Bisphosphonates as a foundation of drug delivery to bone. Curr Pharm Des 2002, 8(21):1929-1944.
32. Zhang S., Gangal G., Uludag H. 'Magic bullets' for bone diseases: progress in rational design of bone-seeking medicinal agents. Chem Soc Rev 2007, 36(3):507-531.
33. Fleisch H. Bisphosphonates in Bone Disease 2000, Academic Press, San Diego, CA. 4 ed.
34. Ezra A., Golomb G. Administration routes and delivery systems of bisphosphonates for the treatment of bone resorption. Adv Drug Deliv Rev 2000, 42(3):175-195.
35. Stepensky D., Kleinberg L., Hoffman A. Bone as an effect compartment: models for uptake and release of drugs. Clin Pharmacokinet 2003, 42(10):863-881.
36. Hirabayashi H., Fujisaki J. Bone-specific drug delivery systems: approaches via chemical modification of bone-seeking agents. Clin Pharmacokinet 2003, 42(15):1319-1330.
37. Fabulet O., Sturtz G.A. Synthesis of gem-bisphosphonic doxorubicinconjugates. Phosphorus Sulfur Silicon Relat Elem 1995, 101(1-4):225-234.
38. Hosain F., Spencer R.P., Couthon H.M., Sturtz G.L. Targeted delivery of antineoplastic agent to bone: biodistribution studies of technetium-99m-labeled gem-bisphosphonate conjugate of methotrexate. J Nucl Med 1996, 37(1):105-107.
39. Sturtz G.L., Couthon H.M., Fabulet O., Mian M.A., Rosini S. Synthesis of gem-bisphosphonic methotrexate conjugates and their biological response towards Walker's osteosarcoma. Eur J Med Chem 1993, 28(11):899-903.
40. Wingen F., Sterz H., Blum H., Moller H., Pittermann W., Pool B.L., et al. Synthesis, antitumor activity, distribution and toxicity of 4-[4-[bis(2-chloroethyl)amino]phenyl]-1-hydroxybutane-1 1-bisphosphonic acid (BAD), a new lost derivative with increased accumulation in rat osteosarcoma. J Cancer Res Clin Oncol 1986, 111(3):209-219.
41. Shipman C.M., Rogers M.J., Apperley J.F., Graham R., Russell G., Croucher P.I. Anti-tumour activity of bisphosphonates in human myeloma cells. Leuk Lymphoma 1998, 32(1-2):129-138.
42. Takahashi R., Shimazaki C., Inaba T., Okano A., Hatsuse M., Okamoto A., et al. A newly developed bisphosphonate, YM529, is a potent apoptosis inducer of human myeloma cells. Leuk Res 2001, 25(1):77-83.
43. Croucher PI, De Raeve H., Perry M., Hijzen A., Shipman C.M., Lippitt J, et al. Zoledronic acid treatment of 5T2MM-bearing mice inhibits the development of myeloma bone disease: evidence for decreased osteolysis, tumor burden and angiogenesis, and increased survival. J Bone Miner Res 2003, 18(3):482-492.
44. Buijs J.T., Que I., Lowik C.W., Papapoulos S.E., van der Pluijm G. Inhibition of bone resorption and growth of breast cancer in the bone microenvironment. Bone 2009, 44:380-386.
45. Hillner B.E., Ingle J.N., Chlebowski R.T., Gralow J., Yee G.C., Janjan N.A., et al. American Society of Clinical Oncology 2003 update on the role of bisphosphonates and bone health issues in women with breast cancer. J Clin Oncol 2003, 21(21):4042-4057.
46. Saarto T., Vehmanen L., Virkkunen P., Blomqvist C. Ten-year follow-up of a randomized controlled trial of adjuvant clodronate treatment in node-positive breast cancer patients. Acta Oncol 2004, 43(7):650-656.
47. Powles T., Paterson A., McCloskey E., Schein P., Scheffler B., Tidy A., et al. Reduction in bone relapse and improved survival with oral clodronate for adjuvant treatment of operable breast cancer [ISRCTN83688026]. Breast Cancer Res 2006, 8(2):R13.
48. Petrut B., Trinkaus M., Simmons C., Clemons M. A primer of bone metastases management in breast cancer patients. Curr Oncol 2008, 15(Supplement 1):S50-S57.
49. Gnant M., Mlineritsch B., Luschin-Ebengreuth G., Kainberger F., Kassmann H., Piswanger-Solkner J.C., et al. Adjuvant endocrine therapy plus zoledronic acid in premenopausal women with early-stage breast cancer: 5-year follow-up of the ABCSG-12 bone-mineral density substudy. Lancet Oncol 2008, 9(9):840-849.
50. Lyseng-Williamson K.A. Zoledronic acid: a review of its use in breast cancer. Drugs 2008, 68(18):2661-2682.
51. Ali S.M., Harvey H.A., Lipton A. Metastatic breast cancer: overview of treatment. Clin Orthop Relat Res 2003, (415 Suppl):S132-S137.