Overview of bisphosphonates

Cancer

Volumn 80, Issue 8 SUPPL., 1997, Pages 1652-1660

  Rogers, Michael J ^a   Watts, Donald J ^b   Russell, R Graham G ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALENDRONIC ACID; BISPHOSPHONIC ACID DERIVATIVE; CLODRONIC ACID; IBANDRONIC ACID; PAMIDRONIC ACID; RISEDRONIC ACID; TILUDRONIC ACID; ZOLEDRONIC ACID;

BONE METASTASIS; BONE MINERALIZATION; CALCIUM METABOLISM; CONFERENCE PAPER; DRUG EFFECT; DRUG STRUCTURE; HUMAN; HYPERCALCEMIA; INTRAVENOUS DRUG ADMINISTRATION; MULTIPLE MYELOMA; ORAL DRUG ADMINISTRATION; OSTEOBLAST; OSTEOCLAST; OSTEOLYSIS; PAGET BONE DISEASE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0030749322     PISSN: 0008543X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-0142(19971015)80:8+<1652::aid-cncr15>3.0.co;2-z     Document Type: Conference Paper

References (91)

1. Fleisch H, Russell RGG, Francis MD. Diphosphonates inhibit formation of calcium phosphate crystals in vitro and pathological calcification in vivo. Science 1969;165:1262-4.
2. Fleisch H, Russell RGG, Francis MD. Diphosphonates inhibit hydroxyapatite dissolution in vitro and bone resorption in tissue culture and in vivo. Science 1969;165:1264-6.
3. Jung A, Bisaz S, Fleisch H. The binding of pyrophosphate and two diphosphonates on hydroxyapatite crystals. Calcif Tissue Res 1973;11:269-80.
4. Bisaz S, Jung A, Fleisch H. Uptake by bone of pyrophosphate, diphosphonates and their technetium derivatives. Clin Sci Mol Med 1978;54:265-72.
5. Russell RGG, Muhlbauer RC, Bisaz S, Williams DA, Fleisch H. The influence of pyrophosphate, condensed phosphates, phosphonates and other phosphate compounds on the dissolution of hydroxyapatite in vitro and on bone resorption induced by parathyroid hormone in tissue culture and in thyroparathyroidectomised rats. Calcif Tissue Res 1970;6:183-96.
6. Geddes AD, D'Souza SM, Ebetino FH, Ibbotson KJ. Bisphosphonates: structure-activity relationships and therapeutic implications. J Bone Miner Res 1994;8:265-306.
7. Shinoda H, Adamek G, Felix R, Fleisch H, Schenk R, Hagan P. Structure-activity relationships of various bisphosphonates. Calcif Tissue Int 1983;35:87-99.
8. Schenk R, Eggli P, Fleisch H, Rosini S. Quantitative morpho-metric evaluation of the inhibitory activity of new aminobis-phosphonates on bone resorption in the rat. Calcif Tissue Int 1986;38:342-9.
9. Boonekamp PM, Löwik CWGM, van der Wee-Pals LJA, van Wijk-van Lennep MLL, Bijvoet OLM. Enhancement of the inhibitory action of APD on the transformation of osteoclast precursors into resorbing cells after dimethylation of the amino group. Bone Miner 1987;2:29-42.
10. Van der Pluijm G, Binderup L, Bramm E, van der Wee-Pals L, de Groot H, Binderup E, et al. Disodium 1-hydroxy-3-(1-pyrrolidinyl)-propylidene-1,1-bisphosphonate (EB-1053) is a potent inhibitor of bone resorption in vitro and in vivo. J Bone Miner Res 1992;7:981-6.
11. Sietsema WK, Ebetino FH, Salvagno AM, Bevan JA. Antiresorptive dose-response relationships across three generations of bisphosphonates. Drugs Exp Clin Res 1989;15:389-96.
12. Green JR, Muller K, Jaeggi KA. Preclinical pharmacology of CGP 42′446, a new, potent, heterocyclic bisphosphonate compound. J Bone Miner Res 1994;9:745-51.
13. Muhlbauer RC, Bauss F, Schenk R, Janner M, Bosies E, Strein K, et al. BM 21.0955, a potent new bisphosphonate to inhibit bone resorption. J Bone Miner Res 1991;6:1003-11.
14. Ebetino FH, Russell RGG. Metabolic bone disease: current therapies and future prospects with bisphosphonates and other agents. In: Sarel S, Mechoulam R, Agranat I, (editors.) Trends in medicinal chemistry 1990. Oxford: Blackwell Scientific Publications, 1992:293-8.
15. Rogers MJ, Watts DJ, Russell RGG, Ji X, Xiong X, Blackburn GM, et al. Inhibitory effects of bisphosphonates on growth of amoebae of the cellular slime mould Dictyostelium discoideum. J Bone Miner Res 1994;9:1029-39.
16. Rogers MJ, Xiong X, Brown RJ, Watts DJ, Russell RGG, et al. Structure-activity relationships of new heterocycle-containing bisphosphonates as inhibitors of bone resorption and as inhibitors of growth of Dictyostelium discoideum amoebae. Mol Pharmacol 1995;47:398-402.
17. Rogers MJ, Xiong X, Brown RJ, Watts DJ, Russell RGG, Bayless AV, et al. Alterations to the phosphonate groups of bisphosphonates decrease their potency as inhibitors of bone resorption and as inhibitors of Dictyostelium growth. Bone Miner 1994;25(Suppl. 1):S69.
18. Mundy GR, Roodman GD. Osteoclast ontogeny and function. J Bone Miner Res 1987;5:209-79.
19. Zaidi M, Towhidul A, Shankar ASM, Bax VS, Bax BE, Moonga CMR, et al. Cellular biology of bone resorption. Biol Rev Camb Philos Soc 1993;68:197-264.
20. Sato M, Grasser W, Endo N, Akins R, Simmons H, Thompson DD, et al. Bisphosphonate action. Alendronate localisation in rat bone and effects on osteoclast ultrastructure. J Clin Invest 1991;88:2095-105.
21. 3H-Etidronate in rat and mouse bones. Bone 1996;19:281-90.
22. 2MBP-coated bone. Bone Miner 1989;6:33-43.
23. Flanagan AM, Chambers TJ. Inhibition of bone resorption by bisphosphonates: interactions between bisphosphonates, osteoclasts and bone. Calcif Tissue Int 1991;49:407-15.
24. Rowe DJ, Hausmann E. The effects of calcitonin and colchicine on the cellular response to diphosphonate. Br J Exp Pathol 1980;61:303-9.
25. Murakami H, Takahashi N, Sasaki T, Udagawa N, Tanaka S, Nakamura I, et al. A possible mechanism of the specific action of bisphosphonates on osteoclasts: tiludronate preferentially affects polarized osteoclasts having ruffled borders. Bone 1995;17:137-44.
26. Mönkkönen J, Taskinen M, Auriola SOK, Urtti A. Growth inhibition of macrophage-like and other cell types by liposome-encapsulated, calcium-bound and free bisphosphonates in vitro. J Drug Target 1994;2:299-308.
27. Rogers MJ, Xiong X, Ji X, Mönkkönen J, Russell RGG, Blackburn GM, et al. Inhibition of growth of Dictyostelium discoideum amoebae by bisphosphonates is dependent on cellular uptake. Pharmacol Res 1997;14:625-30.
28. Carano A, Teitelbaum SA, Konsek JD, Schlesinger PH, Blair HC. Bisphosphonates directly inhibit the bone resorption activity of isolated avian osteoclasts in vitro. J Clin Invest 1990;85:456-61.
29. Hughes DE, Wright KR, Uy HL, Sasaki A, Yoneda T, Roodman GD, et al. Bisphosphonates promote apoptosis in murine osteoclasts in vitro and in vivo. J Bone Miner Res 1995; 10:1478-87.
30. Selander KS, Mönkkönen J, Karhukorpi E-K, Härkönen JP, Nuniemi R, Janen HK. Characteristics of clodronate-induced apoptosis in osteoclasts and macrophages. Mol Pharmacol 1995;50:1127-38.
31. Sato M, Grasser W. Effects of bisphosphonates on isolated rat osteoclasts as examined by reflected light microscopy. J Bone Miner Res 1990;5:31-40.
32. Miller SC, Jee WSS. The effect of dichloromethylene diphosphonate, a pyrophosphate analog, on bone and bone cell structure in the growing rat. Anat Rec 1979;193:439-62.
33. Plasmans CMT, Jap PHK, Kuijpers W, Slooff TJJH. Influence of a diphosphonate on the cellular aspect of young bone tissue. Calcif Tissue Int 1980;32:247-56.
34. 2MDP) on the calcification and resorption of cartilage and bone in the tibial epiphysis and metaphysis of rats. Calcif Tissue Res 1973; 11:196-214.
35. Rowe DJ, Hausmann E. The alteration in osteoclast morphology by diphosphonates in bone organ culture. Calcif Tissue Res 1976;20:53-60.
36. Rowe DJ, Hays SJ. Inhibition of bone resorption by difluoromethylene diphosphonate in organ culture. Metab Bone Dis Rel Res 1983;5:13-6.
37. Wyllie AH, Kerr JFR, Currie AR. Cell death: the significance of apoptosis. Int Rev Cytol 1980;68:251-306.
38. Rogers MJ, Chilton KM, Coxon F, Lawry J, Suri S, Russell RGG. Bisphosphonates induce apoptosis in mouse macrophage-like cells by a nitric-oxide-independent mechanism. J Bone Miner Res 1996;11:1482-91.
39. Shipman CM, Rogers MJ, Apperley JF, Russell RGG, Croucher PI. Bisphosphonates induce apoptosis in human myeloma cells; a novel antitumor activity. Br J Haematol 1997;98:665-72.
40. Luckman S, Ebetino FH, Russell RGG, Rogers MJ. The structure-activity relationships of bisphosphonates for induction of macrophage apoptosis match those for inhibition of bone resorption [abstract]. J Bone Miner Res 1996;11(S1):S396.
41. Felix R, Fleish H. Increase in alkaline phosphatase activity in calvaria cells cultured with diphosphonates. Biochem J 1979;183:73-81.
42. Morgan DB, Monod A, Russell RGG, Fleisch H. Influence of dichloromethylene diphosphonate and calcitonin on bone resorption, lactate production and phosphatase and pyrophosphatase content of mouse calvaria treated with parathyroid hormone in vitro. Calcif Tissue Res 1973;13:287-94.
43. Fast DE, Felix R, Dowse C, Neumann WF, Fleisch H. The effects of diphosphonates on the growth and glycolysis of connective-tissue cells in culture. Biochem J 1978;172:97-107.
44. 2MDP on the metabolism of mouse calvaria in tissue culture. Proc Kon Ned Akad Wet 1979;C82:43-54.
45. Schmidt A, Rutledge SJ, Endo N, Opas EE, Tanaka H, Wesolowski G, et al. Alendronate inhibition of protein tyrosine phosphatase activity. Proc Natl Acad Sci USA 1995;93:3068-73.
46. Murakami H, Takahashi N, Udagawa N, Tanaka S, Nakamura I, Zhang D, et al. Tiludronate inhibits protein tyrosine phosphatase activity in osteoclasts. Bone 1995;16(S1):114S.
47. Boyce BF, Yoneda T, Lowe C, Soriano P, Mundy GR. Requirement of pp60src expression for osteoclasts to form ruffled borders and resorb bone in mice. J Clin Invest 1992;90:1622-7.
48. Baron R, Neff L, Louvard D, Courtoy PJ. Cell-mediated extracellular acidification and bone resorption: evidence for a low pH in resorbing lacunae and localization of a 100-kD lysosomal membrane protein at the osteoclast ruffled border. J Cell Biol 1985;101:2210-22.
49. +-ATPase type in the ruffled borders of osteoclasts. J Cell Biol 1990;111:1305-11.
50. + ATPase. J Bone Miner Res 1996;11:1498-1507.
51. Zimolo Z, Wesolowski G, Rodan GA. Acid extrusion is induced by osteoclast attachment to bone. J Clin Invest 1995;96:2277-83.
52. Rogers M, Russell RGG, Blackburn GM, Williamson MP, Watts, DJ. Metabolism of halogenated bisphosphonates by the cellular slime mould Dictyostelium discoideum. Biochem Biophys Res Commun 1992;189:414-23.
53. Rogers MJ, Ji X, Russell RGG, Blackburn GM, Williamson MP, Bayless AV, et al. Incorporation of bisphosphonates into adenine nucleotides by amoebae of the cellular slime mould Dictyostelium discoideum. Biochem J 1994;303:303-11.
54. Pelorgeas S, Martin J-B, Satre M. Cytotoxicity of dichloromethane diphosphonate and of 1-hydroxyethane-1,1-diphosphonate in the amoebae of the slime mould Dictyostelium discoideum. Biochem Pharmacol 1992;44:2157-63.
55. Rogers MJ, Brown RJ, Hodkin V, Blackburn GM, Russell RGG, Watts DJ. Bisphosphonates are incorporated into adenine nucleotides by human aminoacyl-tRNA synthetase enzymes. Biochem Biophys Res Commun 1996;224:863-9.
56. Frith JC, Mönkkönen J, Russell RGG, Blackburn GM, Rogers MJ. Clodronate and liposome-encapsulated clodronate can be metabolised to a toxic ATP analogue, adenosine 5′-(6,g-dichloromethylen)triphosphate, by mammalian cells in vitro. J Bone Miner Res 1997;12:1358-67.
57. 14C]1-hydroxyethylidene-1,1-bisphosphonate in cultured calvaria cells. Calcif Tiss Int 1984;36:108-13.
58. Amin D, Cornell SA, Gustafson SK, Needle SJ, Ullrich JW, Bilder GE, et al. Bisphosphonates used for the treatment of bone disorders inhibit squalene synthase and cholesterol biosynthesis. J Lipid Res 1992;33:1657-63.
59. Amin D, Cornell SA, Perrone MH, Bilder GE. 1-hydroxy-3-(methylpentylamino)-propylidene-1,1-bisphosphonic acid as a potent inhibitor of squalene synthase. Drug Res 1996; 46:759-62.
60. Zhang FL, Casey PJ. Protein prenylation: molecular mechanisms and functional consequences. Annu Rev Biochem 1996;65:241-69.
61. Coxon FP, Luckman SP, Russell RGG, Rogers MJ. Bisphosphonates inhibit post-translational prenylation of GTP-binding proteins, including ras and rab6. Bone. 1997;20(Suppl)12S.
62. Luckman SP, Coxon FP, Russell RGG, Rogers MJ. Bisphosphonates and mevastatin induce apoptosis in J774 macrophages by inhibition of the mevalonate pathway. Bone. 1997;20(Suppl)110S.
63. Hughes DE, Luckman SP, Russell RGG, Rogers MJ. Involvement of the mevalonate pathway in osteoclast apoptosis and the mechanism of action of bisphosphonates. Bone. 1997;20(Suppl)114S.
64. Hughes DE, MacDonald BR, Russell RGG, Gowen M. Inhibition of osteoclast-like cell formation by bisphosphonates in long-term cultures of human bone marrow. J Clin Invest 1989;83:1930-5.
65. Boonekamp PM, van der Wee-Pals LJA, van Wijk-van Lennep MLL, Wil Thesing C, Bijvoet OLM. Two modes of action of bisphosphonates on osteoclastic resorption of mineralized matrix. Bone Miner 1986;1:27-39.
66. Löwik CWGM, van der Pluijm G, van der Wee-Pals LJA, Bloys van Treslong-de Groot H, Bijvoet OLM. Migration and phenotypic transformation of osteoclast precursors into mature osteoclasts: the effect of a bisphosphonate. J Bone Miner Res 1988;3:185-92.
67. Guenther HL, Guenther HE, Fleisch H. Effects of 1-hydroxyethane-1,1-diphosphonate and dichloromethanediphosphonate on rabbit articular chondrocytes in culture. Biochem J 1979;184:203-14.
68. D'Souza SM, Orcutt CM, Ibbotson KJ. Inhibitory effects of bisphosphonates on rat osteoblast-like cells: correlation with anti-resorptive potency. J Bone Miner Res 1990;5:S90.
69. Sahni M, Guenther HL, Fleisch H, Collin P, Martin TJ. Bisphosphonates act on rat bone resorption through the mediation of osteoblasts. J Clin Invest 1993;91:2004-11.
70. Niskikawa M, Akatsu T, Katayama Y, Yasutomo Y, Kado S, Kugai N, et al. Bisphosphonates act on osteoblastic cells and inhibit osteoclast formation in mouse marrow cultures. Bone 1996;18:9-14.
71. Vitte C, Fleisch H, Guenther HL. Bisphosphonates induce osteoblasts to secrete an inhibitor of osteoclast-mediated resorption. Endocrinology 1996;137:2324-33.
72. Cecchini MG, Fleisch H. Bisphosphonates in vitro specifically inhibit, among the hematopoietic series, the development of the mouse mononuclear phagocyte lineage. J Bone Miner Res 1990;5:1019-27.
73. Cecchini MG, Felix R, Fleisch H, Cooper PH. Effect of bisphosphonates on proliferation and viability of mouse bone marrow-derived macrophages. J Bone Miner Res 1987;2:135-42.
74. Stevenson PH, Stevenson JR. Cytotoxic and migration inhibitory effects of bisphosphonates on macrophages. Calcif Tissue Int 1986;38:227-33.
75. De Vries E, van der Weij JP, v.d. Veen CJP, van Paassen HC, Jager MJ, Sleeboom HP, et al. In vitro effect of (3-amino-1-hydroxypropylidene)-1,1-bisphosphonic acid (APD) on the function of mononuclear phagocytes in lymphocyte proliferation. Immunology 1982;47:157-63.
76. Chambers TJ. Diphosphonates inhibit bone resorption by macrophages in vitro. J Pathol 1980;132:255-62.
77. 2MDP) on rat macrophage-mediated bone resorption in vitro. J Clin Invest 1982; 70:927-33.
78. Adami S, Bhalla AKR, Dorizzi R, Montesanti F, Rosini S, Salvagno G, et al. The acute-phase response after bisphosphonate administration. Calcif Tissue Int 1987;41:326-31.
79. Schweitzer DH, Oostendorp-van de Ruit M, van der Pluijm G, Lowik CWGM, Papapoulos SE. Interleukin-6 and the acute phase response during treatment of patients with Paget's disease with the nitrogen-containing bisphosphonate dimethylaminohydroxypropylidene bisphosphonate. J Bone Miner Res 1995;10:956-62.
80. Pennanen N, Lapinkoki S, Urtti A, Mönkkönen J. Effect of liposomal and free bisphosphonates on the IL-1β, IL-6 and TNFα secretion from RAW 264 cells in vitro. Pharm Res 1996; 12:916-22.
81. Flora L. Comparative antiinflammatory and bone protective effects of two diphosphonates in adjuvant arthritis. Arthritis Rheum 1979;22:340-6.
82. Francis MD, Flora L, King WR. The effects of disodium ethane-1-hydroxy-1,1-diphosphonate on adjuvant induced arthritis in rats. Calcif Tissue Res 1972;9:109-21.
83. Barbier A, Breliere JC, Remandet B, Roncucci R. Studies on the chronic phase of adjuvant arthritis: effect of SR 41319, a new diphosphonate. Ann Rheum Dis 1986;45:67-74.
84. Van Rooijen N. The liposome-mediated macrophage 'suicide' technique. J Immunol Methods 1989;124:1-6.
85. Makkonen N, Hirvonen M-R, Teräväinen T, Savolainen K, Mönkkönen J. Different effects of three bisphosphonates on nitric oxide production by RAW264 macrophage-like cells in vitro. J Pharmacol Exp Ther 1996;277:1097-102.
86. Huitinga I, van Rooijen N, de Groot CJA, Uitdehaag BMJ, Dijkstra CD. Suppression of experimental allergic encephalomyelitis in Lewis rats after elimination of macrophages. J Exp Med 1990;172:1025-33.
87. Van Lent PLEM, van den Bersselaar L, van den Hoek AEM, van de Ende M, van Rooijen N, van den Berg WB. Reversible depletion of synovial lining cells after intraarticular treatment with liposome encapsulated dichloromethylene diphosphonate. Rheumatol Int 1993;13:21-30.
88. Kinne RW, Schmidt-Weber CB, Hoppe R, Buchner E, Palombo-Kinne E, Nurnberg E, et al. Long-term amelioration of rat adjuvant arthritis following systemic elimination of macrophages by clodronate-containing liposomes. Arthritis Rheum 1995;38:1777-90.
89. Fleisch H. Bisphosphonates, pharmacology and use in the treatment of tumour-induced hypercalcaemic and metastatic bone disease. Drugs 1991;42:919-42.
90. Sasaki A, Boyce BF, Story B, Wright KR, Chapman M, Boyce R, et al. Bisphosphonate risedronate reduces metastatic breast cancer burden in bone in nude mice. Cancer Res 1995;55:3551-7.
91. Van der Pluijm G, Vloedgraven H, van Beek E, van der Wee-Pals L, Löwik C, Papapoulos S. Bisphosphonates inhibit the adhesion of breast cancer cells to bone matrices in vitro. J Clin Invest 1996;98:698-705.