Novel insights into actions of bisphosphonates on bone: Differences in interactions with hydroxyapatite

Bone

Volumn 38, Issue 5, 2006, Pages 617-627

  Nancollas, G H ^a   Tang, R ^a   Phipps, R J ^b   Henneman, Z ^a   Gulde, S ^a   Wu, W ^a   Mangood, A ^a   Russell, R G G ^c   Ebetino, F H ^b  

^a UNIVERSITY AT BUFFALO   (United States)

^b PROCTER AND GAMBLE PHARMACEUTICALS   (United States)

^c UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Bisphosphonates; Bone binding affinity; Hydroxyapatite; Osteoporosis; Risedronate; Zeta potential

Indexed keywords

ALENDRONIC ACID; BISPHOSPHONIC ACID DERIVATIVE; CLODRONIC ACID; ETIDRONIC ACID; HYDROXYAPATITE; IBANDRONIC ACID; RISEDRONIC ACID; ZOLEDRONIC ACID;

ALKALINITY; ARTICLE; BINDING AFFINITY; BONE; CORRELATION ANALYSIS; CRYSTALLIZATION; DISSOLUTION; DRUG ABSORPTION; DRUG ADSORPTION; DRUG EFFECT; DRUG POTENCY; IONIC STRENGTH; OSTEOPOROSIS; PH; PROTON TRANSPORT; TREATMENT DURATION; ZETA POTENTIAL;

BONE AND BONES; BONE DENSITY CONSERVATION AGENTS; CRYSTALLIZATION; DIPHOSPHONATES; DURAPATITE; HUMANS; STRESS, MECHANICAL;

EID: 33646089442     PISSN: 87563282     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bone.2005.05.003     Document Type: Article

References (75)

1. Fleisch H., Russell R.G., and Francis M.D. Diphosphonates inhibit hydroxyapatite dissolution in vitro and bone resorption in tissue culture and in vivo. Science 165 (1969) 1262-1264
2. Fleisch H. Bisphosphonates in bone disease. From the laboratory to the patient. 4th ed. (2000), Academic Press, San Diego
3. Fleisch H., Russell R.G., and Straumann F. Effect of pyrophosphate on hydroxyapatite and its implications in calcium homeostasis. Nature 212 (1966) 901-903
4. Russell R.G., Muhlbauer R.C., Bisaz S., Williams D.A., and 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. 6 (1970) 183-196
5. Fleisch H.A., Russell R.G., Bisaz S., Muhlbauer R.C., and Williams D.A. The inhibitory effect of phosphonates on the formation of calcium phosphate crystals in vitro and on aortic and kidney calcification in vivo. Eur. J. Clin. Invest. 1 (1970) 12-18
6. Benedict J.J., The physical chemistry of the diphosphonates-Its relationship to their medical activity. In: Donath A., Courvoisier B., editors. Symposium Cemo, Centre D'Etude des Maladies Osteoarticulatires de Geneve (IV), 1-19. 1982. Geneva, Editions Medicine et Hygiene. Diphosphonates and Bone;1990:7-9.
7. Sunberg R.J., Ebetino F.H., Mosher C.T., and Roof C.F. Designing drugs for stronger bones. Chemtech 21 (1991) 304-309
8. 2MDP) on the calcification and resorption of cartilage and bone in the tibial epiphysis and metaphysis of rats. Calcif. Tissue Res. 11 (1973) 196-214
9. Rogers M.J. New insights into the molecular mechanisms of action of bisphosphonates. Curr. Pharm. Des. 9 (2003) 2643-2658
10. Russell R.G.G., and Rogers M.J. Bisphosphonates: from the laboratory to the clinic and back again. Bone 25 (1999) 97-106
11. Fogelman I., Bessent R.G., Turner J.G., Citrin D.L., Boyce I.T., and Greig W.R. The use of whole-body retention of Tc-99m diphosphonate in the diagnosis of metabolic bone diseases. J. Nucl. Med. 19 (1978) 270-275
12. Hornby S.B., Evans G.P., Hornby S.L., Pataki A., Glatt M., and Green J.R. Long-term zoledronic acid treatment increases bone structure and mechanical strength of long bones of ovariectomized adult rats. Calcif. Tissue Int. 72 (2003) 519-527
13. Glatt M., Pataki A., Evans G.P., Hornby S.B., and Green J.R. Loss of vertebral bone and mechanical strength in estrogen-deficient rats is prevented by long-term administration of zoledronic acid. Osteoporos Int. 15 (2004) 707-715
14. Reid I.R., Brown J.P., Burckhardt P., Horowitz Z., Richardson P., Trechsel U., et al. Intravenous zoledronic acid in postmenopausal women with low bone mineral density. N. Engl. J. Med. 346 (2002) 653-661
15. Tonino R.P., Meunier P.J., Emkey R., Rodriguez-Portales J.A., Menkes C.J., Wasnich R.D., et al. Skeletal benefits of alendronate: 7-year treatment of postmenopausal osteoporotic women. J. Clin. Endocrinol. Metab. 85 (2000) 3109-3115
16. Stock J.L., Bell N.H., Chesnut III C.H., Ensrud K.E., Genant H.K., Harris S.T., et al. Increments in bone mineral density of the lumbar spine and hip and suppression of bone turnover are maintained after discontinuation of alendronate in postmenopausal women. Am. J. Med. 103 (1997) 291-297
17. Khan S.A., Kanis J.A., Vasikaran S., Kline W.F., Matuszewski B.K., Mccloskey E.V., et al. Elimination and biochemical responses to intravenous alendronate in postmenopausal osteoporosis. J. Bone Miner. Res. 12 (1997) 1700-1707
18. Bone H.G., Hosking D., Devogelaer J.P., Tucci J.R., Emkey R.D., Tonino R.P., et al. Ten years' experience with alendronate for osteoporosis in postmenopausal women. N. Engl. J. Med. 350 (2004) 1189-1199
19. Ebetino F.H., and Dansereau S.M. Bisphosphonate antiresorptive structure-activity relationships. In: Bijvoet O.L.M., Fleisch H.A., Canfield R.E., and Russell R.G.G. (Eds). Bisphosphonate on bones (1995), Elsevier Publishing Co., Amsterdam 139-153
20. Ebetino F.H., Francis M.D., Rogers M.J., and Russell R.G.G. Mechanisms of action of etidronate and other bisphosphonates. Rev. Contemp. Pharmacother. 9 (1998) 233-243
21. Dunford J.E., Thompson K., Coxon F.P., Luckman S.P., Hahn F.M., Poulter C.D., et al. Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. J. Pharmacol. Exp. Ther. 296 (2001) 235-242
22. Ebrahimpour A., and Francis M.D. Bisphosphonate therapy in acute and chronic bone boss: physical chemical considerations in bisphosphonate-related therapies. In: Bijvoet O.L.M., Fleisch H.A., Canfield R.E., and Russell R.G.G. (Eds). Bisphosphonate on bones (1995), Elsevier Publishing Co., Amsterdam 125-136
23. Arends J., Schuthof J., van der Lindwen W.H., Bennema P., and van den Berg P.J. Preparation of pure hydroxyapatite single crystals by hydrothermal recrystallization. J. Cryst. Growth 46 (1979) 213-220
24. Koutsoukos P., Amjad Z., Tomson M.B., and Nancollas G.H. Crystallization of calcium phosphates. A constant composition study. J. Am. Chem. Soc. 102 (1980) 1553-1557
25. Ware B.R. Electrophoretic light scattering. Adv. Colloid Interface Sci. 4 (1974) 1-44
26. Hunter R.J. Zeta potential in colloid science (1981), Academic Press, London
27. Traube I., Schoning I., and Weber L.J. Solubility and surface tension. Ber 60B (1927) 1808-1814
28. Semenchenko V.K. Solubility and surface tension. Uspekhi Khimii 3 (1934) 710-751
29. Bagda E. The relation between surface tension and the solubility parameter in liquids. Farbe Lack 84 (1978) 212-215
30. van Oss C.J., Giese R.F., Li Z., Murphy K., Norris J., Chaudhury M.K., et al. Determination of contact angles and pore sizes of porous media by column and thin layer wicking. J. Adhes. Sci. Technol. 6 (1992) 413-428
31. Washburn E.W. Dynamics of capillary flow. Phys. Rev. 17 (1921) 374-375
32. van Oss C.J. Interfacial forces in aqueous media (1994), Marcel Dekker, Inc, New York
33. Garnier P., Voegel J.C., and Frank R.M. Dissolution kinetics of synthetic hydroxyapatite and human enamel crystals. J. Biol. Buccale 4 (1976) 323-330
34. Christoffersen J., Christoffersen M.R., and Kjaergaard N. The kinetics of dissolution of calcium hydroxyapatite in water at constant pH. J. Cryst. Growth 43 (1978) 501-511
35. Chen W.C., and Nancollas G.H. The kinetics of dissolution of tooth enamel-A constant composition study. J. Dent. Res. 65 (1986) 663-668
36. Paschalis E.P., Wikiel K., and Nancollas G.H. Dual constant composition kinetics characterization of apatitic surfaces. J. Biomed. Mater. Res. 28 (1994) 1411-1418
37. Tang R., Hass M., Wu W., Gulde S., and Nancollas G.H. Constant composition dissolution of mixed phases: II. Selective dissolution of calcium phosphates. J. Colloid. Interface Sci. 260 (2003) 379-384
38. Maniatis C.H., Dalas E., Zafiropoulos T.F., and Koutsoukos P.G. Effect of various bis(sulfonamides) on the crystal growth of hydroxyapatite. Langmuir 7 (1991) 1542-1545
39. Gilman H., and Hukins D.W. Seeded growth of hydroxyapatite in the presence of dissolved albumin. J. Inorg. Biochem. 55 (1994) 21-30
40. Koutsoukos P.G., Amjad Z., and Nancollas G.H. The influence of phytate and phosphonate on the crystal growth of fluorapatite and hydroxyapatite. J. Colloid Interface Sci. 83 (1981) 599-605
41. Koutsopoulos S., Pierri E., Dalas E., Tzavellas N., and Klouras N. Effect of ferricenium salts on the crystal growth of hydroxyapatite in aqueous solution. J. Cryst. Growth 218 (2000) 353-358
42. Koutsopoulos S., and Dalas E. Inhibition of hydroxyapatite formation in aqueous solutions by amino acids with hydrophobic side groups. Langmuir 16 (2000) 6739-6744
43. Koutsopoulos S., Dalas E., Tzavellas N., and Klouras N. Inhibition of hydroxyapatite formation in aqueous solutions by hafnocene dichlorides. J. Chem. Soc., Faraday Trans. 93 (1997) 4183-4186
44. Zieba A., Sethuraman G., Perez F., Nancollas G.H., and Cameron D. Influence of organic phosphonates on hydroxyapatite crystal growth kinetics. Langmuir 12 (1996) 2853-2858
45. Fuierer T.A., LoRe M., Puckett S.A., and Nancollas G.H. A mineralization adsorption and mobility study of hydroxyapatite surfaces in the presence of zinc and magnesium ions. Langmuir 10 (1994) 4721-4725
46. Solomons T.W.G. Fundamentals of organic chemistry. 4th ed. (1994), John Wiley & Sons, Inc, New York 100-102
47. Carrington A., McNab I.P., and Montgomerie C.A. Spectroscopy of the hydrogen molecular ion. J. Phys. B: At., Mol. Opt. Phys. 22 (1989) 3551-3586
48. Masoud M.S., Abou Ali S.A., Ali G.Y., and El-Dessouky M.A. Substituent effects on the dissociation constants and the strength of the hydrogen bond in some azo cresol compounds. J. Chem. Eng. Data 28 (1983) 297-300
49. Wu W., and Nancollas G.H. Determination of interfacial tension from crystallization and dissolution data: a comparison with other methods. Adv. Colloid Interface Sci. 79 (1999) 229-279
50. van Beek E.R., Löwik C.W.G.M., Ebetino F.H., and Papapoulos S.E. Binding and antiresorptive properties of heterocycle-containing bisphosphonate analogs: structure-activity relationships. Bone 23 5 (1998) 437-442
51. van Beek E., Löwik C., Que I., and Papapoulos S. Dissociation of binding and antiresorptive properties of hydroxybisphosphonates by substitution of the hydroxyl with an amino group. J. Bone Miner. Res. 11 (1996) 1492-1497
52. Leu C.T., Luegmayr E., Freedman L.P., and Reszka A.A. Relative binding affinities of bisphosphonates for human bone. Bone 34 Suppl 1 (2004) S62
53. van Beek E., Hoekstra M., van de Ruit M., Löwik C., and Papapoulos S. Structural requirements for bisphosphonate actions in vitro. J. Bone Miner. Res. 9 12 (1994) 1875-1882
54. Lowenstam H.A., and Weiner S. On biomineralization (1989), Oxford Univ. Press, Oxford
55. Heywood B.R., Rajam S.R., Birchall J.D., and Mann S. Crystallochemical recognition at organized inorganic-organic interfaces. Biochem. Soc. Trans. 16 (1988) 824-825
56. Mann S. On the nature of boundary-organized biomineralization (BOB). J. Inorg. Biochem. 28 (1986) 363-371
57. Sahin O., and Bulutcu A.N. The effect of surface potential on the growth and dissolution rate dispersion of boric acid. Cryst. Res. Technol. 38 (2003) 56-62
58. Vdovic N., and Kralj D. Electrokinetic properties of spontaneously precipitated calcium carbonate polymorphs: the influence of organic substances. Colloids Surf., A Physicochem. Eng. Asp. 161 (2000) 499-505
59. Cao L.C., Deng G., Boeve E.R., de Bruijn W.C., de Water R., Verkoelen D.F., et al. Zeta potential measurement and particle size analysis for a better understanding of urinary inhibitors of calcium oxalate crystallization. Scanning Microsc. 10 (1996) 401-414
60. Nancollas G.H., and Wu W. The surface, interfacial and electrokinetic properties of biominerals. J. Dispersion Sci. Technol. 19 (1998) 723-738
61. Neilsen A.E. Kinetics of precipitation (1964), The Macmillan Co, New York
62. Cook S.D., Thomas K.A., and Kay J.F. Experimental coating defects in hydroxylapatite-coated implants. Clin. Orthop. 265 (1991) 280-290
63. Wu W., and Nancollas G.H. Interfacial free energies and crystallization in aqueous media. J. Colloid Interface Sci. 182 (1996) 365-373
64. Wu W., and Nancollas G.H. The relationship between surface free-energy and kinetics in the mineralization and demineralization of dental hard tissue. Adv. Dent. Res. 11 (1997) 566-575
65. Wu W., Gerard D.E., and Nancollas G.H. Nucleation at surfaces: the importance of interfacial energy. J. Am. Soc. Nephrol. 10 Suppl 14 (1999) S355-S358
66. Liu Y., Wu W., Sethuraman G., and Nancollas G.H. Intergrowth of calcium phosphates: an interfacial energy approach. J. Cryst. Growth 174 (1997) 386-392
67. Mitchell D.Y., Barr W.H., Eusebio R.A., Stevens K.A., Duke F.P., Russell D.A., et al. Risedronate pharmacokinetics and intra- and inter-subject variability upon single-dose intravenous and oral administration. Pharm. Res. 18 (2001) 166-170
68. Chen T., Berenson J., Vescio R., Swift R., Gilchick A., Goodin S., et al. Pharmacokinetics and pharmacodynamics of zoledronic acid in cancer patients with bone metastases. J. Clin. Pharmacol. 42 (2002) 1228-1236
69. Christiansen C., Phipps R., Burgio D., Sun L., Russell D., Keck B., et al. Comparison of risedronate and alendronate pharmacokinetics at clinical doses. Osteoporos Int. 14 Suppl 7 (2003) S38
70. Francis M.D., Davis T.L., Benedict J.J., and Tofe A.J. Diphosphonates: in vitro adsorption and desorption studies on hydroxyapatite and diffusion in bone. In: Caniggia A. (Ed). Etidronate, proceedings of the 1st international symposium on diphosphonate in therapy. Rome, March 1979 (1980), Instituto Genetili, Via Mazzini, Pisa, Italy 33-50
71. Ravn P., Weiss S.R., Rodriguez-Portales J.A., McClung M.R., Wasnich R.D., Gilchrist N.L., et al. Alendronate in early postmenopausal women: effects on bone mass during long-term treatment and after withdrawal. J. Clin. Endocrinol. Metab. 85 (2000) 1492-1497
72. Fairney A., Kyd P., Thomas E., and Wilson J. The use of cyclical etidronate in osteoporosis: changes after completion of 3 years treatment. Br. J. Rheumatol. 37 (1998) 51-56
73. Watts N., Olszynski W.P., McKeever C.D., Grauer A., and Chines A. Treatment discontinuation effects on bone turnover and BMD with risedronate. Bone 34 Suppl 1 (2004) S99
74. Black D.M., Greenspan S.L., Ensrud K.E., Palermo L., McGowan J.A., Lang T.F., et al. The effects of parathyroid hormone and alendronate alone or in combination in postmenopausal osteoporosis. N. Engl. J. Med. 349 (2003) 1207-1215
75. Eastell R., Barton I., Hannon R.A., Chines A., Garnero P., and Delmas P.D. Relationship of early changes in bone resorption to the reduction in fracture risk with risedronate. J. Bone Miner. Res. 18 (2003) 1051-1056