Bisphosphonates: mechanisms of action

Bibliography

• FLEISCH H: Bisphosphonates in Bone Disease. From the Laboratory to the Patient. Academic Press New York, USA (2000).
   Google Scholar
• FLEISCH H: Bisphosphonates: mechanisms of action. Endocr. Rev. (1998) 19:80–100.
   PubMed Web of Science ®Google Scholar
• RODAN GA: Mechanisms of action of bisphosphonates. Ann. Rev. Pharmacol Toxicol (1998) 38:375–388.
   PubMed Web of Science ®Google Scholar
• RUSSELL RGG, CROUCHER PI, ROGERS MJ: Bisphosphonates: pharmacology, mechanisms of action and clinical uses. Osteoporos. Int. (1999) Suppl. 2:S66–80.
   Google Scholar
• MENSCHUTKIN N: Ueber die Einwirkung des Chloracetyls auf phosphorige Same. Ann. Chem. Pharm. (1865) 133:317–320.
   Google Scholar
• FLEISCH H, RUSSELL RGG, BISAZ S et al.: The influence of pyrophsophate analogues (diphosphonates) on the precipitation and dissolution of calcium phosphate in vitro and in vivo. Calcif Tissue Res. (1968) 2 (Suppl):10-10a.
   Google Scholar
• FRANCIS MD, RUSSELL RGG, FLEISCH H: Diphosphonates inhibit formation of calcium phosphate crystals in vitro and pathological calcification in vivo. Science (1969) 165:1264–1266.
   PubMed Web of Science ®Google Scholar
• FLEISCH H, RUSSELL RGG, FRANCIS MD: Diphosphonates inhibit hydroxyapatite dissolution in vitro and bone resorption in tissue culture and in vivo. Science (1969) 165:1262–1264.
   PubMed Web of Science ®Google Scholar
• JUNG A, BISAZ S, FLEISCH H: The binding of pyrophosphate and two diphosphonates by hydroxyapatite crystals. Calcif Tissue Res. (1973) 11:269–80.
   PubMedGoogle Scholar
• REYNOLDS JJ, MINKIN C, MORGAN DB et al.: The effect of two diphosphonates on the resorption of mouse calvaria in vitro. Calcif Tissue Res. (1972) 10:302–313.
   PubMedGoogle Scholar
• SCHENK R, MERZ WA, MOHLBAUER R et al.: Effect of ethane-1-hydroxy-1,1-diphosphonate (EHDP) and dichloromethylene diphosphonate (C12MDP) on the calcification and resorption of cartilage and bone in the tibial epiphysis and metaphysis of rats. Calcif Tissue Res. (1973) 11:196–214.
   PubMedGoogle Scholar
• GASSER AB, MORGAN DB, FLEISCH HA et al: The influence of two diphosphonates on calcium metabolism in the rat. Clin. Sci. (1972) 43:31–45.
   PubMed Web of Science ®Google Scholar
• RUSSELL RGG, MOHLBAUER RC, BISAZ S et al.: 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.
   PubMedGoogle Scholar
• JUNG A, MERMILLOD B, BARRAS C et al.: Inhibition by two diphosphonates of bone lysis in tumor conditioned media. Cancer Res. (1981) 41:3233–3237.
   PubMed Web of Science ®Google Scholar
• MARTODAM RR, THORNTON KS, SICA DA et al.: The effects of dichloromethylene diphosphonate on hypercalcemia and other parameters of the humoral hypercalcemia of malignancy in the rat Leydig cell tumor. Calcif Tissue Int. (1983) 35:512–519.
   PubMed Web of Science ®Google Scholar
• SASAKI A, BOYCE BF, STORY B et al.: Bisphosphonate risedronate reduces metastatic human breast cancer burden in bone in nude mice. Cancer Res. (1995) 55:3551–3557.
   PubMed Web of Science ®Google Scholar
• MOHLBAUER RC, RUSSELL RGG, WILLIAMS DA et al.: The effects of diphosphonates, polyphosphates and calcitonin on 'immobilisation osteoporosis' in rats. Europ. J. Clin. Invest. (1971) 1:336–344.
   PubMed Web of Science ®Google Scholar
• BALENA R, TOOLAN BC, SHEA M et al.: The effects of 2-year treatment with the aminobisphosphonate alendronate on bone metabolism, bone histomorphometty, and bone strength in ovariectomized nonhuman primates. J. Clin. Invest. (1993) 92:2577–2586.
   PubMed Web of Science ®Google Scholar
• SHOJI K, HORIUCHI H, SHINODA H: Inhibitory effects of a bisphosphonate (risedronate) on experimental periodontitis in rats. J. Periodont. Res. (1995) 30:77–84.
   Web of Science ®Google Scholar
• MASARACHIA P, WEINREB M, BALENA R et al.: Comparison of the distribution of 3H-alendronate and 3H-etidronate in rat and mouse bones. Bone (1996) 19:281–290.
   PubMed Web of Science ®Google Scholar
• HUGHES DE, WRIGHT KR, UY HL et al.: Bisphosphonates promote apoptosis in murine osteoclasts in vitro and in vivo. J. Bone Miner. Res. (1995) 10:1478–1487.
   PubMed Web of Science ®Google Scholar
• SATO M, GRASSER W, ENDO N et al.: Bisphosponate action. Alendronate 1378Expert Op/n. Ther Patents (2001) 11(9) localization in rat bone and effects on osteoclast ultrastructure. J. Clin. Invest. (1991) 88:2095–2105.
   Google Scholar
• FAST DK, FELIX R, DOWSE C et al: The effects of diphosphonates on the growth and glycolysis of connective-tissue cells in culture. Biochem. J. (1978) 172:97–107.
   PubMed Web of Science ®Google Scholar
• DAVID P, NGUYEN, H, BARBIER, A et al.: The bisphosphonate tiludronate is a potent inhibitor of the osteoclast vacuolar H.-ATPase. J Bone Miner. Res. (1996) 11:1498–1507.
   PubMed Web of Science ®Google Scholar
• FELIX R, RUSSELL RGG, FLEISCH H: The effect of several diphosphonates on acid phosphohydrolases and other lysosomal enzymes. Biochim. Biophys. Acta (1976) 429:429–438.
   PubMed Web of Science ®Google Scholar
• OHYA K, YAMADA S, FELIX R et al: Effect of bisphosphonates on prostaglandin synthesis by rat bone cells and mouse calvaria in culture. Clin. Sci. (1985) 9:403–411.
   Google Scholar
• SCHMIDT A, RUTLEDGE SJ, ENDO N et al.: Protein-tyrosine phosphatase activity regulates osteoclast formation and function: inhibition by alendronate. Proc. Natl Acad. Sci. USA (1996) 93:3068–3073.
   PubMed Web of Science ®Google Scholar
• TERONEN O, HEIKKIIÄ P, KONITINEN YT et al: MMP inhibition and downregulation by bisphosphonates. Ann. NY Acad. Sci. (1999) 878:453–465.
   PubMed Web of Science ®Google Scholar
• LUCKMAN SP, COXON FP, EBETINO FH et al.: Heterocycle-containing bisphosphonates cause apoptosis and inhibit bone resorption by preventing protein prenylation: evidence from structure-activity relationships in J774 macrophages. J. Bone Miner. Res. (1998) 13:1668–1678.
   PubMed Web of Science ®Google Scholar
• LUCKMAN SP, HUGHES DE, COXON FP et al.: Nitrogen-containing bisphosphonates inhibit the mevalonate pathway and prevent post-translational prenylation of GTP-binding proteins, including Ras. J. Bone Miner. Res. (1998) 13:581–589.
   PubMed Web of Science ®Google Scholar
• VAN BEEK E, PIETERMAN E, COHEN Let al.: Farnesyl pyrophosphate synthase is the molecular target of nitrogen-containing bisphosphonates. Biochem. Biophys. Res. Comm. (1999) 264:108–11.
   Google Scholar
• BERGSTROM JD, BOSTEDOR RG, MASARACHIA PJ: Alendronate is a specific, nanomolar inhibitor of farnesyl diphosphate synthase. Arch. Biochem. Biophys. (2000) 373:231–241.
   PubMed Web of Science ®Google Scholar
• RESZKA AA, HALASY NAGY JM, Masarachia, PJ et al.: Bisphosphonates act directly on the osteoclast to induce caspase cleavage of Mst1 kinase during apoptosis. A link between inhibition of the mevalonate pathway and regulation of an apoptosis promoting kinase. J. Biol. Chem. (1999) 274:34967–34973.
   Google Scholar
• COXON FP, HELFRICH MH, VAN 'T HOF RJ et al.: Protein geranylgeranylation is required for osteoclast formation, function, and survival: inhibition by bisphosphonates and GGTI-298. J. Bone Miner. Res. (2000) 15:1467–1476.
   Google Scholar
• FISHER JE, ROGERS MJ, HALASY JM: Alendronate mechanism of action: gemylgeraniol, an intermediate in the mevalonate pathway, prevents inhibition of osteoclast formation, bone resorption, and kinase activation in vitro. Proc. Natl. Acad. Sci. USA (1999) 96:133–138.
   PubMed Web of Science ®Google Scholar
• VAN BEEK E, LOWIK C, VAN DER PLUIJM G et al.: The role of geranylgeranylation in bone resorption and its suppression by bisphosphonates in fetal bone explains in vitro: A clue to the mechanism of action of nitrogen-containing bisphosphonates. J. Bone Miner. Res. (1999) 14:722–729.
   Google Scholar
• MARTIN MB, ARNOLD W, HEATH III HT et al.: Nitrogen-containing bisphosphonates as carbocation transition state analogs for isoprenoid biosynthesis. Biochem. Biophys. Res. Comm. (1999) 263:754–758.
   Google Scholar
• DUNFORD JE, THOMPSON K, COXON FP et al.: Strucuture-activity relationships for inhibition of farnesy diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. J. Pharmacol. Exper. Ther. (2001) 296:235–342.
   PubMed Web of Science ®Google Scholar
• ROGERS MJ, BROWN RG, HODKIN A et al.: Bisphosphonates are incorporated into adenine nucleotides by human aminoacyl-tRNA synthetase enzymes. Biochem. Biophys. Res. Commun. (1996) 224:863–869.
   PubMed Web of Science ®Google Scholar
• FRITH JC, MONKKONEN J, BLACKBURN GM et al.: Clodronate and liposome-encapsulated clodronate are metabolised to a toxic ATP analog, adenosine5'(3,y-dichloromethylene)-triphosphate, by mammalian cells in vitro. J. Bone Miner. Res. (1997) 12:1358–1367.
   PubMed Web of Science ®Google Scholar
• FLEISCH H, RUSSELL RGG, BISAZ Set al.: 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. (1970) 1:12–18.
   Google Scholar
• GUENTHER HL, GUENTHER HE, FLEISCH H: The effects of 1-hydroxyethane-1,1-diphosphonate and dichloromethanediphosphonate on collagen synthesis by rabbit articular chondrocytes and rat bone cells. Biochem. J. (1981) 196:293–301.
   PubMed Web of Science ®Google Scholar
• TSUCHIMOTO M, AZUMA Y, HIGUCHI O: Alendronate modulates osteogenesis of human osteoblastic cells in vitro. Jpn. J. Pharmacol. (1994) 66:25–33.
   PubMedGoogle Scholar
• GIULIANI N, PEDRAZZONI M, NEGRI G et al.: Bisphosphonates stimulate formation of osteoblast precursors and mineralized nodules in murine and human bone marrow cultures in vitro and promote early osteoblastogenesis in young and aged mice in vivo. Bone (1998) 22:455–461.
   PubMed Web of Science ®Google Scholar
• REINHOLZ GG, GETZ B, PEDERSON L et al.: Bisphosphonates directly regulate cell proliferation, differentiation, and gene expression in human osteoblasts. Cancer Res. (2000) 60:6001–6007.
   PubMed Web of Science ®Google Scholar
• PLOTKIN LI, WEINSTEIN RS, PARFITT AM. et al.: Prevention of osteocyte and osteoblast apoptosis by bisphosphonates and calcitonin. J. Clin. Invest. (1999) 104:1363–1374.
   Google Scholar
• VAN DER PLUIJM G, VLOEDRAVEN H, VAN BEEK E et al.: Bisphosphonates inhibit the adhesion of breast cancer cells to bone matrices in vitro. J. Clin. Invest. (1996) 98:698–705.
   Google Scholar
• BOISSIER S, MAGNETTO S, FRAPPART Let al: Bisphosphonates inhibit prostate and breast carcinoma cell adhesion to unmineralized and mineralized bone extracellular matrices. Cancer Res. (1997) 57:3890–4389.
   PubMed Web of Science ®Google Scholar
• SHIPMAN CM, ROGERS MJ, APPERLEY JF et al.: Biphosphonates induce apoptosis in human myeloma cell lines: a novel anti-tumour activity. Br. J. Haematol (1997) 98:665–672.
   PubMed Web of Science ®Google Scholar
• SHIPMAN CM, CROUCHER PI, RUSSELL RGG et al.: The bisphosphonate incadronate (YM175) causes apoptosis of human myeloma cells in vitro by inhibiting the mevalonate pathway. Cancer Res. (1998) 58:5294–5297.
   PubMed Web of Science ®Google Scholar
• FRANCIS MD, HOVANCIK K, BOYCE RW: NE-58095: a diphosphonate which prevents bone erosion and preserves joint architecture in experimental arthritis. Int. J. Tissue React. (1989) 11:239-252. 1379 Expert Opin. Ther Patents (2001) 11(9)
   Google Scholar
• DUNN CJ, GALINET LA, WU H et al.: Demonstration of novel anti-arthritic and anti-inflammatory effects of diphosphonates. J. Pharmacol. Exp. Ther. (1993) 266:1691–1698.
   PubMed Web of Science ®Google Scholar
• OSTERMAN T, KIPPO K, LAUREN Let al.: Effect of clodronate on established adjuvant arthritis. Rheumatol Int. (1994) 14:139–147.
   Google Scholar
• BARBERA P, BLOM A, VAN LENT PLEM et al.: Synovial macrophage depletion with clodronate-containing liposomes in rheumatoid arthritis. Arthritis Rheum. (2000) 43:1951–1959.
   Google Scholar
• STURTZ G, COUTHON H, FABULET O et al: Synthesis of gem-bisphosphonic methotrexate conjugates and their biological response towards Walker's osteosarcoma. Eur. J. Med. Chem. (1993) 28:899–903.
   Web of Science ®Google Scholar
• UN JH: Bisphosphonates: a review of theirpharmacokinetic properties. Bone (1996) 18:75–85.
   PubMed Web of Science ®Google Scholar
• PAPAPOULOS SE: Pharmacodynamics of bisphosphonates in man; implications for treatment. IN: Bisphosphonates on Bones. Bijvoet OLM, Fleisch HA, Canfield RE, Russell RGG (Eds) Elsevier, Amsterdam (1995) :231–263.
   Google Scholar
• PORRAS AG, HOLLAND SD, GERTZ BJ: Pharmacokinetics of alendronate. Clin. Pharmacoki net. (1999) 36:315–328.
   PubMed Web of Science ®Google Scholar
• BOULENC X, MARTI E, JOYEUX H et al.: Importance of the paracellular pathway for the transport of new bisphosphonate using the human CACO-2 monolayers model. Biochem. Pharmacol (1993) 46(9) :1591–1600.
   PubMed Web of Science ®Google Scholar
• TROEHLER U, BONJOUR JP, FLEISCH H: Renal secretion of diphosphonates in rats. Kidney Int. (1975) 8:6–13.
   PubMed Web of Science ®Google Scholar
• EZRA A, GOLOMB G: Administration routes and delivery systems of bisphosphonates for the treatment of bone resorption. Adv. Drug Deliv. Rev. (2000) 42:175–195.
   PubMed Web of Science ®Google Scholar
• DE GROEN PC, LUBBE DF, HIRSCH LJ et al..: Esophagitis associated with the use of alendronate. N Engl J. Med. (1996) 355:1016–1021.
   Web of Science ®Google Scholar
• PETER CP, KINDT MV, MAJKA JA: Comparative study of potential for bisphosphonates to damage gastric mucosa of rats. Digest. Dis. Sci. (1998) 43:1009–1015.
   PubMed Web of Science ®Google Scholar
• RESZKA AA, HALASY-NAGY J, RODAN GA: Nitrogen-bisphosphonates block retinoblastoma phosphorylation and cell growth by inhibiting the cholesterol biosynthetic pathway in a keratinocyte model for esophageal irritation. MoL Pharmacol (2001) 59:193–202.
   PubMed Web of Science ®Google Scholar
• FLORAL, HASSING GS, PARFITT AM et al.: Comparative skeletal effects of two diphosphonates in dogs. Metab. Bone Dis. Rel. Res. (1980) 2:389–407.
   Google Scholar
• MASHIBA T, TURNER CH, HIRANO T et al.: Effects of suppressed bone turnover by bisphosphonates on microdamnage accumulation and biomechanical properties in clinically relevant skeletal sites. Bone 28:524–531.
   Google Scholar
• ADAMI S, BHALLA AK, DORIZZI R et al.: The acute-phase response after bisphosphonate administration. Calcif Tissue Int. (1987) 41:326–331.
   PubMed Web of Science ®Google Scholar
• SCHNITZER T, BONE HG, CREPALDI G et al.: Therapeutic equivalence of alendronate 70 mg once-weekly and alendronate 10 mg daily in the treatment of osteoporosis. Aging Clin. E. Res. (2000) 12:1–12.
   Web of Science ®Google Scholar
• TONINO RP, MEUNIER PJ, EMKEY R et al.: Skeletal benefits of alendronate: 7-year treatment of postmenopausal osteoporotic women. J. Clin Endocrinol Metab. (2000) 85:3109–3115
   PubMed Web of Science ®Google Scholar
• GARNERO P, SHIH WJ, GINEYTS E et al.: Comparison of new biochemical markers of bone turnover in late postmenopausal osteoporotic women in response to alendronate treatment. J. Clin. Endocrinol Metab. (1994) 79:1693–1700
   PubMed Web of Science ®Google Scholar