Farnesol and geranylgeraniol prevent activation of caspases by aminobisphosphonates: Biochemical evidence for two distinct pharmacological classes of bisphosphonate drugs

Molecular Pharmacology

Volumn 56, Issue 1, 1999, Pages 131-140

  Benford, Helena L ^a   Frith, Julie C ^a,b   Auriola, Seppo ^c   Mönkkönen, Jukka ^c   Rogers, Michael J ^a  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

^c UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ALENDRONIC ACID; BISPHOSPHONIC ACID DERIVATIVE; CASPASE; CLODRONIC ACID; ETIDRONIC ACID; FARNESOL; GERANYLGERANIOL; GUANINE NUCLEOTIDE BINDING PROTEIN; IBANDRONIC ACID; ISOPRENOID; MEVALONIC ACID; PAMIDRONIC ACID; TILUDRONIC ACID;

ANIMAL CELL; APOPTOSIS; ARTICLE; CONTROLLED STUDY; DRUG INHIBITION; DRUG MECHANISM; ENZYME ACTIVATION; MASS SPECTROMETRY; NONHUMAN; OSTEOLYSIS; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN PROCESSING;

EID: 0032996153     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.56.1.131     Document Type: Article

References (40)

1. Adami S, Bhalla AK, Dorizzi R, Montesanti F, Rosini S, Salvagno G and Lo Cascio V (1987) The acute-phase response after bisphosphonate administration. Calcif Tissue Int 41:326-331.
2. Auriola S, Frith J, Rogers MJ, Koivuniemi A and Mönkkönen J (1997) Identification of adenine nucleotide-containing metabolites of bisphosphonate drugs using ion-pair liquid chromatography-electrospray mass spectrometry. J Chromatogr B 704: 187-195.
3. Boonekamp PM, van der Wee-Pals LJ, van Wijk-van Lennep MM, Thesing CW and Bijvoet OLM (1986) Two modes of action of bisphosphonates on osteoclastic resorption of mineralized matrix. Bone Miner 1:27-39.
4. Boonekamp PM, Lowik CW, van der Wee-Pals LJ, van Wijk-van Lennep ML and Bijvoet OLM (1987) Enhancement of the inhibitory action of APD on the transformation of osteoclast precursors into resorbing cells after dimethylation of the amino group. Bone Miner 2:29-42.
5. Cohen GM (1997) Caspases: The executioners of apoptosis. Biochem J 326:1-16.
6. Coxon FP, Benford HL, Russell RGG and Rogers MJ (1998) Protein synthesis is required for caspase activation and induction of apoptosis by bisphosphonate drugs. Mol Pharmacol 54:631-638.
7. Crick DC, Andres DA and Waechter CJ (1997) Novel salvage pathway utilizing farnesol and geranylgeraniol for protein isoprenylation. Biochem Biophys Res Commun 237:483-487.
8. Ebetino FH, Francis MD, Rogers MJ and Russell RGG (1998) Mechanisms of action of etidronate and other bisphosphonates. Rev Contemp Pharmacother 9:233-243.
9. Flanagan AM and Chambers TJ (1991) Inhibition of bone resorption by bisphosphonates: Interactions between bisphosphonates, osteoclasts, and bone. Calcif Tissue Int 49:407-415.
10. Fleisch H, Russell RGG and Francis MD (1969) Diphosphonates inhibit hydroxyapatite dissolution in vitro and bone resorption in tissue culture and in vivo. Science (Wash DC) 165:1262-1264.
11. Fleisch H (1991) Bisphosphonates. Pharmacology and use in the treatment of tumour-induced hypercalcaemic and metastatic bone disease. Drugs 42:919-944.
12. Fleisch H (1998) Bisphosphonates: Mechanisms of action. Endocrine Rev 19:80-100.
13. Frith JC, Mönkkönen J, Blackburn GM, Russell RGG and Rogers MJ (1997) Clodronate and liposome-encapsulated clodronate are metabolized to a toxic ATP analog, adenosine 5′-(β, γ-dichloromethylene) triphosphate, by mammalian cells in vitro. J Bone Miner Res 12:1358-1367.
14. Geddes AD, D'Souza SM, Ebetino FH and Ibbotson KJ (1994) Bisphosphonates: Structure-activity relationships and therapeutic implications, in Bone and Mineral Research (Heersche JNM, Kanis JA eds) pp 265-306, Elsevier Science BV, Amsterdam.
15. Hughes DE, Wright KR, Uy HL, Sasaki A, Yoneda T, Roodman GD, Mundy GR and Boyce BF (1995) Bisphosphonates promote apoptosis in marine osteoclasts in vitro and in vivo. J Bone Miner Res 10:1478-1487.
16. Inayat-Hussain SH, Couet C, Cohen GM and Cain K (1997) Processing/activation of CPP32-like proteases is involved in transforming growth factor β1-induced apoptosis in rat hepatocytes. Hepalology 25:1516-1526.
17. Lowik CW, Van der Pluijm G, van der Wee-Pals LJ, Van Treslong-De Groot HB and Bijvoet OLM (1988) Migration and phenotypic transformation of osteoclast pre-cursors into mature osteoclasts: The effect of a bisphosphonate. J Bone Miner Res 3:185-192.
18. Luckman SP, Hughes DE, Coxon FP, Russell RGG and Rogers MJ (1998) Nitrogen-containing bisphosphonates inhibit the mevalonate pathway and prevent post-translational prenylation of GTP-binding proteins, including Ras. J Bone Miner Res 13:581-589.
19. Makkonen N, Hirvonen MR, Teravainen T, Savolainen K and Mönkkönen J (1996) Different effects of three bisphosphonates on nitric oxide production by RAW 264 macrophage-like cells in vitro. J Pharmacol Exp Ther 277:1097-1102.
20. Mönkkönen J, Taskinen M, Auriola SO and Urtti A (1994) Growth inhibition of macrophage-like and other cell types by liposome-encapsulated, calcium-bound, and free bisphosphonates in vitro. J Drug Targ 2:299-308.
21. Mundy GR (1995) Bone Remodeling and Its Disorders, Martin Dunitz, London.
22. Murakami H, Takahashi N, Sasaki T, Udagawa N, Tanaka S, Nakamura I, Zhang D, Barbier A and Suda T (1995) A possible mechanism of the specific action of bisphosphonates on osteoclasts: Tiludronate preferentially affects polarized osteoclasts having ruffled borders. Bone 17:137-144.
23. Nakamura M, Ando T, Abe M, Kumagai K and Endo Y (1996) Contrast between effects of aminobisphosphonates and non-aminobisphosphonates on collagen-induced arthritis in mice. Br J Pharmacol 119:205-212.
24. Olkkonen VM and Stenmark H (1997) Role of Rab GTPases in membrane traffic. Int Rev Cytol 176:1-85.
25. Pennanen N, Lapinjoki S, Urtti A and Mönkkönen J (1995) Effect of liposomal and free bisphosphonates on the IL-1β, IL-6 and TNF α secretion from RAW 264 cells in vitro. Pharm Res 12:916-922.
26. 2MDP) on rat macrophage-mediated bone resorption in vitro. J Clin Invest 70:927-933.
27. Reszka AA, Masarachia PJ and Rodan GA (1998) Nitrogen-containing bisphosphonates act directly on the osteoclast: Induction of Mst1 kinase cleavage, mimicked by Lovastatin, is blocked by geranylgeraniol and caspase inhibitors (Abstract). Bone 23:S404.
28. Ridley AJ, Paterson HF, Johnston CL, Diekmann D and Hall A (1992) The small GTP-binding protein rac regulates growth factor-induced membrane ruffling. Cell 70:401-410.
29. Rogers MJ, Russell RGG, Blackburn GM, Williamson MP and Watts DJ (1992) Metabolism of halogenated bisphosphonates by the cellular slime mould Dictyostelium discoideum. Biochem Biophys Res Commun 189:414-423.
30. Rogers MJ, Ji X, Russell RGG, Blackburn GM, Williamson MP, Bayless AV, Ebetino FH and Watts DJ (1994a) Incorporation of bisphosphonates into adenine nucleotides by amoebae of the cellular slime mould Dictyostelium discoideum. Biochem J 303:303-311.
31. Rogers MJ, Watts DJ, Russell RGG, Ji X, Xiong X, Blackburn GM, Bayless AV and Ebetino FH (1994b) Inhibitory effects of bisphosphonates on growth of amoebae of the cellular slime mold Dictyostelium discoideum. J Bone Miner Res 9:1029-1039.
32. Rogers MJ, Xiong X, Brown RJ, Watts DJ, Russell RGG, Bayless AV and Ebetino FH (1995) Structure-activity relationships of new heterocycle-containing bisphosphonates as inhibitors of bone resorption and as inhibitors of growth of Dictyostelium discoideum amoebae. Mol Pharmacol 47:398-402.
33. Rogers MJ, Brown RJ, Hodkin V, Blackburn GM, Russell RGG and Watts DJ (1996a) Bisphosphonates are incorporated into adenine nucleotides by human aminoacyl-tRNA synthetase enzymes. Biochem Biophys Res Commun 224:863-869.
34. Rogers MJ, Chilton KM, Coxon FP, Lawry J, Smith MO, Suri S and Russell RGG (1996b) Bisphosphonates induce apoptosis in mouse macrophage-like cells in vitro by a nitric oxide-independent mechanism. J Bone Miner Res 11:1482-1491.
35. Sahni M, Guenther HL, Fleisch H, Collin P and Martin TJ (1993) Bisphosphonates act on rat bone resorption through the mediation of osteoblasts. J Clin Invest 91:2004-2011.
36. Sato M, Grasser W, Endo N, Akins R, Simmons H, Thompson DD, Golub E and Rodan GA (1991) Bisphosphonate action. Alendronate localization in rat bone and effects on osteoclast ultrastructure. J Clin Invest 88:2095-2105.
37. Sauty A, Pecherstorfer M, Zimmer-Roth I, Fioroni P, Juillerat L, Markert M, Ludwig H, Leuenberger P, Burckhardt P and Thiebaud D (1996) Interleukin-6 and tumor necrosis factor α levels after bisphosphonates treatment in vitro and in patients with malignancy. Bone 18:133-139.
38. Smith R, Russell RGG and Bishop M (1971) Diphosphonates and Paget's disease of bone. Lancet 1:945-947.
39. van Beek E, Hoekstra M, van de Ruit M, Lowik C and Papapoulos S (1994) Structural requirements for bisphosphonate actions in vitro. J Bone Miner Res 9:1875-1882.
40. Zhang D, Udagawa N, Nakamura I, Murakami H, Saito S, Yamasaki K, Shibasaki Y, Morii N, Narumiya S, Takahashi N, (1995) The small GTP-binding protein, rho p21, is involved in bone resorption by regulating cytoskeletal organization in osteoclasts. J Cell Sci 108:2285-2292.