Synthesis and in vivo bioactivity of lipophilic alendronate derivatives against osteoporosis

References

• Abelson A, Ringe JD, Gold DT, Lange JL, Thomas T. (2010). Longitudinal change in clinical fracture incidence after initiation of bisphosphonates. Osteoporos Int 21:1021–1029.
   PubMed Web of Science ®Google Scholar
• Adachi JD, Adami S, Kulkarni PM, Wong M, Stock JL. (2005). Similar proportions of women lose bone mineral density with raloxifene or alendronate treatment. J Clin Densitom 8:273–277.
   PubMed Web of Science ®Google Scholar
• Berry SD, Kiel DP, Donaldson MG, Cummings SR, Kanis JA, Johansson H, Samelson EJ. (2010). Application of the National Osteoporosis Foundation Guidelines to postmenopausal women and men: the Framingham Osteoporosis Study. Osteoporos Int 21:53–60.
   PubMed Web of Science ®Google Scholar
• Blouin J, Dragomir A, Moride Y, Ste-Marie LG, Fernandes JC, Perreault S. (2008). Impact of noncompliance with alendronate and risedronate on the incidence of nonvertebral osteoporotic fractures in elderly women. Br J Clin Pharmacol 66:117–127.
   PubMed Web of Science ®Google Scholar
• Choi A, Gang H, Chun I, Gwak H. (2008). The effects of fatty acids in propylene glycol on the percutaneous absorption of alendronate across the excised hairless mouse skin. Int J Pharm 357:126–131.
   PubMed Web of Science ®Google Scholar
• Coxon FP, Thompson K, Rogers MJ. (2006). Recent advances in understanding the mechanism of action of bisphosphonates. Curr Opin Pharmacol 6:307–312.
   PubMed Web of Science ®Google Scholar
• Dunford JE, Kavanagh K, Oppermann U, Ebetino FH, Russell RGG, Rogers MJ. (2006). Investigations into the kinetic mechanism of inhibition of farnesyl diphosphate synthase by nitrogen containing bisphosphonates. Bone 38:47–48.
   Web of Science ®Google Scholar
• Ebetino FH, Rozé CN, McKenna CE. (2005). Molecular interactions of nitrogen-containing bisphosphonates within farnesyl diphosphate synthase. J Organometal Chem 690:2679–2687.
   Web of Science ®Google Scholar
• Ezra A, Golomb G. (2000). Administration routes and delivery systems of bisphosphonates for the treatment of bone resorption. Adv Drug Deliv Rev 42:175–195.
   PubMed Web of Science ®Google Scholar
• Gittens SA, Bansal G, Zernicke RF, Uludag H. (2005). Designing proteins for bone targeting. Adv Drug Deliv Rev 57:1011–1036.
   PubMed Web of Science ®Google Scholar
• Grima DT, Papaioannou A, Airia P, Ioannidis G, Adachi JD. (2010). Adverse events, bone mineral density and discontinuation associated with generic alendronate among postmenopausal women previously tolerant of brand alendronate: a retrospective cohort study. BMC Musculoskelet Disord 11:68.
   PubMed Web of Science ®Google Scholar
• Gu LJ, Yang BQ, Liu FL.. (2010). Synthesis and biological activity of novel statine derivatives containing ferrocenyl moiety. J Braz Chem Soc 21:58–62.
   Web of Science ®Google Scholar
• Hagino H, Nishizawa Y, Sone T, Morii H, Taketani Y, Nakamura T, Itabashi A, Mizunuma H, Ohashi Y, Shiraki M, Minamide T, Matsumoto T. (2009). A double-blinded head-to-head trial of minodronate and alendronate in women with postmenopausal osteoporosis. Bone 44:1078–1084.
   PubMed Web of Science ®Google Scholar
• Hwang JS, Liou MJ, Ho C, Lin JD, Huang YY, Wang CJ, Tsai KS, Chen JF. (2010). The effects of weekly alendronate therapy in Taiwanese males with osteoporosis. J Bone Miner Metab 28:328–333.
   PubMed Web of Science ®Google Scholar
• Iafisco M, Palazzo B, Falini G, Foggia MD, Bonora S, Nicolis S, Casella L, Roveri N. (2008). Adsorption and conformational change of myoglobin on biomimetic hydroxyapatite nanocrystals functionalized with alendronate. Langmuir 24:4924–4930.
   PubMed Web of Science ®Google Scholar
• Im GI, Qureshi SA, Kenney J, Rubash HE, Shanbhag AS. (2004). Osteoblast proliferation and maturation by bisphosphonates. Biomaterials 25:4105–4115.
   PubMed Web of Science ®Google Scholar
• Ito M, Sone T, Fukunaga M. (2010). Effect of minodronic acid hydrate on hip geometry in Japanese women with postmenopausal osteoporosis. J Bone Miner Metab 28:334–341.
   PubMed Web of Science ®Google Scholar
• Kanis JA, Adams J, Borgström F, Cooper C, Jönsson B, Preedy D, Selby P, Compston J. (2008). The cost-effectiveness of alendronate in the management of osteoporosis. Bone 42:4–15.
   PubMed Web of Science ®Google Scholar
• Leu CT, Luegmayr E, Freedman LP, Rodan GA, Reszka AA. (2006). Relative binding affinities of bisphosphonates for human bone and relationship to antiresorptive efficacy. Bone 38:628–636.
   PubMed Web of Science ®Google Scholar
• Li YC, Majeska RJ, Laudier DM, Mann R, Schaffler MB. (2005). High-dose risedronate treatment partially preserves cancellous bone mass and microarchitecture during long-term disuse. Bone 37:287–295.
   PubMed Web of Science ®Google Scholar
• Lu TL, Hu HJ, Zhao W, Chen T. (2010). RP-HPLC analysis of hydrophobic alendronate amidated derivatives. J Liquid Chromatograph Relat Technol 33:349–361.
   Web of Science ®Google Scholar
• Maalouf MA, Wiemer AJ, Kuder CH, Hohl RJ, Wiemer DF. (2007). Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation. Bioorg Med Chem 15:1959–1966.
   PubMed Web of Science ®Google Scholar
• McLeod K, Kumar S, Smart RSC. (2006). XPS and bioactivity study of the bisphosphonate pamidronate adsorbed onto plasma sprayed hydroxyapatite coatings. Appl Surf Sci 253:2644–2651.
   Web of Science ®Google Scholar
• Monteil M, Guenin E, Migianu E, Lutomski D, Lecouvey M. (2005). Bisphosphonate prodrugs: synthesis of new aromatic and aliphatic 1-hydroxy-1,1-bisphosphonate partial esters. Tetrahedron 61:7528–7537.
   Web of Science ®Google Scholar
• Mukherjee S, Song Y, Oldfield E. (2008). NMR investigations of the static and dynamic structures of bisphosphonates on human bone: a molecular model. J Am Chem Soc 130:1264–1273.
   PubMed Web of Science ®Google Scholar
• Nancollas GH, Tang R, Phipps RJ, Henneman Z, Gulde S, Wu W, Mangood A, Russell RG, Ebetino FH. (2006). Novel insights into actions of bisphosphonates on bone: differences in interactions with hydroxyapatite. Bone 38:617–627.
   PubMed Web of Science ®Google Scholar
• Raiman J, Niemi R, Vepsäläinen J, Yritys K, Järvinen T, Mönkkönen J. (2001). Effects of calcium and lipophilicity on transport of clodronate and its esters through Caco-2 cells. Int J Pharm 213:135–142.
   PubMed Web of Science ®Google Scholar
• Raiman J, Törmälehto S, Yritys K, Junginger HE, Mönkkönen J. (2003). Effects of various absorption enhancers on transport of clodronate through Caco-2 cells. Int J Pharm 261:129–136.
   PubMed Web of Science ®Google Scholar
• Rogers MJ. (2003). New insights into the molecular mechanisms of action of bisphosphonates. Curr Pharm Des 9:2643–2658.
   PubMedGoogle Scholar
• Shull LW, Wiemer AJ, Hohl RJ, Wiemer DF. (2006). Synthesis and biological activity of isoprenoid bisphosphonates. Bioorg Med Chem 14:4130–4136.
   PubMed Web of Science ®Google Scholar
• Troutman JM, Chehade KA, Kiegiel K, Andres DA, Spielmann HP. (2004). Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate. Bioorg Med Chem Lett 14:4979–4982.
   PubMed Web of Science ®Google Scholar
• Vachal P, Hale JJ, Lu Z, Streckfuss EC, Mills SG, MacCoss M, Yin DH, Algayer K, Manser K, Kesisoglou F, Ghosh S, Alani LL. (2006). Synthesis and study of alendronate derivatives as potential prodrugs of alendronate sodium for the treatment of low bone density and osteoporosis. J Med Chem 49:3060–3063.
   PubMed Web of Science ®Google Scholar
• Widler L, Jaeggi KA, Glatt M, Müller K, Bachmann R, Bisping M, Born AR, Cortesi R, Guiglia G, Jeker H, Klein R, Ramseier U, Schmid J, Schreiber G, Seltenmeyer Y, Green JR. (2002). Highly potent geminal bisphosphonates. From pamidronate disodium (Aredia) to zoledronic acid (Zometa). J Med Chem 45:3721–3738.
   PubMed Web of Science ®Google Scholar
• Wright JE, Gittens SA, Bansal G, Kitov PI, Sindrey D, Kucharski C, Uludag H. (2006). A comparison of mineral affinity of bisphosphonate–protein conjugates constructed with disulfide and thioether linkages. Biomaterials 27:769–784.
   PubMed Web of Science ®Google Scholar