Fluorescently labeled risedronate and related analogues: "Magic linker" synthesis

Bioconjugate Chemistry

Volumn 19, Issue 12, 2008, Pages 2308-2310

  Kashemirov, Boris A ^a   Bala, Joy Lynn F ^a   Chen, Xiaolan ^a   Ebetino, F H ^b   Xia, Zhidao ^c   Russell, R Graham G ^c   Coxon, Fraser P ^d   Roelofs, Anke J ^d   Rogers, Michael J ^d   McKenna, Charles E ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b PROCTER AND GAMBLE PHARMACEUTICALS   (United States)

^c UNIVERSITY OF OXFORD   (United Kingdom)

^d UNIVERSITY OF ABERDEEN   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

6 CARBOXYFLUORESCEIN; BISPHOSPHONIC ACID DERIVATIVE; CALCEIN; CARBOXYFLUORESCEIN; CARBOXYLIC ACID; EPOXIDE; FLUORESCENT DYE; HYDROXYAPATITE; PAMIDRONIC ACID; PHOSPHONIC ACID DERIVATIVE; PYRIDINIUM DERIVATIVE; RISEDRONIC ACID;

ARTICLE; BINDING AFFINITY; CONJUGATION; OSTEOCLAST; OSTEOLYSIS; PROTEIN PRENYLATION;

EID: 58149091150     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800369c     Document Type: Article

References (18)

1. Russell, R. G. G. (2007) Bisphosphonates: mode of action and pharmacology. Pediatrics 119 Suppl 2, S150-62.
2. Roelofs, A. J., Thompson, K., Gordon, S., and Rogers, M. J. (2006) Molecular mechanisms of action of bisphosphonates: current status. Clin. Cancer Res. 12, 6222s-6230s.
3. Ebetino, F. H., Roze, C. N., McKenna, C. E., Barnett, B. L., Dunford, J. E., Russell, R. G. G., Mieling, G. E., and Rogers, M. J. (2005) Molecular interactions of nitrogen-containing bisphosphonates within farnesyl diphosphate synthase. J. Organomet. Chem. 690, 2679-2687.
4. Kavanagh, K. L., Guo, K., Dunford, J. E., Wu, X., Knapp, S., Ebetino, F. H., Rogers, M. J., Russell, R. G. G., and Oppermann, U. (2006) The molecular mechanism of nitrogen-containing bisphosphonates as antiosteoporosis drugs. Proc. Natl. Acad. Sci. U.S.A. 103, 7829-7834.
5. Kotsikorou, E., and Oldfield, E. (2003) A quantitative structure-activity relationship and pharmacophore modeling investigation of aryl-X and heterocyclic bisphosphonates as bone resorption agents. J. Med. Chem. 46, 2932-2944.
6. Martin, M. B., Arnold, W., Heath, H. T., III, Urbina, J. A., and Oldfield, E. (1999) Nitrogen-containing bisphosphonates as carbocation transition state analogs for isoprenoid biosynthesis. Biochem. Biophys. Res. Commun. 263, 754-758.
7. Coxon, F. P., Helfrich, M. H., Larijani, B., Muzylak, M., Dunford, J. E., Marshall, D., McKinnon, A. D., Nesbitt, S. A., Horton, M. A., Seabra, M. C., Ebetino, F. H., and Rogers, M. J. (2001) Identification of a novel phosphonocarboxylate inhibitor of Rab geranylgeranyl transferase that specifically prevents Rab prenylation in osteoclasts and macrophages. J. Biol. Chem. 276, 48213-48222.
8. Lueftner, D., Henschke, P., and Possinger, K. (2007) Clinical value of bisphosphonates in cancer therapy. Anticancer Res. 27, 1759-1768.
9. Thompson, K., Rogers, M. J., Coxon, F. P., and Crockett, J. C. (2006) Cytosolic entry of bisphosphonate drugs requires acidification of vesicles after fluid-phase endocytosis. Mol. Pharmacol. 69, 1624-1632.
10. Zaheer, A., Lenkinski, R. E., Mahmood, A., Jones, A. G., Cantley, L. C., and Frangioni, J. V. (2001) In vivo near-infrared fluorescence imaging of osteoblastic activity. Nat. Biotechnol. 19, 1148-1154.
11. Bhushan, K. R., Tanaka, E., and Frangioni, J. V. (2007) Synthesis of conjugatable bisphosphonates for molecular imaging of large animals. Angew. Chem., Int. Ed. 46, 7969-7971.
12. Hirabayashi, H., Sawamoto, T., Fujisaki, J., Tokunaga, Y., Kimura, S., and Hata, T. (2001) Relationship between physicochemical and osteotropic properties of bisphosphonic derivatives: rational design for Osteotropic Drug Delivery System (ODDS). Pharm. Res. 18, 646-651.
13. Maalouf, M. A., Wiemer, A. J., Kuder, C. H., Hohl, R. J., and Wiemer, D. F. (2007) Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation. Bioorg. Med. Chem. 15, 1959-1966.
14. th International Conference on Phosphorus Chemistry, Xiamen, China.
15. Chuiko, A. L., Filonenko, L. P., Borisevich, A. N., and Lozinskii, M. O. (1993) Synthesis and properties of hydroxyaminoalkyl esters of (hydroxyethylidene)bis[phosphonic acid]. Zh. Obshch. Khim. 63, 1070-4.
16. Chen, G., Heim, A., Riether, D., Yee, D., Milgrom, Y., Gawinowicz Mary, A., and Sames, D. (2003) Reactivity of functional groups on the protein surface: development of epoxide probes for protein labeling. J. Am. Chem. Soc. 125, 8130-3.
17. Marma, M. S., Xia, Z., Stewart, C., Coxon, F., Dunford, J. E., Baron, R., Kashemirov, B. A., Ebetino, F. H., Triffitt, J. T., Russell, R. G. G., and McKenna, C. E. (2007) Synthesis and biological evaluation of α-halogenated bisphosphonate and phosphonocarboxylate analogues of risedronate. J. Med. Chem. 50, 5967-5975.
18. Coxon, F. P., Thompson, K., Roelofs, A. J., Ebetino, F. H., and Rogers, M. J. (2008) Visualizing mineral binding and uptake of bisphosphonate by osteoclasts and non-resorbing cells. Bone 42, 848-60.