Synthesis and evaluation of water-soluble polymeric bone-targeted drug delivery systems

Bioconjugate Chemistry

Volumn 14, Issue 5, 2003, Pages 853-859

  Wang, Dong ^a   Miller, Scott ^c   Sima, Monika ^a   Kopečková, Pavla ^a   Kopeček, Jindřich ^a,b  

^a UNIVERSITY OF UTAH   (United States)

^b Department of Electrical and Computer Engineering   (United States)

^c UNIVERSITY OF UTAH SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BONE; CONTROLLED DRUG DELIVERY; HYDROXYAPATITE; TARGETED DRUG DELIVERY;

ALENDRONATE; BONE TARGETING; DELIVERY SYSTEMS; FLUORESCEIN ISOTHIOCYANATE; IN-VITRO; MODEL DRUGS; POLY(N-(2-HYDROXYPROPYL)METHACRYLAMIDE); SYNTHESISED; TARGETED DRUG DELIVERY SYSTEMS; WATERSOLUBLE;

POLYETHYLENE GLYCOLS;

ALENDRONIC ACID; ASPARTIC ACID; FLUORESCEIN ISOTHIOCYANATE; HYDROXYAPATITE; MACROGOL; POLYMER; POLY[N (2 HYDROXYPROPYL)METHACRYLAMIDE];

ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BIOACCUMULATION; BONE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG CONJUGATION; DRUG DEGRADATION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG SCREENING; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HYDROPHOBICITY; IN VITRO STUDY; MALE; MOLECULAR WEIGHT; MOUSE; NONHUMAN;

ANIMALIA;

EID: 0141606725     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc034090j     Document Type: Article

References (34)

1. Marks, S. C., Jr., and Odgren, P. R. (2002) Structure and Development of the Skeleton. Principles of Bone Biology, 2nd ed. (J. P. Bilezikian, L. G. Raisz, and G. A. Rodan, Eds.) pp 3-15, Academic Press, San Diego.
2. Odgren, P. R., and Martin, T. J. (2000) Therapeutic approaches to bone diseases. Science 289, 1508-1514.
3. Ducy, P., Zhang, R., Geoffroy, V., Ridall, A. L., and Karsenty, G. (1997) Osf2/Cbfa1: a transcriptional activator of osteoblast differentiation. Cell 89, 747-754.
4. (a) Takahashi, N., Udagawa, N., Takami, M. and Suda, T. (2002) Cells of Bone: Osteoclast Generation. Principles of Bone Biology, 2nd ed. (J. P. Bilezikian, L. G. Raisz, and G. A. Rodan, Eds.) pp 109-126, Academic Press, San Diego.
5. (b) Väänänen, K., and Zhao, H. (2002) Osteoclast Function: Biology and Mechanism. Principles of Bone Biology, 2nd ed. (J. P. Bilezikian, L. G. Raisz, and G. A. Rodan, Eds.) pp 127-139, Academic Press, San Diego.
6. Capparelli, C., Kostenuik, P. J., Morony, S., Starnes, C., Weimann, B., Van, G., Scully, S., Qi, M., Lacey, D. L., and Dunstan, C. R. (2000) Osteoprotegerin prevents and reverses hypercalcemia in a murine model of humoral hypercalcemia of malignancy. Cancer Res. 60, 783-787.
7. Yamashita, D. S., and Dodds, R. A. (2000) Cathepsin K and the design of inhibitors of cathepsin K. Curr. Pharm. Des. 6, 1-24.
8. Minkin, C., and Jennings, J. M. (1972) Carbonic anhydrase and bone remodeling: sulfonamide inhibition of bone resorption in organ culture. Science 176, 1031-1033.
9. Engleman, V. W., Nickols, G. A., Ross, F. P., Horton, M. A., Griggs, D. W., Settle, S. L., Ruminski, P. G., and Teitelbaum, S. L. (1997) A peptidomimetic antagonist of the αvβ3 integrin inhibits bone resorption in vitro and prevents osteoporosis in vivo. J. Clin. Invest. 99, 2284-2292.
10. Shakespeare, W., Yang, M., Bohacek, R., Cerasoli, F., Stebbins, K., Sundaramoorthi, R., Azimioara, M., Vu, C., Pradeepan, S., Metcalf III, C., Haraldson, C., Merry, T., Dalgarno, D., Narula, S., Hatada, M., Lu, X., van Schravendijk, M. R., Adams, S., Violette, S., Smith, J., Guan, W., Bartlett, C., Herson, J., Iuliucci, J., Weigele, M., and Sawyer, T. (2000) Structure-based design of an osteoclast-selective, nonpeptide Src homology 2 inhibitor with in vivo antiresorptive activity. Proc. Natl. Acad. Sci. U.S.A. 97, 9373-9378.
11. Miller, S. C., and Marks, S. C., Jr. (1994) Effects of prostaglandins on the skeleton. Clin. Plast. Surg. 21, 393-400.
12. Yoshida, K., Oida, H., Kobayashi, T., Maruyama, T., Tanaka, M., Katayama, T., Yamaguchi, K., Segi, E., Tsuboyama, T., Matsushita, M., Ito, K., Ito, Y., Sugimoto, Y., Ushikubi, F., Ohuchida, S., Kondo, K., Nakamura, T., and Narumiya, S. (2002) Stimulation of bone formation and prevention of bone loss by prostaglandin E EP4 receptor activation. Proc. Natl. Acad. Sci. U.S.A. 99, 4580-4585.
13. Mundy, G., Garrett, R., Harris, S., Chan, J., Chen, D., Rossini, G., Boyce, B., Zhao, M., and Gutierrez, G. (1999) Stimulation of bone formation in vitro and in rodents by statins. Science 286, 1946-1949.
14. Lindsay, R., and Nieves, J. (1997) Randomized controlled study of effect of parathyroid hormone on vertebral-bone mass and fracture incidence among postmenopausal women on estrogen with osteoporosis. Lancet 350, 550-555.
15. Rossouw, J. E., Anderson, G. L., Prentice R. L., LaCroix A. Z., Kooperberg C., Stefanick M. L., Jackson R. D., Beresford S. A., Howard B. V., Johnson K. C., Kotchen J. M., and Ockene J. (2002) Risks and benefits of estrogen plus progestin in healthy postmenopausal women. J. Am. Med. Assoc. 288, 321-333.
16. Lacey, J. V., Jr., Mink, P. J., Lubin, J. H., Sherman, M. E., Troisi, R., Hartge, P., Schatzkin, A., and Schairer, C. (2002) Menopausal hormone replacement therapy and risk of ovarian cancer. J. Am. Med. Assoc. 288, 334-341.
17. Pierce, W. M., Jr., and Waite, L. C. (1984) Bone-targeted carbonic anhydrase inhibitors: effect of a proinhibitor on bone resorption in vitro. Proc. Soc. Exp. Bio. Med. 186, 96-102.
18. Orme, M. W., and Labroo, V. M. (1994) Synthesis of β -estradiol-3-benzoate-17-(succinyl-12a-tetracycline): a potential bone-seeking estrogen. Bioorg. Med. Chem. Lett. 4, 1375-1380.
19. Wilson, T. M., Charifson, P. S., Baxter, A. D., and Geddie, N. G. (1996) Bone-targeted drugs. 1. indentification of heterocycles with hydroxyapatite affinity. Bioorg. Med. Chem. Lett. 6, 1043-1046.
20. Bentz, H., and Rosen, D. (1992) Targeted delivery of bone growth factors. EP 0 512 844 A1.
21. Uludag, H., and Yang, J. (2002) Targeting systemically administered proteins to bone by bisphosphonate conjugation. Biotechnol. Prog. 18, 604-611.
22. 99mTc-EC with aminomethylenediphosphonate in the search for a bone tracer with fast clearance from soft tissue. Bioconj. Chem. 13, 16-22.
23. Yokogawa, K., Miya, K., Sekido, T., Higashi, Y., Nomura, M., Fujisawa, R., Morito, K., Masamune, Y., Waki, Y., Kasugai, S., and Miyamoto, K. (2001) Selective delivery of estradiol to bone by aspartic acid oligopeptide and its effects on ovariectomized mice. Endocrinology 142, 1228-1233.
24. Kozak, K. R., Crews, B. C., Ray, J. L., Tai, H. H., Morrow, J. D., and Marnett, L. J. (2001) Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. J. Biol. Chem. 276, 36993-36998.
25. Chan, W. C., and White, P. D. (2000) Basic Procedures. Fmoc Solid-Phase Peptide Synthesis, A Practical Approach. (W. C. Chan and P. D. White, Eds.) pp 41-74, Oxford University Press Inc., New York.
26. Lin, J. H. (1996) Bisphosphonates: a review of their pharmacokinetic properties. Bone 18, 75-85.
27. Yoshida, M., Mahato, R. I., Kawabata, K., Takakura, Y., and Hashida, M. (1996) Disposition characteristics of plasmid DNA in the single-pass rat liver perfusion system. Pharm. Res. 13, 599-603.
28. Fujiwara, M., Baldeschwieler, J. D., and Grubbs, R. H. (1996) Receptor-mediated endocytosis of poly(acrylic acid)conjugated liposomes by macrophages. Biochim. Biophys. Acta 1278, 59-67.
29. Rawls, H. R., and Cabasso, I. (1982) Adsorption of Phosphonylated Polyelectrolytes on Hydroxyapatite. Adsorption on and Surface Chemistry of Hydroxyapatite (D. N. Misra, Ed.) pp 115-128, Plenum Press, New York.
30. Tye, C. E., Rattray, K. R., Warner, K. J., Gordon, J. A., Sodek, J., Hunter, G. K., and Goldberg, H. A. (2003) Delineation of the hydroxyapatite-nucleating domains of bone sialo-protein. J. Biol. Chem. 278, 7949-7955.
31. Howlett, C. R., Dickson, M., and Sheridan, A. K. (1984) The fine structure of the proximal growth plate of the avian tibia: vascular supply. J. Anat. 139, 115-132.
32. Ghandehari, H., Smith, P. L., Ellens, H., Yeh, P.-Y., and Kopeček, J. (1997) Size-dependent permeability of hydrophilic probes across rabbit colonic epithelium. J. Pharm. Exp. Ther., 280, 747-753.
33. w) of N-(2-hydroxypropyl)methacrylamide copolymers on body distribution and rate of excretion after subcutaneous, intraperitoneal, and intravenous administration to rats. J. Biomed. Mater. Res. 21, 1341-1358.
34. Junqueira, L. C., Carneiro, J., and Kelley R. O. (1995) Bone. Basic Histology, 8th ed. (L. C. Junqueira, J. Carneiro, and R. O. Kelley, Eds.) pp 132-151, Appleton & Lange, Connecticut.