Design of dendritic macromolecules containing folate or methotrexate residues

Bioconjugate Chemistry

Volumn 10, Issue 6, 1999, Pages 1115-1121

  Kono, Kenji ^a,b   Liu, Mingjun ^a   Fréchet, Jean M J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMERS; DRUG DELIVERY; ESTERS; NITROGEN COMPOUNDS; ORGANIC ACIDS;

CHAIN-ENDS; CONDENSING AGENTS; DENDRITIC MACROMOLECULES; DENDRITICS; DRUG CARRIER; FOLATES; FOLIC ACIDS; HYDRAZIDE GROUPS; MODEL DRUGS; TUMOUR CELLS;

ETHERS;

EID: 0033230698     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc990082k     Document Type: Article

References (32)

1. Tomalia, D. A., Naylor, A. M., and Goddard, W. A., III (1990) Starburst dendrimers: molecular-level control of size, shape, surface chemistry, topology, and flexibility from atoms to macroscopic matter. Angew. Chem., Int. Ed. Engl. 29, 138-175.
2. Newkome, G. R., Moorefield, C. N., and Vögtle, F. (1996) Dendritic molecules: concepts, syntheses, perspectives, VCH, Weinheim.
3. Fréchet, J. M. J. (1994) Functional polymers and dendrimers: reactivity, molecular architecture, and interfacial energy. Science 263, 1710-1715.
4. Roberts, J., Adams, Y. E., Tomalia, D., Mercer-Smith, J. A., and Lavallee, D. K. (1990) Using starburst dendrimers as linker molecules to radiolabel antibodies. Bioconjugate Chem. 1, 305-308.
5. Singh, P., Moll, F., III, Lin, S. H., Ferzli, C., Kwok, S. Y., Koski, R. K., Saul, R. G., and Cronin, P. (1994) Starburst dendrimers: enhanced performance and flexibility for immunoassays. Clin. Chem. 40, 1845-1849.
6. Barth, R. F., Adams, D. M., Soloway, A. H., Alam, F., and Darby, M. V. (1994) Boranated Starburst dendrimer-monoclonal antibody immunoconjugates: evaluation as a potential delivery system for neutron capture therapy. Bioconjugate Chem. 5, 58-66.
7. Aoi, K., Itoh, K., and Okada, M. (1995) Globular carbohydrate macromolecule "sugar balls". 1. Synthesis of novel sugar-persubstituted poly (amido amine) dendrimers. Macromolecules 28, 5391-5393.
8. Zanini, D., and Roy, R. (1997) Synthesis of new a-thiosialodendrimers and their binding properties to the sialic acid specific lectin from limax flavus. J. Am. Chem. Soc. 119, 2088-2095.
9. Jansen, J. F. G. A., de Brabander-van den Berg, E. M. M., and Meijer, E. W. (1994) Encapsulation of guest molecules into a dendritic box. Science 266, 1226-1229.
10. Newkome, G. R., Moorefield, C. N., Baker, G. R., Johnson, A. W., and Behera, R. K. (1991) Alkane cascade polymers possessing micellar topology: micellanoic acid derivatives. Angew. Chem., Int Ed. Engl. 30, 1176-1178.
11. Newkome, G. R., Moorefield, C. N., Baker, G. R., Saunders, M. J., and Grossman, S. H. (1991) Unimolecular Micelles. Angew. Chem., Int. Ed. Engl. 30, 1178-1180.
12. Hawker, C. J., Wooley, K. L., and Fréchet, J. M. J. (1993) Unimolecular micelles and globular amphiphiles: dendritic macromolecules as novel recyclable solubilization agents. J. Chem. Soc., Perkin Trans. 1, 1287-1297.
13. Liu, M., and Fréchet, J. M. J. (1999) Preparation of water-soluble dendritic unimolecular micelles as potential drug delivery agents. Polym. Mater. Sci. Eng. 80, 167-168.
14. Liu, M., Kono, K., and Fréchet, J. M. J. (1999) Water-soluble dendritic unimolecular micelles: their potential as drug delivery agents. J. Controlled Release (in press).
15. Zhuo, R. X., Du, B., and Lu, Z. R. (1999) In vitro release of 5-fluorouracil with cyclic core dendritic polymer. J. Controlled Release 57, 249-257.
16. Liu, M., Kono, K., and Fréchet, J. M. J. (1999) Water-soluble dendrimer-poly(ethylene glycol) starlike conjugates as potential drug carriers. J. Polym. Sci., Polym. Chem. 37, 3492-3503.
17. Garin-Chesa, P., Campbell, I., Saigo, P. E., Lewis, J. L., Old, L. J., and Lettig, W. J. (1993) Trophoblast and ovarian cancer antigen LK26. Am. J. Pathol. 142, 557-567.
18. Buist, M. R., Molthoff, C. F. M., Kenemans, P., and Meijer, C. J. L. M. (1995) Distribution of OV-TL 3 and Mov18 in normal and malignant ovarian tissue. J. Clin. Pathol. 48, 631-636.
19. Ross, J. F., Chaudhuri, P. K., and Ratnam, M. (1994) Differential regulation of folate receptor isoforms in normal and malignant tissues in vivo and established cell lines. Physiologic and clinical implications. Cancer 73, 2432-2443.
20. Leamon, C. P., and Low, P. S. (1991) Delivery of macromolecules into living cells: A method that exploits folate receptor endocytosis. Proc. Natl. Acad. Sci. U.S.A. 88, 5572-5576.
21. Cho, B. K., Roy, E. J., Patrick, T. A., and Kranz, D. M. (1997) Single-chain Fv/folate conjugates mediate efficient lysis of folate-receptor-positive tumor cells. Bioconjugate Chem. 8, 338-346.
22. Lee, R. J., and Low, P. S. (1994) Delivery of liposomes into cultured KB cells via folate receptor-mediated endocytosis. J. Biol. Chem. 269, 3198-3204.
23. Lee, R. J., and Low, P. S. (1995) Folate-mediated tumor cell targeting of liposome-entrapped doxorubicin in vitro. Biochim. Biophys. Acta 1233, 134-144.
24. Mathias, C. J., Wang S., Lee, R. J., Waters, D. J., Low, P. S., and Green, M. A. (1996) Tumor-selective radiopharmaaceutical targeting via receptor-mediated endocytosis of Gallium-67-deferoxamine-folate. J. Nucl. Med. 37, 1003-1008.
25. Wiener, E. C., Konda, S., Shadron, A., Brechbiel, M., and Gansow, O. (1997) Targeting dendrimer-chelates to tumors and tumor cells expressing the high-affinity folate receptor. Invest. Radiol. 32, 748-754.
26. Wang, S., Lee, R. J., Mathias, C. J., Green, M. A., and Low, P. S. (1996) Synthesis, purification, and tumor cell uptake of 67Ga-deferoxamine-folate, a potential radiopharmaceutical for tumor imaging. Bioconjugate Chem. 7, 56-62.
27. Leon, J. W., Kawa, M., and Fréchet, J. M. J. (1996) Isophthalate ester-terminated dendrimers: versatile nanoscopic building blocks with readily modifiable surface functionalities. J. Am. Chem. Soc. 118, 8847-8859.
28. Vercruysse, K. P., Marecak, D. M., Marecek, J. F., and Prestwich, G. D. (1997) Synthesis and in Vitro degradation of new polyvalent hydrazide cross-linked hydrogels of hyaluronic acid. Bioconjugate Chem. 8, 686-694.
29. Przybylski, M., Fell, E., Ringsdorf, H., and Zaharko, D. (1978) Pharmacologically active polymers, 17: Syntheses and characterization of polymeric derivatives of the antitumor agent metnotrexate. Makromol. Chem. 179, 1719-1733.
30. Ryser, H. J.-P., and Shen, W.-C. (1978) Conjugation of methotrexate to poly(L-lysine) increase drug transport and overcomes drug resistance in cultured cells. Proc. Natl. Acad. Sci. U.S.A. 75, 3867-3870.
31. Abuchowski, A., McCoy, J. R., Palczuk, N. C., van Es, T., and Davis, F. F. (1977) Effect of covalent attachment of poly-(ethylene glycol) on immunogenicity and circulating life of bovine liver catalase. J. Biol. Chem. 252, 3582-3586.
32. Ashihara, Y., Kono, T., Yamazaki, S., and Inada, Y. (1978) Modification of E. coli L-asparaginase with poly(ethylene glycol), disappearance of binding ability to anti-asparaginase serum. Biochem. Biophys. Res. Commun. 83, 358-391.