Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate

Bioconjugate Chemistry

Volumn 10, Issue 5, 1999, Pages 755-763

  Luo, Yi ^a   Prestwich, Glenn D ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CELLS; CONFOCAL MICROSCOPY; CYTOTOXICITY; DISEASES; ESTERS; HYALURONIC ACID; ORGANIC ACIDS;

ANTI-TUMORS; ANTICANCER DRUG; BIOCONJUGATES; CANCER CELL LINES; CELL TARGETING; CELL UPTAKE; CHEMICALLY MODIFIED; DRUG CARRIER; PRODRUGS; SYNTHESISED;

BIOMOLECULES;

EID: 0033200301     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc9900338     Document Type: Article

References (54)

1. Scott, J. E., Secondary structures in hyaluronan solutions: chemical and biological implications; In The Biology of Hyaluronan; C. Foundation, Ed.; J. Wiley & Sons, Ltd.: Chichester, UK, 1989; pp 6-20.
2. Laurent, T. C., Laurent, U. B. G., and Fraser, J. R. E. (1995) Functions of hyaluronan. Ann. Rheum. Dis. 54, 429-432.
3. Larsen, N. E., Leshchiner, E., and Balazs, E. A. (1995) Biocompatibility of Hylan polymers in various tissue compartments. Mater. Res. Soc. Symp. Proc. 394, 149-153.
4. Knudson, C. B., and Knudson, W. (1993) Hyaluronan-Binding proteins in development, tissue homeostasis, and disease. FASEB J. 7, 1233-1241.
5. Turley, E. A., The role of a cell-associated hyaluronan binding protein in fibroblast behavior; In The Biology of Hyaluronan; C. Foundation, Ed.; J. Wiley & Sons, Ltd.: Chichester, UK, 1989; pp 121-137.
6. Underhill, C. B., The interaction of hyaluronate with the cell surface: the hyaluronate receptor and the core protein; In The Biology of Hyaluronan; C. Foundation, Ed.; J. Wiley & Sons, Ltd.: Chichester, UK, 1989; pp 87-106.
7. Entwistle, J., Hall, C. L., and Turley, E. A. (1996) Hyaluronan receptors: regulators of signaling to the cytoskeleton. J. Cell Biochem. 61, 569-577.
8. Vercruysse, K. P., and Prestwich, G. D. (1998) Hyaluronate derivatives in drug delivery. Crit. Rev. Ther. Drug Carr. Syst. 15, 513-555.
9. Freed, L. E., Vunjak-Novakovic, G., Biron, R. J., Eagles, D. B., Lesnoy, D. C., Barlow, S. K., and Langer, R. (1994) Biodegradable polymer scaffolds for tissue engineering. Bio/ Technology 12, 689-693.
10. Prestwich, G. D., Marecak, D. M., Marecek, J. F., Vercruysse, K. P., and Ziebell, M. R., Chemical modification of hyaluronic acid for drug delivery, biomaterials, and biochemical probes; In The Chemistry, Biology, and Medical Applications of Hyaluronan and its Derivatives; T. C. Laurent, Ed.; Portland Press: London, 1998; pp 43-65.
11. Alam, C. A. S., Seed, M. P., and Willoughby, D. A. (1995) Angiostasis and vascular regression in chronic granulomatous inflammation induced by diclofenac in combination with hyaluronan in mice. J. Pharm. Pharmacol. 47, 407-411.
12. Ziegler, J. (1996) Hyaluronan seeps into cancer treatment trials. J. Nat. Cancer Inst. 88, 397-399.
13. Falk, R. E. In PCT Int. Appl. WO 9740841; 1997.
14. Duncan, R., Dimitrijevic, S., and Evagorou, E. G. (1996) The role of polymer conjugates in the diagnosis and treatment of cancer. J. Therap. Polymers Pharmaceut. Sci. 6, 237-263.
15. Brinkley, M. (1992) A brief survey of methods for preparing protein conjugates with dyes, haptens, and cross-linking agents. Bioconjugate Chem. 3, 2-13.
16. Puttnam, D., and Kopecek, J. (1995) Polymer conjugates with anticancer activity. Adv. Polym. Sci. 122, 55-123.
17. Krinick, N. L., and Kopecek, J., Soluble polymers as targetable drug carriers; In Targeted Drug Delivery. Handbook of Experimental Pharmacology; R. L. Juliano, Ed.; Springer-Verlag: Berlin, 1991; pp 105-179.
18. Maeda, H., Seymour, L., and Miyamoto, Y. (1992) Conjugates of anticancer agents and polymers: advantages of macromolecular therapeutics in vivo. Bioconjugate Chem. 3, 351-362.
19. Minko, T., Kopeckova, P., Pozharov, V., and Kopecek, J. (1998) HPMA copolymer bound adriamycin overcomes MDR1 gene encoded resistance in a human ovarian carcinoma cell line. J. Controlled Release 54, 223-233.
20. Akima, K., Ito, H., Iwata, Y., Matsuo, K., Watari, N., Yanagi, M., Hagi, H., Oshima, K., Yagita, A., Atomi, Y., and Tatekawa, I. (1996) Evaluation of antitumor activities of hyaluronate binding antitumor drugs: synthesis, characterization and antitumor activity. J. Drug Targeting 4, 1.
21. Yeo, T. K., Nagy, J. A., Yeo, K. T., Dvorak, H. F., and Toole, B. P. (1996) Increased hyaluronan at sites of attachment to mesentery by CD44-positive mouse ovarian and breast tumor cells. Am. J. Pathol. 148, 1733-1740.
22. Knudson, W. (1996) Tumor-associated hyaluronan: providing an extracellular matrix that facilitates invasion. Am. J. Pathol. 148, 1721-1726.
23. Nelson, R. M., Venot, A., Bevilacqua, M. P., Linhardt, R. J., and Stamenkovic, I. (1995) Carbohydrate-protein interactions in vascular biology. Annu. Rev. Cell Dev. Biol. 11, 601-631.
24. Hall, C. L., Yang, B. H., Yang, X. W., Zhang, S. W., Turley, M., Samuel, S., Lange, L. A., Wang, C., Curpen, G. D., Savani, R. C., Greenberg, A. H., and Turley, E. A. (1995) Overexpression of the hyaluronan receptor RHAMM is transforming and is also required for h-ras transformation. Cell 82, 19-28.
25. Rooney, P., Kumar, S., Ponting, J., and Wang, M. (1995) The role of hyaluronan in tumour neovascularization (review). Int. J. Cancer 60, 632-636.
26. Hoare, K., Savani, R. C., Wang, C., Yang, B., and Turley, E. A. (1993) Identification of hyaluronan binding proteins using a biotinylated hyaluronan probe. Connect. Tissue Res. 30, 117-126.
27. Turley, E. A., Belch, A. J., Poppema, S., and Pilarski, L. M. (1993) Expression and function of a receptor for hyaluronan-mediated motility on normal and malignant lymphocytes-B. Blood 81, 446-453.
28. Gustafson, S., Bjorkman, T., and Westlin, J. E. (1994) Labeling of high molecular weight hyaluronan with I-125-tyrosine: studies in vitro and in vivo in the rat. Glycoconjugate J. 11, 608-613.
29. Gustafson, S., Hyaluronan in drug delivery; In The Chemistry, Biology, and Medical Applications of Hyaluronan and its Derivatives; T. C. Laurent and E. A. Balazs, Ed.; Portland Press: UK, 1997.
30. Gustafson, S., and Bjorkman, T. (1997) Circulating hyaluronan, chondroitin sulphate and dextran sulphate bind to a liver receptor that does not recognize heparin. Glycoconjugate J. 14, 561-568.
31. Samuelsson, C., and Gustafson, S. (1998) Studies on the interaction between hyaluronan and a rat colon cancer cell line. Glycoconjugate J. 15, 169-175.
32. Culty, M., Nguyen, H. A., and Underhill, C. B. (1992) The hyaluronan receptor (CD44) participates in the uptake and degradation of hyaluronan. J. Cell Biol. 116, 1055-1062.
33. Prestwich, G. D., D. M., M., Marecek, J. F., Vercruysse, K. P., and Ziebell, M. R. (1998) Controlled chemical modification of hyaluronic acid: synthesis, applications and biodegradation of hydrazide derivatives. J. Controlled Release 93-103.
34. Teicher, B. A. Cancer Therapeutics: Experimental and Clinical Agents; Humana Press: Totowa, New Jersey, 1997; p 451.
35. Greenwald, R. B., Gilbert, C. W., Pendri, A., Conover, C. D., Xia, J., and Martinez, A. (1996) Drug delivery systems: water soluble taxol 2′-poly(ethylene glycol) ester prodrugs - -design and in vivo effectiveness. J. Med. Chem. 39, 424-431.
36. Pouyani, T., and Prestwich, G. D. In US Patent 5,616, 568; Research Foundation of SUNY: USA, 1997.
37. Pouyani, T., and Prestwich, G. D. (1994) Functionalized derivatives of hyaluronic acid oligosaccharides - drug carriers and novel biomaterials. Bioconjugate Chem. 5, 339-347.
38. Pouyani, T., Harbison, G. S., and Prestwich, G. D. (1994) Novel hydrogels of hyaluronic acid: synthesis, surface morphology, and solid-state NMR. J. Am. Chem. Soc. 116, 7515-7522.
39. Ogura, H., Nagai, S., and Takeda, K. (1980) A novel reagent (N-succinimidyl diphenyl phosphate) for synthesis of active ester and peptide. Tetrahedron Lett. 21, 1467-1468.
40. 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.
41. Kokoshka, J. M., Ireland, C. M., and Barrows, L. R. (1996) Cell-based screen for identification of inhibitors of tubulin polymerization. J. Nat. Prod. 59, 1179-1182.
42. Kreil, G. (1995) Hyaluronidases - a group of neglected enzymes. Protein Sci. 4, 1666-1669.
43. Nicolaou, K. C., Riemer, C., Kerr, M. A., Rideout, D., and Wrasidlo, W. (1993) Design, synthesis and biological activity of protaxols. Nature 364, 464-466.
44. Collis, L., Hall, C., Lange, L., Ziebell, M., Prestwich, G., and Turley, E. (1998) Rapid hyaluronan uptake is associated with enhanced motility: implications for an intracellular mode of action. FEBS Lett. 440, 444-449.
45. Chow, G., Knudson, C. B., Homandberg, G., and Knudson, W. (1995) Increased expression of CD44 in bovine articular chondrocytes by catabolic cellular mediators. J. Biol. Chem. 270, 27734-27741.
46. Lesley, J., and Hyman, R. (1992) CD44 Can be activated to function as an hyaluronic acid receptor in normal murine T-cells. Eur. J. Immunol. 22, 2719-2723.
47. Lesley, J., English, N., Perschl, A., Gregoroff, J., and Hyman, R. (1995) Variant cell lines selected for alterations in the function of the hyaluronan receptor CD44 show differences in glycosylation. J. Exp. Med. 182, 431-437.
48. Perschl, A., Lesley, J., English, N., Trowbridge, I., and Hyman, R. (1995) Role of CD44 cytoplasmic domain in hyaluronan binding. Eur. J. Immunol. 25, 495-501.
49. Asplund, T., and Heldin, P. (1994) Hyaluronan receptors are expressed on human malignant mesothelioma cells but not on normal mesothelial cells. Cancer Res. 54, 4516-4523.
50. Culty, M., Shizari, M., Thompson, E. W., and Underhill, C. B. (1994) Binding and degradation of hyaluronan by human breast cancer cell lines expressing different forms of CD44: correlation with invasive potential. J. Cell. Physiol. 160, 275-286.
51. Hua, Q., Knudson, C. B., and Knudson, W. (1993) Internalization of hyaluronan by chondrocytes occurs via Receptor-Mediated endocytosis. J. Cell Sci. 106, 365-375.
52. Nakabayashi, H., Tsujii, H., Okamoto, Y., and Nakano, H. (1996) Fluorescence-labeled-hyaluronan loading test as an index of hepatic sinusoidal endothelial cell function in the rat. Int. Hepatol. Commun. 5, 345-353.
53. Iida, N., and Bourguignon, L. Y. W. (1997) Coexpression of CD44 variant (v10/ex14) and CD44S in human mammary epithelial cells promotes tumorigenesis. J. Cell. Physiol. 171, 152-160.
54. Bourguignon, L. Y.-W., Zhu, H. B., Chu, A., Iida, N., Zhang, L., and Hung, M. C. (1997) Interaction between the adhesion receptor, CD44, and the oncogene product, p185(HER2), promotes human ovarian tumor cell activation. J. Biol. Chem. 272, 27913-27918.