Skip to main content

Use of Functionalized Poly(Ethylene Glycol)s for Modification of Polypeptides

  • Chapter
Poly(Ethylene Glycol) Chemistry

Part of the book series: Topics in Applied Chemistry ((TAPP))

Abstract

The unique properties of poly(ethylene glycol) (or PEG) and its general compatibility with polypeptide materials facilitated development of a variety of different applications of this polymer.1–11 A marked proportion of these applications involve the use of covalently linked polypeptide-PEG adducts (reviewed elsewhere5–11). For example, a number of PEG-enzymes were shown to be useful as catalysts, soluble and active in organic solvents.7 Due to the affinity to the upper phase of PEG/Dextran and PEG/salt two-phase systems, PEG-modified proteins were proven useful both as diagnostic tools8 and in preparative separations of biological cells.9

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. I. N. Topchieva, Usp. Khim. 49, 494.

    Google Scholar 

  2. N. Topchieva, Russ. Chem. Rev. 49, 260 (1980).

    Article  Google Scholar 

  3. K. C. Ingham, Methods Enzymol. 104, 351 (1984).

    Article  PubMed  CAS  Google Scholar 

  4. H. Walter and G. Johansson, Anal. Biochem. 155, 215 (1986).

    Article  PubMed  CAS  Google Scholar 

  5. E. Merrill and E. W. Salzman, Am. Soc. Artif. Internal Organs J. 6, 60 (1983).

    CAS  Google Scholar 

  6. M. Mutter and E. Bayer, in: The Peptides (E. Gross and J. Meienhofer, eds.), Vol. 2, p. 285, Academic Press, New York (1979).

    Google Scholar 

  7. V. N. R. Pillai and M. Mutter, Acc. Chem. Res. 14, 122 (1981).

    Article  CAS  Google Scholar 

  8. Y. Inada, K. Takahashi, T. Yoshimoto, A. Ajima, A. Matsushima, and Y. Saito, Trends in Biotechnol. 4, 190 (1986).

    Article  CAS  Google Scholar 

  9. B. Mattiason, Methods Enzymol. 92, 498 (1983).

    Article  Google Scholar 

  10. D. E. Brooks, K. A. Sharp, and S. J. Stocks, Makromol. Chem., Macromol. Symp. 17, 387 (1988).

    Article  CAS  Google Scholar 

  11. A. Abuchowski and F. F. Davis, in: Enzymes as Drugs (J. Holsenberg and J. Roberts, eds.), p. 367, Wiley, New York (1981).

    Google Scholar 

  12. S. Dreborg and E. B. Åkerblom, Crit. Rev. Therap. Drug Carrier Syst. 6, 315 (1990).

    CAS  Google Scholar 

  13. J. M. Harris, J. Macromol. Sci., Rev. Macromol. Chem. Phys. C25, 325 (1985).

    Article  CAS  Google Scholar 

  14. S. Zalipsky, C. Gilon, and A. Zilkha, J. Macromol. Sci. Chem. A21, 839 (1984).

    CAS  Google Scholar 

  15. S. Zalipsky, C. Gilon, and A. Zilkha, Eur. Polym. J. 19, 1177 (1983).

    Article  CAS  Google Scholar 

  16. D. A. Herold, K. Keil, and D. E. Bruns, Biochem. Pharmacol. 38, 73 (1989).

    Article  PubMed  CAS  Google Scholar 

  17. H. F. Smyth, Jr., C. P. Carpenter, and C. S. Weil, J. Am. Pharm. Assoc. 39, 349 (1950).

    CAS  Google Scholar 

  18. A. J. Johnson, M. H. Karpatkin, and J. Newman, Br. J. Hematol. 21, 21 (1971).

    Article  CAS  Google Scholar 

  19. C. B. Shaffer and F. H. Critchfield, J. Am. Pharm. Assoc. 36, 152 (1947).

    CAS  Google Scholar 

  20. E. C. Dittmann, Naunyn-Schmeideberg’s Arch. Pharmacol. 276, 199 (1973).

    Article  CAS  Google Scholar 

  21. A. W. Richter and E. Åkerblom, Int. Arch. Allergy Appl. Immunol. 70, 124 (1983).

    Article  PubMed  CAS  Google Scholar 

  22. F. F. Davis, T. Van Es, and N. C. Palczuk, U.S. Patent 4,179,337 (1979).

    Google Scholar 

  23. E Kawai, CRC Crit. Rev. Biotechnol. 6, 273 (1987).

    Article  CAS  Google Scholar 

  24. G. P. Royer and G. M. Ananthramaiah, J. Am. Chem. Soc. 101, 3394 (1979).

    Article  CAS  Google Scholar 

  25. J. D. Glass, L. Silver, J. Sondheimer, C. S. Pande, and J. Coderre, Biopolymers 18, 383 (1979).

    Article  CAS  Google Scholar 

  26. K. Ulbrich, J. Strohalm, and J. Kopecek, Makromol. Chem. 187, 1131 (1986).

    Article  CAS  Google Scholar 

  27. P. Pasta, S. Riva, and G. Carrea, FEBS Lett. 236, 329 (1988).

    Article  PubMed  CAS  Google Scholar 

  28. A. Abuchowski, T. Van Es, N. C. Palczuk, and F. F. Davis, J. Biol. Chem. 252, 3578 (1977).

    PubMed  CAS  Google Scholar 

  29. T. P. King, L. Kochoumian, and L. M. Lichtenstein, Arch. Biochem. Biophys. 178, 442 (1977)

    Article  PubMed  CAS  Google Scholar 

  30. T. P. King, L. Kochoumian, and N. Chiorazzi, J. Exp. Med. 149, 424 (1979).

    Article  PubMed  CAS  Google Scholar 

  31. Y. Ashihara, T. Kono, S. Yamazaki, and Y. Inada, Biochem. Biophys. Res. Commun. 93, 385 (1978).

    Article  Google Scholar 

  32. H. F. Gaertner and A. J. Puigserver, Proteins 3, 130 (1988).

    Article  PubMed  CAS  Google Scholar 

  33. S. G. Shafer and J. M. Harris, J. Polym. Sci., Polym. Chem. Ed. 24, 375 (1986).

    Article  CAS  Google Scholar 

  34. M. Z. Atassi, in: Immunochemistry of Proteins (M. Z. Atassi, ed.), Vol. 1, p. 1, Plenum Press, New York (1977).

    Chapter  Google Scholar 

  35. K. J. Wieder, N. C. Palczuk, T. Van Es, and F. F. Davis, J. Biol. Chem. 254, 12579 (1979).

    PubMed  CAS  Google Scholar 

  36. S. Davis, A. Abuchowski, Y. K. Park, and F. F. Davis, Clin. Exp. Immunol. 46, 649 (1981).

    PubMed  CAS  Google Scholar 

  37. K. Yoshinaga and J. M. Harris, J. Bioact. Compatible Polym. 4, 17 (1989).

    Article  Google Scholar 

  38. A. Matsushima, H. Nishimura, Y. Ashihara, Y. Yokota, and Y. Inada, Chem. Lett., 113 (1980).

    Google Scholar 

  39. H. Nishimura, K. Takahashi, K. Sakurai, K. Fujinuma, Y. Imamura, M. Ooba, and Y Inada, Life Sci. 33, 1467 (1983).

    Article  PubMed  CAS  Google Scholar 

  40. K. Takahashi, A. Ajima, T. Yoshimoto, M. Okada, A. Matsushima, Y. Tamaura, and Y. Inada, J. Org. Chem. 50, 3414 (1985).

    Article  CAS  Google Scholar 

  41. C. C. Jackson, J. L. Charlton, K. Kuzminski, G. M. Lang, and A. H. Sehon, Anal. Biochem. 165, 114 (1987).

    Article  PubMed  CAS  Google Scholar 

  42. A. Yoshimoto, S. G. Chao, Y. Saito, I. Imamura, H. Wada, and Y Inada, Enzyme 36, 261 (1986).

    PubMed  CAS  Google Scholar 

  43. M. Rubinstein, U.S. Patent 4,101,380 (1978).

    Google Scholar 

  44. M. Joppich and P. L. Luisi, Makromol. Chem. 180, 1381 (1979).

    Article  CAS  Google Scholar 

  45. A. Abuchowski, G. Kazo, C. R. Verhoest, T. Van Es, D. Kafkewitz, M. L. Nucci, A. T. Viau, and F. F. Davis, Cancer Biochem. Biophys. 7, 175 (1984).

    PubMed  CAS  Google Scholar 

  46. M. S. Hershfield, R. H. Buckley, M. L. Greenberg, A. L. Melton, R. Schiff, C. Hatem, J. Kirtzberg, M. L. Markert, R. H. Kobayashi, A. L. Kobayashi, and A. Abuchowski, N. Engl. J. Med. 316, 589 (1987).

    Article  PubMed  CAS  Google Scholar 

  47. K. B. Hadley and P. H. Sato, Enzyme 42, 225 (1989).

    PubMed  CAS  Google Scholar 

  48. K. Iwasaki, Y Iwashita, and T. Okami, U.S. Patent 4,670,417 (1987).

    Google Scholar 

  49. V. N. Katre, M. J. Knauf, and W. J. Laird, Proc. Natl. Acad. Sci. U.S.A. 84, 1487 (1987).

    Article  PubMed  CAS  Google Scholar 

  50. E. Boccu, R. Largajolli, and F. M. Veronese, Z. Naturforsch. 38c, 94 (1983).

    CAS  Google Scholar 

  51. D. Larwood and E. Szoka, J. Labelled Compd. Radiopharm. 21, 603 (1984).

    Article  CAS  Google Scholar 

  52. C. O. Beauchamp, S. L. Gonias, D. P. Menapace, and S. V. Pizzo, Anal. Biochem. 131, 25 (1983).

    Article  PubMed  CAS  Google Scholar 

  53. L. Tondelli, M. Laus, A. S. Angeloni, and P. Ferruti, J. Controlled Release 1, 251 (1985).

    Article  CAS  Google Scholar 

  54. C. Beauchamp, P. E. Daddona, and D. P. Menapace, in: Adv. Exp. Med. Biol. (C.H.M.M. DeDruyn, H. A. Simmons, and M. Muller, eds.), 165A, 47 (1984).

    Google Scholar 

  55. H. Berger and S. V. Pizzo, Blood 71, 1641 (1988).

    PubMed  CAS  Google Scholar 

  56. F. M. Veronese, R. Largajolli, E. Boccu, C. A. Benassi, and O. Schiavon, Appl. Biochem. Biotechnol. 11, 141 (1985).

    Article  PubMed  CAS  Google Scholar 

  57. S. Zalipsky, Patent pending; S. Zalipsky, R. Seltzer, and S. Meron-Rudolph, Biotechnol. Appl. Biochem. 15, 100 (1992).

    Article  PubMed  CAS  Google Scholar 

  58. S. Zalipsky, R. Seltzer, and K. Nho, Polym. Prepr., Am. Chem. Soc, Div. Polym. Chem. 31(2), 173 (1990); in: Polymeric Drugs and Drug Delivery Systems (R. L. Dunn and R. M. Ottenbrite, eds.), p. 91, ACS Symposium Series 469, Washington, DC (1991).

    CAS  Google Scholar 

  59. A. Nathan, S. Zalipsky, and J. Kohn, Polym. Prepr., Am. Chem. Soc, Div. Polym. Chem. 31(2), 213 (1990).

    CAS  Google Scholar 

  60. A. Buckmann, M. Morr, and G. Johansson, Makromol. Chem. 182, 1379 (1981).

    Article  Google Scholar 

  61. M. Leonard, J. Neel, and E. Dellacherie, Tetrahedron 40, 1581 (1984).

    Article  CAS  Google Scholar 

  62. S. Zalipsky and G. Barany, J. Bioact. Compat. Polym. 5, 227 (1990).

    Article  CAS  Google Scholar 

  63. G. Johansson, J. Chromatogr. 368, 309 (1986).

    Article  CAS  Google Scholar 

  64. F. M. Veronese, P. Caliceti, A. Pastorino, O. Schiavon, L. Sartore, L. Banci, and L. M. Scolaro, J. Controlled Release 10, 145 (1989).

    Article  CAS  Google Scholar 

  65. T. Yoshimoto, M. Nakata, S. Yamaguchi, T. Funada, Y. Saito, and Y. Inada, Biotechnol. Lett. 8, 771 (1986).

    Article  CAS  Google Scholar 

  66. D. E. Nitecki, L. Aldwin, and M. Moreland in: Peptide Chemistry 1987 (T. Shiba and S. Sakakibara, eds.), p. 243, Protein Res. Foundation, Osaka (1988).

    Google Scholar 

  67. K. Shimizu, T. Nakahara, and T. Kinoshita, U.S. Patent 4,495,285 (1985).

    Google Scholar 

  68. K. Shimizu, T. Nakahara, T. Kinoshita, J. Takatsuka, and M. Igarashi, U.S. Patent 4,640,835 (1987).

    Google Scholar 

  69. A. J. Garman and S. B. Kalindjian, FEBS Lett. 223, 361 (1987).

    Article  PubMed  CAS  Google Scholar 

  70. A. J. Garman, U.S. Patent 4,935,465 (1990).

    Google Scholar 

  71. T. P. King and C. Weiner, Int. J. Peptide Protein Res. 16, 147 (1980).

    Article  CAS  Google Scholar 

  72. S. Zalipsky, F. Albericio, U. Slomczynska, and G. Barany, Int. J. Peptide Protein Res. 30, 740 (1987).

    Article  CAS  Google Scholar 

  73. J. M. Harris, E. C. Struck, M. G. Case, M. S. Paley, M. Yalpani, J. M. Van Alstine, and D. E. Brooks, J. Polym. Sci., Polym. Chem. Ed. 22, 341 (1984).

    Article  CAS  Google Scholar 

  74. K. Nilsson and K. Mosbach, Methods Enzymol. 104, 56 (1984).

    Article  PubMed  CAS  Google Scholar 

  75. C. Delgado, J. N. Patel, G. E. Francis, and D. Fisher, Biotechnol. Appl. Biochem. 12, 119 (1990).

    PubMed  CAS  Google Scholar 

  76. P. Bohlen, S. Stein, W. Dairman, and S. Udenfriend, Arch. Biochem. Biophys. 155, 213 (1973).

    Article  PubMed  CAS  Google Scholar 

  77. S. J. Stocks, A. J. M. Jones, C. W. Ramey, and D. E. Brooks, Anal. Biochem. 154, 232 (1986).

    Article  PubMed  CAS  Google Scholar 

  78. A. S. E A. Habeeb, Anal. Biochem. 14, 328 (1966).

    Article  PubMed  CAS  Google Scholar 

  79. N. Yamasaki, A. Matsuo, and H. Isobe, Agric. Biol. Chem. 52, 2125 (1988).

    Article  CAS  Google Scholar 

  80. L. Sartore, R Caliceti, O. Schiavon, P. Ferruti, E. Ranucci, and F. M. Veronese, Proc. Int. Symp. Control. Rel. Bioact. Mater. 17, 208 (1990).

    Google Scholar 

  81. S. Zalipsky and G. Barany, Polym. Prepr., Am. Chem. Soc, Div. Polym. Chem. 27(1), 1 (1986).

    CAS  Google Scholar 

  82. H. Ueno and M. Fujino, Eur. Patent Appl. 0236987 (1987).

    Google Scholar 

  83. C. S. Pande, M. Pelzig, and J. D. Glass, Proc. Natl. Acad. Sci. U.S.A. 77, 895 (1980).

    Article  PubMed  CAS  Google Scholar 

  84. J. D. Glass, R. Miller, and G. Wesolowski, in: Peptides Structure and Function (D. Rich, ed.), p. 209, Pierce Chemical Co., Rockford, IL (1981).

    Google Scholar 

  85. J. D. Glass, M. Pelzig, and C. S. Pande, in: Peptides 1978 (I. Z. Siemion and G. Kupryszewski, eds.), p. 235, Wroclav University Press, Poland (1979).

    Google Scholar 

  86. A. Sano, H. Maeda, Y. Kai, and K. Ono, Eur. Patent Appl. 0340741 (1989).

    Google Scholar 

  87. R. J. Goodson and N. V. Katre, Bio/Technology 8, 343 (1990).

    Article  PubMed  CAS  Google Scholar 

  88. S. Romani, W. Gohring, L. Moroder, and E. Wunsch, in: Chemistry of Peptides and Proteins (W. Voelter, E. Bayer, Y. A. Ovchinnikov, and E. Wunsch, eds.), Vol. 2, p. 29, Walter de Gruyter, Berlin (1984).

    Google Scholar 

  89. A. Pollak and G. M. Whitesides, J. Am. Chem. Soc. 98, 289 (1976).

    Article  CAS  Google Scholar 

  90. M. Kimura, Y. Matsumura, Y. Miyauchi, and H. Maeda, Proc. Soc. Exp. Biol. Med. 188, 364 (1988).

    Article  PubMed  CAS  Google Scholar 

  91. M. Urrutigoity and J. Souppe, Biocatalysis 2, 145 (1989).

    Article  CAS  Google Scholar 

  92. M.-T. Babonneau, R. Jacquier, R. Lazaro, and P. Viallefont, Tetrahedron Lett. 30, 2787 (1989).

    Article  CAS  Google Scholar 

  93. K. Yoshinaga, S. G. Shafer, and J. M. Harris, J. Bioact. Compatible Polym. 2, 49 (1987).

    Article  CAS  Google Scholar 

  94. C. Visco, C. A. Benassi, F. M. Veronese, and P. A. Maglioli, Il Farmaco 42, 549 (1987).

    CAS  Google Scholar 

  95. K. V. Savoca, A. Abuchowski, T. Van Es, F. F. Davis, and N. C. Palczuk, Biochem. Biophys. Acta 578, 47 (1979).

    Article  PubMed  CAS  Google Scholar 

  96. Y. Kamisaki, H. Wada, T. Yaguara, A. Matsushima, and Y. Inada, J. Pharmacol. Exp. Ther. 216, 410 (1981).

    PubMed  CAS  Google Scholar 

  97. T. Yoshimoto, T. Mihama, K. Takahashi, Y. Saito, Y. Tamaura, and Y. Inada, Biochem. Biophys. Res. Commun. 145, 908 (1987).

    Article  PubMed  CAS  Google Scholar 

  98. C. Pina, D. Clark, and H. Blanch, Biotechnol. Tech. 3, 333 (1989).

    Article  CAS  Google Scholar 

  99. A. Matsushima, M. Okada, and Y. Inada, FEBS Lett. 178, 275 (1984).

    Article  PubMed  CAS  Google Scholar 

  100. T. Nishio, K. Takahashi, T. Tsuzuki, T. Yoshimoto, Y. Kodera, A. Matsushima, Y. Saito, and Y. Inada, J. Biotechnol. 8, 39 (1988).

    Article  CAS  Google Scholar 

  101. Y. Inada, H. Nishimura, K. Takahashi, T. Yoshimoto, A. R. Saha, and Y. Inada, Biochem. Biophys. Res. Commun. 122, 845 (1984).

    Article  PubMed  CAS  Google Scholar 

  102. A. Matsushima, M. Okada, K. Takahashi, T. Yoshimoto, and Y. Inada, Biochem. Int. 11, 551 (1985).

    CAS  Google Scholar 

  103. Y. Kodera, K. Takahashi, H. Nishimura, A. Matsushima, Y. Saito, and Y. Inada, Biotechnol. Lett. 8, 881 (1986).

    Article  CAS  Google Scholar 

  104. J. S. Beckman, R. L. Minor, C. W. White, J. E. Repine, G. M. Rosen, and B. A. Freeman, J. Biol. Chem. 263, 6884 (1988).

    PubMed  CAS  Google Scholar 

  105. P. S. Pyatak, A. Abuchowski, and F. F. Davis, Res. Commun. Chem. Pathol. Pharmacol. 29, 113 (1980).

    PubMed  CAS  Google Scholar 

  106. P. McGoff, A. C. Baziotis, and R. Maskiewicz, Chem. Pharm. Bull. 36, 3079 (1988).

    Article  PubMed  CAS  Google Scholar 

  107. K. Miyata, Y. Nakagawa, M. Nakamura, T. Ito, K. Sugo, T. Fujita, and K. Tomoda, Agric. Biol. Chem. 52, 1575 (1988).

    Article  CAS  Google Scholar 

  108. A. Abuchowski and F. F. Davis, Biochem. Biophys. Acta 578, 41 (1979).

    Article  PubMed  CAS  Google Scholar 

  109. U. Bagert and K.-H. Rohm, Biochem. Biophys. Acta 999, 36 (1989).

    Article  PubMed  CAS  Google Scholar 

  110. H. Neumann and A. Lustig, Eur. J. Biochem. 109, 475 (1980).

    Article  PubMed  CAS  Google Scholar 

  111. M. Leonard and E. Dellacherie, Makromol. Chem. 189, 1809 (1988).

    Article  CAS  Google Scholar 

  112. S. Zalipsky, F. Albericio, and G. Barany, in: Peptides: Structure and Function (V. J. Hruby and K. H. Kopple, eds.), p. 257, Pierce Chemical Co., Rockford, IL (1985).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1992 Springer Science+Business Media New York

About this chapter

Cite this chapter

Zalipsky, S., Lee, C. (1992). Use of Functionalized Poly(Ethylene Glycol)s for Modification of Polypeptides. In: Harris, J.M. (eds) Poly(Ethylene Glycol) Chemistry. Topics in Applied Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-0703-5_21

Download citation

  • DOI: https://doi.org/10.1007/978-1-4899-0703-5_21

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-0705-9

  • Online ISBN: 978-1-4899-0703-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics