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
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References
I. N. Topchieva, Usp. Khim. 49, 494.
N. Topchieva, Russ. Chem. Rev. 49, 260 (1980).
K. C. Ingham, Methods Enzymol. 104, 351 (1984).
H. Walter and G. Johansson, Anal. Biochem. 155, 215 (1986).
E. Merrill and E. W. Salzman, Am. Soc. Artif. Internal Organs J. 6, 60 (1983).
M. Mutter and E. Bayer, in: The Peptides (E. Gross and J. Meienhofer, eds.), Vol. 2, p. 285, Academic Press, New York (1979).
V. N. R. Pillai and M. Mutter, Acc. Chem. Res. 14, 122 (1981).
Y. Inada, K. Takahashi, T. Yoshimoto, A. Ajima, A. Matsushima, and Y. Saito, Trends in Biotechnol. 4, 190 (1986).
B. Mattiason, Methods Enzymol. 92, 498 (1983).
D. E. Brooks, K. A. Sharp, and S. J. Stocks, Makromol. Chem., Macromol. Symp. 17, 387 (1988).
A. Abuchowski and F. F. Davis, in: Enzymes as Drugs (J. Holsenberg and J. Roberts, eds.), p. 367, Wiley, New York (1981).
S. Dreborg and E. B. Åkerblom, Crit. Rev. Therap. Drug Carrier Syst. 6, 315 (1990).
J. M. Harris, J. Macromol. Sci., Rev. Macromol. Chem. Phys. C25, 325 (1985).
S. Zalipsky, C. Gilon, and A. Zilkha, J. Macromol. Sci. Chem. A21, 839 (1984).
S. Zalipsky, C. Gilon, and A. Zilkha, Eur. Polym. J. 19, 1177 (1983).
D. A. Herold, K. Keil, and D. E. Bruns, Biochem. Pharmacol. 38, 73 (1989).
H. F. Smyth, Jr., C. P. Carpenter, and C. S. Weil, J. Am. Pharm. Assoc. 39, 349 (1950).
A. J. Johnson, M. H. Karpatkin, and J. Newman, Br. J. Hematol. 21, 21 (1971).
C. B. Shaffer and F. H. Critchfield, J. Am. Pharm. Assoc. 36, 152 (1947).
E. C. Dittmann, Naunyn-Schmeideberg’s Arch. Pharmacol. 276, 199 (1973).
A. W. Richter and E. Åkerblom, Int. Arch. Allergy Appl. Immunol. 70, 124 (1983).
F. F. Davis, T. Van Es, and N. C. Palczuk, U.S. Patent 4,179,337 (1979).
E Kawai, CRC Crit. Rev. Biotechnol. 6, 273 (1987).
G. P. Royer and G. M. Ananthramaiah, J. Am. Chem. Soc. 101, 3394 (1979).
J. D. Glass, L. Silver, J. Sondheimer, C. S. Pande, and J. Coderre, Biopolymers 18, 383 (1979).
K. Ulbrich, J. Strohalm, and J. Kopecek, Makromol. Chem. 187, 1131 (1986).
P. Pasta, S. Riva, and G. Carrea, FEBS Lett. 236, 329 (1988).
A. Abuchowski, T. Van Es, N. C. Palczuk, and F. F. Davis, J. Biol. Chem. 252, 3578 (1977).
T. P. King, L. Kochoumian, and L. M. Lichtenstein, Arch. Biochem. Biophys. 178, 442 (1977)
T. P. King, L. Kochoumian, and N. Chiorazzi, J. Exp. Med. 149, 424 (1979).
Y. Ashihara, T. Kono, S. Yamazaki, and Y. Inada, Biochem. Biophys. Res. Commun. 93, 385 (1978).
H. F. Gaertner and A. J. Puigserver, Proteins 3, 130 (1988).
S. G. Shafer and J. M. Harris, J. Polym. Sci., Polym. Chem. Ed. 24, 375 (1986).
M. Z. Atassi, in: Immunochemistry of Proteins (M. Z. Atassi, ed.), Vol. 1, p. 1, Plenum Press, New York (1977).
K. J. Wieder, N. C. Palczuk, T. Van Es, and F. F. Davis, J. Biol. Chem. 254, 12579 (1979).
S. Davis, A. Abuchowski, Y. K. Park, and F. F. Davis, Clin. Exp. Immunol. 46, 649 (1981).
K. Yoshinaga and J. M. Harris, J. Bioact. Compatible Polym. 4, 17 (1989).
A. Matsushima, H. Nishimura, Y. Ashihara, Y. Yokota, and Y. Inada, Chem. Lett., 113 (1980).
H. Nishimura, K. Takahashi, K. Sakurai, K. Fujinuma, Y. Imamura, M. Ooba, and Y Inada, Life Sci. 33, 1467 (1983).
K. Takahashi, A. Ajima, T. Yoshimoto, M. Okada, A. Matsushima, Y. Tamaura, and Y. Inada, J. Org. Chem. 50, 3414 (1985).
C. C. Jackson, J. L. Charlton, K. Kuzminski, G. M. Lang, and A. H. Sehon, Anal. Biochem. 165, 114 (1987).
A. Yoshimoto, S. G. Chao, Y. Saito, I. Imamura, H. Wada, and Y Inada, Enzyme 36, 261 (1986).
M. Rubinstein, U.S. Patent 4,101,380 (1978).
M. Joppich and P. L. Luisi, Makromol. Chem. 180, 1381 (1979).
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).
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).
K. B. Hadley and P. H. Sato, Enzyme 42, 225 (1989).
K. Iwasaki, Y Iwashita, and T. Okami, U.S. Patent 4,670,417 (1987).
V. N. Katre, M. J. Knauf, and W. J. Laird, Proc. Natl. Acad. Sci. U.S.A. 84, 1487 (1987).
E. Boccu, R. Largajolli, and F. M. Veronese, Z. Naturforsch. 38c, 94 (1983).
D. Larwood and E. Szoka, J. Labelled Compd. Radiopharm. 21, 603 (1984).
C. O. Beauchamp, S. L. Gonias, D. P. Menapace, and S. V. Pizzo, Anal. Biochem. 131, 25 (1983).
L. Tondelli, M. Laus, A. S. Angeloni, and P. Ferruti, J. Controlled Release 1, 251 (1985).
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).
H. Berger and S. V. Pizzo, Blood 71, 1641 (1988).
F. M. Veronese, R. Largajolli, E. Boccu, C. A. Benassi, and O. Schiavon, Appl. Biochem. Biotechnol. 11, 141 (1985).
S. Zalipsky, Patent pending; S. Zalipsky, R. Seltzer, and S. Meron-Rudolph, Biotechnol. Appl. Biochem. 15, 100 (1992).
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).
A. Nathan, S. Zalipsky, and J. Kohn, Polym. Prepr., Am. Chem. Soc, Div. Polym. Chem. 31(2), 213 (1990).
A. Buckmann, M. Morr, and G. Johansson, Makromol. Chem. 182, 1379 (1981).
M. Leonard, J. Neel, and E. Dellacherie, Tetrahedron 40, 1581 (1984).
S. Zalipsky and G. Barany, J. Bioact. Compat. Polym. 5, 227 (1990).
G. Johansson, J. Chromatogr. 368, 309 (1986).
F. M. Veronese, P. Caliceti, A. Pastorino, O. Schiavon, L. Sartore, L. Banci, and L. M. Scolaro, J. Controlled Release 10, 145 (1989).
T. Yoshimoto, M. Nakata, S. Yamaguchi, T. Funada, Y. Saito, and Y. Inada, Biotechnol. Lett. 8, 771 (1986).
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).
K. Shimizu, T. Nakahara, and T. Kinoshita, U.S. Patent 4,495,285 (1985).
K. Shimizu, T. Nakahara, T. Kinoshita, J. Takatsuka, and M. Igarashi, U.S. Patent 4,640,835 (1987).
A. J. Garman and S. B. Kalindjian, FEBS Lett. 223, 361 (1987).
A. J. Garman, U.S. Patent 4,935,465 (1990).
T. P. King and C. Weiner, Int. J. Peptide Protein Res. 16, 147 (1980).
S. Zalipsky, F. Albericio, U. Slomczynska, and G. Barany, Int. J. Peptide Protein Res. 30, 740 (1987).
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).
K. Nilsson and K. Mosbach, Methods Enzymol. 104, 56 (1984).
C. Delgado, J. N. Patel, G. E. Francis, and D. Fisher, Biotechnol. Appl. Biochem. 12, 119 (1990).
P. Bohlen, S. Stein, W. Dairman, and S. Udenfriend, Arch. Biochem. Biophys. 155, 213 (1973).
S. J. Stocks, A. J. M. Jones, C. W. Ramey, and D. E. Brooks, Anal. Biochem. 154, 232 (1986).
A. S. E A. Habeeb, Anal. Biochem. 14, 328 (1966).
N. Yamasaki, A. Matsuo, and H. Isobe, Agric. Biol. Chem. 52, 2125 (1988).
L. Sartore, R Caliceti, O. Schiavon, P. Ferruti, E. Ranucci, and F. M. Veronese, Proc. Int. Symp. Control. Rel. Bioact. Mater. 17, 208 (1990).
S. Zalipsky and G. Barany, Polym. Prepr., Am. Chem. Soc, Div. Polym. Chem. 27(1), 1 (1986).
H. Ueno and M. Fujino, Eur. Patent Appl. 0236987 (1987).
C. S. Pande, M. Pelzig, and J. D. Glass, Proc. Natl. Acad. Sci. U.S.A. 77, 895 (1980).
J. D. Glass, R. Miller, and G. Wesolowski, in: Peptides Structure and Function (D. Rich, ed.), p. 209, Pierce Chemical Co., Rockford, IL (1981).
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).
A. Sano, H. Maeda, Y. Kai, and K. Ono, Eur. Patent Appl. 0340741 (1989).
R. J. Goodson and N. V. Katre, Bio/Technology 8, 343 (1990).
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).
A. Pollak and G. M. Whitesides, J. Am. Chem. Soc. 98, 289 (1976).
M. Kimura, Y. Matsumura, Y. Miyauchi, and H. Maeda, Proc. Soc. Exp. Biol. Med. 188, 364 (1988).
M. Urrutigoity and J. Souppe, Biocatalysis 2, 145 (1989).
M.-T. Babonneau, R. Jacquier, R. Lazaro, and P. Viallefont, Tetrahedron Lett. 30, 2787 (1989).
K. Yoshinaga, S. G. Shafer, and J. M. Harris, J. Bioact. Compatible Polym. 2, 49 (1987).
C. Visco, C. A. Benassi, F. M. Veronese, and P. A. Maglioli, Il Farmaco 42, 549 (1987).
K. V. Savoca, A. Abuchowski, T. Van Es, F. F. Davis, and N. C. Palczuk, Biochem. Biophys. Acta 578, 47 (1979).
Y. Kamisaki, H. Wada, T. Yaguara, A. Matsushima, and Y. Inada, J. Pharmacol. Exp. Ther. 216, 410 (1981).
T. Yoshimoto, T. Mihama, K. Takahashi, Y. Saito, Y. Tamaura, and Y. Inada, Biochem. Biophys. Res. Commun. 145, 908 (1987).
C. Pina, D. Clark, and H. Blanch, Biotechnol. Tech. 3, 333 (1989).
A. Matsushima, M. Okada, and Y. Inada, FEBS Lett. 178, 275 (1984).
T. Nishio, K. Takahashi, T. Tsuzuki, T. Yoshimoto, Y. Kodera, A. Matsushima, Y. Saito, and Y. Inada, J. Biotechnol. 8, 39 (1988).
Y. Inada, H. Nishimura, K. Takahashi, T. Yoshimoto, A. R. Saha, and Y. Inada, Biochem. Biophys. Res. Commun. 122, 845 (1984).
A. Matsushima, M. Okada, K. Takahashi, T. Yoshimoto, and Y. Inada, Biochem. Int. 11, 551 (1985).
Y. Kodera, K. Takahashi, H. Nishimura, A. Matsushima, Y. Saito, and Y. Inada, Biotechnol. Lett. 8, 881 (1986).
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).
P. S. Pyatak, A. Abuchowski, and F. F. Davis, Res. Commun. Chem. Pathol. Pharmacol. 29, 113 (1980).
P. McGoff, A. C. Baziotis, and R. Maskiewicz, Chem. Pharm. Bull. 36, 3079 (1988).
K. Miyata, Y. Nakagawa, M. Nakamura, T. Ito, K. Sugo, T. Fujita, and K. Tomoda, Agric. Biol. Chem. 52, 1575 (1988).
A. Abuchowski and F. F. Davis, Biochem. Biophys. Acta 578, 41 (1979).
U. Bagert and K.-H. Rohm, Biochem. Biophys. Acta 999, 36 (1989).
H. Neumann and A. Lustig, Eur. J. Biochem. 109, 475 (1980).
M. Leonard and E. Dellacherie, Makromol. Chem. 189, 1809 (1988).
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).
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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
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