Abstract
Superoxide dismutase (SOD) from bovine erythrocytes was conjugated with sodium hyaluronate (HA) with a mean molecular weight of 106 to have greater anti-inflammatory activity in vivo. Amino groups of SOD were coupled with carboxyl groups in the hyaluronate molecule using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide. The HA-SOD conjugate was composed of 1.5 mol of SOD molecule per 1 mol of hyaluronate on the average, and retained 70% of the activity of unmodified SOD. The conjugate was essentially non-immunogenic in mice, and exhibited much higher anti-inflammatory activities than HA or SOD in models of inflammatory diseases such as ischemic oedema of the foot-pad in mice, carrageenin-induced pleurisy and adjuvant arthritis in rats.
Similar content being viewed by others
References
Brigham KL (1986) Chest 6: 859-63.
Gardner TJ, Stewart JR, Casale AS, Downey JM, Chambers DE (1983) Surgery 94: 423-27.
Suematsu M, Suzuki M, Kitahara T, Miura S, Suzuki K, Hibi T, Watanabe M, Nagata H, Asakura H, Tsuchiya M (1987) J Clin Lab Immunol 24: 125-28.
Oda T, Akaike T, Hamamoto T, Suzuki F, Hirano T, Maeda H (1989) Science 244: 974-76.
Inada Y, Matsushima A, Hiroto M, Nishimura H, Kodera Y (1995) Adv Biomed Engineer/Biotechnol 52: 130-50.
Inada Y, Kodera Y, Matsushima A, Nishimura H (1992) In Synthesis of Biocomposite Materials (Imanishi Y, ed) pp 85-108. Tokyo: CRC Press.
Pyatak PS, Abuchowski A, Davis SS (1980) Res Commun Chem Pathol Pharmacol 29: 113-27.
White CW, Jackson JH, Abuchowski A, Kazo GM, Mimmack RF, Berger EM, Freeman BA, McCord JM, Repine JE (1989) J Appl Physiol 66: 584-90.
Walther FJ, Nunez FL, David-Cu R, Hill KE (1993) Pediatr Res 33: 332-35.
Stone WC, Bjorling DE, Southard JH, Galbreath EJ, Lindsay WA (1992) Am J Vet Res 53: 2153-56.
Kawasaki S, Sugiyama S, Ishiguro N, Ozawa T, Miura T (1993) Eur Surg Res 25: 129-36.
Maksimenko AV, Petrov AD, Caliceti P, Konovalova GG, Grigoryeva EL, Schiavon O, Tischenko EG, Lankin VZ, Veronese FM (1995) Drug Delivery 2: 39-43.
Conforti A, Franco L, Milanino R, Velo GP, Boccu E, Largajolli E, Schiavon O, Veronese FM (1987) Pharmacol Res Commun 19: 287-94.
Sato H, Takahashi T, Ide H, Fukushima T, Tabata M, Sekine F, Kobayashi K, Negishi M, Miwa Y (1988) Arthr Rheum 31: 63-71.
Tanaka H, Kito Y, Katsuramaki T, Tanaka M, Kitabayashi M, Fujimori S, Umemoto J, Nanba K (1992) Folia Pharmacol Jpn 100: 77-86.
Yamada N, Uzuki M, Ohnuma E, Ishiyama T, Inoue H, Fukamachi T, Rikimaru A, Sawai T (1994) Jpn J Inflammation 14: 303-11.
Namiki O (1996) J Joint Surg 15: 113-19.
Steinman HM (1974) J Biol Chem 249: 7326-33.
Inoue Y, Nagasawa K (1982) Carbohydrate Res 111: 113-25.
Bitter T, Müir HM (1962) Anal Biochem 4: 330-34.
Lowry OH, Rosenbrough NJ, Farr AL, Randall RJ (1951) J Biol Chem 193: 265-75.
Habeeb AFSA (1966) Anal Biochem 14: 328-36.
McCord JM, Fridovich I (1969) J Biol Chem 244: 6049-55.
Voller A, Bidwell D, Bartlett A (1976) In Manual of Clinical Immunology (Rose NR and Friedman H, eds) pp 506-12. Washington DC: American Society for Microbiology.
Oyanagui Y, Sato S, Okajima T (1988) Free Rad Res Comms 4: 385-96.
Oh-ishi S, Tsuji N, Hayashi I (1989) Japan Pharmacol 50: 11-18.
Shingu M, Takahashi S, Suenaga Y, Ichibangase Y, Nobunaga M (1994) Rheumatol Int 14: 77-81.
Ohno H, Takayanagi N, Murase J, Iwata H (1983) Folia Pharmacol Jpn 82: 375-81.
Herp A (1980) In he Carbohydrates: Chemistry and Biochemistry, 2nd edition (Pigman W and Horton D, eds) vol 1B, pp 1276-97. New York: Academic Press.
Robert AG, Wai WM (1980) Arthr Reum 23: 445-62.
Yim MB, Chock PB, Stadtman ER (1990) Proc Natl Acad Sci º SA 87: 5006-10.
Sato K, Akaike T, Kohno M, MaedaH (1992) J Biol Chem 267: 25371-77.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sakurai, K., Miyazaki, K., Kodera, Y. et al. Anti-inflammatory activity of superoxide dismutase conjugated with sodium hyaluronate. Glycoconj J 14, 723–728 (1997). https://doi.org/10.1023/A:1018521501289
Issue Date:
DOI: https://doi.org/10.1023/A:1018521501289