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Acid glycosaminoglycans and their chemical modification

Abstract

The modern state of chemical modification of hyaluronic acid, chondroitin sulfates, and heparin is considered, and the possible application of modified glycosaminoglycans as potential drugs is discussed.

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Abbreviations

CS:

chondroitin sulfate

CS-4 and CS-6:

chondroitin-4 and chondroitin-6 sulfates

DS:

dermatan sulfate

EDC:

1-ethyl-3-[3-dimethylamino)propyl]carbodiimide

GlcA:

D-glucuronic acid

GlcNAc:

N-acetyl-D-glucosamine

HA:

hyaluronic acid

HEP:

heparin

GAG:

glycosaminoglycan

HONSu:

N-hydroxysuccinimide

IdoA and IdoA2S:

iduronic acid and its 2-sulfate

References

  1. Cowmen, M.K. and Matsuoka, S., Carbohydr. Res., 2005, vol. 340, no. (5), pp. 791–809.

    Article  CAS  Google Scholar 

  2. Prydz, K. and Dalen, K.T., J. Cell Sci., 2000, vol. 113, pp. 192–205.

    Google Scholar 

  3. Laurent, T.C. and Fraser, R.E., FASEB J., 1992, vol. 6, pp. 2398–2404.

    Google Scholar 

  4. Vercruysse, K.P. and Prestwich, G.D., Therapeutic Drug Carrier Systems, 1998, vol. 15, no. (5), pp. 513–555.

    CAS  Google Scholar 

  5. Fernandez, C., Hattan, C.M., and Kerns, R.J., Carbohydr. Res., 2006, vol. 341, no. (10), pp. 1253–1265.

    CAS  PubMed  Article  Google Scholar 

  6. Volpi, N., Curr. Med. Chem., 2006, vol. 13, pp. 1799–1810.

    CAS  PubMed  Article  Google Scholar 

  7. Carbohydrate analysis. A practical approach, Chaplin, M.F. and Kennedy, J.F., Eds., Oxford, Washington DC: IRL, 1986.

    Google Scholar 

  8. Sugahara, K., Schwartz, N., and Dorfman, A., J. Biol. Chem., 1979, vol. 254, pp. 6252–6261.

    CAS  PubMed  Google Scholar 

  9. van den Rijn, I., J. Bacteriol., 1983, vol. 156, pp. 1059–1065.

    PubMed  Google Scholar 

  10. Abetamann, V., Kern, H.F., and Elsaesser, H.-P., Clin. Cancer Res., 1996, vol. 2, pp. 1607–1618.

    CAS  PubMed  Google Scholar 

  11. Scott, J.E., Heatley, F., Moorcroft, D., and Olavesen, A.H., Biochem. J., 1981, vol. 199, pp. 829–832.

    CAS  PubMed  Google Scholar 

  12. Scott, J.E. and Heatley, F., Biochem. J., 1982, vol. 207, pp. 139–144.

    CAS  PubMed  Google Scholar 

  13. Scott, J.E. and Heatley, F., Biochem. J., 1984, vol. 220, pp. 197–205.

    CAS  PubMed  Google Scholar 

  14. Scott, J.E. and Heatley, F., Proc. Natl. Acad. Sci. USA, 1999, vol. 96, pp. 4850–4855.

    CAS  PubMed  Article  Google Scholar 

  15. Scott, J.E. and Heatley, F., Biomacromolecules, 2002, vol. 3, pp. 547–553.

    CAS  PubMed  Article  Google Scholar 

  16. Scott, J.E., Heatley, F., and Wood, B., Biochemistry, 1995, vol. 34, pp. 15 467–15 474.

    CAS  Google Scholar 

  17. Malmstrom, A., Biochem. J., 1991, vol. 198, pp. 669–675.

    Google Scholar 

  18. Scott, J.E., FASEB J., 1992, vol. 6, pp. 2639–2645.

    CAS  PubMed  Google Scholar 

  19. Ferro, D.R., Provasoli, A., and Ragazzi, M., Carbohydr. Res., 1990, vol. 195, pp. 157–167.

    CAS  PubMed  Article  Google Scholar 

  20. Forster, M.J. and Mulloy, B., Biopolymers, 1993, vol. 33, pp. 575–588.

    CAS  Article  Google Scholar 

  21. Hagner-McWhirter A., Lindahl, U., Li, J., Biochem. J., 2000, vol. 347, pp. 69–75.

    CAS  PubMed  Article  Google Scholar 

  22. Lindahl, U., Backstron, G., Thunberg, L., and Leder, I.G., Proc. Natl. Acad. Sci. USA, 1980, vol. 77, pp. 6551–6555.

    CAS  PubMed  Article  Google Scholar 

  23. Lindahl, U., Lidholt, K., Spillman, D., and Kjellen, L., Thrombosis Res., 1994, vol. 75, pp. 1–32.

    CAS  Article  Google Scholar 

  24. Ferro, D.R., Provasoli, A., Ragazzi, M., Torri, G., Casu, B., Gatti, G., Jasquinet, J.-C., Sinay, P., Petitou, M., and Choay, J., J. Am. Chem. Soc., 1986, vol. 108, pp. 6773–6778.

    CAS  Article  Google Scholar 

  25. Sanderson, P.N., Huckerby, T.N., and Nieduszynski, I.A., Biochem. J., 1987, vol. 243, pp. 175–181.

    CAS  PubMed  Google Scholar 

  26. Mulloy, B., Forster, M.J., Jones, Ch., and Davies, D.B., Biochem. J., 1993, vol. 293, pp. 849–858.

    CAS  PubMed  Google Scholar 

  27. Mikhailov, D., Mayo, K.H., Vlahov, I., Toida, T., Perlin, A., and Linhardt, R.J., Biochem. J., 1996, vol. 318, pp. 93–102.

    CAS  PubMed  Google Scholar 

  28. Mikhailov, D., Linhardt, R.J., and Mayo, K.H., Biochem. J., 1997, vol. 328, pp. 51–61.

    CAS  PubMed  Google Scholar 

  29. Hricovini, M., Guerrini, M., and Bisio, A., Eur. J. Biochem., 1999, vol. 261, pp. 789–801.

    CAS  PubMed  Article  Google Scholar 

  30. Mulloy, B. and Forster, M.J., Glycobiology, 2000, vol. 10, pp. 1147–1156.

    CAS  PubMed  Article  Google Scholar 

  31. Cavalieri, F., Chiessi, E., Paci, M., Paradossi, G., Flabiani, A., and Cesaro, A., Macromolecules, 2001, vol. 34, pp. 99–109.

    CAS  Article  Google Scholar 

  32. Hricovini, M., Guerrini, M., Bisio, A., Petitou, M., Torri, G., and Casu, B., Biochem. J., 2001, vol. 359, pp. 265–272.

    CAS  PubMed  Article  Google Scholar 

  33. Nieduszynski, I.A., Biochem. J., 1973, vol. 135, pp. 729–733.

    CAS  PubMed  Google Scholar 

  34. Scott, J.E. and Tigwell, M.J., Biochem. J., 1978, vol. 173, pp. 103–114.

    CAS  PubMed  Google Scholar 

  35. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya volna, 2005.

    Google Scholar 

  36. Johns, D.B., Rodgers, K.E., and Donahue, W.D., Fertil. Steril., 1997, vol. 68, no. 1, pp. 37–42.

    CAS  PubMed  Article  Google Scholar 

  37. Kyotaro, H., Jpn. Patent 63215617, 1988.

  38. Imperatori, D., EP Patent 0378519, 1990.

  39. Gazzani, G., EP Patent 297455, 1989.

  40. Bashkatov, S.A., Borisova, N.A., Davletov, E.G., Dzhemilev, U.M., Vakhitov, V.A., Alekhin, E.K., Shcheglov, A.N., Brazhenko, A.V., Ponedel’kina, I.Yu., Chemeris, A.V., Pakhomov, D.V., Valinurova, Yu.P., and Shemagomov, D.V., RF Patent 2130304, 1999.

  41. Borisova, N.A., Bashkatov, S.A., Davletov, E.G., Dzhemilev, U.M., Vakhitov, V.A., Alekhin, E.K., Shcheglov, D.V., Brazhenko, A.V., Ponedel’kina, I.Yu., Chemeris, A.V., Pakhomov, D.V., Tunik, V.F., and Naimushin, A.A., RF Patent 2140786, 1999.

  42. Damian, J.G., US Patent 5631242, 1997.

  43. Falk, R.E. and Asculai, S.S., US Patent No. 6114314, 2000.

  44. Samoilenko, I.I. and Samoilenko, O.I., RF Patent 2142898, 2000.

  45. Samoilenko, I.I., Samoilenko, O.I., Khorosheva, T.V., Mordvintseva, E.Yu., and Khmelenko, T.I., RF Patent 2182008, 2002.

  46. Ceschel, G.C., Maffei, P., Lombardi, B.S., Ronchi, C., and Rossi, C., Drug Dev. Ind. Pharm., 2001, vol. 27, pp. 541–547.

    CAS  PubMed  Article  Google Scholar 

  47. Matsumoto, Y., Yamamoto, I., Watanabe, Y., and Matsumoto, M., Biol. Pharm. Bull., 1995, vol. 18, pp. 1744–1749.

    CAS  PubMed  Google Scholar 

  48. Moor, A.R. and Willoughby, D.A., Int. J. Tissue React., 1995, vol. 17, no. 4, pp. 153–156.

    Google Scholar 

  49. Barabash, L.S., Barabash, N.A., and Zhuravleva, I.Yu., Bioprotezy klapanov serdtsa: problemy i perspektivy (Biological Protheses of Heart Valves: Problems and Proapects), Kemerovo: Kemerovskii poligrafkombinat, 1995.

    Google Scholar 

  50. Bychkov, S.M., Vopr. Med. Khim., 1981, no. 6, pp. 726–735.

  51. Lapierre, F., Holme, K., and Lam, L., Glycobiology, 1996, vol. 6, pp. 355–366.

    CAS  PubMed  Article  Google Scholar 

  52. Rider, C.C., Glyconj. J., 1997, vol. 14, pp. 639–642.

    CAS  Article  Google Scholar 

  53. Harrop, H.A. and Rider, C.C., Glycobiology, 1998, vol. 8, no. (2), pp. 131–137.

    CAS  PubMed  Article  Google Scholar 

  54. Crum, R., Szabo, S., and Folkman, J., Science, 1985, vol. 230, pp. 1375–1378.

    CAS  PubMed  Article  Google Scholar 

  55. Smith, P.K., Mallia, A.K., and Hermanson, G.T., Anal. Biochem., 1980, vol. 109, pp. 466–473.

    CAS  PubMed  Article  Google Scholar 

  56. Yazhebinski, Dzh. and Tonska, S., Acta. Pol. Pharm., 1986, vol. 43, pp. 454–460.

    Google Scholar 

  57. Ponedel’kina, I.Yu., Karabanov, Yu.P., Bashkatov, S.A., Vakhitov, V.A., Dzhemilev, U.M., Davletov, E.G., Gataullin, N.G., Kostromina, L.E., Izhbul’din, R.I., Kamalov, A.P., Chemeris, A.V., and Shchekin, S.V., RF Patent 2137507, 1999.

  58. Ponedel’kina, I.Yu., Karabanov, Yu.P., Bashkatov, S.A., Dzhemilev, U.M., Vakhitov, V.A., Davletov, E.G., Gataullin, N.G., Kamalov, A.P., Kostromina, L.E., Izhbul’din, R.I., Chemeris, A.V., and Shchekin, S.V., RF Patent 2152217, 2000.

  59. Ponedel’kina, I.Yu., Karabanov, Yu.P., Bashkatov, S.A., Dzhemilev, U.M., Vakhitov, V.A., Davletov, E.G., Gataullin, N.G., Kostromina, L.E., Izhbul’din, R.I., Chemeris, A.V., and Shchekin, S.V., RF Patent 2155593, 2000.

  60. Ponedel’kina, I.Yu., Sibagatullin, N.G., Bashkatov, S.A., Dzhemilev, U.M., Plechev, V.V., Gataullin, N.G., Abu Khashum Madzhid, M., Sufiyarova, R.Sh., and Parfenova, T.I., RF Patent No. 2241414, 2004.

  61. Diakun, G.P., Edwards, H.E., Allen, J.C., Phillips, G.O., and Gundall, R.B., Anal. Biochem., 1979, vol. 94, pp. 378–382.

    CAS  PubMed  Article  Google Scholar 

  62. Mabe, P., Valiente, A., Soto, V., Cornejo, V., and Raimann, E., Clin. Chim. Acta, 2004, vol. 345, pp. 135–140.

    CAS  PubMed  Article  Google Scholar 

  63. Tadashi, U., Yoshiaki, T., and Shinji, N., EP Patent 0544259 (1992).

  64. Denuziere, D., Ferrier, O., Damour, O., and Domard, A., Biomaterials, 1998, vol. 19, pp. 1275–1285.

    CAS  PubMed  Article  Google Scholar 

  65. Denuziere, A., Ferrier, D., and Domard, A., Carbohydr. Res., 1996, vol. 29, pp. 317–323.

    CAS  Google Scholar 

  66. Denuziere, A., Ferrier, D., and Damour, O., Ann. Pharm. Fr., 2000, vol. 58, pp. 47–53.

    CAS  PubMed  Google Scholar 

  67. Kofuji, K., Ito, T., Marata, Y., and Kawashima, S., Biol. Pharm. Bull., 2002, vol. 25, pp. 268–271.

    CAS  PubMed  Article  Google Scholar 

  68. Baumann, H. and Keller, R., J. Membr. Sci., 1991, vol. 61, pp. 253–268.

    CAS  Article  Google Scholar 

  69. Xinghang, M., Fazal, M.S., and Wan, K.S., J. Colloid Interface Sci., 1991, vol. 147, pp. 251–261.

    Article  Google Scholar 

  70. Scott, J.E., Biochem. J., 1961, vol. 81, pp. 418–424.

    CAS  PubMed  Google Scholar 

  71. Stacey, M. and Barker, S., Carbohydrates of Living Tissues, D. Van Nostrand Company, London, 1964. Translated under the title Uglevody zhivykh tkanei, Moscow: Mir, 1965.

    Google Scholar 

  72. You, N., Oya, T., and Sato, I., US Patent 6673919, 2004.

  73. Warren, C. and Manley, G., Clin. Chim. Acta, 1981, vol. 116, pp. 369–380.

    CAS  PubMed  Article  Google Scholar 

  74. Szeitli, J. And Dosa E., US Patent 4105760, 1978.

  75. Plate, N.A. and Vasil’ev, A.E., Fiziologicheski Aktivhye Polimery (Physiologically Active Polymers), Moscow: Khimiya, 1986.

    Google Scholar 

  76. D’sousa, A.J. and Topp, E.M., J. Pharm. Sci., 2004, vol. 93, pp. 1962–1979.

    Article  CAS  Google Scholar 

  77. Glass, J.R., Dickerson, K.T., Stecker, K., and Polarek, J.W., Biomaterials, 1996, vol. 17, pp. 1101–1109.

    CAS  PubMed  Article  Google Scholar 

  78. Keuren, J.F., Wielders, S.J., Driessen, A., Verhoever, M., Hendriks, M., and Lindhout, T., Arterioscler. Thromb. Vasc. Biol., 2004, vol. 24, pp. 613–617.

    CAS  PubMed  Article  Google Scholar 

  79. Jiang, B., Drouet, E., Milas, M., and Rinaudo, M., Carbohydr. Res., 2000, vol. 327, pp. 455–461.

    CAS  PubMed  Article  Google Scholar 

  80. Crescenzi, V., Francescangeli, A., Renier, D., and Bellini, D., Macromolecules, 2000, vol. 34, pp. 6367–6372.

    Article  CAS  Google Scholar 

  81. Cera, C., Terbojevich, M., Cosani, A., and Palumbo, M., Int. J. Biol. Macromol., 1988, vol. 10, pp. 66–73.

    CAS  Article  Google Scholar 

  82. Barbucci, R., Cialdi, G., and Magnani, A., WO Patent No. 39525751, 1995.

  83. Barbucci, R., Lamponi, S., Magnani, A., Poletti, L.F., Rhodes, N.P., Sobel, M., and Williams, D.F., J. Thromb. Thrombolysis, 1998, vol. 6, pp. 109–115.

    CAS  PubMed  Article  Google Scholar 

  84. Magnani, A., Albanese, A., Lamponi, S., and Barbucci, R., Thromb. Res., 1996, vol. 81, pp. 383–395.

    CAS  PubMed  Article  Google Scholar 

  85. Barbucci, R., Magnani, A., Lamponi, S., and Casolaro, M., Macromol. Symp., 1996, vol. 105, pp. 1–8.

    CAS  Google Scholar 

  86. Ogawa, D., Shikata, K., Matsuda, M., Akima, K., Iwahash, M., Okada, S., Tsuchiyama, Y., Shikata, Y., Wada, J., and Makino, H., Nephron. Exp. Nephrol., 2005, vol. 99, pp. 26–32.

    Article  CAS  Google Scholar 

  87. Cen, L., Neoh, K.G., Li, Y., and Kang, E.T., Biomacromolecules, 2004, vol. 5, pp. 2238–2246.

    CAS  PubMed  Article  Google Scholar 

  88. Chen, G., Ito, Y., Imanishi, Y., Magnani, A., Lamponi, S., and Barbucci, R., Bioconj. Chem., 1997, vol. 8, pp. 730–734.

    CAS  Article  Google Scholar 

  89. Nadkarni, V.D., Toida, T.G., Van, C.L., Schubert, R.L., Weiler, J.M., Hansen, K.P., Caldwell, E.O., and Linhart, R.J., Carbohydr. Res., 1996, vol. 290, pp. 87–96.

    CAS  PubMed  Article  Google Scholar 

  90. Maruyama, T., Toida, T., Imanari, T., Yu, G., and Linhard, R., Carbohydr. Res., 1998, vol. 306, pp. 35–43.

    CAS  PubMed  Article  Google Scholar 

  91. Yates, E.A., Santini, F., Guerrini, M., Naggi, A., Torri, G., and Casu, B., Carbohydr. Res., 1996, vol. 294, pp. 15–27.

    CAS  PubMed  Google Scholar 

  92. Toida, T., Maruyama, T., and Ogita, Y., Int. J. Biol. Macromol., 1999, vol. 26, pp. 233–241.

    CAS  PubMed  Article  Google Scholar 

  93. Mascellani, G., Liverani, L., Bianchini, P., Parma, B., Torri, G., Bisio, A., Guerrini, M., and Casu, B., Biochem. J., 1993, vol. 296, pp. 639–648.

    CAS  PubMed  Google Scholar 

  94. Bossennec, V., Petitou, M. and Perly, B., Biochem. J., 1990, vol. 267, pp. 625–630.

    CAS  PubMed  Google Scholar 

  95. Inoue, Y. and Nagasawa, K., Carbohydr. Res., 1976, vol. 46, pp. 87–95.

    CAS  PubMed  Article  Google Scholar 

  96. Baumann, H., Scheen, H., Huppertz, B., and Keller, R., Carbohydr. Res., 1998, vol. 308, pp. 381–388.

    CAS  PubMed  Article  Google Scholar 

  97. Hara, S., Yoshida, K., and Ishihara, M., US Patent 6545136, 2003.

  98. Hricovini, M., Guerrini, M., Torri, G., Piani, S., and Ungarelli, F., Carbohydr. Res., 1995, vol. 277, pp. 11–23.

    CAS  PubMed  Article  Google Scholar 

  99. Naggi, A., Cristofano, B., Bisio, A., Torri, G., and Casu, B., Carbohydr. Res., 2001, vol. 336, pp. 283–290.

    CAS  PubMed  Article  Google Scholar 

  100. Santini, F., Bisio, A., and Guerrini, M., Carbohydr. Res., 1997, vol. 302, pp. 103–108.

    CAS  Article  Google Scholar 

  101. Benedetti, L.M., Stella, V.J., and Topp, E.M., J. Controll. Rel., 1990, vol. 13, pp. 33–41.

    CAS  Article  Google Scholar 

  102. Kyyronen, K., Hume, L., Benedetti, L., Urtti, A., Topp, E., and Stella, V., Int. J. Pharm., 1992, vol. 80, p. 161.

    CAS  Article  Google Scholar 

  103. Hume, L., Topp, E.M., and Stella, V., Pharm. Res., 1990, vol. 7, p. 174.

    Google Scholar 

  104. Hunt, J.A., Joshi, H.N., Stella, V.J., and Topp, E.M., J. Controll. Rel., 1990, vol. 12, pp. 159–169.

    CAS  Article  Google Scholar 

  105. Ruiz-Cardona, L., Sanzgiri, Y.D., Benedetti, L.M., Stella, V.J., and Topp, E.M., Biomaterials, 1996, vol. 17, pp. 1639–1643.

    CAS  PubMed  Article  Google Scholar 

  106. Ishidami, Y., Gama, J., and Kawaguchi, Y., Jpn. Patent 03143540, 1991.

  107. Perbellini, A. and Ventura, C., Patent WO 2004063364, 2004.

  108. You, N., Oya, T., and Sato, I., Jpn. Patent 6673919, 2004.

  109. Takehisa, M., Minoo, M., and Katsukiyo, S., US Patent 5763504, 1998.

  110. Petitou, M., Lormeau, J.C., and Choay, J., Fr. Patent 2634485, 1990.

  111. Foley, K.M., Amaya, E., and Griffin, C.C., EP Patent 0256880, 1988.

  112. Barzu, T., Level, M., Petitou, M., Lormeau, J.C., Choay, J., Schols, D., Baba, M., Pauwels, R., Witvrouw, M., and De Clercq, E., J. Med. Chem., 1993, vol. 36, no. (23), pp. 3546–3555.

    CAS  PubMed  Article  Google Scholar 

  113. Sportoletty, G. and Baglioni, A., Fr. Patent 8112070, 1981.

  114. Sportoletty, G. and Pagella, P., US Patent 4717719, 1988.

  115. Lopalco, L., Ciccomascolo, F., Lanza, P., Zopetti, G., Caramazza, I., Leoni, F., Beretta, A., and Siccardi, A., AIDS Res. Hum. Retroviruses, 1994, vol. 10, pp. 87–93.

    Google Scholar 

  116. Franchesco, V. and Aurelio, R., EP Patent 0341745, 1989.

  117. Young, J.J., Cheng, K.M., Tsou, T.L., Liu, H.W., and Wang, H.J., J. Biomater. Sci. Polym. Ed., 2004, vol. 15, pp. 767–780.

    CAS  PubMed  Article  Google Scholar 

  118. Maelson, T. and Lindquist, B., WO Patent 9009401, 1990.

  119. Katukiyo, S., Yoshio, U., and Kenkyush, T. EP Patent 0161887, 1985.

  120. Tomihata, K. and Ikada, Y., J. Biomed. Mat. Res., 1997, vol. 37, pp. 243–251.

    CAS  Article  Google Scholar 

  121. Del Soldato, P., Torri, G., Bolla, M., Mazzoni, G., Monopoli, A., and Naggi, A., EP Patent 1340771, 2003.

  122. Bolla, M., Monopoli, A., Del Soldato, P., Torri, G., Naggi, A., and Cacu, B., EP Patent 1340772, 2003.

  123. Moczar, E. and Hornebeck, W., Int. J. Biol. Macromol., 1991, vol. 13,, pp. 261–262.

    CAS  PubMed  Google Scholar 

  124. Clayette, P., Moczar, E., Mabondzo, A., Martin, M., Toutain, B., Marce, D., and Dormont, D., AIDS Res. Hum. Retroviruses, 1996, vol. 12, pp. 63–69.

    CAS  PubMed  Article  Google Scholar 

  125. Kuo, J., Swann, D.A., and Prestwich, G.D., Bioconj. Chem., 1991, vol. 2, pp. 232–241.

    CAS  Article  Google Scholar 

  126. Taylor, R.L. and Conrad, H.E., Biochemistry, 1972, vol. 11, pp. 1383–1388.

    CAS  PubMed  Article  Google Scholar 

  127. Mikolajczyk, M. and Kielbasinsky, P., Tetrahedron, 1981, vol. 37, pp. 233–284.

    CAS  Article  Google Scholar 

  128. Williams, A. and Ibrahim, I.T., Chem. Rev., 1981, vol. 6, pp. 589–636.

    Article  Google Scholar 

  129. Nakajima, N. and Ikada, Y., Bioconj. Chem., 1995, vol. 6, pp. 123–130.

    CAS  Article  Google Scholar 

  130. Pouyani, T., Kuo, J., Harbison, G.S., and Prestwich, G.D., J. Am. Chem. Soc., 1992, vol. 114, pp. 5972–5976.

    CAS  Article  Google Scholar 

  131. Inoe, Y. and Nagasawa, K., Carbohydr. Res., 1982, vol. 111, pp. 113–125.

    Article  Google Scholar 

  132. Pouyani, T. and Prestwich, G.D., Bioconj. Chem., 1994, vol. 5, pp. 339–347.

    CAS  Article  Google Scholar 

  133. Bulpitt, C.A., Sherwood, Ch.H., and Sadozai, Kh.K., US Patent 6620927, 2003.

  134. Sadozai, K.K., Kuo, J.W., Sherwood, Ch.H., and Anica, T., US Patent 2002071855, 2002.

  135. Oliveira, G.B., Carvalho, L.B., and Silva, M.P., Biomaterials, 2003, vol. 24, pp. 4777–4783.

    CAS  PubMed  Article  Google Scholar 

  136. Pumphrey, C.Y., Theus, A.M., Li, Sh., Parrish, R.S., and Sanderson, R.D., Cancer Res., 2002, vol. 62, pp. 3722–3728.

    CAS  PubMed  Google Scholar 

  137. Akima, K., Iwata, Y., Matsuo, K., and Watari, N., EP Patent 0506976 B1, 1992.

  138. Akima, K., Ito, H., Iwata, Y., Matsuo, K., Watari, N., Yanagi, M., Hagi, H., Oshima, K., Yagita, A., Atomi, Y., and Tatekawa, I., J. Drug. Target, 1996, vol. 4, pp. 1–8.

    CAS  PubMed  Article  Google Scholar 

  139. Ogamo, A.K., Matzuzaki, K., Uchiyama, H., and Nagasawa, K., Carbohydr. Res., 1982, vol. 105, pp. 69–85.

    CAS  PubMed  Article  Google Scholar 

  140. Danishefsky, I. and Siskovic, E., Carbohydr. Res., 1971, vol. 16, pp. 199–201.

    CAS  Article  Google Scholar 

  141. Calias, P. and Miller, R. US Patent 6610669, 2003.

  142. Ponedel’kina, I.Yu., Odinokov, V.N., Vakhrusheva, T.S., Golikova, M.T., Khalilov, L.M., and Dzhemilev, U.M., Bioorg. Khim., 2005, vol. 31, pp. 90–95; Rus. J. Bioorg. Chem., 2005, vol. 31, pp. 82–86.

    PubMed  Google Scholar 

  143. Ponedel’kina, I.Yu., Khasanov, A.G., Kunafin, M.S., Mrikh, O.V., Bashkatov, S.A., Dzhemilev, U.M., Temirbulatov, V.M., Parfenova, T.I., Sufiyarova, R.Sh., and Kayumov, F.A., RF Patent 2191782, 2002.

  144. Ponedel’kina, I.Yu., Odinokov, V.N., Lukina, E.S., Tuumkina, T.V., Khalilov, L.M., and Dzhemilev, U.M., Bioorg. Khim., 2006, vol. 32, pp. 524–529; Rus. J. Bioorg. Chem., 2005, vol. 32, pp. 472–477.

    PubMed  Google Scholar 

  145. Prestwich, G.D., Marecak, D.M., Marecak, J.F., Vercruysse, K.P., and Ziebell, M.R., J. Controll. Rel., 1998, vol. 53, p. 99.

    Article  Google Scholar 

  146. Pouyani, T. and Prestwich, G.D., US Patent 5616568, 1997.

  147. Pouyani, T. and Prestwich, G.D., US Patent 5652347, 1997.

  148. Derbyshire, E.J., Yang, Y.C., Li, S., Comin, G.A., Belloir, J., and Thorpe, F.E., Biochim. Biophys. Acta, 1996, vol. 1310, pp. 86–96.

    PubMed  Article  Google Scholar 

  149. Kirker, K.R., Luo, Y., Nielson, J.H., Shelby, J., and Prestwich, G.D., Biomaterials, 2002, vol. 23, pp. 3661–3671.

    CAS  PubMed  Article  Google Scholar 

  150. Shu, X.Z., Liu, Y., Roberts, M.C., and Prestwich, G.D., Biomacromolecules, 2002, vol. 3, pp. 1304–1311.

    CAS  PubMed  Article  Google Scholar 

  151. Pouyani, T., Harbison, G.S., and Prestwich, G.D., J. Am. Chem. Soc., 1994, vol. 116, pp. 7515–7522.

    CAS  Article  Google Scholar 

  152. Vercruysse, K.P., Marecak, D.M., Marecak, J.F., and Prestwich, G.D., Bioconj. Chem, 1997, vol. 8, pp. 686–694.

    CAS  Article  Google Scholar 

  153. Chang, Ch.H., Liu, H.C., Lin, C.C., Chou, C.H., and Lin, F.H., Biomaterials, 2003, vol. 24, pp. 4853–4858.

    CAS  PubMed  Article  Google Scholar 

  154. Taguchi, T., Ikoma, T., and Tanaka, J., J. Biomed. Mater. Res., 2002, vol. 61, pp. 330–336.

    CAS  PubMed  Article  Google Scholar 

  155. Osborne, C.S., Barbenel, J.C., Smith, D., Savakis, M., and Grant, M.H., Med. Biol. Eng. Comput., 1998, vol. 36, pp. 129–134.

    CAS  PubMed  Article  Google Scholar 

  156. Zhang, L., Ma, D., Wang, F., and Zhang, Q., Artif. Cells Blood Substit. Immobil. Biotechnol., 2002, vol. 30, pp. 319–332.

    CAS  PubMed  Article  Google Scholar 

  157. Laemmel, E. and Penhoat, J., J. Biomed. Mater. Res., 1998, vol. 39, pp. 446–452.

    CAS  PubMed  Article  Google Scholar 

  158. Hennink, W.E., Feijen, J., Ebert, C.D., and Kim, S.W., Thromb. Res., 1983, vol. 29, pp. 1–13.

    CAS  PubMed  Article  Google Scholar 

  159. Chandy, T., Das, G.S., Wilson, R.F., and Rao, G.H., Int. J. Artif. Organs, 1999, vol. 22, pp. 547–558.

    CAS  PubMed  Google Scholar 

  160. Wissink, M.J., Beernink, R.A., Pieper, J.S., Poot, A.A., Engbers, G.H., Beugeling, T.L., van Aken, W.G., and Feijen, J., Biomaterials, 2001, vol. 22, pp. 151–163.

    CAS  PubMed  Article  Google Scholar 

  161. Sakurai, K., Miyazaki, K., Kodera, Y., Nishimura, H., Shingi, M., and Inada, Y., Glycoconj. J., 1997, vol. 14, pp. 723–728.

    CAS  PubMed  Article  Google Scholar 

  162. Wang, A., Cao, T., Tang, H., Liang, X., Salley, S.O., and Ng, K.Y., Colloid. Surf. Biointerfaces, 2005, vol. 43, pp. 245–255.

    CAS  Article  Google Scholar 

  163. Venkataramani, E.S., Senatore, F.A., Feola, M.L., and Tran, R.M., Surgery, 1986, vol. 6, pp. 735–741.

    Google Scholar 

  164. Zhao, Y., Zhao, R., Shangguan, D., Xiong, S., and Liu, G., Biomed. Chromatogr, 2001, vol. 15, pp. 487–492.

    CAS  PubMed  Article  Google Scholar 

  165. Akima, K., Iwata, Y., Matsuo, K., and Warari, N., US Patent 5733891, 1998.

  166. Luo, Y. and Prestwich, G.D., Bioconjug. Chem., 2001, vol. 12, pp. 1085–1088.

    CAS  PubMed  Article  Google Scholar 

  167. Luo, Y.K. and Prestwich, G.D., Bioconjug. Chem., 1999, vol. 10, pp. 755–763.

    CAS  PubMed  Article  Google Scholar 

  168. Moon, H.T., Lee, Y.K., Han, J.K., and Byun, Y., Biomaterials, 2001, vol. 22, pp. 281–289.

    CAS  PubMed  Article  Google Scholar 

  169. Byun, Y. and Moon, H.T., WO Patent 0234312, 2002.

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Correspondence to I. Yu. Ponedel’kina.

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Original Russian Text © I.Yu. Ponedel’kina, E.S. Lukina, V.N. Odinokov, 2008, published in Bioorganicheskaya Khimiya, 2008, Vol. 34, No. 1, pp. 5–28.

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Ponedel’kina, I.Y., Lukina, E.S. & Odinokov, V.N. Acid glycosaminoglycans and their chemical modification. Russ J Bioorg Chem 34, 1–23 (2008). https://doi.org/10.1134/S1068162008010019

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Key words

  • acid glycosaminoglycans
  • chemical modification
  • properties
  • application