Advertisement

Russian Chemical Bulletin

, Volume 61, Issue 4, pp 781–795 | Cite as

Chitosan conjugates with biologically active compounds: design strategies, properties, and targeted drug delivery

  • A. S. Berezin
  • E. A. Lomkova
  • Yu. A. Skorik
Reviews

Abstract

This review summarizes the current research on the development of biologically active polymer compounds based on chitosan and its derivatives; it systematizes approaches taken for the design of conjugates based on a given polymer, and it covers the latest trends in the development of targeted drug delivery systems. An analysis of published data shows that the conjugation of biologically active substances with chitosan and its derivatives results in promising materials for use as drug delivery systems and for the control of the properties of the biologically active substances.

Key words

polysaccharides chitin chitosan polymer modifications drug delivery systems polymer nanoparticles chemotherapy antioxidant activity antibacterial activity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    D. Labarre, G. Ponchel, C. Vauthier, Biomedical, Pharmaceutical Polymers, Pharmaceutical Press, London, Chicago, 2011.Google Scholar
  2. 2.
    R. Langer, Nature, 1998, 392, 5.Google Scholar
  3. 3.
    R. A. A. Muzzarelli, C. Muzzarelli, Polysaccharides 1: Structure, Characterization and Use, Springer-Verlag Berlin, Berlin, 2005, p. 151.Google Scholar
  4. 4.
    M. Kumar, R. A. A. Muzzarelli, C. Muzzarelli, H. Sashiwa, A. J. Domb, Chem. Rev., 2004, 104, 6017.CrossRefGoogle Scholar
  5. 5.
    T. Kean, M. Thanou, Adv. Drug Delivery Rev., 2010, 62, 3.CrossRefGoogle Scholar
  6. 6.
    I. A. Sogias, A. C. Williams, V. V. Khutoryanskiy, Biomacromolecules, 2008, 9, 1837.CrossRefGoogle Scholar
  7. 7.
    M. Rinaudo, Progress in Polymer Science, 2006, 31, 603.CrossRefGoogle Scholar
  8. 8.
    R. A. A. Muzzarelli, C. Muzzarelli, Chitosan in Pharmacy, Chemistry, Atec edizioni, Grottammare (Italy), 2002.Google Scholar
  9. 9.
    H. Sashiwa, S. I. Aiba, Progress in Polymer Science, 2004, 29, 887.CrossRefGoogle Scholar
  10. 10.
    J. H. Park, G. Saravanakumar, K. Kim, I. C. Kwon, Adv. Drug Delivery Rev., 2010, 62, 28.CrossRefGoogle Scholar
  11. 11.
    E. Lee, J. Lee, I. H. Lee, M. Yu, H. Kim, S. Y. Chae, S. Jon, J. Med. Chem., 2008, 51, 6442.CrossRefGoogle Scholar
  12. 12.
    F. Q. Hu, L. N. Liu, Y. Z. Du, H. Yuan, Biomaterials, 2009, 30, 6955.CrossRefGoogle Scholar
  13. 13.
    Y. Kato, H. Onishi, Y. Machida, Current Pharmaceutical Biotechnology, 2003, 4, 303.CrossRefGoogle Scholar
  14. 14.
    C. Dufes, A. G. Schatzlein, L. Tetley, A. I. Gray, D. G. Watson, J. C. Olivier, W. Couet, I. F. Uchegbu, Pharmaceutical Research, 2000, 17, 1250.CrossRefGoogle Scholar
  15. 15.
    C. Mura, D. Valenti, C. Floris, R. Sanna, M. A. De Luca, A. M. Fadda, G. Loy, Eur. J. Med. Chem., 2011, 46, 4142.CrossRefGoogle Scholar
  16. 16.
    N. Todorova, M. Krysteva, K. Maneva, D. Todorov, J. Bioactive and Compatible Polymers, 1999, 14, 178.Google Scholar
  17. 17.
    M. Kumar, Reactive Functional Polymers, 2000, 46, 1.CrossRefGoogle Scholar
  18. 18.
    V. Dodane, V. D. Vilivalam, Pharmaceutical Sci. Technol. Today, 1998, 1, 246.CrossRefGoogle Scholar
  19. 19.
    Y. Kato, H. Onishi, Y. Machida, Biomaterials, 2004, 25, 907.CrossRefGoogle Scholar
  20. 20.
    E. Vavrikova, J. Mandikova, F. Trejtnar, K. Horvati, S. Bosze, J. Stolarikova, J. Vinsova, Carbohydr. Polym., 2011, 83, 1901.CrossRefGoogle Scholar
  21. 21.
    J. Holappa, T. Nevalainen, P. Soininen, M. Elomaa, R. Safin, M. Masson, T. Jarvinen, Biomacromolecules, 2005, 6, 858.CrossRefGoogle Scholar
  22. 22.
    M. Masson, J. Holappa, M. Hjalmarsdottir, O. V. Runarsson, T. Nevalainen, T. Jarvinen, Carbohydr. Polym., 2008, 74, 566.CrossRefGoogle Scholar
  23. 23.
    M. K. S. Batista, M. Gallemi, A. Adeva, C. A. R. Gomes, P. Gomes, Synth. Commun., 2009, 39, 1228.CrossRefGoogle Scholar
  24. 24.
    J. Vinsova, E. Vavrikova, Current Pharmaceutical Design, 2008, 14, 1311.CrossRefGoogle Scholar
  25. 25.
    K. Hojo, M. Maeda, Y. Mu, H. Kamada, Y. Tsutsumi, Y. Nishiyama, T. Yoshikawa, K. Kurita, L. H. Block, T. Mayumi, K. Kawasaki, J. Pharm. Pharmacology, 2000, 52, 67.CrossRefGoogle Scholar
  26. 26.
    E. B. Denkbas, E. Ozturk, N. Ozdemir, K. Kececi, J. Biomaterials App., 2004, 18, 291.CrossRefGoogle Scholar
  27. 27.
    G. H. He, X. Chen, Y. H. Yin, H. Zheng, X. Xiong, Y. M. Du, Carbohydr. Polym., 2011, 83, 1274.CrossRefGoogle Scholar
  28. 28.
    H. Tang, P. Zhang, T. L. Kieft, S. J. Ryan, S. M. Baker, W. P. Wiesmann, S. Rogelj, Acta Biomaterialia, 2010, 6, 2562.CrossRefGoogle Scholar
  29. 29.
    K. Kurita, H. Yoshino, K. Yokota, M. Ando, S. Inoue, S. Ishii, S. I. Nishimura, Macromolecules, 1992, 25, 3786.CrossRefGoogle Scholar
  30. 30.
    H. Sashiwa, Y. Shigemasa, Carbohydr. Polym., 1999, 39, 127.CrossRefGoogle Scholar
  31. 31.
    X. X. Jin, J. T. Wang, J. Bai, Carbohydr. Res., 2009, 344, 825.CrossRefGoogle Scholar
  32. 32.
    Z. Guo, R. Xing, S. Liu, Z. Zhong, X. Ji, L. Wang, P. Li, Carbohydr. Res., 2007, 342, 1329.CrossRefGoogle Scholar
  33. 33.
    A. L. Kjoniksen, B. Nystrom, T. Nakken, O. Palmgren, T. Tande, Polymer Bull., 1997, 38, 71.CrossRefGoogle Scholar
  34. 34.
    K. Kurita, S. Mori, Y. Nishiyama, M. Harata, Polymer Bull., 2002, 48, 159.CrossRefGoogle Scholar
  35. 35.
    Y. Omura, Y. Taruno, Y. Irisa, M. Morimoto, H. Saimoto, Y. Shigemasa, Tetrahedron Lett., 2001, 42, 7273.CrossRefGoogle Scholar
  36. 36.
    F. H. Wang, D. R. Zhang, C. X. Duan, L. J. Jia, F. F. Feng, Y. Liu, Y. C. Wang, L. L. Hao, Q. A. Zhang, Carbohydr. Polym., 2011, 84, 1192.CrossRefGoogle Scholar
  37. 37.
    H. Onishi, Y. Saito, M. Sasatsu, Y. Machida, Intern. J. Pharmaceutics, 2011, 410, 17.CrossRefGoogle Scholar
  38. 38.
    A. Bernkop-Schnurch, M. E. Krajicek, J. Controlled Release, 1998, 50, 215.CrossRefGoogle Scholar
  39. 39.
    R. Smoum, A. Rubinstein, M. Srebnik, Bioconj. Chem., 2006, 17, 1000.CrossRefGoogle Scholar
  40. 40.
    M. Sato, H. Onishi, J. Takahara, Y. Machida, T. Nagai, Biol. Pharm. Bull., 1996, 19, 1170.CrossRefGoogle Scholar
  41. 41.
    S. K. Sahu, S. Maiti, T. K. Maiti, S. K. Ghosh, P. Pramanik, Macromolecular Biosci., 2011, 11, 285.CrossRefGoogle Scholar
  42. 42.
    Y. J. Son, J. S. Jang, Y. W. Cho, H. Chung, R. W. Park, I. C. Kwon, I. S. Kim, J. Y. Park, S. B. Seo, C. R. Park, S. Y. Jeong, J. Controlled Release, 2003, 91, 135.CrossRefGoogle Scholar
  43. 43.
    Y. Song, H. Onishi, T. Nagai, Chem. Pharm. Bull., 1992, 40, 2822.CrossRefGoogle Scholar
  44. 44.
    M. Werle, B. Loretz, D. Entstrasser, F. Foger, J. Drug Targeting, 2007, 15, 327.CrossRefGoogle Scholar
  45. 45.
    S. J. Yang, F. H. Lin, K. C. Tsai, M. F. Wei, H. M. Tsai, J. M. Wong, M. J. Shieh, Bioconj. Chem., 2010, 21, 679.CrossRefGoogle Scholar
  46. 46.
    V. B. Morris, C. P. Sharma, J. Colloid Interface Sci., 2010, 348, 360.CrossRefGoogle Scholar
  47. 47.
    C. E. Kast, C. Valenta, M. Leopold, A. Bernkop-Schnurch, J. Controlled Release, 2002, 81, 347.CrossRefGoogle Scholar
  48. 48.
    P. Yousefpour, F. Atyabi, E. Vasheghani-Farahani, A.-A. M. Movahedi, R. Dinarvand, Int. J. Nanomedicine, 2011, 6, 1977.Google Scholar
  49. 49.
    A. Ghanem, D. Skonberg, J. Appl. Polymer Sci., 2002, 84, 405.CrossRefGoogle Scholar
  50. 50.
    F.-L. Mi, S.-H. Yu, C.-K. Peng, H.-W. Sung, S.-S. Shyu, H.-F. Liang, M.-F. Huang, C.-C. Wang, Polymer, 2006, 47, 4348.CrossRefGoogle Scholar
  51. 51.
    D. G. Rando, C. A. Brandt, E. I. Ferreira, Revista Brasileira de Ciencias Farmaceuticas, 2004, 40, 335.Google Scholar
  52. 52.
    T. Schmitz, E. Grabovac, T. E. Palmberger, M. H. Hoffer, A. Bemkop-Schnurch, Int. J. Pharmaceutics, 2008, 347, 79.CrossRefGoogle Scholar
  53. 53.
    J. S. Park, T. H. Han, K. Y. Lee, S. S. Han, J. J. Hwang, D. H. Moon, S. Y. Kim, Y. W. Cho, J. Controlled Release, 2006, 115, 37.CrossRefGoogle Scholar
  54. 54.
    K. Kurita, H. Ikeda, Y. Yoshida, M. Shimojoh, M. Harata, Biomacromolecules, 2002, 3, 1.CrossRefGoogle Scholar
  55. 55.
    K. Kurita, H. Ikeda, M. Shimojoh, J. Yang, Polym. J., 2007, 39, 945.CrossRefGoogle Scholar
  56. 56.
    K. Kurita, H. Yoshino, S. I. Nishimura, S. Ishii, Carbohydr. Polym., 1993, 20, 239.CrossRefGoogle Scholar
  57. 57.
    C. Liu, H. Baumann, Carbohydr. Res., 2002, 337, 1297.CrossRefGoogle Scholar
  58. 58.
    C. H. Kim, J. W. Choi, H. J. Chun, K. S. Choi, Polymer Bull., 1997, 38, 387.CrossRefGoogle Scholar
  59. 59.
    P. Fernandez-Saiz, M. J. Ocio, J. M. Lagaron, Biopolymers, 2006, 83, 577.CrossRefGoogle Scholar
  60. 60.
    G. J. Tsai, W. H. Su, J. Food Protection, 1999, 62, 239.Google Scholar
  61. 61.
    H. Liu, Y. M. Du, X. H. Wang, L. P. Sun, Int. J. Food Microbiology, 2004, 95, 147.CrossRefGoogle Scholar
  62. 62.
    Y. L. Chen, C. C. Chou, Food Microbiology, 2005, 22, 29.CrossRefGoogle Scholar
  63. 63.
    I. M. Helander, E. L. Nurmiaho-Lassila, R. Ahvenainen, J. Rhoades, S. Roller, Int. J. Food Microbiology, 2001, 71, 235.CrossRefGoogle Scholar
  64. 64.
    L. Y. Zheng, J. A. F. Zhu, Carbohydr. Polym., 2003, 54, 527.CrossRefGoogle Scholar
  65. 65.
    N. Liu, X. G. Chen, H. J. Park, C. G. Liu, C. S. Liu, X. H. Meng, L. J. Yu, Carbohydr. Polym., 2006, 64, 60.CrossRefGoogle Scholar
  66. 66.
    S. Tokura, K. Ueno, S. Miyazaki, N. Nishi, Macromolecular Symposia, 1997, 120, 1.CrossRefGoogle Scholar
  67. 67.
    Y. J. Jeon, P. J. Park, S. K. Kim, Carbohydr. Polym., 2001, 44, 71.CrossRefGoogle Scholar
  68. 68.
    T. C. Yang, C. C. Chou, C. F. Li, Int. J. Food Microbiology, 2005, 97, 237.CrossRefGoogle Scholar
  69. 69.
    H. K. No, N. Y. Park, S. H. Lee, S. P. Meyers, Int. J. Food Microbiology, 2002, 74, 65.CrossRefGoogle Scholar
  70. 70.
    Z. S. Jia, D. F. Shen, W. L. Xu, Carbohydr. Res., 2001, 333, 1.CrossRefGoogle Scholar
  71. 71.
    W. M. Xie, P. X. Xu, W. Wang, Q. Liu, Carbohydr. Polym., 2002, 50, 35.CrossRefGoogle Scholar
  72. 72.
    R. Muzzarelli, R. Tarsi, O. Filippini, E. Giovanetti, G. Biagini, P. E. Varaldo, Antimicrobial Agents and Chemotherapy, 1990, 34, 2019.CrossRefGoogle Scholar
  73. 73.
    X. F. Liu, Y. L. Guan, D. Z. Yang, Z. Li, K. De Yao, J. Applied Polym. Sci., 2001, 79, 1324.CrossRefGoogle Scholar
  74. 74.
    L. C. Wang, X. G. Chen, D. Y. Zhong, Q. C. Xu, J. Materials Science-Materials in Medicine, 2007, 18, 1125.CrossRefGoogle Scholar
  75. 75.
    Y. A. Skorik, C. A. R. Gomes, M. Vasconcelos, Y. G. Yatluk, Carbohydr. Res., 2003, 338, 271.CrossRefGoogle Scholar
  76. 76.
    A. V. Pestov, Y. A. Skorik, G. Kogan, Y. G. Yatluk, J. Appl. Polym. Sci., 2008, 108, 119.CrossRefGoogle Scholar
  77. 77.
    R. Jayakumar, N. Nwe, S. Tokura, H. Tamura, Int. J. Biol. Macromolecules, 2007, 40, 175.CrossRefGoogle Scholar
  78. 78.
    R. H. Huang, Y. M. Du, L. S. Zheng, H. Liu, L. H. Fan, Reactive Functional Polymers, 2004, 59, 41.CrossRefGoogle Scholar
  79. 79.
    H. Caner, E. Yilmaz, O. Yimaz, Carbohydr. Polym., 2007, 69, 318.CrossRefGoogle Scholar
  80. 80.
    Y. Hu, Y. Du, J. Yang, J. F. Kennedy, X. Wang, L. Wang, Carbohydr. Polym., 2007, 67, 66.CrossRefGoogle Scholar
  81. 81.
    S. P. Chen, G. Z. Wu, H. Y. Zeng, Carbohydr. Polym., 2005, 60, 33.CrossRefGoogle Scholar
  82. 82.
    M. Krysteva, N. Todorova, K. Maneva, D. Todorov, C. Dimitrov, Biotechnology Biotechnological Equipment, 1997, 11, A30.Google Scholar
  83. 83.
    R. Mehvar, J. Controlled Release, 2000, 69, 1.CrossRefGoogle Scholar
  84. 84.
    Y. H. Song, H. Onishi, Y. Machida, T. Nagai, J. Controlled Release, 1996, 42, 93.CrossRefGoogle Scholar
  85. 85.
    Y. Nishiyama, T. Yoshikawa, K. Kurita, K. Hojo, H. Kamada, Y. Tsutsumi, T. Mayumi, K. Kawasaki, Chem. Pharm. Bull., 1999, 47, 451.CrossRefGoogle Scholar
  86. 86.
    Y. Zheng, Y. Yi, Y. P. Qi, Y. T. Wang, W. A. Zhang, M. Du, Bioorg. Med. Chem. Lett., 2006, 16, 4127.CrossRefGoogle Scholar
  87. 87.
    A. Zhu, T. Chen, L. Yuan, H. Wu, P. Lu, Carbohydr. Polym., 2006, 66, 274.CrossRefGoogle Scholar
  88. 88.
    Y. H. Song, H. Onishi, T. Nagai, Int. J. Pharmaceutics, 1993, 98, 121.CrossRefGoogle Scholar
  89. 89.
    L. Illum, Pharmaceutical Research, 1998, 15, 1326.CrossRefGoogle Scholar
  90. 90.
    O. Felt, P. Buri, R. Gurny, Drug Development Industrial Pharmacy, 1998, 24, 979.CrossRefGoogle Scholar
  91. 91.
    Y. H. Song, H. Onishi, T. Nagai, Biolog. Pharmaceut. Bull., 1993, 16, 48.CrossRefGoogle Scholar
  92. 92.
    T. Ouchi, M. Tada, M. Matsumoto, Y. Ohya, K. Hasegawa, Y. Arai, K. Kadowaki, S. Akao, T. Matsumoto, S. Suzuki, M. Suzuki, Reactive Functional Polymers, 1998, 37, 235.CrossRefGoogle Scholar
  93. 93.
    J. Cha, W. B. Lee, C. R. Park, Y. W. Cho, C. H. Ahn, I. C. Kwon, Macromolecular Research, 2006, 14, 573.CrossRefGoogle Scholar
  94. 94.
    C. Dufes, J. M. Muller, W. Couet, J. C. Olivier, I. F. Uchegbu, A. G. Schatzlein, Pharmaceutical Research, 2004, 21, 101.CrossRefGoogle Scholar
  95. 95.
    G. Kogan, Y. A. Skorik, I. Zitnanova, L. Krizkova, Z. Durackova, C. A. R. Gomes, Y. G. Yatluk, J. Krajcovic, Toxicology Applied Pharmacology, 2004, 201, 303.CrossRefGoogle Scholar
  96. 96.
    K. W. Kim, R. L. Thomas, Food Chem., 2007, 101, 308.CrossRefGoogle Scholar
  97. 97.
    P. J. Chien, F. Sheu, W. T. Huang, M. S. Su, Food Chem., 2007, 102, 1192.CrossRefGoogle Scholar
  98. 98.
    A. S. Koryagin, E. A. Erofeeva, N. O. Yakimovich, E. A. Aleksandrova, L. A. Smirnova, A. V. Mal’kov, Bull. Experiment. Biol. Med., 2006, 142, 461.CrossRefGoogle Scholar
  99. 99.
    R. Weerakkody, D. Labbett, L. J. Cheng, S. L. Kosaraju, Food Biophysics, 2011, 6, 127.CrossRefGoogle Scholar
  100. 100.
    J. C. Fernandes, P. Eaton, H. Nascimento, M. S. Giao, O. S. Ramos, L. Belo, A. Santos-Silva, M. E. Pintado, F. X. Malcata, Carbohydr. Polym., 2010, 79, 1101.CrossRefGoogle Scholar
  101. 101.
    M. Curcio, F. Puoci, F. Iemma, O. I. Parisi, G. Cirillo, U. G. Spizzirri, N. Picci, J. Agricultural Food Chem., 2009, 57, 5933.CrossRefGoogle Scholar
  102. 102.
    C. H. Peng, Y. T. Wang, Y. R. Tang, J. Appl. Polymer Sci., 1998, 70, 501.CrossRefGoogle Scholar
  103. 103.
    T. Feng, Y. Du, J. Li, Y. Wei, P. Yao, Eur. Food Research Technology, 2007, 225, 133.CrossRefGoogle Scholar
  104. 104.
    R. E. Xing, S. Liu, Z. Y. Guo, H. H. Yu, P. B. Wang, C. P. Li, Z. Li, P. C. Li, Bioorg. Med. Chem., 2005, 13, 1573.CrossRefGoogle Scholar
  105. 105.
    R. E. Xing, H. H. Yu, S. Liu, W. W. Zhang, Q. B. Zhang, Z. Li, P. C. Li, Bioorg. Med. Chem., 2005, 13, 1387.CrossRefGoogle Scholar
  106. 106.
    Z. Zhong, X. Ji, R. Xing, S. Liu, Z. Guo, X. Chen, P. Li, Bioorg. Med. Chem., 2007, 15, 3775.CrossRefGoogle Scholar
  107. 107.
    X. Ji, Z. Zhong, X. Chen, R. Xing, S. Liu, L. Wang, P. Li, Bioorg. Med. Chem. Lett., 2007, 17, 4275.CrossRefGoogle Scholar
  108. 108.
    B. O. Jung, S. J. Chung, S. B. Lee, J. Appl. Polymer Sci., 2006, 99, 3500.CrossRefGoogle Scholar
  109. 109.
    Z. Guo, H. Liu, X. Chen, X. Ji, P. Li, Bioorg. Med. Chem. Lett., 2006, 16, 6348.CrossRefGoogle Scholar
  110. 110.
    S. Mitra, U. Gaur, P. C. Ghosh, A. N. Maitra, J. Controlled Release, 2001, 74, 317.CrossRefGoogle Scholar
  111. 111.
    J. H. Park, S. Kwon, M. Lee, H. Chung, J. H. Kim, Y. S. Kim, R. W. Park, I. S. Kim, S. B. Seo, I. C. Kwon, S. Y. Jeong, Biomaterials, 2006, 27, 119.CrossRefGoogle Scholar
  112. 112.
    E. Lee, H. Kim, I. H. Lee, S. Jon, J. Controlled Release, 2009, 140, 79.CrossRefGoogle Scholar
  113. 113.
    S. Y. Chae, S. Son, M. Lee, M. K. Jang, J. W. Nah, J. Controlled Release, 2005, 109, 330.CrossRefGoogle Scholar
  114. 114.
    P. Chan, M. Kurisawa, J. E. Chung, Y. Y. Yang, Biomaterials, 2007, 28, 540.CrossRefGoogle Scholar
  115. 115.
    S. K. Sahu, S. K. Mallick, S. Santra, T. K. Maiti, S. K. Ghosh, P. Pramanik, J. Materials Sci.-Materials Med., 2010, 21, 1587.CrossRefGoogle Scholar
  116. 116.
    D. Bhattacharya, M. Das, D. Mishra, I. Banerjee, S. K. Sahu, T. K. Maiti, P. Pramanik, Nanoscale, 2011, 3, 1653.CrossRefGoogle Scholar
  117. 117.
    Z. H. Wang, Z. Y. Wang, C. S. Sun, C. Y. Wang, T. Y. Jiang, S. L. Wang, Biomaterials, 2010, 31, 908.CrossRefGoogle Scholar
  118. 118.
    Y. Zheng, Z. Cai, X. R. Song, B. Yu, Y. Q. Bi, Q. H. Chen, D. Zhao, J. P. Xu, S. X. Hou, Int. J. Pharmaceutics, 2009, 382, 262.CrossRefGoogle Scholar
  119. 119.
    V. B. Morris, C. P. Sharma, Int. J. Pharmaceutics, 2010, 389, 176.CrossRefGoogle Scholar
  120. 120.
    M. Dash, F. Chiellini, R. M. Ottenbrite, E. Chiellini, Progress Polym. Sci., 2011, 36, 981.CrossRefGoogle Scholar
  121. 121.
    Y. Ohya, M. Shiratani, H. Kobayashi, T. Ouchi, J. Macromolecular Sci.-Pure Appl. Chem., 1994, A31, 629.Google Scholar
  122. 122.
    C. C. Chiu, Y. T. Lin, S. L. Sun, K. H. Sung, L. F. Wang, J. Biomaterials Sci.-Polymer Ed., 2011, 22, 1487.CrossRefGoogle Scholar
  123. 123.
    R. D. Broadwell, B. J. Baker-Cairns, P. M. Friden, C. Oliver, J. C. Villegas, Experimental Neurology, 1996, 142, 47.CrossRefGoogle Scholar
  124. 124.
    J. Q. Wang, X. Y. Tao, Y. F. Zhang, D. Z. Wei, Y. H. Ren, Biomaterials, 2010, 31, 4426.CrossRefGoogle Scholar
  125. 125.
    B. Lu, D. Q. Wu, H. Zheng, C. Y. Quan, X. Z. Zhang, R. X. Zhuo, Molecular Biosystems, 2010, 6, 2529.CrossRefGoogle Scholar
  126. 126.
    E. M. Kim, H. J. Jeong, I. K. Park, C. S. Cho, C. G. Kim, H. S. Bom, J. Nuclear Medicine, 2005, 46, 141.Google Scholar
  127. 127.
    T. H. Kim, I. K. Park, J. W. Nah, Y. J. Choi, C. S. Cho, Biomaterials, 2004, 25, 3783.CrossRefGoogle Scholar
  128. 128.
    M. Hashimoto, M. Morimoto, H. Saimoto, Y. Shigemasa, T. Sato, Bioconj. Chem., 2006, 17, 309.CrossRefGoogle Scholar
  129. 129.
    S. E. Cook, I. K. Park, E. M. Kim, H. J. Jeong, T. G. Park, Y. J. Choi, T. Akaike, C. S. Cho, J. Controlled Release, 2005, 105, 151.CrossRefGoogle Scholar
  130. 130.
    A. H. Lin, Y. M. Liu, Y. Huang, J. B. Sun, Z. F. Wu, M. Zhang, Q. N. Ping, Int. J. Pharmaceutics, 2008, 359, 247.CrossRefGoogle Scholar
  131. 131.
    Y. Park, H. Y. Hong, H. J. Moon, B. H. Lee, I. S. Kim, I. C. Kwon, I. Rhee, J. Controlled Release, 2008, 128, 217.CrossRefGoogle Scholar
  132. 132.
    M. K. Yoo, S. K. Kang, J. H. Choi, I. K. Park, H. S. Na, H. C. Lee, E. B. Kim, N. K. Lee, J. W. Nah, Y. J. Choi, C. S. Cho, Biomaterials, 2010, 31, 7738.CrossRefGoogle Scholar
  133. 133.
    T. M. Allen, Nature Reviews Cancer, 2002, 2, 750.CrossRefGoogle Scholar
  134. 134.
    A. Gabizon, A. T. Horowitz, D. Goren, D. Tzemach, F. Mandelbaum-Shavit, M. M. Qazen, S. Zalipsky, Bioconj. Chem., 1999, 10, 289.CrossRefGoogle Scholar
  135. 135.
    Y. Y. Liang, L. M. Zhang, Biomacromolecules, 2007, 8, 1480.CrossRefGoogle Scholar
  136. 136.
    X. Y. Zhang, F. H. Chen, J. Z. Ni, Drug Delivery, 2009, 16, 280.CrossRefGoogle Scholar
  137. 137.
    E. E. Hassan, J. M. Gallo, J. Drug Targeting, 1993, 1, 7.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • A. S. Berezin
    • 1
  • E. A. Lomkova
    • 1
  • Yu. A. Skorik
    • 1
  1. 1.Saint Petersburg State Chemical Pharmaceutical AcademySaint PetersburgRussian Federation

Personalised recommendations