Chemical and Technological Advances in Chitins and Chitosans Useful for the Formulation of Biopharmaceuticals

Chitosan-Based Systems for Biopharmaceuticals: Delivery, Targeting and Polymer Therapeutics

Volumn , Issue , 2012, Pages 1-21

  Muzzarelli, Riccardo A A ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

Chitin and chitosan nanofibrils; Chitins and chitosans in biomedical applications; Chitins and chitosans, in biopharmaceutical formulation; Chitosan hydrogels, and new drug delivery systems; Chitosan nanosystems for hydrophilic, lipophilic drug delivery; Chitosan, as safe (GRAS) material; Chitosan, general aspects; Electrospun nanofibers; Novel strategies in ocular disorder treatment; Safety of chitins and chitosans

Indexed keywords

EID: 84885551237     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781119962977.ch1     Document Type: Chapter

References (108)

1. Muzzarelli, R.A.A., Boudrant, J., Meyer, D., Manno, N., DeMarchis, M. and Paoletti, M.G. (2011) Current views on fungal chitin/chitosan, human chitinases, food preservation, glucans, pectins and inulin: A tribute to Henri Braconnot, precursor of the carbohydrate polymers science, on the chitin bicentennial. Carbohydr. Polym., DOI information: 10.1016/j.carbpol.2011.09.063.
2. Kean, T. and Thanou, M. (2010) Biodegradation, biodistribution and toxicity of chitosan. Adv. Drug Deliv. Rev., 62, 3-11.
3. Bhattarai, N., Gunn, J. and Zhang, M. (2010) Chitosan-based hydrogels for controlled, localized drug delivery. Adv. Drug Deliv. Rev., 62, 83-99.
4. Carreira, A.S., Gonçalves, F.A.M.M., Mendonça, P.V. et al. (2010) Temperature and pH responsive polymers based on chitosan: applications and new graft copolymerization strategies based on living radical polymerization. Carbohydr. Polym., 80, 618-630.
5. de la Fuente, M., Ravina, M., Paolicelli, P. et al. (2010) Chitosan-based nanostructures: a delivery platform for ocular therapeutics. Adv. Drug Deliv. Rev., 62, 100-117.
6. Oyarzun-Ampuero, F.A., Garcia-Fuentes, M., Torres, D. and Alonso, M.J. (2010) Chitosan-coated lipid nanocarriers for therapeutic applications. J. Drug Deliv. Sci. Technol., 20, 259-265.
7. Bowman, K. and Leong, K.W. (2006) Chitosan nanoparticles for oral drug and gene delivery. Int. J. Nanomedicine, 1, 117-128.
8. Kim, I.Y., Seo, S.J., Moon, H.S. et al. (2008) Chitosan and its derivatives for tissue engineering applications. Biotechnol. Adv., 26, 1-21.
9. Chopra, S., Mahdi, S., Kaur, J. et al. (2006) Advances and potential applications of chitosan derivatives as mucoadhesive biomaterials in modern drug delivery. J. Pharm. Pharmacol., 58, 1021-1032.
10. Werle, M., Takeuchi, H. and Bernkop-Schnürch, A. (2009) Modified chitosans for oral drug delivery. J. Pharm. Sci., 98, 1643-1656.
11. Muzzarelli, R.A.A. and Muzzarelli, C. (2005) Chitin nanofibrils, in Chitin and Chitosan, Opportunities and Challenges (ed. P.K. Dutta), SSM International, Contai, India.
12. Muzzarelli, R.A.A. and Muzzarelli, C. (2009) Chitin and chitosan hydrogels, in Handbook of Hydrocolloids, 2nd edn (eds G.O. Phillips and P.A. Williams), Woodhead Publishing Ltd., Cambridge, UK.
13. Muzzarelli, R.A.A. (2009) Genipin-crosslinked chitosan hydrogels as biomedical and pharmaceutical aids. Carbohydr. Polym., 77, 1-9.
14. Muzzarelli, R.A.A. (2009) Chitins and chitosans for the repair of wounded skin, nerve, cartilage and bone. Carbohydr. Polym., 76, 167-182.
15. Muzzarelli, R.A.A. (2010) Chitosan scaffolds for bone regeneration, in Chitin, Chitosan and Their Derivatives: Biological Activities and Applications (ed. S.K. Kim), CRC Press, Boca Raton, FL, USA.
16. Muzzarelli, R.A.A. (2011) Chitosan composites with inorganics, morphogenetic proteins and stem cells, for bone regeneration. Carbohydr. Polym., 83, 1433-1445.
17. Muzzarelli, R.A.A. (2010) Enhanced biochemical efficacy of oligomeric and partially depolymerized chitosans, in Chitosan: Manufacture, Properties and Usages (ed. F. Columbus), Nova Publishers, Hauppauge, NY, USA.
18. Muzzarelli, R.A.A. (2011) Chitin nanostructures in living organisms, in Chitin Formation and Diagenesis (ed. N.S. Gupta), Springer Science, Dordrecht, Germany.
19. Jayakumar, R., Prabaharan, M., Nair, S.V. et al. (2010) Novel carboxymethyl derivatives of chitin and chitosan materials and their biomedical applications. Prog. Mater. Sci., 55, 675-709.
20. Liu, Z., Zhang, Z., Zhou, C. and Jiao, Y. (2010) Hydrophobic modifications of cationic polymers for gene delivery. Prog. Polym. Sci., 35, 1144-1162.
21. Kristiansen, K.A., Potthast, A. and Christensen, B.E. (2010) Periodate oxidation of polysaccharides for modification of chemical and physical properties. Carbohydr. Res., 345, 1264-1271.
22. Hamman, J.H. (2010) Chitosan based polyelectrolyte complexes as potential carrier materials in drug delivery systems. Mar. Drugs, 8, 1305-1322.
23. Kumari, A.,Yadav, S.K. andYadav, S.C. (2010) Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf. B Biointerfaces, 75, 1-18.
24. Jayakumar, R., Menon, D., Manzoor, K. et al. (2010) Biomedical applications of chitin and chitosan based nanomaterials-a short review. Carbohydr. Polym., 82, 227-232.
25. Zhang, J., Xia, W., Liu, P. et al. (2010) Chitosan modification and pharmaceutical/biomedical applications. Mar. Drugs, 8, 1962-1987.
26. Ogawa, K., Yui, T. and Okuyama, K. (2004) Three D structures of chitosan. Int. J. Biol. Macromol., 34, 1-8.
27. Yui, T., Taki, N., Sugiyama, J. and Hayashi, S. (2007) Exhaustive crystal structure search and crystal modeling of beta-chitin. Int. J. Biol. Macromol., 40, 336-344.
28. Muzzarelli, R.A. (2010) Chitins and chitosans as immunoadjuvants and non-allergenic drug carriers. Mar. Drugs, 8, 292-312.
29. Da Silva, C.A., Pochard, P., Lee, C.G. and Elias, J.A. (2010) Chitin particles are multifaceted immune adjuvants. Am. J. Respir. Crit. Care Med., 182, 1482-1491.
30. Amidi, M., Mastrobattista, E., Jiskoot, W. and Hennink, W.E. (2010) Chitosan-based delivery systems for protein therapeutics and antigens. Adv. Drug Deliv. Rev., 62, 59-82.
31. Baldrick, P. (2010) The safety of chitosan as a pharmaceutical excipient. Regul. Toxicol. Pharmacol., 56, 290-299.
32. Reichert, W.M., Visser, A.E., Swatloski, R.P. et al. (2001) Derivatization of chitin in room temperature ionic liquids. 222nd ACS National Meeting, Chicago, IL, USA.
33. Reichert, W.M., Visser, A.E., Swatloski, R.P. et al. (2001) Solubilization and derivatization of chitin in room temperature ionic liquids. 221st ACS National Meeting, San Diego, CA, USA.
34. Spear, S.K., Reichert,W.M., Swatloski, R.P. and Rogers, R.D. (2001) Ionic liquids as benign solvents for extraction of astaxanthin and solubilization of chitin. 221st ACS National Meeting, San Diego, CA, USA.
35. Swatloski, R.P., Spear, S.K., Holbrey, J.D. and Rogers, R.D. (2002) Dissolution of cellose with ionic liquids. J. Am. Chem. Soc., 124, 4974-4975.
36. Xie, H., Zhang, S. and Li, S. (2006) Chitin and chitosan dissolved in ionic liquids as reversible sorbents ofCO2. Green Chem., 8, 630-633.
37. Yamazaki, S., Takegawa, A., Kaneko, Y. et al. (2010) High/low temperature operation of electric double layer capacitor utilizing acidic cellulose-chitin hybrid gel electrolyte. J. Power Sources, 195, 6245-6249.
38. Yamazaki, S., Takegawa, A., Kaneko, Y. et al. (2010) Performance of electric double-layer capacitor with acidic cellulose-chitin hybrid gel electrolyte. J. Electrochem. Soc., 157, A203-A208.
39. Takegawa, A., Murakami, M.-A., Kaneko, Y. and Kadokawa, J.-I. (2010) Preparation of chitin/cellulose composite gels and films with ionic liquids. Carbohydr. Polym., 79, 85-90.
40. Prasad, K., Murakami, M.A., Kaneko, Y. et al. (2009) Weak gel of chitin with ionic liquid, 1-allyl-3-methylimidazolium bromide. Int. J. Biol. Macromol., 45, 221-225.
41. Wu, Y., Sasaki, T., Irie, S. and Sakurai, K. (2008) A novel biomass-ionic liquid platform for the utilization of native chitin. Polymer, 49, 2321-2327.
42. Wang, W.T., Zhu, J., Wang, X.L. et al. (2010) Dissolution behavior of chitin in ionic liquids. J. Macromol. Sci. B, 49, 528-541.
43. Qin, Y., Lu, X., Sun, N. and Rogers, R.D. (2010) Dissolution or extraction of crustacean shells using ionic liquids to obtain high molecular weight purified chitin and direct production of chitin films and fibers. Green Chem., 12, 968-971.
44. Zhang, Z., Li, C., Wang, Q. and Zhao, Z.K. (2009) Efficient hydrolysis of chitosan in ionic liquids. Carbohydr. Polym., 78, 685-689.
45. Mine, S., Izawa, H., Kaneko, Y. and Kadokawa, J. (2009) Acetylation of alpha-chitin in ionic liquids. Carbohydr. Res., 344, 2263-2265.
46. Liu, B.K., Wu, Q., Xu, J.M. and Lin, X.F. (2007) N-methylimidazole significantly improves lipase-catalysed acylation of ribavirin. Chem. Commun. (Camb)., 295-297.
47. Lu, X., Hu, J., Yao, X. et al. (2006) Composite system based on chitosan and room-temperature ionic liquid: direct electrochemistry and electrocatalysis of hemoglobin. Biomacromolecules, 7, 975-980.
48. Itoh, T., Nishimura, Y., Kashiwagi, M, and Onaka, M. (2003) Efficient lipase-catalyzed enantioselective acylation in an ionic liquid solvent system, in Ionic Liquids as Green Solvents, vol. 856 (eds R.D. Rogers and K.R. Seddon), American Chemical Society, Washington, DC, USA.
49. Park, S., Viklund, F., Hult, K. and Kazlauskas, R.J. (2003) Vacuum-driven lipase-catalysed direct condensation of L-ascorbic acid and fatty acids in ionic liquids: synthesis of a natural surface active antioxidant. Green Chem., 5, 715-719.
50. Ifuku, S., Nogi, M., Abe, K. et al. (2009) Preparation of chitin nanofibers with a uniform width as alpha-chitin from crab shells. Biomacromolecules, 10, 1584-1588.
51. Ifuku, S., Nogi, M., Yoshioka, M. et al. (2010) Fibrillation of dried chitin into 10-20 nm nanofibers by a simple grinding method under acidic conditions. Carbohydr. Polym., 81, 134-139.
52. Ifuku, S., Morooka, S., Morimoto, M. and Saimoto, H. (2010) Acetylation of chitin nanofibers and their transparent nanocomposite films. Biomacromolecules, 11, 1326-1330.
53. Fan, Y., Saito, T. and Isogai, A. (2008) Preparation of chitin nanofibers from squid pen beta-chitin by simple mechanical treatment under acid conditions. Biomacromolecules, 9, 1919-1923.
54. Watthanaphanit, A., Supaphol, P., Tamura, H. et al. (2008) Fabrication, structure, and properties of chitin whiskerreinforced alginate nanocomposite fibers. J. Appl. Polym. Sci., 110, 890-899.
55. Tzoumaki, M.V., Moschakis, T. and Biliaderis, C.G. (2010) Metastability of nematic gels made of aqueous chitin nanocrystal dispersions. Biomacromolecules, 11, 175-181.
56. Chang, P.R., Jian, R., Yu, J. and Ma, X. (2010) Starch-based composites reinforced with novel chitin nanoparticles. Carbohydr. Polym., 80, 421-426.
57. Watthanaphanit, A., Supaphol, P., Tamura, H. et al. (2010) Wet-spun alginate/chitosan whiskers nanocomposite fibers: preparation, characterization and release characteristic of the whiskers. Carbohydr. Polym., 79, 738-746.
58. Phongying, S., Aiba, S.-I. and Chirachanchai, S. (2007) Direct chitosan nanoscaffold formation via chitin whiskers. Polymer, 48, 393-400.
59. Fan, Y., Saito, T. and Isogai, A. (2010) Individual chitin nano-whiskers prepared from partially deacetylated a-chitin by fibril surface cationization. Carbohydr. Polym., 79, 1046-1051.
60. Hariraksapitak, P. and Supaphol, P. (2010) Preparation and properties of a-chitin-whisker-reinforced hyaluronangelatin nanocomposite scaffolds. J. Appl. Polym. Sci., 117, 3406-3418.
61. Hafner, A., Lovric, J.,Voinovich, D. and Filipovic-Grcic, J. (2009) Melatonin-loaded lecithin/chitosan nanoparticles: physicochemical characterisation and permeability through Caco-2 cell monolayers. Int. J. Pharm., 381, 205-213.
62. Yerlikaya, F., Aktas, Y. and Capan, Y. (2010) LC-UV determination of melatonin from chitosan nanoparticles. Chromatographia, 71, 967-970.
63. Kofuji, K., Nakamura, M., Isobe, T. et al. (2008) Stabilization of a-lipoic acid by complex formation with chitosan. Food Chem., 109, 167-171.
64. Muzzarelli, R.A.A., Morganti, P., Morganti, G. et al. (2007) Chitin nanofibrils/chitosan glycolate composites as wound medicaments. Carbohydr. Polym., 70, 274-284.
65. Azeredo, H.M., Mattoso, L.H.,Avena-Bustillos, R.J. et al. (2010) Nanocellulose reinforced chitosan composite films as affected by nanofiller loading and plasticizer content. J. Food Sci., 75, N1-N7.
66. Junkasem, J., Rujiravanit, R., Grady, B.P. and Supaphol, P. (2010) X-ray diffraction and dynamic mechanical analyses of a-chitin whisker-reinforced poly(vinyl alcohol) nanocomposite nanofibers. Polym. Int., 59, 85-91.
67. Jayakumar, R., Prabaharan, M., Nair, S.V. and Tamura, H. (2010) Novel chitin and chitosan nanofibers in biomedical applications. Biotechnol. Adv., 28, 142-150.
68. Yao, F., Chena, W., Wang, H. et al. (2003) A study on cytocompatible poly(chitosan-g-L-lactic acid). Polymer, 44, 6435-6441.
69. Toffey, A. and Classer, W.G. (1999) Chitin derivatives. II. Time-temperature-transformation cure diagrams of the chitosan amidization process. J. Appl. Polym. Sci., 73, 1879-1889.
70. Toffey, A., Samaranayake, G., Frazier, C.E. and Glasser, W.G. (1996) Chitin derivatives. I. Kinetics of the heatinduced conversion of chitosan to chitin. Journal of Applied Polymer Science, 60, 75-85.
71. Qu, X.,Wirsén, A. and Albertsson, A.C. (1999) Structural change and swelling mechanism of pH-sensitive hydrogels based on chitosan and D,L-lactic acid. J. Appl. Polym. Sci., 74, 3186-3192.
72. Qu, X., Wirsén, A., and Albertsson, A.C. (1999) Synthesis and characterization of pH-sensitive hydrogels based on chitosan and D,L-lactic acid. J. Appl. Polym. Sci., 74, 3193-3202.
73. Muzzarelli, R.A.A. and Muzzarelli, C. (2005) Chitosan chemistry: relevance to the biomedical sciences, in Advances in Polymer Science (ed. T. Heinze), Springer Verlag, Berlin, Germany.
74. Cooper, A., Bhattarai, N., Kievit, F.M. et al. (2011) Electrospinning of chitosan derivative nanofibers with structural stability in an aqueous environment. Phys. Chem. Chem. Phys. doi: 10.1039/C0CP02909B
75. Skotak, M., Leonov, A.P., Larsen, G. et al. (2008) Biocompatible and biodegradable ultrafine fibrillar scaffold materials for tissue engineering by facile grafting of L-lactide onto chitosan. Biomacromolecules, 9, 1902-1908.
76. Chen, J.W., Tseng, K.F., Delimartin, S. et al. (2008) Preparation of biocompatible membranes by electrospinning. Desalination, 233, 48-54.
77. Klossner, R.R., Queen, H.A., Coughlin, A.J. and Krause, W.E. (2008) Correlation of chitosan's rheological properties and its ability to electrospin. Biomacromolecules, 9, 2947-2953.
78. Seo, H., Matsumoto, H., Hara, S. et al. (2005) Preparation of polysaccharide nanofiber fabrics by electrospray deposition: additive effects of poly(ethylene oxide). Polym. J., 37, 391-398.
79. Lin, Y.C., Tan, F.J., Marra, K.G. et al. (2009) Synthesis and characterization of collagen/hyaluronan/chitosan composite sponges for potential biomedical applications. Acta Biomater., 5, 2591-2600.
80. Wu, Y., Hu, Y., Cai, J. et al. (2008) Coagulation property of hyaluronic acid-collagen/chitosan complex film. J. Mater. Sci. Mater. Med., 19, 3621-3629.
81. Chen, J., Li, Q., Xu, J. et al. (2005) Study on biocompatibility of complexes of collagen-chitosan-sodium hyaluronate and cornea. Artif. Organs, 29, 104-113.
82. He, P., Davis, S.S. and Illum, L. (1998) In vitro evaluation of the mucoadhesive properties of chitosan microspheres. Int. J. Pharm., 166, 75-88.
83. Snyman, D., Hamman, J.H. and Kotzé, A.F. (2003) Evaluation of the mucoadhesive properties of N-trimethyl chitosan chloride. Drug Dev. Ind. Pharm., 29, 61-69.
84. Sogias, I.A.,Williams, A.C. and Khutoryanskiy,V.V. (2008) Why is chitosan mucoadhesive? Biomacromolecules, 9, 1837-1842.
85. Luppi, B., Bigucci, F., Mercolini, L. et al. (2009) Novel mucoadhesive nasal inserts based on chitosan/hyaluronate polyelectrolyte complexes for peptide and protein delivery. J. Pharm. Pharmacol., 61, 151-157.
86. Bertram, U. and Bodmeier, R. (2006) In situ gelling, bioadhesive nasal inserts for extended drug delivery: in vitro characterization of a new nasal dosage form. Eur. J. Pharm. Sci., 27, 62-71.
87. Perioli, L., Ambrogi,V.,Venezia, L. et al. (2008) Chitosan and a modified chitosan as agents to improve performances of mucoadhesive vaginal gels. Colloids Surf. B Biointerfaces, 66, 141-145.
88. Giunchedi, P., Genta, I., Conti, B. et al. (1998) Preparation and characterization of ampicillin loaded methylpyrrolidinone chitosan and chitosan microspheres. Biomaterials, 19, 157-161.
89. Perioli, L., Ambrogi, V., Pagano, C. et al. (2009) FG90 chitosan as a new polymer for metronidazole mucoadhesive tablets for vaginal administration. Int. J. Pharm., 377, 120-127.
90. Muzzarelli, C., Tosi, G., Francescangeli, O. and Muzzarelli, R.A. (2003) Alkaline chitosan solutions. Carbohydr. Res., 338, 2247-2255.
91. Muzzarelli, C., Stanic, V., Gobbi, L. et al. (2004) Spray-drying of solutions containing chitosan together with polyuronans and characterisation of the microspheres. Carbohydr. Polym., 57, 73-82.
92. Gavini, E., Rassu, G., Muzzarelli, C. et al. (2008) Spray-dried microspheres based on methylpyrrolidinone chitosan as new carrier for nasal administration of metoclopramide. Eur. J. Pharm. Biopharm., 68, 245-252.
93. Colonna, C., Genta, I., Perugini, P. et al. (2006) 5-methyl-pyrrolidinone chitosan films as carriers for buccal administration of proteins. AAPS PharmSciTech, 7, 70.
94. Mattioli-Belmonte, M., Nicoli-Aldini, N., De Benedittis, A. et al. (1999) Morphological study of bone regeneration in the presence of 6-oxychitin. Carbohydr. Polym., 40, 23-27.
95. Muzzarelli, R.A.A., Muzzarelli, C., Cosani, A. and Terbojevich, M. (1999) 6-oxychitins, novel hyaluronan-like regiospecifically carboxylated chitins. Carbohydr. Polym., 39, 361-367.
96. Eaton, P., Fernandes, J.C., Pereira, E. et al. (2008) Atomic force microscopy study of the antibacterial effects of chitosans on Escherichia coli and Staphylococcus aureus. Ultramicroscopy, 108, 1128-1134.
97. Helander, I.M., Nurmiaho-Lassila, E.L., Ahvenainen, R. et al. (2001) Chitosan disrupts the barrier properties of the outer membrane of gram-negative bacteria. Int. J. Food Microbiol., 71, 235-244.
98. Li, X.-F., Feng, X.-Q., Yang, S. et al. (2010) Chitosan kills Escherichia coli through damage to be of cell membrane mechanism. Carbohydr. Polym., 79, 493-499.
99. Liu, H., Du, Y., Wang, X. and Sun, L. (2004) Chitosan kills bacteria through cell membrane damage. Int. J. Food Microbiol., 95, 147-155.
100. Muzzarelli, R., Tarsi, R., Filippini, O. et al. (1990) Antimicrobial properties of N-carboxybutyl chitosan. Antimicrob. Agents Chemother., 34, 2019-2023.
101. Tayel, A.A., Moussa, S., Opwis, K. et al. (2010) Inhibition of microbial pathogens by fungal chitosan. Int. J. Biol. Macromol., 47, 10-14.
102. Davydova, V.N., Bratskaya, S.Y., Gorbach, V.I. et al. (2008) Comparative study of electrokinetic potentials and binding affinity of lipopolysaccharides-chitosan complexes. Biophys. Chem., 136, 1-6.
103. Martinez, L.R., Mihu, M.R., Han, G. et al. (2010) The use of chitosan to damage Cryptococcus neoformans biofilms. Biomaterials, 31, 669-679.
104. Liu, H., Huang, N., Leng, Y. et al. (2010) Inhibition of bacterial adherence on the surface of biliary stent materials modified with chitosan. J. Wuhan Univ. Technol. Mater. Sci. Ed., 25, 795-798.
105. Saxena, S., Ray, A.R. and Gupta, B. (2010) Chitosan immobilization on polyacrylic acid grafted polypropylene monofilament. Carbohydr. Polym., 82, 1315-1322.
106. Muzzarelli, R.A.A. (2010) Chitosans: new vectors for gene therapy, in Handbook of Carbohydrate Polymers: Development, Properties and Applications (eds R. Ito and Y. Matsuo), Nova Publishers, Hauppauge, NY, USA.
107. Jayakumar, R., Chennazhi, K.P., Muzzarelli, R.A.A. et al. (2010) Chitosan conjugated DNA nanoparticles in gene therapy. Carbohydr. Polym., 79, 1-8.
108. Salem, M.L., Demcheva, M., Gillanders, W.E. et al. (2010) Poly-N-acetyl glucosamine gel matrix as a non-viral delivery vector for DNA-based vaccination. Anticancer Res., 30, 3889-3894.