Biodegradation, biodistribution and toxicity of chitosan

Advanced Drug Delivery Reviews - Tập 62 - Trang 3-11 - 2010
T. Kean1, M. Thanou2
1Case Western Reserve University, Orthopaedics Department, Cleveland, Ohio, 44106, USA
2King's College London, Pharmaceutical Sciences Division, London, SE1 9NH, United Kingdom

Tài liệu tham khảo

Onishi, 1999, Biodegradation and distribution of water-soluble chitosan in mice, Biomaterials, 20, 175, 10.1016/S0142-9612(98)00159-8 Tommeraas, 2001, Preparation and characterisation of fluorescent chitosans using 9-anthraldehyde as fluorophore, Carbohydr. Res., 336, 291, 10.1016/S0008-6215(01)00275-0 Hejazi, 2002, Stomach-specific anti-h. Pylori therapy. I: preparation and characterization of tetracyline-loaded chitosan microspheres, Int. J. Pharm., 235, 87, 10.1016/S0378-5173(01)00985-1 Richardson, 1999, Potential of low molecular mass chitosan as a DNA delivery system: biocompatibility, body distribution and ability to complex and protect DNA, Int. J. Pharm., 178, 231, 10.1016/S0378-5173(98)00378-0 Banerjee, 2002, Preparation, characterization and biodistribution of ultrafine chitosan nanoparticles, Int. J. Pharm., 243, 93, 10.1016/S0378-5173(02)00267-3 Soane, 1999, Evaluation of the clearance characteristics of bioadhesive systems in humans, Int. J. Pharm., 178, 55, 10.1016/S0378-5173(98)00367-6 Hsu, 2002, Free radical degradation of chitosan with potassium persulfate, Polym. Degrad. Stab., 75, 73, 10.1016/S0141-3910(01)00205-1 Zoldners, 2005, Influence of ascorbic acid on the stability of chitosan solutions, Carbohydr. Polym., 60, 215, 10.1016/j.carbpol.2005.01.013 KEGG Pathway, Amino sugar and nucleotide sugar metabolism. 2009, Kanehisa Laboratories. T. Kean, M. Thanou, Chitin and chitosan—sources, production and medical applications, in: P.A. Williams, R. Arshady (Eds.), Desk reference of Natural Polymers, their Sources, Chemistry and Applications, Kentus Books, London, 2009, pp. 327–361. Funkhouser, 2007, Chitinase family gh18: evolutionary insights from the genomic history of a diverse protein family, BMC Evol. Biol., 7, 96, 10.1186/1471-2148-7-96 Huet, 2008, X-ray structure of papaya chitinase reveals the substrate binding mode of glycosyl hydrolase family 19 chitinases, Biochemistry, 47, 8283, 10.1021/bi800655u Collinge, 1993, Plant chitinases, Plant J., 3, 31, 10.1046/j.1365-313X.1993.t01-1-00999.x Kasprzewska, 2003, Plant chitinases—regulation and function, Cell Mol. Biol. Lett., 8, 809 Yang, 2007, The controlling biodegradation of chitosan fibers by n-acetylation in vitro and in vivo, J. Mater. Sci. Mater. Med., 18, 2117, 10.1007/s10856-007-3013-x Xu, 1996, Chitosan film acylation and effects on biodegradability, Macromolecules, 29, 3436, 10.1021/ma951638b Correa, 1982, Endochitinase, a mannan-associated enzyme from Saccharomyces cerevisiae, J. Biol. Chem., 257, 1392, 10.1016/S0021-9258(19)68204-9 Molinari, 2007, Identification and partial characterisation of a chitinase from Nile tilapia, Oreochromis niloticus, Comp. Biochem. Physiol. B Biochem. Mol. Biol., 146, 81, 10.1016/j.cbpb.2006.09.004 Boot, 2001, Identification of a novel acidic mammalian chitinase distinct from chitotriosidase, J. Biol. Chem., 276, 6770, 10.1074/jbc.M009886200 Hartl, 2008, Acidic mammalian chitinase is secreted via an adam17/epidermal growth factor receptor-dependent pathway and stimulates chemokine production by pulmonary epithelial cells, J. Biol. Chem., 283, 33472, 10.1074/jbc.M805574200 Zhu, 2004, Acidic mammalian chitinase in asthmatic th2 inflammation and il-13 pathway activation, Science, 304, 1678, 10.1126/science.1095336 Stirling, 1974, Nn′-diacetylchitobiase activity in Tay–Sachs disease and Sandhoff's disease, Biochem. J., 141, 597, 10.1042/bj1410597 Kuranda, 1986, A di-n-acetylchitobiase activity is involved in the lysosomal catabolism of asparagine-linked glycoproteins in rat liver, J. Biol. Chem., 261, 5803, 10.1016/S0021-9258(17)38454-5 Hollak, 1994, Marked elevation of plasma chitotriosidase activity. A novel hallmark of Gaucher disease, J. Clin. Invest., 93, 1288, 10.1172/JCI117084 Renkema, 1995, Purification and characterization of human chitotriosidase, a novel member of the chitinase family of proteins, J. Biol. Chem., 270, 2198, 10.1074/jbc.270.5.2198 Malaguarnera, 2006, Chitotriosidase: the yin and yang, Cell. Mol. Life Sci., 63, 3018, 10.1007/s00018-006-6269-2 Senel, 2004, Potential applications of chitosan in veterinary medicine, Adv. Drug Deliv. Rev., 56, 1467, 10.1016/j.addr.2004.02.007 Zhang, 2002, In vitro degradation of chitosan by bacterial enzymes from rat cecal and colonic contents, Biomaterials, 23, 2761, 10.1016/S0142-9612(02)00011-X Lu, 2009, Controlling the degradation of covalently cross-linked carboxymethyl chitosan utilizing bimodal molecular weight distribution, J. Biomater. Appl., 23, 435, 10.1177/0885328208091661 Kafedjiiski, 2007, Evaluation of in vitro enzymatic degradation of various thiomers and cross-linked thiomers, Drug Dev. Ind. Pharm., 33, 199, 10.1080/03639040600762651 Rao, 1997, Use of chitosan as a biomaterial: studies on its safety and hemostatic potential, J. Biomed. Mater. Res., 34, 21, 10.1002/(SICI)1097-4636(199701)34:1<21::AID-JBM4>3.0.CO;2-P Kittur, 2003, Low molecular weight chitosans-preparation by depolymerization with Aspergillus niger pectinase, and characterization, Carbohydr. Res., 338, 1283, 10.1016/S0008-6215(03)00175-7 Kittur, 2005, Chitooligosaccharides—preparation with the aid of pectinase isozyme from Aspergillus niger and their antibacterial activity, Carbohydr. Res., 340, 1239, 10.1016/j.carres.2005.02.005 McConnell, 2008, An investigation into the digestion of chitosan (noncrosslinked and crosslinked) by human colonic bacteria, J. Pharm. Sci., 97, 3820, 10.1002/jps.21271 Verheul, 2009, Influence of the degree of acetylation on the enzymatic degradation and in vitro biological properties of trimethylated chitosans, Biomaterials, 30, 3129, 10.1016/j.biomaterials.2009.03.013 Ma, 2003, Collagen/chitosan porous scaffolds with improved biostability for skin tissue engineering, Biomaterials, 24, 4833, 10.1016/S0142-9612(03)00374-0 Ishihara, 2003, Controlled release of fibroblast growth factors and heparin from photocrosslinked chitosan hydrogels and subsequent effect on in vivo vascularization, J. Biomed. Mater. Res. A., 64, 551, 10.1002/jbm.a.10427 Langoth, 2006, Thiolated chitosans: design and in vivo evaluation of a mucoadhesive buccal peptide drug delivery system, Pharm. Res., 23, 573, 10.1007/s11095-005-9533-5 Hirano, 1988, Bio-compatibility of chitosan by oral and intravenous administrations Kato, 2000, Evaluation of n-succinyl-chitosan as a systemic long-circulating polymer, Biomaterials, 21, 1579, 10.1016/S0142-9612(00)00044-2 Suzuki, 1998, Biodistribution and kinetics of holmium-166-chitosan complex (dw-166hc) in rats and mice, J. Nucl. Med., 39, 2161 Banerjee, 2005, Labeling efficiency and biodistribution of technetium-99m labeled nanoparticles: interference by colloidal tin oxide particles, Int. J. Pharm., 289, 189, 10.1016/j.ijpharm.2004.09.022 Zhang, 2008, Pharmacokinetics, biodistribution, efficacy and safety of n-octyl-o-sulfate chitosan micelles loaded with paclitaxel, Biomaterials, 29, 1233, 10.1016/j.biomaterials.2007.11.029 Alexis, 2008, Factors affecting the clearance and biodistribution of polymeric nanoparticles, Mol. Pharmacol., 5, 505, 10.1021/mp800051m Gupta, 2005, Synthesis and surface engineering of iron oxide nanoparticles for biomedical applications, Biomaterials, 26, 3995, 10.1016/j.biomaterials.2004.10.012 Line, 2000, Reduction of background activity through radiolabeling of antifibrin fab′ with 99mtc-dextran, J. Nucl. Med., 41, 1264 Zhang, 2008, Biological evaluation of n-octyl-o-sulfate chitosan as a new nano-carrier of intravenous drugs, Eur. J. Pharm. Sci., 33, 415, 10.1016/j.ejps.2008.01.012 Kato, 2000, Biological fate of highly-succinylated n-succinyl-chitosan and antitumor characteristics of its water-soluble conjugate with mitomycin c at i.v. And i.p. administration into tumor-bearing mice, Biol. Pharm. Bull., 23, 1497, 10.1248/bpb.23.1497 Kumar, 2000, A review of chitin and chitosan applications, React. Funct. Polym., 46, 1, 10.1016/S1381-5148(00)00038-9 Xu, 2007, Mechanism study of chitosan on lipid metabolism in hyperlipidemic rats, Asia Pac. J. Clin. Nutr., 16, 313 Chae, 2005, Influence of molecular weight on oral absorption of water soluble chitosans, J. Control. Release, 102, 383, 10.1016/j.jconrel.2004.10.012 Zheng, 2007, Chitosan nanoparticle as gene therapy vector via gastrointestinal mucosa administration: results of an in vitro and in vivo study, Life Sci., 80, 388, 10.1016/j.lfs.2006.09.040 Ishii, 2001, Mechanism of cell transfection with plasmid/chitosan complexes, Biochim. Biophys. Acta, 1514, 51, 10.1016/S0005-2736(01)00362-5 Leong, 1998, DNA-polycation nanospheres as non-viral gene delivery vehicles, J. Control. Release, 53, 183, 10.1016/S0168-3659(97)00252-6 Park, 2003, Visualization of transfection of hepatocytes by galactosylated chitosan-graft-poly(ethylene glycol)/DNA complexes by confocal laser scanning microscopy, Int. J. Pharm., 257, 103, 10.1016/S0378-5173(03)00133-9 Janes, 2001, Chitosan nanoparticles as delivery systems for doxorubicin, J. Control. Release, 73, 255, 10.1016/S0168-3659(01)00294-2 Nam, 2009, Cellular uptake mechanism and intracellular fate of hydrophobically modified glycol chitosan nanoparticles, J. Control. Release, 135, 259, 10.1016/j.jconrel.2009.01.018 Dodane, 1998, Pharmaceutical applications of chitosan, Pharm. Sci. Technol. Today, 1, 246, 10.1016/S1461-5347(98)00059-5 Thanou, 2001, Oral drug absorption enhancement by chitosan and its derivatives, Adv. Drug Delivery Rev., 52, 117, 10.1016/S0169-409X(01)00231-9 Illum, 1998, Chitosan and its use as a pharmaceutical excipient, Pharm. Res., 15, 1326, 10.1023/A:1011929016601 Wedmore, 2006, A special report on the chitosan-based hemostatic dressing: experience in current combat operations, J. Trauma, 60, 655, 10.1097/01.ta.0000199392.91772.44 Carreño-Gómez, 1997, Evaluation of the biological properties of soluble chitosan and chitosan microspheres, Int. J. Pharm., 148, 231, 10.1016/S0378-5173(96)04847-8 Sgouras, 1990 Wan, 2004, Poly(amidoamine) salt form: effect on ph-dependent membrane activity and polymer conformation in solution, Biomacromolecules, 5, 1102, 10.1021/bm040007z Schipper, 1996, Chitosans as absorption enhancers for poorly absorbable drugs. 1: influence of molecular weight and degree of acetylation on drug transport across human intestinal epithelial (caco-2) cells, Pharm. Res., 13, 1686, 10.1023/A:1016444808000 Schipper, 1999, Chitosans as absorption enhancers of poorly absorbable drugs. 3: influence of mucus on absorption enhancement, Eur. J. Pharm. Sci., 8, 335, 10.1016/S0928-0987(99)00032-9 Thanou, 1999, Effects of n-trimethyl chitosan chloride, a novel absorption enhancer, on caco-2 intestinal epithelia and the ciliary beat frequency of chicken embryo trachea, Int. J. Pharm., 185, 73, 10.1016/S0378-5173(99)00126-X Kean, 2005, Trimethylated chitosans as non-viral gene delivery vectors: cytotoxicity and transfection efficiency, J. Control. Release, 103, 643, 10.1016/j.jconrel.2005.01.001 Baruch, 2006, Alginate–chitosan complex coacervation for cell encapsulation: effect on mechanical properties and on long-term viability, Biopolymers, 82, 570, 10.1002/bip.20509 Jumaa, 2002, A new lipid emulsion formulation with high antimicrobial efficacy using chitosan, Eur. J. Pharm. Biopharm., 53, 115, 10.1016/S0939-6411(01)00191-6 Guo, 2006, Novel derivatives of chitosan and their antifungal activities in vitro, Carbohydr. Res., 341, 351, 10.1016/j.carres.2005.11.002 Pujals, 2008, In vitro evaluation of the effectiveness and cytotoxicity of meglumine antimoniate microspheres produced by spray drying against Leishmania infantum, Parasitol. Res., 102, 1243, 10.1007/s00436-008-0901-z Hirano, 1991, Enhancement of serum lysozyme activity by injecting a mixture of chitosan oligosaccharides intravenously in rabbits, Agric. Biol. Chem., 55, 2623 Song, 1993, Conjugate of mitomycin c with n-succinyl-chitosan: in vitro drug release properties, toxicity and antitumor activity, Int. J. Pharm., 98, 121, 10.1016/0378-5173(93)90048-K Ono, 2000, Photocrosslinkable chitosan as a biological adhesive, J. Biomed. Mater. Res., 49, 289, 10.1002/(SICI)1097-4636(200002)49:2<289::AID-JBM18>3.0.CO;2-M Azad, 2004, Chitosan membrane as a wound-healing dressing: characterization and clinical application, J. Biomed. Mater. Res. B Appl. Biomater., 69, 216, 10.1002/jbm.b.30000 Ishihara, 2001, Acceleration of wound contraction and healing with a photocrosslinkable chitosan hydrogel, Wound Repair Regen., 9, 513, 10.1046/j.1524-475x.2001.00513.x Kim, 2006, Long-term clinical outcome of phase iib clinical trial of percutaneous injection with holmium-166/chitosan complex (milican) for the treatment of small hepatocellular carcinoma, Clin. Cancer Res., 12, 543, 10.1158/1078-0432.CCR-05-1730 Gades, 2003, Chitosan supplementation and fecal fat excretion in men, Obes. Res., 11, 683, 10.1038/oby.2003.97 Arai, 1968, Toxicity of chitosan, Bull. Tokai Reg. Fish. Res. Lab., 56, 89 Sonaje, 2009, In vivo evaluation of safety and efficacy of self-assembled nanoparticles for oral insulin delivery, Biomaterials, 30, 2329, 10.1016/j.biomaterials.2008.12.066 Illum, 1994, Chitosan as a novel nasal delivery system for peptide drugs, Pharm. Res., 11, 1186, 10.1023/A:1018901302450 FDA. Alphabetical listing of gras notices. 2009 [cited May 14th 2009]; Available from: http://www.cfsan.fda.gov/~rdb/opagras1.html. Brenner, 1978, Glomerular permselectivity: barrier function based on discrimination of molecular size and charge, Am. J. Physiol., 234, F455 Miyauchi, 2007, Characterization of lysozymes from three shellfish, Fish. Sci., 73, 1404 Garcia-Alonso, 1990, Purification and properties of beta-n-acetylhexosaminidase a from pig brain, Int. J. Biochem., 22, 645, 10.1016/0020-711X(90)90043-3 Sanon, 2005, N-acetyl-beta-d-hexosaminidase from Trichomonas vaginalis: substrate specificity and activity of inhibitors, Biomed. Pharmacother., 59, 245, 10.1016/j.biopha.2004.09.013 Akeboshi, 2007, Production of recombinant beta-hexosaminidase a, a potential enzyme for replacement therapy for Tay–Sachs and Sandhoff diseases, in the methylotrophic yeast Ogataea minuta, Appl. Environ. Microbiol., 73, 4805, 10.1128/AEM.00463-07 Fu, 2003, Characterization of three chitosanase isozymes isolated from a commercial crude porcine pepsin preparation, J. Agric. Food Chem., 51, 1042, 10.1021/jf020675g Andronopoulou, 2003, Purification and characterization of a new hyperthermostable, allosamidin-insensitive and denaturation-resistant chitinase from the hyperthermophilic archaeon thermococcus chitonophagus, Extremophiles, 7, 43, 10.1007/s00792-002-0294-3 Watanabe, 1999, Family 19 chitinases of streptomyces species: characterization and distribution, Microbiology, 145, 3353, 10.1099/00221287-145-12-3353 Wiwat, 1999, Purification and characterization of chitinase from Bacillus circulans no.4.1, Curr. Microbiol., 39, 134, 10.1007/s002849900434 Martinou, 2002, Expression, purification, and characterization of a cobalt-activated chitin deacetylase (cda2p) from Saccharomyces cerevisiae, Protein Expr. Purif., 24, 111, 10.1006/prep.2001.1547 Ye, 2009, Enhanced cytotoxicity of core modified chitosan based polymeric micelles for doxorubicin delivery, J. Pharm. Sci., 98, 704, 10.1002/jps.21464 Opanasopit, 2007, Effect of salt forms and molecular weight of chitosans on in vitro permeability enhancement in intestinal epithelial cells (caco-2), Pharm. Dev. Technol., 12, 447, 10.1080/10837450701555901 Mao, 2005, Synthesis, characterization and cytotoxicity of poly(ethylene glycol)-graft-trimethyl chitosan block copolymers, Biomaterials, 26, 6343, 10.1016/j.biomaterials.2005.03.036 Murata, 1997, Design of quaternary chitosan conjugate having antennary galactose residues as a gene delivery tool, Carbohydr. Polym., 32, 105, 10.1016/S0144-8617(96)00154-3