Synthesis and characterization of chitosan-based biomaterials modified with different active groups and their relationship with cytotoxicity

Yinghui Lv , Xiguang Chen , Qizhao Wang , Ye Wang , Jing Zhang , Chengsheng Liu , Chenguang Liu , Xianghong Meng , Lejun Yu

Journal of Wuhan University of Technology Materials Science Edition ›› 2007, Vol. 22 ›› Issue (4) : 695 -700.

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Journal of Wuhan University of Technology Materials Science Edition ›› 2007, Vol. 22 ›› Issue (4) : 695 -700. DOI: 10.1007/s11595-006-4695-5
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Synthesis and characterization of chitosan-based biomaterials modified with different active groups and their relationship with cytotoxicity

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Abstract

The cytotoxicity profile of three chitosan derivatives with different affinity to water was evaluated in vitro. The derivatives selected were carboxymethylated-chitosan (CMCH), linoleic acid modified-chitosan (LACH) and deoxycholic acid modified-chitosan (DACH), respectively, and the results of FTIR and NMR confirmed the successful modification. Cytotoxicity of these polymers was investigated via the red blood cell lysis assay and the MTT assay. The red blood cell lysis test showed that CH elicited a certain level of red blood cell toxicity, while CMCH, LACH and DACH all displayed low membrane damaging effects, with the hemolysis rates of 2.385%, 1.560% and 4.404%, respectively, which comes well within permissible limit (5%). The MTT assay revealed that CH exhibited significant inhibitory effect on fibroblast proliferation at higher concentration, while its three derivatives showed no cytotoxicity. CMCH had stimulatory effects on fetal mouse fibroblast proliferation. Differences in cytotoxicity of CH and its derivatives may result from the specific chemical modifications leading to the alteration of molecular charge density and type of the cationic functionalities, structure and sequence, and conformational flexibility.

Keywords

carboxymethylated-chitosan (CMCH) / linoleic acid modified-chitosan (LACH) / deoxycholic acid modified-chitosan (DACH) / cytotoxicity

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Yinghui Lv, Xiguang Chen, Qizhao Wang, Ye Wang, Jing Zhang, Chengsheng Liu, Chenguang Liu, Xianghong Meng, Lejun Yu. Synthesis and characterization of chitosan-based biomaterials modified with different active groups and their relationship with cytotoxicity. Journal of Wuhan University of Technology Materials Science Edition, 2007, 22(4): 695-700 DOI:10.1007/s11595-006-4695-5

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References

[1]

Ouchi T., Nishizawa H., Ohya Y. Aggregation Phenomenon of PEG-grafted Chitosan in Aqueous Solution[J]. Polymer, 1998, 39(21): 5171-5175.

[2]

Holme K. R., Perlin A. S. Chitosan N-sulfate. A Water-soluble Polyelectrolyte[J]. Carbohyd. Res., 1997, 302(1–2): 7-12.

[3]

Krause T. J., Goldsmith N. K., Ebner S., . An Inhibitor of Cell Proliferation Associated with Adhesion Formation is Suppressed by N,O-carboxymethyl Chitosan[J]. J. Invest. Surg., 1998, 11(2): 105-113.

[4]

Uchegbu I. F., Sadiq L., Arastoo M., . Quaternary Ammonium Palmitoyl Glycol Chitosan—a New Polysoap for Drug Delivery[J]. Int. J. Pharm., 2001, 224(1–2): 185-199.

[5]

Liu C. G., Desai K. G. H., Chen X. G., . Linolenic-Acid Modified Chitosan for Formation of Self-Assembled Nanoparticles[J]. J. Agr. Food. Chem., 2005, 53(2): 437-441.

[6]

Chen X. G., Lee C. M., Park H. J. O/W Emulsification for the Self-aggregation and Nanoparticle Formation of Linoleic Acid Modified Chitosan in the Aqueous System[J]. J. Agr. Food. Chem., 2003, 51(10): 3135-3139.

[7]

Lee K. Y., Kim Y. H., Kwon I. C., . Self-aggregates of Deoxycholic Acid-modified Chitosan as a Novel Carrier of Adriamycin[J]. Colloid. Polym. Sci., 2000, 278(12): 1216-1219.

[8]

Chen X. G., Wang Z., Liu W. S., . The Effect of Carboxymethyl-chitosan on Proliferation and Collagen Secretion of Normal and Keloid Skin Fibroblasts[J]. Biomaterials, 2002, 23(23): 4609-4614.

[9]

Kim K., Kwon S., Park J. H., . Physicochemical Characterizations of Self-assembled Nanoparticles of Glycol Chitosan-deoxycholic Acid Conjugates[J]. Biomacromolecules, 2005, 6(2): 1154-1158.

[10]

Lee K. Y., Known I. C., Kim Y. H., . Preparation of Chitosan Self-aggregates as a Gene Delivery System[J]. J. Control. Release., 1998, 51(2–3): 213-220.

[11]

Liu X. F., Guan Y. L., Yang D. Z., . Antibacterial Action of Chitosan and Carboxymethylated Chitosan[J]. J. Appl. Polym. Sci., 2001, 79(7): 1324-1335.

[12]

Lee K. Y., Jo W. H., Kwon I. C., . Structural Determination and Interior Polarity of Self-aggregates Prepared from Deoxycholic Acid-modified Chitosan in Water[J]. Macromolecules, 1998, 31: 378-383.

[13]

Rinaudo M., Dung P. L., Gey C., . Substituent Distribution on O, N-carboxymethylchitosans by 1H and 13C NMR[J]. In.t. J. Biol. Macromol., 1992, 14(3): 122-128.

[14]

Parnham M. J., Wetzig H. Toxicity Screening of Liposomes[J]. Chem. Phys. Lipids., 1993, 64(1–3): 263-274.

[15]

Hansen M. B., Nielsen S. E., BerK g. Re-examination and Further Development of a Precise and Rapid Dye Method for Measuring Cell Growth/Cell Kill[J]. J. Immunol. Methods, 1989, 119(2): 203-210.

[16]

Brugnerotto J., Lizardi J., Goycoolea F. M., . An Infrared Investigation in Relation with Chitin and Chitosan Characterization[J]. Polymer., 2001, 42(8): 3569-3580.

[17]

Chen X. G., Park H. J. Chemical Characteristics of O-carboxymethyl Chitosans Related to the Preparation Conditions[J]. Carbohyd. Polym., 2003, 53(4): 355-359.

[18]

Ragnhild J., Hjerde N., Varum K. M., . Chemical Composition of O-(carboxymethyl)-chitins in Relation to Lysozyme Degradation Rates[J]. Carbohyd. Polym., 1997, 34(3): 131-139.

[19]

Setchell K. D. R., Kritchevsky D., Nair P. P. The Bile Acid: Chemistry, Physiology, and Metabolism. Volume 4: Methods and Applications[M], 1988. New York: Plenum Press. 68

[20]

Rao S. B., Sharma C. P. Use of Chitosan as a Biomaterial: Studies on its Safety and Hemostatic Potential[J]. J. Biomed. Mater. Res., 1997, 34(1): 21-28.

[21]

Howling G. I., Dettmar P. W., Goddard P. A., . The Effect of Chitin and Chitosan on the Proliferation of Human Skin Fibroblasts and Keratinosytes in vitro[J]. Biomaterials, 2001, 22(22): 2959-2966.

[22]

Fischer D., Li Y., Ahlemeyer B., . In vitro Cytotoxicity Testing of Polycations: Influence of Polymer Structure on Cell Viability and Hemolysis[J]. Biomaterials, 2003, 24(7): 1121-1131.

[23]

Quinton P. M., Phillpot C. W. A Role for Anionic Sites in Epithelial Architecture. Effect of Cationic Polymers on Cell Membrane Structure[J]. J. Cell. Biol., 1973, 56(3): 787-796.

[24]

Dekie L., Toncheva V., Dubruel P., . Poly-L-glutamic Acid Derivatives as Vectors for Gene Therapy[J]. J. Control. Rel., 2000, 65(1–2): 187-202.

[25]

Choksakulnimitr S., Masuda S., Tokuda H., . In vitro Cytotoxicity of Macromolecules in Different Cell Culture Systems[J]. J. Control. Rel., 1995, 34(3): 233-241.

[26]

Ryser H. J. A Membrane Effect of Basic Polymers Dependent on Molecular Size[J]. Nature, 1967, 215(104): 934-936.

[27]

Hirano S., Noishiki Y., Kinugawa J. Chitin and Chitosan for use as Novel Biomedical Material[J]. Polym. Mater. Sci. Eng., 1985, 53: 649-653.

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