Abstract
Chitosan was modified by conjugating coupling with linolenic acid through the l-ethyl-3-(3-dimethylaminopropyyl) carbodiimide (EDC)-mediated reaction. The degree of substitution 1.8% (i.e. 1.8 linolenic acid group per 100 anhydroglucose units) was measured by 1H NMR. The critical aggregation concentration (CAC) of the self-aggregate of hydrophobically modified chitosan was determined by measuring the fluorescence intensity of the pyrene as a fluorescent probe. The CAC value in phosphate-buffered saline (PBS) solution (pH7.4) was 5 × 10−2 mgmL−1. The average particle size of self- aggregates of hydrophobically modified chitosan in PBS solution (pH7.4) was 210.8 nm with a unimodal size distribution ranging from 100 to 500 nm. Transmission electron microscopy (TEM) study showed that the formation of near spherical shape nanoparticles has enough structural integrity. The loading ability of hydrophibically modified chitosan (LA-chitosan) was investigated by using bovine serum albumin (BSA) as the model. The loading capacity of self-aggregated nanoparticles increases (19.85% ±0.04% to 37.57% ±0.25%) with the concentration of BSA (O.l–O.5 mgmL−1)
Similar content being viewed by others
References
Akiyoshi, K., 2002. Superamolecular design for biological applications: hydrophobic effects. Yui, N., ed., CRC Press, Boca Raton; London; New York; Washington, D.C., 13–24.
Akiyoshi, K., and J. Sunamoto, 1996. Supramolecular assembly hydrophobized polysaccharides. Superamolecular Sci., 3: 157–163.
Akiyoshi, K., S. Kobayashi, S. Shichibe, D. Mix, and M. Baudys, 1998. Self-assembled hydrogel nanoparticle of cholesterol-bearing pullulan as a carrier of protein drugs: complexation and stabilization of insulin. J. Control. Rel., 54: 313–320.
Amiji, M.M., 1995. Pyrene fluorescence study of chitosan self-association in aqueous solution. Carbohydr. Polym., 26: 211–213.
Calvo, P., C. Remunan-Lopez, J.L. Vila-Jato, and M.J. Alonso, 1997. Novel hydrophilic chitosan-polyethylene oxide nanoparticles as protein carriers. J. Appl. Polym. Sci., 63: 125–132.
Chen, X. G., C. M. Lee, and H. J. Park, 2003. O/W emulsification for the self-aggregation and nanoparticle formation of linoleic acid-modified chitosan in the aqueous system. J. Agric. Food Chem., 51: 3135–3139.
Hejazi, R., and M. Amiji, 2002. Polymer Biomaterials: Chitosan-based Delivery Systems: Physicochenical Properties and Pharmaceutical Applications. 2nd edition. Dumitriu. S., ed., Marcel Dekker, New York, 213–238.
Hjerde, R.J.N., K.M. Varum, H. Grasdalen, S. Tokura, and O. Smidsrød, 1997. Chemical composition of O-(carboxymethy)-chitins in relation to lysozyme degradation rates. Carbohyd. Polym., 34: 131–139.
Hwang, K.T., S.T. Jung, G.D. Lee, M.S. Chinnan, and Y.S. Park, 2002. Controlling molecular weight and degree of deacetylation of chitosan by response surface methodology. J. Agricul. Food Chem., 50: 1876–1882.
Jahreis, G., J. Kraft, F. Tischendorf, F. Schone, and C. V. Loeffelholz, 2000. Conjugated linoleic acids: physiological effects in animal and man with special regard to body composition. Eur. J. Lipid Sci. Technol., 102: 695–703.
Kalyanasundaram, K., and J. K. Thomas, 1977. Raman spectroscopy of uncomplexed valinomycin. 2. Nonpolar and polar solution. J. Am. Chem. Soc., 99: 2039–2044.
Kim, Y.H., S.H. Gihm, and C.R. Park, 2001. Structural characteristics of size-controlled self-aggregates of deoxycholic acid-modified chitosan and their application as a DNA delivery carrier. Bioconjugate Chem., 12: 932–938.
Ko, J.A., H.J. Park, Y.S. Hwang, and J.B. Park, 2003. Chitosan microparticle preparation for controlled drug release by response surface methology. J. Microencapsulation, 20: 791–797.
Lee, D.W., S.J. Park, J.B. Park, and H.J. Park, 2003. Preparation and release characteristics of polymer-coated and blended alginate microsphere. J. Microencapsulation, 20: 179–192.
Lee, K.Y., I.C. Kwon, Y.H. Kim, W.H. Jo, and S.Y. Jeong, 1998a. Preparation of chitosan self-aggregates as a gene delivery system. J. Control. Rel., 51: 213–220.
Lee, K.Y., W.H. Jo, I.C. Kwon, Y.H. Kim, and S.Y. Jeong, 1998b. Physicochemical characteristics of self-aggregates of hydrophobically modified chitosans. Langmuir, 14: 2 329–2 332.
Lee, K.Y., Y.H. Kim, I.C. Kwon, W.H. Jo, and S.Y. Jeong, 2000. Self-aggregates of deoxycholic acid-modified chitosan as a novel carrier of adriamycin Colloid. Polym Sci., 278: 1216–1219.
Liu, L., C. Li, X. Li, Z. Yuan, Y. An, et al, 2001. Biodegradable polylactide/poly(ethylene glycol)/polylactide triblock copolymer micelles as anticancer drug carriers. J. Appl. Polym. Sci., 80: 1976–1982.
Liu, W. G., X. Zhang, S. J. Sun, G. J. Sun, and K. D. Yao, 2003. N-Alkylated chitosan as a potential nonviral vector for gene transfection. Bioconjugate Chem., 14: 782–789.
Magny, B., I. Iliopolous, R. Zana, and R. Audebert, 1994. Mixed micelles formed by cationic surfactants and anionic hydrophobically modified polyelectrolytes. Langmuir, 10: 3180–3187.
Miwa, A., A. Ishibe, M. Nakano, T. Yamahira, and S. Itai, 1998. Development of novel chitosan derivatives as micellar carriers of taxol. Pharm. Res., 15: 1844–1850.
Na, K., T. B. Lee, K. H. Park, E. K. Shin, Y. B. Lee, et al., 2003. Self-assembled nanoparticles of hydrophobically-modified polysaccharide bearing vitamin H as a targeted anti-cancer drug delivery system. European J. Phar. Sci., 18: 165–173.
Nichifor, M., A. Lopes, A. Carpov, and E. Melo, 1999. Aggregation in water of dextran hydrophobically modified with bile acids. Macromolecules, 32: 7 078–7 085.
Nishikawa, T., K. Akiyoshi, and J. Sunamoto, 1996. Macromolecular complexation between bovine serum albumin and the self-assembled hydrogel nanoparticle of hydrophobized polysaccharides. J. Am. Chem. Soc., 118: 6110–6115.
Prabha, S., W. Z. Zhou, J. Panyam, and V. Labhasetwar, 2002. Size-dependency of nanoparticle-mediated gene transfection: studies with fractionated nanoparticles. Int. J. Pharm., 244: 105–115.
Ravi Kumar V., 2000. A review of chitin and chitosan applications. Reactive and Functional Polymers., 46: 1–27.
Sashiwa, H., and Y. Shigemasa, 1999. Chemical modification of chitin and chitosan 2: preparation and water soluble property of N-acylated or N-alkylated partially deacetylated chitins. Carbohydr. Polym., 39: 127–138.
Shigemasa, Y., H. Matsuura, H. Sashiwa, and H. Saimoto, 1996. Evaluation of different absorbance ratios from infrared spectroscopy for analyzing the degree of deacetylation in chitin. Int. J. Biol. Macromol., 18: 237–242.
Whitesides, G. M., J. P. Mathias, and C. T. Sato, 1991. Molecular self-assembly and nanochemistry- a chemical strategy for the synthesis of nanostructures. Science, 254: 1312–1319.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Liu, C., Desai Kashappa, G.H., Chen, X. et al. Preparation and charaterization of self-assembled nanoparticles based on linolenic-acid modified chitosan. J Ocean Univ. China 4, 234–239 (2005). https://doi.org/10.1007/s11802-005-0039-x
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11802-005-0039-x