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Preparation and charaterization of self-assembled nanoparticles based on linolenic-acid modified chitosan

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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)

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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.

    Google Scholar 

  • Akiyoshi, K., and J. Sunamoto, 1996. Supramolecular assembly hydrophobized polysaccharides. Superamolecular Sci., 3: 157–163.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • Amiji, M.M., 1995. Pyrene fluorescence study of chitosan self-association in aqueous solution. Carbohydr. Polym., 26: 211–213.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • Kalyanasundaram, K., and J. K. Thomas, 1977. Raman spectroscopy of uncomplexed valinomycin. 2. Nonpolar and polar solution. J. Am. Chem. Soc., 99: 2039–2044.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • Ravi Kumar V., 2000. A review of chitin and chitosan applications. Reactive and Functional Polymers., 46: 1–27.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

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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

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