Synthesis and Biological Activity of Drug Delivery System Based on Chitosan Nanocapsules
Affiliation(s)
1 Department of Chemistry, College of Science, King Faisal University, Hofuf, Kingdom of Saudi Arabia. 2 Textile Research Division, National Research Center, Cairo, Egypt. 3 Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt.
1 Department of Chemistry, College of Science, King Faisal University, Hofuf, Kingdom of Saudi Arabia. 2 Textile Research Division, National Research Center, Cairo, Egypt. 3 Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt.
ABSTRACT
Chitosan nanocapsules containing naproxen as an active ingredient were synthesized by ionic gelation method in presence of polyanion tripolyphosphate as a crosslinker. The morphology and diameter of the prepared chitosan nanoparticles was characterized using scanning electron microscopy and transition electron microscopy. Different factors affecting on the size diameter of chitosan nanoparticles such as stirring time and temperature, pH values as well as chitosan concentration were studied. Different factors affecting on the immobilization of naproxen into chitosan nanoparticles such as time, temperature and pH values were optimized. Synthesized naproxen/chitosan nanocapsules were assessed against both Gram positive bacterial strain such as Bacillus subtilis and Staphylococcus aureus and Gram negative bacterial strain such as Pseudomonas aeruginosa and Escherichia coli. Also, the antifungal activity of the naproxen/chitosan nanocapsules against Saccharomyces cerevisiae was demonstrated. Super oxide dismutase like activity of naproxen/chitosan nanocapsules will be determined.
Chitosan nanocapsules containing naproxen as an active ingredient were synthesized by ionic gelation method in presence of polyanion tripolyphosphate as a crosslinker. The morphology and diameter of the prepared chitosan nanoparticles was characterized using scanning electron microscopy and transition electron microscopy. Different factors affecting on the size diameter of chitosan nanoparticles such as stirring time and temperature, pH values as well as chitosan concentration were studied. Different factors affecting on the immobilization of naproxen into chitosan nanoparticles such as time, temperature and pH values were optimized. Synthesized naproxen/chitosan nanocapsules were assessed against both Gram positive bacterial strain such as Bacillus subtilis and Staphylococcus aureus and Gram negative bacterial strain such as Pseudomonas aeruginosa and Escherichia coli. Also, the antifungal activity of the naproxen/chitosan nanocapsules against Saccharomyces cerevisiae was demonstrated. Super oxide dismutase like activity of naproxen/chitosan nanocapsules will be determined.
KEYWORDS
Chitosan, Naproxen, Nanocapsules, Drug Delivery Systems, Antimicrobial, Antioxidant, DNA Degradation
Chitosan, Naproxen, Nanocapsules, Drug Delivery Systems, Antimicrobial, Antioxidant, DNA Degradation
Cite this paper
Gouda, M. , Elayaan, U. and Youssef, M. (2014) Synthesis and Biological Activity of Drug Delivery System Based on Chitosan Nanocapsules. Advances in Nanoparticles, 3, 148-158. doi: 10.4236/anp.2014.34019.
Gouda, M. , Elayaan, U. and Youssef, M. (2014) Synthesis and Biological Activity of Drug Delivery System Based on Chitosan Nanocapsules. Advances in Nanoparticles, 3, 148-158. doi: 10.4236/anp.2014.34019.
References
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http://dx.doi.org/10.1016/j.colsurfa.2009.06.021 [18] Zhang, K., Zheng, L.L., Zhang, X.H., Chen, X. and Yang, B. (2006) Silica-PMMA Core-Shell and Hollow Nanospheres. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 277, 145-150.
http://dx.doi.org/10.1016/j.colsurfa.2005.11.049 [19] Liu, H.X., Wang, C.Y., Gao, Q.X., Chen, J.X., Ren, B.Y. and Tong, Z. (2009) Facile Fabrication of Well-Defined Hydrogel Beads with Magnetic Nanocomposite Shells. International Journal of Pharmaceutics, 376, 92-98.
http://dx.doi.org/10.1016/j.ijpharm.2009.04.031 [20] Szarpak, A., Cui, D., Dubreuil, F., De Geest, B.G., De Cock, L.J., Picart, C. and Ly-Velty, R.A. (2010) Designing Hyaluronic Acid-Based Layer-by-Layer Capsules as a Carrier for Intracellular Drug Delivery. Biomacromolecules, 11, 713-720.
http://dx.doi.org/10.1021/bm9012937 [21] Endo, Y., Sato, K. and Anzai, J.I. (2010) Preparation of Avidin-Containing Polyelectrolyte Microcapsules and Their Uptake and Release Properties. Polymer Bulletin, 66, 711-720.
http://dx.doi.org/10.1007/s00289-010-0375-x [22] Taqieddin, E. and Amiji, M. (2004) Enzyme Immobilization in Novel Alginate-Chitosan Core-Shell Microcapsules. Biomaterials, 25, 1937-1942.
http://dx.doi.org/10.1016/j.biomaterials.2003.08.034 [23] Tang, Y.F., Zhao, Y.Y., Li, Y. and Du, Y.M. (2010) A Thermo-Sensitive Chitosan/Poly(Vinyl Alcohol) Hydrogel Containing Nanoparticles for Drug Delivery. Polymer Bulletin, 64, 791-804.
http://dx.doi.org/10.1007/s00289-009-0214-0 [24] Harrington, P.J. and Lodewijk, E. (1997) Large-Scale Synthetic Process for (S)-Naproxen by Syntex. Organic Process Research Development, 1, 72-76.
http://dx.doi.org/10.1021/op960009e [25] Rollas, S. and Kucukguzel, S.G. (2007) Biological Activities of Hydrazone Derivatives. Molecules, 12, 1910-1939.
http://dx.doi.org/10.3390/12081910 [26] Sriram, D., Yogeeswari, P. and Devakaram, R.V. (2006) Synthesis, in Vitro and in Vivo Antimycobacterial Activities of Diclofenac Acid Hydrazones and Amides. Bioorganic Medicinal Chemistry, 14, 3113-3118.
http://dx.doi.org/10.1016/j.bmc.2005.12.042 [27] Munoz-Muniz, O. and Juaristi, E. (2003) Enantioselective Protonation of Prochiralenolates in the Asymmetric Synthesis of (S)-Naproxen. Tetrahedron Letters, 44, 2023-2026.
http://dx.doi.org/10.1016/S0040-4039(03)00217-X [28] Tang, Z.X., Qian, J.Q. and Shi, L.E. (2007) Preparation of Chitosan Nanoparticles as Carrier for Immobilized Enzyme. Applied Biochemistry and Biotechnology, 136, 77-97.
http://dx.doi.org/10.1007/BF02685940 [29] Syedakulsum, Padmalatha, M., Sandeep, K., Saptasila, B. and Vidyasagar, G. (2011) Spectrophotometric Methods for the Determination of Naproxen sodium in Pure and Pharmaceutical Dosage Forms. International Journal of Research in Pharmaceutical and Biomedical Sciences, 2, 1303-1307. [30] Genthner, F.J., Hook, L.A. and Strohl, W.R. (1985) Determination of the Molecular Mass of Bacterial Genomic DNA and Plasmid Copy Number by High-Pressure Liquid Chromatography. Applied and Environmental Microbiology, 50, 1007-1013. [31] Sambrook, J., Fritsch, E.F. and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press, Cold Spring Harbor. [32] Laemmli, U.K. (1970) Cleavage of Structural Proteins during the Assembly of the Head of Bacteriophage T4. Nature, 227, 680-685. [33] Bauer, A.W., Kirby, W.M., Sherris, J.C. and Turck, M. (1966) Antibiotic Susceptibility Testing by a Standardized Single Disk Method. Journal of Clinical Pathology, 45, 493-496.
http://dx.doi.org/10.1038/227680a0 [34] Bridges, S.M. and Salin, M.L. (1981) Distribution of Iron Containing Superoxide Dismutase in Vascular Plants. Plant Physiology, 68, 275-278.
http://dx.doi.org/10.1104/pp.68.2.275
[1] Juang, R.S., Wu, F.C. and Tseng, R.L. (2001) Solute Adsorption and Enzyme Immobilizationon Chitosan Beads Prepared from Shrimp Shell Wastes. Bioresource Technology, 80, 187-193.
http://dx.doi.org/10.1016/S0960-8524(01)00090-6 [2] Monteiro, O.A. and Airoldi, C. (1999) Some Studies of Crosslinking Chitosan Glutaraldehyde Interaction of Homogeneous System. International Journal of Biological Macromolecules, 26, 119-128.
http://dx.doi.org/10.1016/S0141-8130(99)00068-9 [3] Denkbas, E.B., Kilicay, E., Birlikseven, C. and Ozturk, E. (2002) Magnetic Chitosan Microspheres: Preparation and Characterization. Reactive and Functional Polymers, 50, 225-232.
http://dx.doi.org/10.1016/S1381-5148(01)00115-8 [4] Selmer-Olsen, E., Ratnaweera, H.C. and Pehrson, R. (1996) Novel Treatment Process for Dairy Wastewater with Chitosan Produced from Shrimp-Shell Waste. Water Science and Technology, 34, 33-40.
http://dx.doi.org/10.1016/S0273-1223(96)00818-9 [5] Kucera, J. (2004) Fungal Myceliumthe Source of Chitosan for Chromatography. Journal of Chromatography B, 808, 69-73.
http://dx.doi.org/10.1016/j.jchromb.2004.05.023 [6] Chiou, S.H. and Wu, W.T. (2004) Immobilization of Candida Rugosa Lipase on Chitosan with Activation of Hydroxyl Group. Biomaterials, 25, 197-204.
http://dx.doi.org/10.1016/S0142-9612(03)00482-4 [7] Mi, F.L., Kuan, C.Y., Shyu, S.S., Lee, S.T. and Chang, S.F. (2000)The Study of Gelation Kinetics and Chain-Relaxation Properties of Glutaraldehyde-Cross-Linked Chitosan Gel and Their Effects on Microspheres Preparation and Drug Release. Carbohydrate Polymers, 41, 389-396.
http://dx.doi.org/10.1016/S0144-8617(99)00104-6 [8] Berthold, A., Cremer, K. and Kreuter, J. (1996) Preparation and Characterization of Chitosan Microspheres as Drug Carrier for Prednisolone Sodium Phosphate as Model for Anti-Inflammatory Drugs. Journal of Controlled Release, 39, 17-25.
http://dx.doi.org/10.1016/0168-3659(95)00129-8 [9] Tian, X.X. and Groves, M.J. (1999) Formulation and Biological Activity of Antineoplastic Proteoglycans Derived from Mycobacterium vaccae in Chitosan Nanoparticles. Journal of Pharmacology and Pharmacotherapeutics, 51, 151-157.
http://dx.doi.org/10.1211/0022357991772268 [10] Du, J., Chen, Y., Han, C. and Schmidt, M. (2003) Organic/Inorganic Hybrid Vesicles Based on a Reactive Block Copolymer. Journal of the American Chemical Society, 125, 14710-14711.
http://dx.doi.org/10.1021/ja0368610 [11] Clark, C.G. and Wooley, K.L. (2001) Dendrimers and Other Dendritic Polymers. In: Tomalia, D.A., Ed., Regioselectively-Crosslinked Nanostructures, Wiley, New York, 166-174. [12] Peyratout, C.S. and Dahne, L. (2004) Tailor-Made Polyelectrolyte Microcapsules: From Multilayers to Smart Containers. Angewandte Chemie International Edition, 43, 3762-3783.
http://dx.doi.org/10.1002/anie.200300568 [13] Sukhorukov, G.B., Rogach, A.L., Zebli, B., Liedl, T., Skirtach, A.G. and Parak, W.J. (2005) Nanoengineered Polymer Capsules: Tools for Detection, Controlled Delivery, and Site-Specific Manipulation. Small, 1, 194-200.
http://dx.doi.org/10.1002/smll.200400075 [14] Bédard, M.F., De Geest, B.G., Skirtach, A.G., Mohwaldb, H. and Sukhorukov, G.B. (2010) Polymeric Microcapsules with Light Responsive Properties for Encapsulation and Release. Advances in Colloid and Interface Science, 158, 2-14.
http://dx.doi.org/10.1016/j.cis.2009.07.007 [15] Li, X.D., Lu, T., Xu, J.J., Hu, Q.L. and Shen, J.C. (2009) A Study of Properties of “Micelle-Enhanced” Polyelectrolyte Capsules: Structure, Encapsulation and in Vitro Release. Acta Biomaterialia, 5, 2122-2131.
http://dx.doi.org/10.1016/j.actbio.2009.01.045 [16] Li, G., Feng, Y.Q., Gao, P. and Li, X.G. (2008) Preparation of Mono-Dispersed Polyurea-Urea Formaldehyde Double Layered Microcapsules. Polymer Bulletin, 60, 725-731.
http://dx.doi.org/10.1007/s00289-008-0894-x [17] Zhao, M.W., Zheng, L.Q., Bai, X.T., Li, N. and Yu, L. (2009) Fabrication of Silica Nanoparticles and Hollow Spheres Using Ionic Liquid Microemulsion Droplets as Temdishes. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 346, 229-236.
http://dx.doi.org/10.1016/j.colsurfa.2009.06.021 [18] Zhang, K., Zheng, L.L., Zhang, X.H., Chen, X. and Yang, B. (2006) Silica-PMMA Core-Shell and Hollow Nanospheres. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 277, 145-150.
http://dx.doi.org/10.1016/j.colsurfa.2005.11.049 [19] Liu, H.X., Wang, C.Y., Gao, Q.X., Chen, J.X., Ren, B.Y. and Tong, Z. (2009) Facile Fabrication of Well-Defined Hydrogel Beads with Magnetic Nanocomposite Shells. International Journal of Pharmaceutics, 376, 92-98.
http://dx.doi.org/10.1016/j.ijpharm.2009.04.031 [20] Szarpak, A., Cui, D., Dubreuil, F., De Geest, B.G., De Cock, L.J., Picart, C. and Ly-Velty, R.A. (2010) Designing Hyaluronic Acid-Based Layer-by-Layer Capsules as a Carrier for Intracellular Drug Delivery. Biomacromolecules, 11, 713-720.
http://dx.doi.org/10.1021/bm9012937 [21] Endo, Y., Sato, K. and Anzai, J.I. (2010) Preparation of Avidin-Containing Polyelectrolyte Microcapsules and Their Uptake and Release Properties. Polymer Bulletin, 66, 711-720.
http://dx.doi.org/10.1007/s00289-010-0375-x [22] Taqieddin, E. and Amiji, M. (2004) Enzyme Immobilization in Novel Alginate-Chitosan Core-Shell Microcapsules. Biomaterials, 25, 1937-1942.
http://dx.doi.org/10.1016/j.biomaterials.2003.08.034 [23] Tang, Y.F., Zhao, Y.Y., Li, Y. and Du, Y.M. (2010) A Thermo-Sensitive Chitosan/Poly(Vinyl Alcohol) Hydrogel Containing Nanoparticles for Drug Delivery. Polymer Bulletin, 64, 791-804.
http://dx.doi.org/10.1007/s00289-009-0214-0 [24] Harrington, P.J. and Lodewijk, E. (1997) Large-Scale Synthetic Process for (S)-Naproxen by Syntex. Organic Process Research Development, 1, 72-76.
http://dx.doi.org/10.1021/op960009e [25] Rollas, S. and Kucukguzel, S.G. (2007) Biological Activities of Hydrazone Derivatives. Molecules, 12, 1910-1939.
http://dx.doi.org/10.3390/12081910 [26] Sriram, D., Yogeeswari, P. and Devakaram, R.V. (2006) Synthesis, in Vitro and in Vivo Antimycobacterial Activities of Diclofenac Acid Hydrazones and Amides. Bioorganic Medicinal Chemistry, 14, 3113-3118.
http://dx.doi.org/10.1016/j.bmc.2005.12.042 [27] Munoz-Muniz, O. and Juaristi, E. (2003) Enantioselective Protonation of Prochiralenolates in the Asymmetric Synthesis of (S)-Naproxen. Tetrahedron Letters, 44, 2023-2026.
http://dx.doi.org/10.1016/S0040-4039(03)00217-X [28] Tang, Z.X., Qian, J.Q. and Shi, L.E. (2007) Preparation of Chitosan Nanoparticles as Carrier for Immobilized Enzyme. Applied Biochemistry and Biotechnology, 136, 77-97.
http://dx.doi.org/10.1007/BF02685940 [29] Syedakulsum, Padmalatha, M., Sandeep, K., Saptasila, B. and Vidyasagar, G. (2011) Spectrophotometric Methods for the Determination of Naproxen sodium in Pure and Pharmaceutical Dosage Forms. International Journal of Research in Pharmaceutical and Biomedical Sciences, 2, 1303-1307. [30] Genthner, F.J., Hook, L.A. and Strohl, W.R. (1985) Determination of the Molecular Mass of Bacterial Genomic DNA and Plasmid Copy Number by High-Pressure Liquid Chromatography. Applied and Environmental Microbiology, 50, 1007-1013. [31] Sambrook, J., Fritsch, E.F. and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press, Cold Spring Harbor. [32] Laemmli, U.K. (1970) Cleavage of Structural Proteins during the Assembly of the Head of Bacteriophage T4. Nature, 227, 680-685. [33] Bauer, A.W., Kirby, W.M., Sherris, J.C. and Turck, M. (1966) Antibiotic Susceptibility Testing by a Standardized Single Disk Method. Journal of Clinical Pathology, 45, 493-496.
http://dx.doi.org/10.1038/227680a0 [34] Bridges, S.M. and Salin, M.L. (1981) Distribution of Iron Containing Superoxide Dismutase in Vascular Plants. Plant Physiology, 68, 275-278.
http://dx.doi.org/10.1104/pp.68.2.275