Modifications of Chitosan for Use in Nanoparticulate Drug Delivery Systems

DOI:

https://doi.org/10.37285/ijpsn.2013.6.4.3

Authors

  • D. Gowtham Kumar
  • Naresh R
  • K. Rakesh Varma
  • Nagasen D
  • Sudheer B
  • Sai Kishore V

Abstract

Nanoparticles with naturally occurring biodegradable polymers have emerged as potential carriers of various therapeutic agents. Chitosan, a cationic polysaccharide, is one of such biodegradable polymers, which has been extensively exploited for the preparation of nanoparticles with several therapeutic agents. In recent years, the area of focus has shifted from chitosan to chitosan derivatized polymers due to its vastly improved properties such as better drug retention capability, improved permeation, enhanced mucoadhesion, and sustained release of therapeutic agents. Chitosan derivatized polymers are primarily the quaternized chitosan derivatives, chitosan cyclodextrin complexes, thiolated chitosan, pegylated chitosan, chitosan combined with sugar ligands, chitosan with cholanic acid, chitosan-linolenic acid and chitosan-DTPA. This review article covers the various modifications of chitosan, their preparation procedures and various works done with them. 

 

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Keywords:

Chitosan, Nanoparticles, Cyclodextrin, cholanic acid;, linolenic acid, DTPA, PEG

Downloads

Published

2013-12-31

How to Cite

1.
Kumar DG, R N, Varma KR, D N, B S, V SK. Modifications of Chitosan for Use in Nanoparticulate Drug Delivery Systems. Scopus Indexed [Internet]. 2013 Dec. 31 [cited 2024 Nov. 19];6(4):2210-8. Available from: https://ijpsnonline.com/index.php/ijpsn/article/view/683

Issue

Section

Review Articles

References

Aiba S (1993). Reactivity of partially N-acetylated chitosan in aqueous media. Makromolekulare Chemie, 194(1): 65–75.

Akiyoshi K, Sunamoto J (1996). Supramolecular assembly hydrophobized polysaccharides. Supramol Sci 3: 157-163.

Anitha A, S Maya and N Deepa (2011). Efficient water soluble O-carboxymethyl chitosan nanocarrier for the delivery of curcumin to cancer cells. Carbohydrate Polymers 83: 452–461.

Berger J, Reist M, Mayer J.M, Felt O and Gurny R (2004). Structure and interactions in chitosan hydrogels formed by complexation or aggregation for biomedical applications. Eur J Pharm Biopharm 57: 35-52.

Bernkop-Schnurch A, Hornof M, Guggi D (2004). Thiolated chitosans. Eur J Pharm Biopharm 57(1): 9–17.

Bravo-Osuna I, Ponchel G, Vauthier C (2007). Tuning of shell and core characteristics of chitosan-decorated acrylic nanoparticles, Eur JPharm Sci., 30(2): 143–54.

Burstein D, Velyvis J, Scott K. T, Stock K. W, Kim Y. J and Jaramillo D (2001). Protocol issues for delayed Gd(DTPA)(2)-enhanced MRI: (dGEMRIC) for clinical evaluation of articular cartilage. Magnetic Resonance in Medicine 45(1): 36–41.

Canaple L, Beuf O, Armenean M, Hasserodt J, Samarut J and Janier M (2008). Fast screening of paramagnetic molecules in zebrafish embryos by MRI. NMR in Biomedicine, 21(2): 129–137.

Challa R, Ahuja A, Ali J and Khar RK (2005). Cyclodextrins in drug delivery: An updated review. AAPS PharmSciTech, 6: E329–E357.

Chen XG, Lee C. M and Park HJ (2003). OM emulsification for the self-aggregation and nanoparticle formation of linoleic acid-modified chitosan in the aqueous system. J Agril Food Chem 51: 3135-3139.

Chen XG, Lee CM, Park HJ (2003). J. Agric. Food Chem 8: 31-35.

Couvreur P, Lemarchand C and Gref R (2004). Polysaccharide-decorated nanoparticles. Eur J Pharm Biopharmaceutics 58(2): 327-341.

Darras V, Nelea M, innik FM, Buschmann MD (2010). Chitosan modified with gadolinium diethylenetriaminepentaacetic acid for magnetic resonance imaging of DNA/chitosan nanoparticles, Carbohydrate Polymers 80: 1137–1146.

Don-Gon Kim, Joong-Kuen Kwonl, Young-II Jeong, MiKyeong Jang and Jaw Woon Nah (2008) Preparation and spectroscopic characterization of methoxy poly(ethylene glycol) grafted low molecular weight water-soluble chitosan. Applied Chemistry 12: 29-32.

Dos Santos KS, Coelho JF, Ferreira P, Pinto I, Lorenzetti SG, Ferreira EI (2006). Synthesis and characterization of membranes obtained by graft copolymerization of 2-hydroxyethyl methacrylate and acrylic acid onto chitosan. Int J Pharm 310(1–2): 37–45.

Duceppe N and M Tabrizian (2010). Advances in using chitosan based nanoparticles for in vitro and in vivo drug and gene delivery. Expert Opinion on Drug Delivery 7:1191–1207.

Durand A, Rouzes C, Leonard M and Dellacherie E (2002). Surface activity and emulsification properties of hydrophobically modified dextrans, J Colloid and Interface Science, 253(1): 217-223.

Fan C, W Gao, Z Chen (2011). Tumor selectivity of stealth multi-functionalized superparamagnetic iron oxide nanoparticles. Int J Pharm 404: 180–190.

Fang Y, Huang M F, Liu L, Zhang G B and Yuan G B (2006). Preparation of chitosan derivative with polyethylene glycol side chains for porous structure without specific processing technique. Int J Biological Macromolecules 38(3-5): 191-196.

Franco P, Senso A, Oliveros L and Minguillon C (2001). Covalently bonded polysaccharide derivatives as chiral stationary phases in high-performance liquid chromatography. J. Chromatogr A, 906: 155-170.

Gonil P, Sajomsang W (2011). Novel quaternized chitosan containing β-cyclodextrin moiety: Synthesis, characterization and antimicrobial activity. Carbohydr. Polym 83: 905–913.

Gorochovceva N, Naderi A, Dedinaite A and Makuska R (2005). Chitosan-Npoly( ethylene glycol) brush copolymers: Synthesis and adsorption on silica surface. European Polymer J 41: 2653-2662.

Guibal E (2004). Interactions of metal ions with chitosan-based sorbents: a review. Separ Purific. Techn 38: 43-74.

Harris J M, Struk E C, Case M G, Paley M S, Yalpani M, Van Alstin J M and Brooks D E (1984). Synthesis and Characterization of Poly( ethylene Glycol) Derivatives. J Polym Sci. Polym. Chem. Ed. 22: 341–352.

Hirano (1999). Chitin and chitosan as novel biotechnological materials, Polym Int; 48: 732–734.

Janes K A, Calvo P and Alonso M J (2001). Polysaccharide colloidal particles as delivery systems for macromolecules, Adv. Drug Deliv. Rev 47: 83–97.

Jiang HL, Kim YK, Lee SM, Park MR, Kim EM, Jin YM, Arote R, Jeong HJ, Song SC, Cho MH and Cho CS (2010). Galactosylated chitosan-g-PEI/DNA complexes loaded poly(organophosphazene) hydrogel as a hepatocyte targeting gene delivery system. Arch. Pharm. Res 33: 551.

Kato Y, Onishi H and Machida Y (2004). N-succinyl-chitosan as a drug carrier: water insoluble and water-soluble conjugates, Biomaterials, 25: 907-915, ISSN 0142-9612

Kean T and Thanou M (2010). Biodegradation, biodistribution and toxicity of chitosan, Advanced Drug Delivery Reviews 62: 3–11.

Kennedy S D, Szczepaniak L S, Gibson S L, Hilf R, Foster T H and Bryant R G (1994). Quantitative MRI of Gd–DTPA uptake in tumors – Response to photodynamic therapy. Magnetic Resonance in Medicine 31(3): 292–301.

Kim K, Kwon S, Park J H, Chung H, Jeong S Y, Kwon I C and Kim I S (2005). Physicochemical characterizations of self-assembled nanoparticles of glycol chitosan-deoxycholic acid conjugates. Biomacromolecules, 6(2): 1154–1158.

Kurita K (2001). Controlled functionalization of the polysaccharide chitin. Progress in Polymer Science 26(9): 1921-1971.

Kwon GS (2003). Polymeric micelles for delivery of poorly water-soluble compounds. Critical Reviews in Therapeutic Drug Carrier Systems 20(5): 357-403.

Kwon JHPS, Chung H, Kwon IC, Jeong SY (2003). Physicochemical Characteristics of Self-Assembled Nanoparticles Based on Glycol Chitosan Bearing 5-beta-Cholanic Acid. Langmuir 19: 10188–10193.

Lee RJ and Low PS (1994). Delivery of liposomes into cultured KB cells via folate receptor-mediated endocytosis. J Biol Chem 269(5): 3198–3204.

Leonard M, Rouzes C, Durand A and Dellacherie E (2003). Influence of polymeric surfactants on the properties of drug-loaded PLA nanospheres. Colloids and Surfaces B-Biointerfaces 32(2): 125-135.

Li Y, Zhang S, X Meng, X Chen and G Ren (2011). The preparation and characterization of a novel amphiphilic oleoylcarboxymethyl chitosan self-assembled nanoparticles, Carbohydrate Polymers 83: 130–136.

Liang J, F Li, Y Fang (2011). Synthesis, characterization and cytotoxicity studies of chitosan-coated tea polyphenols nanoparticles, Colloids and Surfaces B, 82: 297–301.

M M Issa, M Koping-Hoggard, K Tommeraas (2006). Targeted gene delivery with trisaccharide-substituted chitosan oligomers in vitro and after lung administration in vivo. J Control Rel 115: 103–112.

Ma Z, Lim TM, Lim LY (2005). Pharmacological activity of peroral chitosan–insulin nanoparticles in diabetic rats. Int J Pharm 293(1–2): 271–280.

Maestrelli F, Garcia-Fuentes M, Mura P, Alonso MJ (2006). A new drug nanocarrier consisting of chitosan and hydroxypropylcyclodextrin. Eur J Pharm Biopharm 63(2): 79–86.

Martien R, Loretz B, Thaler M, Majzoob S, Bernkop-Schnurch (2007). Chitosan–thioglycolic acid conjugate: An alternative carrier for oral nonviral gene delivery. J Biomed Mater Res A; 82(1): 1–9.

Moghaddam FA, Atyabi F and Dinarvand R (2009). Preparation and invitro evaluation of mucoadhesion and permeation enhancement of thiolated chitosan–pHEMA core–shell nanoparticles. Nanomedicine 5(2): 208–15.

Opanasopit P, Ngawhirunpat T, Chaidedgumjorn A Rojanarata, T Apirakaramwong, A Phongying, S Choochottiros and Chirachanchai S (2006). Incorporation of camptothecin into N-phthaloyl chitosan-g-mPEG self-assembly micellar system, European Journal of Pharmaceutics and Biopharmaceutics 64(3): 269-276.

Ouchi T, Nishizawa H and Ohya Y (1998). Aggregation phenomenon of PEG-grafted chitosan in aqueous solution. Polymer 39: 5171-5175.

Park YK, Y H Park, B A Shin (2000). Galactosylated chitosan-graft-dextran as hepatocyte-targeting DNA carrier. J Control Rel 69: 97–108.

Payne GF, Yi HM, Wu LQ, Bentley WE, Ghodssi R, Rubloff GW and Culver JN (2005). Biofabrication with chitosan, Biomacromolecules 6(6): 2881-2894.

Perbacher, S Zou, T Bettinger, AM Steffan and JS Remy (1998). Chitosan-based vector/DNA complexes for gene delivery: biophysical characteristics and transfection ability. Pharmaceutical Research, 15: 1332–1339.

Petter RC, Salek JS, Sikorski CT (1990). Cooperative binding by aggregated mono-6-(alkylamino)-β-cyclodextrins, J. Am. Chem. Soc. 112: 3860–3868.

Rabea EI, Badawy MET, Stevens CV, Smagghe G and Steurbaut W (2003). Chitosan as antimicrobial Agent: applications and mode of action, Biomacromolecules, 4: 1457- 1465.

Roberts GAF (1992). Solubility and solution behaviour of chitin and chitosan, In: Roberts GAF, ed. Chitin Chemistry, MacMillan, Houndmills. 274-329.

Rodrigues J S, Santos-Magalhaes N S, Coelho L C B, Couvreur P, Ponchel G and Gref R (2003). Novel core (polyester)-shell(polysaccharide) nanoparticles: protein loading and surface modification with lectins, J Control Rel 92: 103-112.

Sailaja AK, P Amareshwar, P Chakravarty (2010). Chitosan nanoparticles as a drug delivery system. RJPBCS 1: 475.

Saito H, Wu Sato T, Nagasaki T, Sakairi N and Shinkai S (2004). 6-Amino-6 deoxychitosan-Preparation and application as plasmid vector in COS-1 cells, Chem. Lett 33: 340-341.

Saito H, Wu X, Harris J M and Hoffman AS (1997). Graft copolymers of poly(ethylene glycol) (PEG) and chitosan, Macromol. Rapid Commun 18: 547-550.

Shi X, Du Y, J Yang, B Zhang, and L Sun (2006). Effect of degree of substitution and molecular weight of carboxymethyl chitosan nanoparticles on doxorubicin delivery, J Applied Polymer Sci 100(6): 4689–4696.

Sinha V R, Singla A K, Wadhawan S, Kaushik R, Kumria R, Bansal K and Dhawan S (2004). Chitosan microspheres as a potential carrier for drugs, Int. J. Pharm. 274: 1-33.

Szejtli J (2004). Past, present, and future of cyclodextrin research, Pure and Applied Chemistry 76: 1825–1845.

Turner JL, Pan D, Plummer R, Chen Z, Whittaker AK and Wooley KL (2005). Synthesis of gadolinium-labeled shell cross-linked nanoparticles for magnetic resonance imaging applications, Advanced Functional Materials 15(8): 1248–1254.

Varma A J, Deshpande S V and Kennedy J F (2004). Metal complexation by chitosan and its derivatives: a review. Carbohydrate Polymers 55: 77-93.

Weissleder R, Bogdanov A J and Papisov M (1995). Handbook of targeted delivery of imaging agents, Boca Raton, FL: CRC Press.

Whitesides GM, Mathias JP, Sato CT (1991). Molecular self assembly and nanochemistry; A chemical strategy for the synthesis of nanostructures, Science 254: 1312-1319.

Widmer WR, Turk MJ, Breur GJ (2002). Folate-targeted imaging of activated macrophages in rats with adjuvant induced arthritis. Arthritis and Rheumatism 46: 1947–1955.

Yi Zhou, Jian-hai Chen, He Wang, Cheng-xi Wang, Jian-ye Zhang, Yi-wen Tao, Guodong Zheng, Hong-yan Xie and Yi Zhou (2011). Synthesis and characterization of folate poly(ethylene glycol) chitosan graft-polyethylenimine as a non-viral carrier for tumor-targeted gene delivery. African J Biotech 10(32): 6120-6129.

Yoo HS, Lee JE, Chung H, Kwon IC, Jeong SY (2005). Self-assembled nanoparticles containing hydrophobically modified glycol chitosan for gene delivery. J Control Rel 103: 235–243.