Skip to main content
Log in

Preparation and evaluation of O-carboxymethyl chitosan/cyclodextrin nanoparticles as hydrophobic drug delivery carriers

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

In present study, novel composite nanocarriers comprised of O-carboxymethyl chitosan/β-cyclodextrin (O-CMC/β-CD) nanoparticles (NPS) were prepared and used to improve the bioavailability of hydrophobic drugs. Ibuprofen (IBU) was selected as a model drug and chitosan/β-CD (CS/β-CD) NPS were also prepared as control. The prepared NPS were characterized by FT-IR spectroscopy and X-ray diffraction. IBU entrapment of up to 93.25 ± 2.89% was obtained as determined by UV spectrophotometer. The NPS were spherical in shape with average particle sizes of 166 nm. The in vitro release studies were performed in simulated gastric medium (pH 1.2) and simulated intestinal medium (pH 6.8). The release rate of IBU from the O-CMC/β-CD NPS was slower than CS/β-CD NPS in simulated gastric medium. However, the converse tendency was observed in simulated intestinal medium. These results suggested that O-CMC/β-CD NPS were more suitable for the oral delivery of hydrophobic drugs compared with the CS/β-CD NPS.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Levis KA, Lane ME, Corrigan OI (2003) Effect of buffer media composition on the solubility and effective permeability coefficient of ibuprofen. Int J Pharm 253:49–59

    Article  CAS  Google Scholar 

  2. Terao K, Nakata D, Fukumi H, Schmid G, Arima H, Hirayama F, Uekama K (2006) Enhancement of oral bioavailability of coenzyme Q10 by complexation with γ-cyclodextrin in healthy adults. Nutr Res 26:503–508

    Article  CAS  Google Scholar 

  3. Chang YH, Xiao L, Du YM (2009) Preparation and properties of a novel thermosensitive N-trimethyl chitosan hydrogel. Polym Bull 63:53–545

    Article  Google Scholar 

  4. Tang YF, Zhao YY, Li Y, Du YM (2010) A thermosensitive chitosan/poly(vinyl alcohol) hydrogel containing nanoparticles for drug delivery. Polym Bull 64:791–804

    Article  CAS  Google Scholar 

  5. Lertsutthiwong P, Rojsitthisak P, Nimmannit U (2009) Preparation of turmeric oil-loaded chitosan-alginate biopolymeric nanocapsules. Mater Sci Eng C 29:856–860

    Article  CAS  Google Scholar 

  6. Du YM, Xia ZY, Lu R (1997) Blend films of chitosan/starch. J Wuhan Univ Nat Sci 2(2):220–224

    Article  CAS  Google Scholar 

  7. Feng T, Du YM, Li J, Wei YN, Yao PJ (2007) Antioxidant activity of half N-acetylated water-soluble chitosan in vitro. Eur Food Res Technol 225:133–138

    Article  CAS  Google Scholar 

  8. Chang YH, Xiao L, Du YM (2009) Preparation and properties of a novel thermosensitive N-trimethyl chitosan hydrogel. Polym Bull 63:531–545

    Article  CAS  Google Scholar 

  9. Soppimath KS, Aminabhavi TM, Kulkarni AR, Rudzinski WE (2001) Biodegradable polymeric nanoparticles as drug delivery devices. J Control Release 70:1–20

    Article  CAS  Google Scholar 

  10. Trapania A, Sitterbergb J, Bakowskyb U, Kissel T (2009) The potential of glycol chitosan nanoparticles as carrier for low water soluble drugs. Int J Pharm 375:97–106

    Article  Google Scholar 

  11. Desirée TO, Carmen RL, Alonso MJ (2009) Chitosan/cyclodextrin nanoparticles can efficiently transfect the airway epithelium in vitro. Eur J Pharm Biopharm 71:257–263

    Article  Google Scholar 

  12. Trapani A, Lopedota A, Franco M, Cioffi N, Ieva E, Marcos GF, Alonso MJ (2010) A comparative study of chitosan and chitosan/cyclodextrin nanoparticles as potential carriers for the oral delivery of small peptides. Eur J Pharm Biopharm 75:26–32

    Article  CAS  Google Scholar 

  13. Zhang YF, Yin P, Zhao XQ, Wang J, Wang J, Wang CD, Ren L, Zhang QQ (2009) O-Carboxymethyl-chitosan/organosilica hybrid nanoparticles as non-viral vectors for gene delivery. Mater Sci Eng C 29:2045–2049

    Article  CAS  Google Scholar 

  14. Dev A, Mohan JC, Sreeja V, Tamura H, Patzke GR, Hussain F, Weyeneth S, Naira SV, Jayakumar R (2010) Novel carboxymethyl chitin nanoparticles for cancer drug delivery applications. Carbohydr Polym 79:1073–1079

    Article  CAS  Google Scholar 

  15. Cai ZS, Song ZB, Shang SB, Yang CS (2007) Study on the flocculating properties of quaternized carboxymethyl chitosan. Polym Bull 59:655–665

    Article  CAS  Google Scholar 

  16. Sun LP, Du YM, Fan LH, Chen X, Yang JH (2006) Preparation, characterization and antimicrobial activity of quaternized carboxymethyl chitosan and application as pulp-cap. Polymer 47:1796–1804

    Article  CAS  Google Scholar 

  17. Lamkin S, Fraiz A (2009) An acid/base disturbance from ibuprofen toxicity. J Emerg Nurs 35:584–585

    Article  Google Scholar 

  18. He JX, Wang Y, Cui SZ, Gao YY, Wang SY (2010) Structure and properties of silk fibroin/carboxymethyl chitosan blend films. Polym Bull 59:395–409

    Article  Google Scholar 

  19. Lamprecht A, Saumet JL, Roux J, Benoit JP (2004) Lipid nanocarriers as drug delivery system for ibuprofen in pain treatment. Int J Pharm 278:407–414

    Article  CAS  Google Scholar 

  20. Higuchi T, Connors KA (1965) Phase-solubility techniques. Adv Anal Chem Instrum 4:117–212

    CAS  Google Scholar 

  21. Williams RO, Mahaguna V, Sriwongjanya M (1998) Characterization of an inclusion complex of cholesterol and hydroxypropyl-b-cyclodextrin. Eur J Pharm Biopharm 46:355–360

    Article  CAS  Google Scholar 

  22. Stella VJ, Rao VM, Zannou EA, Zia V (1999) Mechanisms of drug release from cyclodextrin complexes. Adv Drug Deliver Res 36:3–16

    Article  CAS  Google Scholar 

  23. Araujo MVG, Vieira EKB, Lazaro GS, Conegero LS, Ferreria OP, Almeida LE, Barreto LS, Cost NBa, Gimenez IF (2007) Inclusion complexes of pyrimethamine in 2-hydroxypropyl-b-cyclodextrin: characterization, phase solubility and molecular modelling. Bioorgan Med Chem 15:5752–5759

    Article  Google Scholar 

  24. Anitha A, Rani VVD, Krishna R, Sreeja V, Selvamurugan N, Nair SV, Tamura H, Jayakumar R (2009) Synthesis, characterization, cytotoxicity and antibacterial studies of chitosan, O-carboxymethyl and N,O-carboxymethyl chitosan nanoparticles. Carbohydr Polym 78:672–677

    Article  CAS  Google Scholar 

  25. Sun SL, Wang AQ (2006) Adsorption kinetics of Cu (II) ions using N, O-carboxymethyl-chitosan. J Hazard Mater 131:103–111

    Article  CAS  Google Scholar 

  26. Yoksana R, Jirawutthiwongchai J, Arpo K (2010) Encapsulation of ascorbyl palmitate in chitosan nanoparticles by oil-in-water emulsion and ionic gelation processes. Colloid Surf B 76:292–297

    Article  Google Scholar 

  27. Rokhade AP, Agnihotri SA, Patil SA, Mallikarjuna NN, Kulkarni PV, Aminabhavi TM (2006) Semi-interpenetrating polymer network microspheres of gelatin and sodium carboxymethyl cellulose for controlled release of ketorolac tromethamine. Carbohydr Polym 65:243–252

    Article  CAS  Google Scholar 

  28. Mundargi RC, Shelke NB, Aminabhavi TM (2008) Formulation and in vitro evaluation of novel starch-based tableted microspheres for controlled release of ampicillin. Carbohydr Polym 71:42–53

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by Chongqing University Postgraduates’ Science and Innovation Fund (201005A1A0010333) and 211 Project Innovation Personnel Training Plan Items of Chongqing University (S-09103).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jingou Ji.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ji, J., Hao, S., Liu, W. et al. Preparation and evaluation of O-carboxymethyl chitosan/cyclodextrin nanoparticles as hydrophobic drug delivery carriers. Polym. Bull. 67, 1201–1213 (2011). https://doi.org/10.1007/s00289-011-0449-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-011-0449-4

Keywords

Navigation