10.1007/s40204-015-0044-0

Modeling and optimization of degree of folate grafted on chitosan and carboxymethyl-chitosan

PDF HTML
  • S. Esfandiarpour-Boroujeni1,
  • S. Bagheri-Khoulenjani*2,
  • H. Mirzadeh1,
  1. Department of Polymer and Color Engineering, Amirkabir University of Technology, Tehran, IR
  2. Department of Polymer and Color Engineering, Amirkabir University of Technology, Tehran, IR Cancer Model Research Centre, Cancer Institute of Iran, Tehran University of Medical Sciences, Tehran, IR
Cover Image

Published in Issue 2015-11-19

How to Cite

Esfandiarpour-Boroujeni, S., Bagheri-Khoulenjani, S., & Mirzadeh, H. (2015). Modeling and optimization of degree of folate grafted on chitosan and carboxymethyl-chitosan. Progress in Biomaterials, 5(1 (March 2016). https://doi.org/10.1007/s40204-015-0044-0
Crossref
Scopus
Google Scholar
Europe PMC

Abstract

Abstract Chitosan is a cationic polysaccharide with great properties and so is considered as an attractive biopolymer. However, chitosan shows its antibacterial activity only in acidic environment and this restricts its uses. So water-soluble chitosan derivatives such as carboxymethyl chitosan could be good candidates for such biomedical applications. Modified chitosan with hydrophobic functional groups such as folate (FA) is able to make self-assembled nanoparticles in aqueous media. One of the most important factors affecting the properties of resulting nanoparticles such as size, morphology, amount and efficiency of drug loading and also drug release profile is the amount of FA groups grafted on the chitosan chains. In this study FA modified chitosan and carboxymethyl chitosan have been synthesized using folic acid, N -hydroxy succinimide (NHS), N , N -dicyclohexylcarbodiimide (DCC) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC). The effect of molecular weight, degree of substitution of carboxymethyl hydrophilic group and primary molar ratio of folic acid to chitosan/carboxymethyl chitosan (CMCS) on degree of substitution of folate functional groups grafted on chitosan chains was modeled using a statistical software package (Design of Expert 8, Trial version). Degree of substitution of grafted folate was measured using UV/Vis spectroscopy. Results show that degree of substitution of CMC and molar ratio of folic acid to chitosan/carboxymethyl chitosan has direct effect on substitution degree of folate and molecular weight has an inverse impact. Also results show that molar ratio of folic acid to chitosan/(CMCS) has the most effect on substitution degree of folate and the proposed model is statistically valid to predict degree of substitution of FA groups on chitosan chains.

Keywords

  • Folic acid modified chitosan,
  • Carboxymethyl chitosan,
  • Modeling of substitution degree,
  • Design experiments
PDF HTML

References

  1. Bagheri-Khoulenjani et al. (2009) Effect of fabrication process parameters on the size of gelatin/nanohydroxyapatite microspheres 22(4) (pp. 285-294)
  2. Bagheri-Khoulenjani et al. (2009) An investigation on the short-term biodegradability of chitosan with various molecular weights and degrees of deacetylation 78(4) (pp. 773-778) https://doi.org/10.1016/j.carbpol.2009.06.020
  3. Bhavsar et al. (2006) Formulation optimization for the nanoparticles-in-microsphere hybrid oral delivery system using factorial design 110(2) (pp. 422-430) https://doi.org/10.1016/j.jconrel.2005.11.001
  4. de Oliveira et al. (2014) Effects of post-harvest treatment using chitosan from Mucor circinelloides on fungal pathogenicity and quality of table grapes during storage (pp. 211-219) https://doi.org/10.1016/j.fm.2014.06.007
  5. Ge and Luo (2005) Preparation of carboxymethyl chitosan in aqueous solution under microwave irradiation 340(7) (pp. 1351-1356) https://doi.org/10.1016/j.carres.2005.02.025
  6. Jaikumar et al. (2015) Injectable alginate-O-carboxymethyl chitosan/nano fibrin composite hydrogels for adipose tissue engineering (pp. 318-326) https://doi.org/10.1016/j.ijbiomac.2014.12.037
  7. Larsson et al. (2013) Biomedical applications and colloidal properties of amphiphilically modified chitosan hybrids 38(9) (pp. 1307-1328) https://doi.org/10.1016/j.progpolymsci.2013.06.009
  8. Li et al. (2008) Preparation, characterization and aggregation behavior of amphiphilic chitosan derivative having poly (l-lactic acid) side chains 72(1) (pp. 60-66) https://doi.org/10.1016/j.carbpol.2007.07.042
  9. Majedi et al. (2013) Microfluidic assisted self-assembly of chitosan based nanoparticles as drug delivery agents 13(2) (pp. 204-207) https://doi.org/10.1039/C2LC41045A
  10. Möglich et al. (2006) End-to-end distance distributions and intrachain diffusion constants in unfolded polypeptide chains indicate intramolecular hydrogen bond formation 103(33) (pp. 12394-12399) https://doi.org/10.1073/pnas.0604748103
  11. Montgomery DC, Montgomery DC (1984) Design and analysis of experiments, vol 7. Wiley, New York
  12. Nam et al. (2013) Encapsulation of paclitaxel into lauric acid-O-carboxymethyl chitosan-transferrin micelles for hydrophobic drug delivery and site-specific targeted delivery 457(1) (pp. 124-135) https://doi.org/10.1016/j.ijpharm.2013.09.021
  13. Novoa-Carballal et al. (2013) Chitosan hydrophobic domains are favored at low degree of acetylation and molecular weight 54(8) (pp. 2081-2087) https://doi.org/10.1016/j.polymer.2013.02.024
  14. Prabaharan (2015) Chitosan-based nanoparticles for tumor-targeted drug delivery (pp. 1313-1322) https://doi.org/10.1016/j.ijbiomac.2014.10.052
  15. Sahu et al. (2010) In vitro evaluation of folic acid modified carboxymethyl chitosan nanoparticles loaded with doxorubicin for targeted delivery 21(5) (pp. 1587-1597) https://doi.org/10.1007/s10856-010-3998-4
  16. Sun and Wang (2006) Adsorption kinetics of Cu (II) ions using N, O-carboxymethyl-chitosan 131(1) (pp. 103-111) https://doi.org/10.1016/j.jhazmat.2005.09.012
  17. Tan and Liu (2011) Preparation and characterization of self-assemblied nanoparticles based on folic acid modified carboxymethyl chitosan 22(5) (pp. 1213-1220) https://doi.org/10.1007/s10856-011-4302-y
  18. Wang et al. (2011) Preparation and characterizations of a novel deoxycholic acid-O-carboxymethylated chitosan–folic acid conjugates and self-aggregates 84(3) (pp. 1192-1200) https://doi.org/10.1016/j.carbpol.2011.01.017
  19. Yang et al. (2010) Folic acid-conjugated chitosan nanoparticles enhanced protoporphyrin IX accumulation in colorectal cancer cells 21(4) (pp. 679-689) https://doi.org/10.1021/bc9004798
  20. Yang et al. (2014) Advances in self-assembled chitosan nanomaterials for drug delivery 32(7) (pp. 1301-1316) https://doi.org/10.1016/j.biotechadv.2014.07.007
  21. Zhao et al. (2008) Targeted drug delivery via folate receptors (pp. 309-319) https://doi.org/10.1517/17425247.5.3.309