Quaternized chitosan

Just recently a series of other quaternized chitosan derivatives have been synthesized and characterized, namely, A,A-dimethyl, A-ethyl chitosan (DMEC) (Bayat et al. 2006), A-methyl, A,A-diethyl chitosan (DEMC) (Avadi et al. 2004) and A,A,A-triethyl chitosan (TEC) (Avadi et al. 2003). In a comprehensive study (Sadeghi et al. 2008a, b) the four quaternized derivatives of chitosan, trimethyl chitosan (TMC), diethylmethyl chitosan (DEMC), triethyl chitosan (TEC) and dimethylethyl chitosan (DMEC) with degree of substitution of approximately 50% were synthesized and their effect on the permeability of insulin across intestinal Caco-2 monolayers was studied and compared with chitosan both in free-soluble form and in nanoparticulate systems. Trans-epithelial electrical resistance (TEER) studies revealed that all four chitosan derivatives in free-soluble forms were able to decrease the TEER value in the following order TMC>DEMC>TEC = DMEC>chitosan, indicating their... 

Another very attractive application of nanoparticles is the oral gene delivery. For example, quaternized chitosan-trimethylated chitosan was shown to have... 

Table 3.2 Anionic conductivity values for quaternized chitosan.

G. (2002). Quaternized chitosan oligomers as novel gene delivery vectors in epithelial cell lines. Biomaterials, 23(1), 153-159. 

Jonker, C., Hamman, J. H., Kotze, A. F. (2002). Intestinal paracellular permeation enhancement with quaternized chitosan In situ and in vitro evaluation, Int I. Pharm.. 238,205-213. 

M. Ignatova, N. Manolova, I. Rashkov, Novel antibacterial fibers of quaternized chitosan and poly (vinyl pyrrolidone) prepared by electrospinning, Eur. Polym. J. 43 (2007) 1112-1122. 

Quaternized chitosan was developed by the reaction of chitosan with methyl iodide under basic conditions. After quaternization, the obtained N,N,N-trimethyl chitosan chloride (TMC) was soluble at neutral pH. The TMC makes it possible to prepare gene polyplexes over a wide pH range compared with the unmodified chitosan. The protonation of the amino group was pH independent when it was trimethylated, which favored the solubility of chitosan derivatives at physiological pH and the formation of polyplexes with DNA and siRNA. The presence of more positive charges contributed to better colloidal stability arising from both electrostatic stabilization and static effects. The size of the gene polyplexes obtained with trimethyl chitosan was reduced when compared with those formed with the... 

Synonyms Chitosan, 2,3-dihydroxypropyl-2-hydroxy-3-(trimethylammonio)propyl ether, chloride Dihydroxypropyl chitosan trimonium chloride Quaternized chitosan... 

Quaternized chitosan. See Polyquatemium-29, QuatexS. SeeSteartrimonium hydroxyethyl hydrolyzed collagen Quat Keratin QTM-30. See Hydroxypropyltrimonium hydrolyzed keratin Quat Keratin WKP. See Cocodimonium hydroxypropyl hydrolyzed keratin Quat-Pro E. See Triethonium hydrolyzed collagen ethosulfate Quat-Pro S 30] Quat-Pro S. See Hydroxypropyltrimonium hydrolyzed collagen Quatrene CB] Quatrene CB-50, Quatrene CB-80] Quatrene MB-50, Quatrene MB-80. See Benzalkonium chloride... 

The presence of fetal calf serum (FCS) did not affect the transfection efficiency of the chitoplexes, whereas the transfection efficiency of DOTAP-DNA complexes was decreased. Cells remained 100% viable in the presence of chitosan oligomers whereas viability of DOTAP treated cells decreased to 50% in both cell lines. Both DOTAP-DNA lipoplexes and chitoplexes resulted in less transfection efficiency in Caco-2 cell cultures than in COS-1 cells however, quaternized chitosan oligomers proved to be superior to DOTAP. The effects on the viability of Caco-2 cells were similar to the effects observed in COS-1 cells. This report is also in line with the earlier one suggesting that chitosan-DNA complexes present suitable characteristics and less cytotoxic compared to lipid gene carriers and thus has the potential to be used as gene delivery vectors. 

Wang T, Xu Q, Wu Y, Zeng A, Li M, Gao H. Quaternized chitosan (QCS)/poly (aspartic acid) nanoparticles as a protein drug-delivery system. Carbohydr Res. 2009 344(7) 908-14. 

Xu R, Xin S, Zhou X, Li W, Cao F, Feng X, Deng H. Quaternized chitosan-organic rectorite intercalated composites based nanoparticles for protein controlled release. Int J Pharm. 2012 438(l-2) 258-65. 

Bayat A, Dorkoosh FA, Dehpour AR, Moezi L, Larijani B, Junginger HE, Morteza RT. Nanoparticles of quaternized chitosan derivatives as a carrier for colon delivery of insulin Ex vivo and in vivo studies. Int J Pharm. 2008 356(l-2) 259-66. 

Guo Z, Liu H, Chen X, Ji X, Li P (2006) Hydroxyl radicals scavenging activity of N-substituted chitosan and quaternized chitosan. Bioorg Med Chem Lett 16 6348-6350... 

Guo Z, Xing R, Liu S, Zhong Z, Ji X, WangL, Li P (2007) Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan. Carbohydr Res 342 1329-1332... 

Hu, Y. Wang, M Wang, D. Gao, X Gao, C. (2008). Feasibility study on surface modification of cation exchange membranes by quaternized chitosan for improving its selectivity. Journal of Membrane Scietux, 319. 5-9. 

Stabilizers Kathon LX Dowicil 75, paraquat dichloride, quaternized chitosan ... 

Wan, Y Peppley, B., Creber, K.A.M., and Bui, V.T. (2010) Anion-exchange membranes composed of quaternized-chitosan derivatives for alkaline fuel cells. Journal of Power Sources, 195,... 

Bracamonte, M. V., S. Bollo, P. Labbe, G. A. Rivas, and N. E. Eerreyra. 2011. Quaternized chitosan as support for the assembly of gold nanoparticles and glucose oxidase Physicochemical characterization of the platform and evaluation of its biocatalytic activity. Electrochim. Acta 56 1316-1322. 

Huang, R., Chen, G., Yang, B., and Gao, C. 2008. Positively charged composite nanofiltration membrane from quaternized chitosan by toluene diisocyanate cross-liuldng. Sep. Purif. Technol. 61 424-429. 

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