Methylated N-(4-N,N-dimethylaminocinnamyl) chitosan enhances paracellular permeability across Caco-2 cells

References

• Artursson, P., Lindmark, T., Davis, S.S., Illum, L. (1994). Effect of chitosan on the permeability of monolayers of intestinal epithelial cells (Caco-2). Pharm Res. 11:1358–61.
   PubMed Web of Science ®Google Scholar
• Balimane, P.V., Chong, S. (2005). Cell culture-based models for intestinal permeability: a critique. Drug Discov Today. 10:335–43.
   PubMed Web of Science ®Google Scholar
• Borchard, G., Lueszen, H.L., Boer, D.A.G., Verhoef, J.C., Lehr, C.M., Junginger, H.E. (1996). The potential of mucoadhesive polymers in enhancing intestinal peptide drug absorption. III. Effects of chitosan-glutamate and carbomer on epithelial tight junctions in vitro. J Contr Rel. 39:131–8.
   Web of Science ®Google Scholar
• Brugnerotto, J., Lizardi, J., Goycoolea, F.M., Argüelles-Monal, W., Desbrières, J., Rinaudo, M. (2001). An infrared investigation in relation with chitin and chitosan characterization. Polymer. 42:3569–80.
   Web of Science ®Google Scholar
• Cano-Cebrian, M.J., Zornoza, T., Granero, L., Polache, A. (2005). Intestinal absorption enhancement via the paracellular route by fatty acids, chitosans and others: a target for drug delivery. Curr Drug Deliv. 2:9–22.
   PubMedGoogle Scholar
• Chae, Y., Jang, M.K., Nah, J.W. (2005). Influence of molecular weight on oral absorption of water soluble chitosans. J Contr Rel. 102:383–94.
   PubMed Web of Science ®Google Scholar
• Colo, D.G., Burgalassi, S., Zambito, Y., Monti, D., Chetoni, P. (2004). Effects of different N-trimethylchitosans on in vitro/in vivo ofloxacin transcorneal permeation. J Pharm Sci. 93:2851–62.
   PubMed Web of Science ®Google Scholar
• Crini, G., Torri, G., Guerrini, M., Morcellet, M., Weltrowski, M., Martel, B. (1997). NMR characterization of N-benzyl sulfonated derivatives of chitosan. Carbohyd Polym. 33:145–51.
   Web of Science ®Google Scholar
• Domard, A., Rinaudo, M., Terrassin, C. (1986). New method for the quaternization of chitosan. Int J Biol Macromol. 8:105–7.
   Web of Science ®Google Scholar
• Illum, L., Farraj, N.F., Davis, S.S. (1994). Chitosan as a novel nasal delivery system for peptide drugs. Pharm Res. 11:1186–9.
   PubMed Web of Science ®Google Scholar
• Jintapattanakit, A., Mao, S., Kissel, T., Junyaprasert, V.B. (2008). Physicochemical properties and biocompatibility of N-trimethyl chitosan: effect of quaternization and dimethylation. Eur J Pharm Biopharm. 70:563–71.
   PubMed Web of Science ®Google Scholar
• Kotze, A.F., Lueβen, H.L., Leeuw, B.J., Boer, D.B.G., Verhoef, J.C., Junginger, H.E. (1998). Comparison of the effect of different chitosan salts and N-trimethyl chitosan chloride on the permeability of intestinal epithelial cells (Caco-2). J Contr Rel. 51:35–46.
   PubMed Web of Science ®Google Scholar
• Kowapradit, J., Opanasopit, P., Ngawhiranpat, T., Apirakaramwong, A., Rojanarata, T., Ruktanonchai, U., Sajomsang, W. (2008). Methylated N-(4-N,N-dimethylaminobenzyl) chitosan, a novel chitosan derivative, enhances paracellular permeability across intestinal epithelial cells (Caco-2). AAPS PharmSciTechnol. 9:1143–52.
   PubMed Web of Science ®Google Scholar
• Lapierre, L.A. (2000). The molecular structure of the tight junction. Adv Drug Deliv Rev. 41:255–64.
   PubMed Web of Science ®Google Scholar
• Madara, J.L. (1987). Intestinal absorptive cell tight junction are linked to cytoskeleton. Am J Physiol. 253:C171–5.
   PubMed Web of Science ®Google Scholar
• McEwan, G., Jepson, M., Hirst, B., Simmons, N. (1993). Polycation-induced enhancement of epithelial paracellular permeability is independent of tight junctional characteristics. Biochim Biophys Acta. 1148:51–60.
   PubMed Web of Science ®Google Scholar
• Portero, A., Remunan-Lopez, C., Nielsen, H.M. (2002). The potential of chitosan in enhancing peptide and protein absorption across the TR146 cell culture model-an in vitro model of the buccal epithelium. Pharm Res. 19:169–74.
   PubMed Web of Science ®Google Scholar
• Rabea, E.I., Badawy, I.M.E., Rogge, T.M., Stevens, C.V., Hofte, M., Steurbaut, W., Smagghe, G. (2005). Insecticidal and fungicidal activity of new synthesized chitosan derivatives. Pest Manag Sci. 61:951–60.
   PubMed Web of Science ®Google Scholar
• Ross, B.P., Toth, I. (2005). Gastrointestinal absorption of heparin by lipidization or coadministration with penetration enhancers. Curr Drug Deliv. 2:277–87.
   PubMedGoogle Scholar
• Sajomsang, W., Tantayanon, S., Tangpasuthadol, V., Daly, W.H. (2008b). Synthesis of methylated chitosan containing aromatic moieties: chemoselectivity and effect on molecular weight. Carbohyd Polym. 72:740–50.
   Web of Science ®Google Scholar
• Sajomsang, W., Tantayanon, S., Tangpasuthadol, V., Thatte, M., Daly, W.H. (2008a). Synthesis and characterization of N-aryl chitosan derivatives. Int J Biol Macromol. 43:79–87.
   PubMed Web of Science ®Google Scholar
• Sandri, G., Rossi, S., Ferrari, F., Bonferoni, M.C., Muzzarelli, C., Caramella, C. (2004). Assessment of chitosan derivatives as buccal and vaginal penetration enhancers. Eur J Pharm Sci. 21:351–9.
   PubMed Web of Science ®Google Scholar
• Sashiwa, H., Shigemasa, Y. (1999). Chemical modification of chitin and chitosan 2: preparation and water soluble property of N-acylated or N-alkylated partially deacetylated chitins. Carbohyd Polym. 39:127–38.
   Web of Science ®Google Scholar
• Schipper, N.G., Olsson, S., Hoogstraate, J.A., Boer, D.A.G., Varum, K.M., Artursson, P. (1997). Chitosans as absorption enhancers for poorly absorbable drugs II: mechanism of absorption enhancement. Pharm Res. 14:923–9.
   PubMed Web of Science ®Google Scholar
• Sieval, A.B., Thanou, M., Kotze, A.F., Verhoef, J.C., Brussee, J., Junginger, H.E. (1998). Preparation and NMR characterization of highly substituted trimethyl chitosan chloride. Carbohyd Polym. 36:157–65.
   Web of Science ®Google Scholar
• Snyman, D., Hamman, J.H., Kotze, J.S., Rollings, J.E., Kotzé, A.F. (2002). The relationship between the absolute molecular weight and the degree of quaternisation of N-trimethyl chitosan chloride. Carbohyd Polym. 50:145–50.
   Web of Science ®Google Scholar
• Tanima, B., Susmita, M., Ajay, K.S. (2002). Preparation, characterization and biodistribution of ultrafine chitosan nanoparticles. Int J Pharm. 243:93–105.
   PubMedGoogle Scholar
• Thanoo, B.C., Sunny, M.C., Jayakrishnan, A. (1992). Crosslinked chitosan microspheres: preparation and evaluation as a matrix for the controlled release of pharmaceuticals. J Pharm Pharmacol. 44:283–6.
   PubMed Web of Science ®Google Scholar
• Thanou, M., Verhoef, J.C., Junginger, H.E. (2001). Chitosan and its derivatives as intestinal absorption enhancers. Adv Drug Deliv Rev. 50:91–101.
   PubMed Web of Science ®Google Scholar