N-alkylation of highly quaternized chitosan derivatives affects the paracellular permeation enhancement in bronchial epithelia in vitro

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 86, Issue 1, 2014, Pages 55-63

  Benediktsdóttir, Berglind Eva ^a   Gudjónsson, Thórarinn ^a   Baldursson, Ólafur ^b   Másson, Már ^a  

^a UNIVERSITY OF ICELAND   (Iceland)

^b LANDSPITALI UNIVERSITY HOSPITAL   (Iceland)

Author keywords

Airway drug delivery; Chitosan; N quaternary derivatives; Permeation enhancement; Tight junctions; TMC

Indexed keywords

CHITOSAN DERIVATIVE; CLAUDIN 4; F ACTIN; FLUORESCEIN ISOTHIOCYANATE DEXTRAN; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CELL VIABILITY; CONTROLLED STUDY; ELECTRIC RESISTANCE; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPOPHILICITY; LUNG ALVEOLUS EPITHELIUM; MACROMOLECULE; STRUCTURE ACTIVITY RELATION;

AIRWAY DRUG DELIVERY; CHITOSAN; N-QUATERNARY DERIVATIVES; PERMEATION ENHANCEMENT; TIGHT JUNCTIONS; TMC;

ALKYLATION; BRONCHI; CELL LINE; CELL SURVIVAL; CHITOSAN; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG CARRIERS; EPITHELIAL CELLS; HUMANS; PERMEABILITY; QUATERNARY AMMONIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; TIGHT JUNCTIONS;

EID: 84896735024     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2013.04.002     Document Type: Article

References (55)

1. Beyond Borders. Global Biotechnology Report 2012, Ernst & Young. Available from: < http://www.ey.com/Publication/vwLUAssets/Beyond-borders- 2012/$FILE/Beyond-borders-2012.pdf >.
2. J.S. Patton Mechanisms of macromolecule absorption by the lungs Adv. Drug Deliv. Rev. 19 1996 3 36
3. A. Tronde, B. Nordén, H. Marchner, A.-K. Wendel, H. Lennernäs, and U.H. Bengtsson Pulmonary absorption rate and bioavailability of drugs in vivo in rats: structure-absorption relationships and physicochemical profiling of inhaled drugs J. Pharm. Sci. 92 2003 1216 1233
4. B. Benediktsdóttir, A. Arason, S. Halldórsson, T. Gudjónsson, M. Másson, and Ó. Baldursson Drug delivery characteristics of the progenitor bronchial epithelial cell line VA10 Pharm. Res. 30 2013 781 791
5. K. Shin, V.C. Fogg, and B. Margolis Tight junctions and cell polarity Annu. Rev. Cell Dev. Biol. 22 2006 207 235
6. N.G.M. Schipper, K.M. Vårum, and P. Artursson Chitosans as absorption enhancers for poorly absorbable drugs. 1: Influence of molecular weight and degree of acetylation on drug transport across human intestinal epithelial (Caco-2) cells Pharm. Res. 13 1996 1686 1692
7. A.F. Kotze, H.L. Luessen, B.J. de Leeuw, B.G. de Boer, J.C. Verhoef, and H.E. Junginger Comparison of the effect of different chitosan salts and N-trimethyl chitosan chloride on the permeability of intestinal epithelial cells (Caco-2) J. Control. Release 51 1998 35 46
8. M. Thanou, B.I. Florea, M.W.E. Langemeyer, J.C. Verhoef, and H.E. Junginger N-trimethylated chitosan chloride (TMC) improves the intestinal permeation of the peptide drug buserelin in vitro (Caco-2 cells) and in vivo (rats) Pharm. Res. 17 2000 27 31
9. N.G.M. Schipper, S. Olsson, J.A. Hoogstraate, A.G. deBoer, K.M. Vårum, and P. Artursson Chitosans as absorption enhancers for poorly absorbable drugs 2: mechanism of absorption enhancement Pharm. Res. 14 1997 923 929
10. J. Smith, E. Wood, and M. Dornish Effect of chitosan on epithelial cell tight junctions Pharm. Res. 21 2004 43 49
11. C.-M. Lehr, J.A. Bouwstra, E.H. Schacht, and H.E. Junginger In vitro evaluation of mucoadhesive properties of chitosan and some other natural polymers Int. J. Pharm. 78 1992 43 48
12. H. Onishi, and Y. Machida Biodegradation and distribution of water-soluble chitosan in mice Biomaterials 20 1999 175 182
13. P. Baldrick The safety of chitosan as a pharmaceutical excipient Regul. Toxicol. Pharmacol. 56 2010 290 299
14. L. Illum, N.F. Farraj, and S.S. Davis Chitosan as a novel nasal delivery system for peptide drugs Pharm. Res. 11 1994 1186 1189
15. B.I. Florea, M. Thanou, H.E. Junginger, and G. Borchard Enhancement of bronchial octreotide absorption by chitosan and N-trimethyl chitosan shows linear in vitro/in vivo correlation J. Control. Release 110 2006 353 361
16. M.W. Anthonsen, and O. Smidsrod Hydrogen-ion titration of chitosans with varying degrees of N-acetylation by monitoring induced H-1-NMR chemical-shifts Carbohydr. Polym. 26 1995 303 305
17. J.K. Sahni, S. Chopra, F.J. Ahmad, and R.K. Khar Potential prospects of chitosan derivative trimethyl chitosan chloride (TMC) as a polymeric absorption enhancer: synthesis, characterization and applications J. Pharm. Pharmacol. 60 2008 1111 1119
18. R.A.A. Muzzarelli, and F. Tanfani The N-permethylation of chitosan and the preparation of N-trimethyl chitosan iodide Carbohydr. Polym. 5 1985 297 307
19. C.H. Kim, J.W. Choi, H.J. Chun, and K.S. Choi Synthesis of chitosan derivatives with quaternary ammonium salt and their antibacterial activity Polym. Bull. 38 1997 387 393
20. P. Ledung, M. Milas, M. Rinaudo, and J. Desbrieres Water-soluble derivatives obtained by controlled chemical modifications of chitosan Carbohydr. Polym. 24 1994 209 214
21. A.B. Sieval, M. Thanou, A.F. Kotze, J.E. Verhoef, J. Brussee, and H.E. Junginger Preparation and NMR characterization of highly substituted N-trimethyl chitosan chloride Carbohydr. Polym. 36 1998 157 165
22. A. Polnok, G. Borchard, J.C. Verhoef, N. Sarisuta, and H.E. Junginger Influence of methylation process on the degree of quaternization of N-trimethyl chitosan chloride Eur. J. Pharm. Biopharm. 57 2004 77 83
23. R.J. Verheul, M. Amidi, S. van der Wal, E. van Riet, W. Jiskoot, and W.E. Hennink Synthesis, characterization and in vitro biological properties of O-methyl free N,N,N-trimethylated chitosan Biomaterials 29 2008 3642 3649
24. R.J. Verheul, M. Amidi, M.J. van Steenbergen, E. van Riet, W. Jiskoot, and W.E. Hennink Influence of the degree of acetylation on the enzymatic degradation and in vitro biological properties of trimethylated chitosans Biomaterials 30 2009 3129 3135
25. A.M.M. Sadeghi, F.A. Dorkoosh, M.R. Avadi, M. Weinhold, A. Bayat, F. Delie, R. Gurny, B. Larijani, M. Rafiee-Tehrani, and H.E. Junginger Permeation enhancer effect of chitosan and chitosan derivatives: comparison of formulations as soluble polymers and nanoparticulate systems on insulin absorption in Caco-2 cells Eur. J. Pharm. Biopharm. 70 2008 270 278
26. B.E. Benediktsdottir, V.S. Gaware, O.V. Runarsson, S. Jonsdottir, K.J. Jensen, and M. Masson Synthesis of N, N, N-trimethyl chitosan homopolymer and highly substituted N-alkyl-N, N-dimethyl chitosan derivatives with the aid of di-tert-butyldimethylsilyl chitosan Carbohydr. Polym. 86 2011 1451 1460
27. M.H. Ottoy, K.M. Varum, and O. Smidsrod Compositional heterogeneity of heterogeneously deacetylated chitosans Carbohydr. Polym. 29 1996 17 24
28. B.E. Benediktsdóttir, K.K. Sørensen, M.B. Thygesen, K.J. Jensen, T. Gudjónsson, Ó. Baldursson, and M. Másson Regioselective fluorescent labeling of N, N, N-trimethyl chitosan via oxime formation Carbohydr. Polym. 90 2012 1273 1280
29. S. Halldorsson, V. Asgrimsson, I. Axelsson, G.H. Gudmundsson, M. Steinarsdottir, O. Baldursson, and T. Gudjonsson Differentiation potential of a basal epithelial cell line established from human bronchial explant In Vitro Cell. Dev. - Anim. 43 2007 283 289
30. R. Scherließ The MTT assay as tool to evaluate and compare excipient toxicity in vitro on respiratory epithelial cells Int. J. Pharm. 411 2011 98 105
31. S. Franzdottir, I. Axelsson, A. Arason, O. Baldursson, T. Gudjonsson, and M. Magnusson Airway branching morphogenesis in three dimensional culture Respir. Res. 11 2010 162
32. K.A. Foster, M.L. Avery, M. Yazdanian, and K.L. Audus Characterization of the Calu-3 cell line as a tool to screen pulmonary drug delivery Int. J. Pharm. 208 2000 1 11
33. N.R. Mathias, J. Timoszyk, P.I. Stetsko, J.R. Megill, R.L. Smith, and D.A. Wall Permeability characteristics of Calu-3 human bronchial epithelial cells: in vitro-in vivo correlation to predict lung absorption in rats J. Drug Target. 10 2002 31 40
34. J. Fogh, J.M. Fogh, and T. Orfeo 127 Cultured human tumor-cell lines producing tumors in nude mice J. Natl. Cancer I 59 1977 221 226
35. C.J. Watson, M. Rowland, and G. Warhurst Functional modeling of tight junctions in intestinal cell monolayers using polyethylene glycol oligomers Am. J. Physiol. - Cell Physiol. 281 2001 C388 C397
36. S. Lu, A.W. Gough, W.F. Bobrowski, and B.H. Stewart Transport properties are not altered across Caco-2 cells with heightened TEER despite underlying physiological and ultrastructural changes J. Pharm. Sci. 85 1996 270 273
37. S.Y. Yee In vitro permeability across Caco3 cells (colonic) can predict in vivo (small intestinal) absorption in man - fact or myth Pharm. Res. 14 1997 763 766
38. R. Rosenthal, D. Günzel, C. Finger, S.M. Krug, J.F. Richter, J.-D. Schulzke, M. Fromm, and S. Amasheh The effect of chitosan on transcellular and paracellular mechanisms in the intestinal epithelial barrier Biomaterials 33 2012 2791 2800
39. A.F. Kotze, M.M. Thanou, H.L. Luessen, B.G. de Boer, J.C. Verhoef, and H.E. Junginger Effect of the degree of quaternization of N-trimethyl chitosan chloride on the permeability of intestinal epithelial cells (Caco-2) Eur. J. Pharm. Biopharm. 47 1999 269 274
40. C. Jonker, J.H. Hamman, and A.F. Kotze Intestinal paracellular permeation enhancement with quaternised chitosan: in situ and in vitro evaluation Int. J. Pharm. 238 2002 205 213
41. P. Ashton, K.A. Walters, K.R. Brain, and J. Hadgraft Surfactant effects in percutaneous absorption I. Effects on the transdermal flux of methyl nicotinate Int. J. Pharm. 87 1992 261 264
42. A. Nokhodchi, J. Shokri, A. Dashbolaghi, D. Hassan-Zadeh, T. Ghafourian, and M. Barzegar-Jalali The enhancement effect of surfactants on the penetration of lorazepam through rat skin Int. J. Pharm. 250 2003 359 369
43. A.F. Kotze, M.M. Thanou, H.L. Luebetaen, A.G. de Boer, J.C. Verhoef, and H.E. Junginger Enhancement of paracellular drug transport with highly quaternized N-trimethyl chitosan chloride in neutral environments: in vitro evaluation in intestinal epithelial cells Caco-2 J. Pharm. Sci. 88 1999 253 257
44. A.F. Kotze, H.L. Luessen, B.J. deLeeuw, B.G. deBoer, J.C. Verhoef, and H.E. Junginger N-trimethyl chitosan chloride as a potential absorption enhancer across mucosal surfaces: In vitro evaluation in intestinal epithelial cells (Caco-2) Pharm. Res. 14 1997 1197 1202
45. M.M. Thanou, A.F. Kotze, T. Scharringhausen, H.L. Luessen, A.G. de Boer, J.C. Verhoef, and H.E. Junginger Effect of degree of quaternization of N-trimethyl chitosan chloride for enhanced transport of hydrophilic compounds across intestinal Caco-2 cell monolayers J. Control. Release 64 2000 15 25
46. L. Kudsiova, and M.J. Lawrence A comparison of the effect of chitosan and chitosan-coated vesicles on monolayer integrity and permeability across Caco-2 and 16HBE14o-cells J. Pharm. Sci. 97 2008 3998 4010
47. P. Artursson, T. Lindmark, S.S. Davis, and L. Illum Effect of chitosan on the permeability of monolayers of intestinal epithelial-cells (Caco-2) Pharm. Res. 11 1994 1358 1361
48. V. Dodane, M. Amin Khan, and J.R. Merwin Effect of chitosan on epithelial permeability and structure Int. J. Pharm. 182 1999 21 32
49. F.A. Dorkoosh, C.A.N. Broekhuizen, G. Borchard, M. Rafiee-Tehrani, J.C. Verhoef, and H.E. Junginger Transport of octreotide and evaluation of mechanism of opening the paracellular tight junctions using superporous hydrogel polymers in Caco-2 cell monolayers J. Pharm. Sci. 93 2004 743 752
50. T.-H. Yeh, L.-W. Hsu, M.T. Tseng, P.-L. Lee, K. Sonjae, Y.-C. Ho, and H.-W. Sung Mechanism and consequence of chitosan-mediated reversible epithelial tight junction opening Biomaterials 32 2011 6164 6173
51. D. Vllasaliu, R. Exposito-Harris, A. Heras, L. Casettari, M. Garnett, L. Illum, and S. Stolnik Tight junction modulation by chitosan nanoparticles: comparison with chitosan solution Int. J. Pharm. 400 2010 183 193
52. J.L. Madara Intestinal absorptive cell tight junctions are linked to cytoskeleton Am. J. Physiol. - Cell Physiol. 253 1987 C171 C175
53. S. Frisch, and H. Francis Disruption of epithelial cell-matrix interactions induces apoptosis J. Cell Biol. 124 1994 619 626
54. X. Jia, X. Chen, Y. Xu, X. Han, and Z. Xu Tracing transport of chitosan nanoparticles and molecules in Caco-2 cells by fluorescent labeling Carbohydr. Polym. 78 2009 323 329
55. M. Huang, E. Khor, and L.-Y. Lim Uptake and cytotoxicity of chitosan molecules and nanoparticles: effects of molecular weight and degree of deacetylation Pharm. Res. 21 2004 344 353