Effects of molecular weight and pyridinium moiety on water-soluble chitosan derivatives for mediated gene delivery

Carbohydrate Polymers

Volumn 91, Issue 2, 2013, Pages 508-517

  Sajomsang, Warayuth ^a   Gonil, Pattarapond ^a   Ruktanonchai, Uracha Rungsardthong ^a   Petchsangsai, Maleenart ^a   Opanasopit, Praneet ^b   Puttipipatkhachorn, Satit ^c  

^a NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY   (Thailand)

^b SILPAKORN UNIVERSITY   (Thailand)

^c MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Chitosan; Gene delivery; Methylated N (3 pyridylmethyl) chitosan chloride; Molecular weight; Pyridinium trimethyl ammonium ratio; Quaternized chitosan

Indexed keywords

CELL LINES; DELOCALIZATIONS; GENE DELIVERY; GENE TRANSFECTION; HETEROCYCLIC RINGS; HUMAN HEPATOMAS; HYDROPHOBIC EFFECT; METHYLATED N-(3-PYRIDYLMETHYL) CHITOSAN CHLORIDE; NITROGEN ATOM; NONVIRAL VECTORS; PHOSPHORUS ATOM; PHYSICOCHEMICAL PROPERTY; POSITIVE CHARGES; PYRIDINE RINGS; PYRIDINIUM; TRANSFECTION EFFICIENCY; WATER-SOLUBLE CHITOSAN;

AMMONIUM COMPOUNDS; CELL CULTURE; CHITOSAN; CHLORINE COMPOUNDS; DNA; EFFICIENCY; GENE TRANSFER; GENES;

MOLECULAR WEIGHT;

CHITOSAN; DNA; DRUG DERIVATIVE; NANOCONJUGATE; PYRIDINIUM DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CELL SURVIVAL; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECT; GENE TRANSFER; GENETIC TRANSFECTION; HUMAN; METABOLISM; METHODOLOGY; MOLECULAR WEIGHT; TRANSMISSION ELECTRON MICROSCOPY; TUMOR CELL LINE;

CELL LINE, TUMOR; CELL SURVIVAL; CHITOSAN; DNA; GENE TRANSFER TECHNIQUES; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR WEIGHT; NANOCONJUGATES; PYRIDINIUM COMPOUNDS; QUATERNARY AMMONIUM COMPOUNDS; TRANSFECTION;

EID: 84868336004     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2012.08.053     Document Type: Article

References (45)

1. W.F. Anderson Human gene therapy Science 256 1992 808 813
2. D.G. Anderson, A. Akinc, N. Hossain, and R. Langer Structure/property studies of polymeric gene delivery using a library of poly(β-amino esters) Molecular Therapy 11 2005 426 434
3. J.M. Benns, J.S. Choi, R.I. Mahato, J.S. Park, and S.W. Kim pH-sensitive cationic polymer gene delivery vehicle: N-Ac-poly(l-histidine)-graft-poly(l- lysine) comb shaped polymer Bioconjugate Chemistry 11 2000 637 645
4. O. Boussif, F. Lezoualc'h, M.A. Zanta, M.D. Mergny, D. Scherman, and B. Demeneix A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: Polyethylenimine The Proceedings of the National Academy of Sciences of the United States of America 92 1995 7297 7301
5. K. Corsi, F. Chellat, L. Yahia, and J.C. Fernandes Mesenchymal stem cells, MG63 and HEK293 transfection using chitosan-DNA nanoparticles Biomaterials 24 2003 1255 1264
6. I.Y. Farber, and A.J. Domb Cationic polysaccharides for gene delivery Materials Science and Engineering C 27 2007 595 598
7. X. Gao, K.S. Kim, and D. Liu Nonviral gene delivery: What we know and what is next The American Association Pharmaceutical Scientists Journal 9 2007 E92 E104
8. O. Germershaus, S. Mao, J. Sitterberg, U. Bakowsky, and T. Kissel Gene delivery using chitosan, trimethyl chitosan or polyethylenglycol-graft-trimethyl chitosan block copolymers: Establishment of structure-activity relationships in vitro Journal of Controlled Release 125 2008 145 154
9. K.V. Gersdorff, N.N. Sanders, R. Vandenbroucke, S.C. De Smedt, E. Wagner, and M. Ogris The internalization route resulting in successful gene expression depends on both cell line and polyethylenimine polyplex type Molecular Therapy 14 2006 745 753
10. C. Goncalves, E. Mennesson, R. Fuchs, J.P. Gorvel, P. Midoux, and C. Pichon Macropinocytosis of polyplexes and recycling of plasmid via the clathrin-dependent pathway impair the transfection efficiency of human hepato-carcinoma cells Molecular Therapy 10 2004 373 385
11. J.J. Green, R. Langer, and D.G. Anderson A combinatorial polymer library approach yields insight into non-viral gene delivery Accounts of Chemical Research 41 2008 749 979
12. S. Grosse, Y. Aron, G. Thevenot, D. Francois, M. Monsigny, and I. Fajac Potocytosis and cellular exit of complexes as cellular pathways for gene delivery by polycations The Journal of Gene Medicine 7 2005 1275 1286
13. J. Guy, D. Drabek, and M. Antoniou Delivery of DNA into mammalian cells by receptor-mediated endocytosis and gene therapy Molecular Biotechnology 3 1995 237 248
14. M. Hashimoto, M. Morimoto, H. Saimoto, Y. Shigemasa, and T. Sato Lactosylated chitosan for DNA delivery into hepatocytes: The effect of lactosylation on the physicochemical properties and intracellular trafficking of pDNA/chitosan complexes Bioconjugate Chemistry 17 2006 309 316
15. S. Hong, A.U. Bielinska, A. Mecke, B. Keszler, J.L. Beals, and X. Shi Interaction of poly(amidoamine) dendrimers with supported lipid bilayers and cells: Hole formation and the relation to transport Bioconjugate Chemistry 15 2004 774 782
16. M. Huang, E. Khor, and L.Y. Lim Uptake and cytotoxicity of chitosan molecules and nanoparticles: Effects of molecular weight and degree of deacetylation Pharmaceutical Research 21 2004 344 353
17. R. Jayakumar, K.P. Chennazhi, R.A.A. Muzzarelli, H. Tamura, S.V. Nair, and N. Selvamurugan Chitosan conjugated DNA nanoparticles in gene therapy Carbohydrate Polymers 79 2010 1 8
18. M.A. Ilies, B.H. Johnson, F. Makori, A. Miller, W.A. Seitz, and E.B. Thompson Pyridinium cationic lipids in gene delivery: An in vitro and in vivo comparison of transfection efficiency versus a tetraalkylammonium congener Archives of Biochemistry Biophysics 435 2005 217 226
19. M.A. Ilies, W.A. Seitz, I. Ghiviriga, B.H. Johnson, A. Miller, and E.B. Thompson Pyridinium cationic lipids in gene delivery: A structure-activity correlation study Journal of Medicinal Chemistry 47 2004 3744 3754
20. T. Ishii, Y. Okahata, and T. Sato Mechanism of cell transfection with plasmid/chitosan complexes Biochimica et Biophysica Acta 1514 2001 51 64
21. K.A. Janes, and M.J. Alonso Depolymerized chitosan nanoparticles for protein delivery: Preparation and characterization Journal of Applied Polymer Science 88 2003 2769 2776
22. T. Kean, S. Roth, and M. Thanou Trimethylated chitosans as non-viral gene delivery vectors: Cytotoxicity and transfection efficiency Journal of Controlled Release 103 2005 643 653
23. T. Kiang, J. Wen, H.W. Lim, and K.W. Leong The effect of the degree of chitosan deacetylation on the efficiency of gene transfection Biomaterials 25 2004 5293 5301
24. T.H. Kim, H.L. Jiang, D. Jere, I.K. Park, M.H. Cho, and J.W. Nah Chemical modification of chitosan as a gene carrier in vitro and in vivo Progress in Polymer Science 32 2007 726 753
25. D.K. Knight, S.N. Shapka, and B.G. Amsden Structure, depolymerization, and cytocompatibility evaluation of glycol chitosan Journal of Biomedical Materials Research Part A 83 2007 787 798
26. M. Kurisawa, M. Yokoyama, and T. Okano Transfection efficiency increases by incorporating hydrophobic monomer units into polymeric gene carriers Journal of Controlled Release 68 2000 1 8
27. J.M. Layman, S.M. Ramirez, M.D. Green, and T.E. Long Influence of polycation molecular weight on poly(2-dimethylaminoethyl methacrylate)-mediated DNA delivery in vitro Biomacromolecules 10 2009 1244 1252
28. S. Li, and L. Huang Nonviral gene therapy: Promises and challenges Gene Therapy 7 2000 31 34
29. Y. Liu, and T.M. Reineke Poly(glycoamidoamine)s for gene delivery. Structural effects on cellular internalization, buffering capacity, and gene expression Bioconjugate Chemistry 18 2007 19 30
30. B. Lu, Y.X. Sun, Y.Q. Li, X.Z. Zhang, and R.Z. Zhuo N-succinyl-chitosan grafted with low molecular weight polyethylenimine as a serum-resistant gene vector Molecular Biosystems 5 2009 629 637
31. M. Manunta, B.J. Nichols, P. Hong Tan, P. Sagoo, J. Harper, and A.J. George Gene delivery by dendrimers operates via different pathways in different cells, but is enhanced by the presence of caveolin Journal of Immunological Methods 314 2006 134 146
32. A.A.P. Meekel, A. Wagenaar, J. Smisterova, J.E. Kroeze, P. Haadsma, and B. Bosgraaf Synthesis of pyridinium amphiphiles used for transfection and some characteristics of amphiphile/DNA complex formation European Journal of Organic Chemistry 4 2000 665 673
33. K.A. Mislick, and J.D. Baldeschwieler Evidence for the role of proteoglycans in cation-mediated gene transfer The Proceedings of the National Academy of Sciences of the United States of America 93 1996 12349 12354
34. M. Ogris, P. Steinlein, S. Carotta, S. Brunner, and E. Wagner DNA/polyethylenimine transfection particles: Influence of ligands, polymer size and PEGylation on internalisation and gene expression The American Association Pharmaceutical Scientists PharmSci 3 2001 43 53
35. P. Opanasopit, W. Sajomsang, U. Ruktanonchai, V. Mayen, T. Rojanarata, and T. Ngawhirunpat Methylated N-(4-pyridinylmethyl) chitosan as a novel effective safe gene carrier International Journal of Pharmaceutics 364 2008 127 134
36. D. Pijper, E. Bulten, J. Šmisterová, A. Wagenaar, D. Hoekstra, and J.B.F.N. Engberts Novel biodegradable pyridinium amphiphiles for gene delivery European Journal of Organic Chemistry 22 2003 4406 4412
37. J. Rejman, A. Bragonzi, and M. Conese Role of clathrin- and caveolae-mediated endocytosis in gene transfer mediated by lipo- and polyplexes Molecular Therapy 12 2005 468 474
38. A. Roosjen, J. Šmisterová, C. Driessen, J.T. Anders, A. Wagenaar, and D. Hoekstra Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery European Journal of Organic Chemistry 7 2002 1271 1277
39. W. Sajomsang, U. Ruktanonchai, P. Gonil, V. Mayen, and P. Opanasopit Methylated N-aryl chitosan derivative/DNA complex nanoparticles for gene delivery: Synthesis and structure-activity relationships Carbohydrate Polymers 78 2009 743 752
40. W. Sajomsang, U. Rungsardthong Ruktanonchai, P. Gonil, and C. Warin Quaternization of N-(3-pyridylmethyl) chitosan derivatives: Effects of the degree of quaternization, molecular weight and ratio of N-methylpyridinium and NNN-trimethyl ammonium moieties on bactericidal activity Carbohydrate Polymers 82 2010 1143 1152
41. I. Solodin, C.S. Brown, M.S. Bruno, C.Y. Chow, E.H. Jang, and R.J. Debs A novel series of amphiphilic imidazolinium compounds for in vitro and in vivo gene delivery Biochemistry 34 1995 13537 13544
42. M.X. Tang, and F.C. Szoka The influence of polymer structure on the interactions of cationic polymers with DNA and morphology of the resulting complexes Gene Therapy 4 1997 823 832
43. I. Van Der Woude, A. Wagenaar, A.A.P. Meekel, M.B.A. Ter Beest, M.H.J. Ruiters, and J.B.F.N. Engberts Novel pyridinium surfactants for efficient, nontoxic in vitro gene delivery The Proceedings of the National Academy of Sciences of the United States of America 94 1997 1160 1165
44. 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
45. W. Weecharangsan, P. Opanasopit, T. Ngawhirunpat, T. Rojanarata, and A. Apirakaramwong Chitosan lactate as a nonviral gene delivery vector in COS-1 cells The American Association Pharmaceutical Scientists PharmSciTech 7 2006 E74 E79