Effect of N-pyridinium positions of quaternized chitosan on transfection efficiency in gene delivery system

Carbohydrate Polymers

Volumn 104, Issue 1, 2014, Pages 17-22

  Sajomsang, Warayuth ^a   Gonil, Pattarapond ^a   Ruktanonchai, Uracha Rungsardthong ^a   Petchsangsai, Maleenart ^b   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; N pyridylmethyl chitosan; Quaternized chitosan; Transfection efficiency

Indexed keywords

COMPLEX FORMATIONS; DEGREE OF QUATERNIZATION; GENE DELIVERY; GENE DELIVERY SYSTEMS; POSITIVE CHARGES; QUATERNIZED CHITOSANS; REDUCTIVE AMINATION; TRANSFECTION EFFICIENCY;

ALKYLATION; CELL CULTURE; CHITOSAN; CHLORINE COMPOUNDS; CYTOTOXICITY; EFFICIENCY; GENE TRANSFER; TRANSMISSION ELECTRON MICROSCOPY;

MOLECULAR BIOLOGY;

CHITOSAN; GREEN FLUORESCENT PROTEIN; METHYLATED N-(4-PYRIDINYLMETHYL)CHITOSAN;

ANALOGS AND DERIVATIVES; CHEMISTRY; GENETIC TRANSFECTION; GENETICS; HUMAN; PLASMID; PROCEDURES; TUMOR CELL LINE;

CELL LINE, TUMOR; CHITOSAN; GREEN FLUORESCENT PROTEINS; HUMANS; PLASMIDS; TRANSFECTION;

EID: 84893202558     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2013.12.077     Document Type: Article

References (23)

1. Y. Gao, Z. Zhang, L. Chen, W. Gu, and Y. Li Chitosan N-betainates/DNA self-assembly nanoparticles for gene delivery: In vitro uptake and transfection efficiency International Journal of Pharmaceutics 371 2009 156 162
2. O. Germershaus, S. Mao, J. Sitterberg, U. Bakowsky, and T. Kissel Gene delivery using chitosan, trimethyl chitosan or polyethyleneglycol-graft- trimethyl chitosan block copolymers: Establishment of structure-activity relationships in vitro Journal of Controlled Release 125 2008 145 154
3. M.A. Ilies, W.A. Seitz, I. Ghiviriga, B.H. Johnson, A. Miller, and E.B. Thompson et al. Pyridinium cationic lipids in gene delivery: A structure-activity correlation study Journal of Medicinal Chemistry 47 2004 3744 3754
4. 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
5. 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
6. T.H. Kim, H.L. Jiang, D. Jere, I.K. Park, M.H. Cho, and J.W. Nah et al. Chemical modification of chitosan as a gene carrier in vitro and in vivo Progress in Polymer Science 32 2007 726 753
7. 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
8. 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
9. R.A.A. Muzzarelli Chitosans: New vectors for gene therapy R. Ito, Y. Matsuo, Handbook of carbohydrate polymers: Development, properties and applications 2010 Nova Publ. Hauppauge NY, USA 583 604
10. R.A.A. Muzzarelli Chitins and chitosans as immunoadjuvants and non-allergenic drug carriers Marine Drugs 8 2 2010 292 312
11. R.A.A. Muzzarelli Nanochitins and nanochitosans, paving the way to eco-friendly and energy-saving exploitation of marine resources Polymer Science: A Comprehensive Reference 10 2012 153 164
12. 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
13. D. Pijper, E. Bulten, J. Šmisterová, A. Wagenaar, D. Hoekstra, and J.B.F.N. Engberts et al. Novel biodegradable pyridinium amphiphiles for gene delivery European Journal of Organic Chemistry 22 2003 4406 4412
14. T. Rojanarata, M. Petchsangsai, P. Opanasopit, T. Ngawhirunpat, U. Ruktanonchai, and W. Sajomsang et al. Methylated N-(4-N,N-dimethylaminobenzyl) chitosan for novel effective gene carriers European Journal of Pharmaceutics and Biopharmaceutics 70 2008 207 214
15. S. Safari, F.A. Dorkoosha, M. Soleimani, M.H. Zarrintan, H. Akbari, and B. Larijani et al. N-Diethylmethyl chitosan for gene delivery to pancreatic cancer cells and the relation between charge ratio and biologic properties of polyplexes via interpolations polynomial International Journal of Pharmaceutics 420 2011 350 357
16. W. Sajomsang Synthetic methods and applications of chitosan containing pyridylmethyl moiety and its quaternized derivatives: A review Carbohydrate Polymers 80 2010 631 647
17. W. Sajomsang, S. Tantayanon, V. Tangpasuthadol, M. Thatte, and W.H. Daly Synthesis and characterization of N-aryl chitosan derivatives International Journal of Biological Macromolecules 43 2008 79 87
18. 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
19. 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
20. W. Sajomsang, P. Gonil, U. Ruktanonchai, M. Petchsangsai, P. Opanasopit, and S. Puttipipatkhachorn Effects of molecular weight and pyridinium moiety on water-soluble chitosan derivatives for mediated gene delivery Carbohydrate Polymers 91 2013 508 517
21. A.B. Sieval, M. Thanou, A.F. Kotze, J.C. Verhoef, J. Brussee, and H.E. Junginger Preparation and NMR characterization of highly substituted trimethyl chitosan chloride Carbohydrate Polymers 36 1998 157 165
22. 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 et al. Novel pyridinium surfactants for efficient, nontoxic in vitro gene delivery Proceedings of the National Academy of Sciences of the United States of America 94 1997 1160 1165
23. W. Weecharangsan, P. Opanasopit, T. Ngawhirunpat, T. Rojanarata, and A. Apirakaramwong Chitosan lactate as a nonviral gene delivery vector in COS-1 cells American Association Pharmaceutical Scientists PharmSciTech 7 2006 E74 E79