Methylated N-aryl chitosan derivative/DNA complex nanoparticles for gene delivery: Synthesis and structure-activity relationships

Carbohydrate Polymers

Volumn 78, Issue 4, 2009, Pages 743-752

  Sajomsang, Warayuth ^a   Ruktanonchai, Uracha ^a   Gonil, Pattarapond ^a   Mayen, Varissaporn ^a   Opanasopit, Praneet ^b  

^a NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY   (Thailand)

^b SILPAKORN UNIVERSITY   (Thailand)

Author keywords

Chitosan; DNA; Gene carrier; Methylated N aryl chitosan derivatives

Indexed keywords

AROMATIC MOIETIES; ATOMIC FORCE; ATR FTIR; CHEMICAL STRUCTURE; CHITOSAN DERIVATIVES; COMPLEX NANOPARTICLES; GEL ELECTROPHORESIS; GENE CARRIER; GENE DELIVERY; GREEN FLUORESCENCE PROTEINS; H NMR SPECTROSCOPY; HUH-7 CELLS; HUMAN HEPATOMA CELLS; METHYLATED N-ARYL CHITOSAN DERIVATIVES; MICROSCOPIC TECHNIQUES; MTT ASSAYS; N , N , N-TRIMETHYL CHITOSAN CHLORIDE; PLASMID DNA; REDUCTIVE AMINATION; STRUCTURE ACTIVITY RELATIONSHIPS; TRANSFECTION EFFICIENCY; ZETA-POTENTIALS;

CHITOSAN; CHLORINE COMPOUNDS; CYTOTOXICITY; DNA; ELECTROPHORESIS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GELATION; GENE TRANSFER; GENES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEIC ACIDS; SYNTHESIS (CHEMICAL);

CHITIN;

EID: 69749085890     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2009.06.006     Document Type: Article

References (40)

1. Allen M.J., Bradbury E.M., and Balhorn R. AFM analysis of DNA-protamine complexes bound to mica. Nucleic Acids Research 25 (1997) 2221-2226
2. Anderson D.G., Akinc A., Hossain N., and Langer R. Structure/property studies of polymeric gene delivery using a library of poly(β-amino esters). Molecular Therapy 11 (2005) 426-434
3. Boussif O., Lezoualc'h F., Zanta M.A., Mergny M.D., Scherman D., Demeneix B., et al. A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: Polyethylenimine. Proceedings of the National Academy of Sciences of the USA 92 (1995) 7297-7301
4. Brugnerotto J., Lizardi J., Goycoolea F.M., Argüelles-Monal W., Desbrières J., and Rinaudo M. An infrared investigation in relation with chitin and chitosan characterization. Polymer 42 (2001) 3569-3580
5. Chae S.Y., Son S., Lee M., Jang M.K., and Nah J.W. Deoxycholic acid-conjugated chitosan oligosaccharide nanoparticles for efficient gene carrier. Journal of Controlled Release 109 (2005) 330-344
6. Check E. Gene therapy put on hold as third child develops cancer. Nature 433 (2005) 561
7. Corsi K., Chellat F., Yahia L., and Fernandes J.C. Mesenchymal stem cells, MG63 and HEK293 transfection using chitosan-DNA nanoparticles. Biomaterials 24 (2003) 1255-1264
8. Crini G., Torri G., Guerrini M., Morcellet M., Weltrowski M., and Martel B. NMR characterization of N-benzyl sulfonated derivatives of chitosan. Carbohydrate Polymers 33 (1997) 145-151
9. Doody A.M., Korley J.N., Dang K.P., Zawaneh P.N., and Putnam D. Characterizing the structure/function parameter space of hydrocarbon-conjugated branched polyethylenimine for DNA delivery in vitro. Journal of Controlled Release 116 (2006) 227-237
10. Elisabete C., Douglas D.B., and Sergio P.C.F. Methylation of chitosan with iodomethane: Effect of reaction conditions on chemoselectivity and degree of substitution. Macromolecular BioScience 3 (2003) 571-576
11. Germershaus O., Mao S., Sitterberg J., Bakowsky U., and Kissel T. 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
12. Golan R., Pietrasanta L.I., Hsieh W., and Hansma H.G. DNA toroids: Stages in condensation. Biochemistry 38 (1999) 14069-14076
13. Guy J., Drabek D., and Antoniou M. Delivery of DNA into mammalian cells by receptor-mediated endocytosis and gene therapy. Molecular Biotechnology 3 (1995) 237-248
14. Hollon T. Researchers and regulators reflect on first gene therapy death. Nature Medicine 6 (2000) 6-14
15. Kean T., Roth S., and Thanou M. Trimethylated chitosans as non-viral gene delivery vectors: Cytotoxicity and transfection efficiency. Journal of Controlled Release 103 (2005) 643-653
16. Kim C.H., Choi J.W., Chun H.J., and Choi K.S. Synthesis of chitosan derivatives with quaternary ammonium salt and their antibacterial activity. Polymer Bulletin 38 (1997) 387-393
17. Kim T.H., Jiang H.L., Jere D., Park I.K., Cho M.H., Nah J.W., et al. Chemical modification of chitosan as a gene carrier in vitro and in vivo. Progress in Polymer Science 32 (2007) 726-753
18. Kneuer C., Sameti M., Bakowsky U., Schietstel T., Schirra H., Schmidt H., et al. A nonviral DNA delivery system based on surface modified silica-nanoparticles can efficiently transfect cells in vitro. Bioconjugate Chemistry 11 (2000) 926-932
19. Köping-Höggård M., Tubulekas I., Guan H., Edwards K., Nilsson M., Vårum K.M., et al. Chitosan as a nonviral gene delivery system. Structure-property relationships and characteristics compared with polyethylenimine in vitro and after lung administration in vivo. Gene Therapy 8 (2001) 1108-1121
20. 1H NMR method for the determination of the degree of deacetylation of chitosan. Journal of Pharmaceutical and Biomedical Analysis 32 (2003) 1149-1158
21. Lee K.Y., Kwon I.C., Kim Y.H., Jo W.H., and Jeong S.Y. Preparation of chitosan self-aggregates as a gene delivery system. Journal of Controlled Release 51 (1998) 213-220
22. Lv H., Zhang S., Wang B., Cui S., and Yan J. Toxicity of cationic lipids and cationic polymers in gene delivery. Journal of Controlled Release 114 (2006) 100-109
23. Mansouri S., Cuie Y., Winnik F., Shi Q., Lavigne P., Benderdour M., et al. Characterization of folate-chitosan-DNA nanoparticles for gene therapy. Biomaterials 27 (2006) 2060-2065
24. Mansouri S., Lavigne P., Corsi K., Benderdour M., Beaumont E., and Fernandes J.C. Chitosan-DNA nanoparticles as non-viral vectors in gene therapy: Strategies to improve transfection efficacy. European Journal of Pharmaceutics and Biopharmaceutics 57 (2004) 1-8
25. Martin A.L., Davies M.C., Rackstraw B.J., Roberts C.J., Stolnik S., Tendler S.J.B., et al. Observation of DNA-polymer condensate formation in real time at a molecular level. Federation of European Biochemical Societies Letters 480 (2000) 106-112
26. Merdan T., Kopeček J., and Kissel T. Prospects for cationic polymers in gene and oligonucleotide therapy against cancer. Advanced Drug Delivery Reviews 54 (2002) 715-758
27. Murata J., Ohya Y., and Ouchi T. Design of quaternary chitosan conjugate having antennary galactose residues as a gene delivery tool. Carbohydrate Polymers 32 (1997) 105-109
28. Nomura T., Nakajima S., Kawabata K., Yamashita F., Takakura Y., and Hashita M. Intratumoral pharmacokinetics and in-vivo gene expression of naked plasmid DNA and its cationic liposome complexes after direct gene transfer. Cancer Research 57 (1997) 2681-2686
29. Ogris M., Steinlein P., Carotta S., Brunner S., and Wagner E. DNA/polyethylenimine transfection particles: Influence of ligands, polymer size and PEGylation on internalisation and gene expression. American Association of Pharmaceutical Scientists 3 3 (2001) 43-53
30. Ogris M., Steinlein P., Kursa M., Mechtler K., Kircheis R., and Wagner E. The size of DNA/transferrin-PEI complexes is an important factor for gene expression in cultured cells. Gene Therapy 5 (1998) 1425-1433
31. Putnam D. Polymers for gene delivery across length scales. Natural Materials 5 (2006) 439-451
32. Sajomsang W., Tantayanon S., Tangpasuthadol V., and Daly W.H. Synthesis of methylated chitosan containing aromatic moieties: Chemoselectivity and effect on molecular weight. Carbohydrate Polymers 72 (2008) 740-750
33. Sieval A.B., Thanou M., Kotzé A.F., Verhoef J.C., Brussee J., and Junginger H.E. Preparation and NMR characterization of highly substituted N-trimethyl chitosan chloride. Carbohydrate Polymers 36 (1998) 157-165
34. Snyman D., Hamman J.H., and Kotze A.F. Evaluation of the mucoadhesive properties of N-trimethyl chitosan chloride. Drug Development and Industrial Pharmacy 29 (2003) 61-69
35. Thanou M., Florea B.I., Geldof M., Junginger H.E., and Borchard G. Quaternized chitosan oligomers as novel gene delivery vectors in epithelial cell lines. Biomaterials 23 (2002) 153-159
36. Tian H., Xiong W., Wei J., Wang Y., Chen X., Jing X., et al. Gene transfection of hyperbranched PEI grafted by hydrophobic amino acid segment PBLG. Biomaterials 28 (2007) 2899-2907
37. Wagner E., Kircheis R., and Walker G.F. Targeted nucleic acid delivery into tumors: New avenues for cancer therapy. Biomedicine and Pharmacotherapy 58 (2004) 152-161
38. Weecharangsan W., Opanasopit P., Ngawhirunpat T., Rojanarata T., and Apirakaramwong A. Chitosan lactate as a nonviral gene delivery vector in COS-1 cells. American Association of Pharmaceutical Scientists 7 3 (2006) E74-E79
39. Wong S.Y., Pelet J.M., and Putman D. Polymer systems for gene delivery - Past, present, and future. Progress in Polymer Science 32 (2007) 799-837
40. Zhang S., Xu Y., Wang B., Qiao W., Liu D., and Li Z. Cationic compounds used in lipoplexes and polyplexes for gene delivery. Journal of Controlled Release 100 (2004) 165-180