Hexanoic acid and polyethylene glycol double grafted amphiphilic chitosan for enhanced gene delivery: Influence of hydrophobic and hydrophilic substitution degree

Molecular Pharmaceutics

Volumn 11, Issue 3, 2014, Pages 982-994

  Layek, Buddhadev ^a   Haldar, Manas K ^a   Sharma, Gitanjali ^a   Lipp, Lindsey ^a   Mallik, Sanku ^a   Singh, Jagdish ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

chitosan; gene delivery; hexanoic acid; poly(ethylene glycol); transfection

Indexed keywords

CHITOSAN; DEOXYRIBONUCLEASE I; HEXANOIC ACID; MACROGOL; PLASMID DNA; DNA; GREEN FLUORESCENT PROTEIN; HEXANOIC ACID DERIVATIVE; MACROGOL DERIVATIVE; MONOMETHOXYPOLYETHYLENE GLYCOL; NANOPARTICLE; POLYMER;

ADSORPTION; ARTICLE; BLOOD COMPATIBILITY; CELL MEMBRANE PERMEABILITY; CELL VIABILITY; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONJUGATION; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; DNA BINDING; EMBRYO; ENZYME DEGRADATION; GENE EXPRESSION; GENE TARGETING; GENETIC TRANSFECTION; HEMOLYSIS; HUMAN; HUMAN CELL; HYDROPHILICITY; HYDROPHOBICITY; IN VITRO GENE TRANSFER; IN VITRO STUDY; MTT ASSAY; NONVIRAL GENE DELIVERY SYSTEM; PARTICLE SIZE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ZETA POTENTIAL; ADMINISTRATION AND DOSAGE; ANIMAL; CHEMICAL PHENOMENA; CHEMISTRY; ERYTHROCYTE; GEL MOBILITY SHIFT ASSAY; GENE TRANSFER; GENETICS; HEK293 CELL LINE; HELA CELL LINE; INFRARED SPECTROSCOPY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLASMID; RAT;

ANIMALS; CAPROATES; CHITOSAN; DNA; ELECTROPHORETIC MOBILITY SHIFT ASSAY; ERYTHROCYTES; GENE TRANSFER TECHNIQUES; GREEN FLUORESCENT PROTEINS; HEK293 CELLS; HELA CELLS; HEMOLYSIS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MAGNETIC RESONANCE SPECTROSCOPY; NANOPARTICLES; PLASMIDS; POLYETHYLENE GLYCOLS; POLYMERS; RATS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84901741345     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400633r     Document Type: Article

References (46)

1. McCormick, F. Cancer Gene Therapy: Fringe or Cutting Edge Nat. Rev. Cancer 2001, 1, 130-141
2. Opalinska, J. B.; Gewirtz, A. M. Nucleic-Acid Therapeutics: Basic Principles and Recent Applications Nat. Rev. Drug Discovery 2002, 1, 503-514
3. Al-Dosari, M. S.; Gao, X. Nonviral Gene Delivery: Principle, Limitations, and Recent Progress AAPS J. 2009, 11, 671-681
4. Kim, T.; Jiang, H.; Jere, D.; Park, I.; Cho, M.; Nah, J.; Choi, Y.; Akaike, T.; Cho, C. Chemical Modification of Chitosan as a Gene Carrier In Vitro and In Vivo Prog. Polym. Sci. 2007, 32, 726-753
5. Giacca, M.; Zacchigna, S. Virus-Mediated Gene Delivery for Human Gene Therapy J. Controlled Release 2012, 161, 377-88
6. Ginn, S. L.; Alexander, I. E.; Edelstein, M. L.; Abedi, M. R.; Wixon, J. Gene Therapy Clinical Trials Worldwide to 2012-an Update J. Gene Med. 2013, 15, 65-77
7. Hollon, T. Researchers and Regulators Reflect on First Gene Therapy Death Nat. Med. 2000, 6, 6
8. Check, E. Gene Therapy Put on Hold as Third Child Develops Cancer Nature 2005, 433, 561
9. Jones, C. H.; Chen, C. K.; Ravikrishnan, A.; Rane, S.; Pfeifer, B. A. Overcoming Nonviral Gene Delivery Barriers: Perspective and Future Mol. Pharmaceutics 2013, 10.1021/mp400467x
10. Remaut, K.; Sanders, N. N.; De Geest, B. G.; Braeckmans, K.; Demeester, J.; De Smedt, S. C. Nucleic Acid Delivery: Where Material Sciences and Bio-Sciences Meet Mater. Sci. Eng. R 2007, 58, 117-161
11. Mao, S.; Sun, W.; Kissel, T. Chitosan-Based Formulations for Delivery of DNA and siRNA Adv. Drug Delivery Rev. 2010, 62, 12-27
12. Saranya, N.; Moorthi, A.; Saravanan, S.; Pandima Devi, M.; Selvamurugan, N. Chitosan and Its Derivatives for Gene Delivery Int. J. Biol. Macromol. 2011, 48, 234-238
13. Yan, J.; Du, Y. Z.; Chen, F. Y.; You, J.; Yuan, H.; Hu, F. Q. Effect of Proteins with Different Isoelectric Points on the Gene Transfection Efficiency Mediated by Stearic Acid Grafted Chitosan Oligosaccharide Micelles Mol. Pharmaceutics 2013, 10, 2568-2577
14. Chang, K. L.; Higuchi, Y.; Kawakami, S.; Yamashita, F.; Hashida, M. Efficient Gene Transfection by Histidine-Modified Chitosan through Enhancement of Endosomal Escape Bioconjugate Chem. 2010, 21, 1087-1095
15. Yang, X.; Yuan, X.; Cai, D.; Wang, S.; Zong, L. Low Molecular Weight Chitosan in DNA Vaccine Delivery via Mucosa Int. J. Pharm. 2009, 375, 123-132
16. Lu, B.; Wang, C. F.; Wu, D. Q.; Li, C.; Zhang, X. Z.; Zhuo, R. X. Chitosan Based Oligoamine Polymers: Synthesis, Characterization, and Gene Delivery J. Controlled Release 2009, 137, 54-62
17. Chan, P.; Kurisawa, M.; Chung, J. E.; Yang, Y. Y. Synthesis and Characterization of Chitosan-g-Poly (ethylene glycol)-Folate as a Non-Viral Carrier for Tumor-Targeted Gene Delivery Biomaterials 2007, 28, 540-549
18. Chiu, Y. L.; Ho, Y. C.; Chen, Y. M.; Peng, S. F.; Ke, C. J.; Chen, K. J.; Mi, F. L.; Sung, H. W. The Characteristics, Cellular Uptake and Intracellular Trafficking of Nanoparticles Made of Hydrophobically-Modified Chitosan J. Controlled Release 2010, 146, 152-159
19. Layek, B.; Singh, J. Amino Acid Grafted Chitosan for High Performance Gene Delivery: Comparison of Amino Acid Hydrophobicity on Vector and Polyplex Characteristics Biomacromolecules 2013, 14, 485-494
20. Liu, W. G.; Zhang, X.; Sun, S. J.; Sun, G. J.; Yao, K. D.; Liang, D. C.; Guo, G.; Zhang, J. Y. N-Alkylated Chitosan as a Potential Nonviral Vector for Gene Transfection Bioconjugate Chem. 2003, 14, 782-789
21. Hu, F. Q.; Zhao, M. D.; Yuan, H.; You, J.; Du, Y. Z.; Zeng, S. A Novel Chitosan Oligosaccharide-Stearic Acid Micelles for Gene Delivery: Properties and In Vitro Transfection Studies Int. J. Pharmaceutics 2006, 315, 158-166
22. Lee, K. Y.; Kwon, I. C.; Jo, W. H.; Jeong, S. Y. Complex Formation Between Plasmid DNA and Self-Aggregates of Deoxycholic Acid-Modified Chitosan Polymer 2005, 46, 8107-8112
23. Son, S. H.; Chae, S. Y.; Choi, C. Y.; Kim, M. Y.; Ngugen, V. G.; Jang, M. K.; Nah, J. W.; Kweon, J. K. Preparation of a Hydrophobized Chitosan Oligosaccharide for Application as an Efficient Gene Carrier Macromol. Res. 2004, 12, 573-580
24. Park, I. K.; Park, Y. H.; Shin, B. A.; Choi, E. S.; Kim, Y. R.; Akaike, T.; Cho, C. S. Galactosylated Chitosan-Graft-Dextran as Hepatocyte-Targeting DNA Carrier J. Controlled Release 2000, 9, 97-108
25. Jiang, X.; Dai, H.; Leong, K. W.; Goh, S. H.; Mao, H. Q.; Yang, Y. Y. Chitosan-g-PEG/DNA Complexes Deliver Gene to the Rat Liver via Intrabiliary and Intraportal Infusions J. Gene Med. 2006, 8, 477-487
26. Zhang, Y.; Chen, J.; Zhang, Y.; Pan, Y.; Zhao, J.; Ren, L.; Liao, M.; Hu, Z.; Kong, L.; Wang, J. A Novel PEGylation of Chitosan Nanoparticles for Gene Delivery Biotechnol. Appl. Biochem. 2007, 46, 197-204
27. Park, I. K.; Ihm, J. E.; Park, Y. H.; Choi, Y. J.; Kim, S. I.; Kim, W. J.; Akaike, T.; Cho, C. S. Galactosylated Chitosan (GC)-Graft-Poly(vinyl pyrrolidone) (PVP) as Hepatocyte-Targeting DNA Carrier: Preparation and Physicochemical Characterization of GC-Graft-PVP/DNA Complex (1) J. Controlled Release 2003, 86, 349-359
28. Wang, B.; He, C.; Tang, C.; Yin, C. Effects of Hydrophobic and Hydrophilic Modifications on Gene Delivery of Amphiphilic Chitosan Based Nanocarriers Biomaterials 2011, 32, 4630-4638
29. Layek, B.; Singh, J. N-hexanoyl, N-octanoyl and N-decanoyl Chitosans: Binding Affinity, Cell Uptake, and Transfection Carbohydr. Polym. 2012, 89, 403-410
30. Working, P. K.; Newman, M. S.; Johnson, J.; Cornacoff, J. B. Safety of Poly(ethylene glycol) and Poly(ethylene glycol) Derivatives. In Polyethylene Glycol Chemistry and Biological Applications; Harris, J. M.; Zalipsky, S., Eds.; American Chemical Society: Washington, DC, 1997; p 45.
31. Kurita, K.; Ikeda, H.; Yoshida, Y.; Shimojoh, M.'; Harata, M. Chemoselective Protection of Amino Groups of Chitosan by Controlled Phthaloylation: Facile Preparation of a Precursor Useful for Chemical Modifications Biomacromolecules 2002, 3, 1-4
32. Malhotra, M.; Lane, C.; Tomaro-Duchesneau, C.; Saha, S.; Prakash, S. A Novel Method for Synthesizing PEGylated Chitosan Nanoparticles: Strategy, Preparation, and In Vitro Analysis Int. J. Nanomed. 2011, 6, 485-494
33. Zhang, J.; Chen, X. G.; Peng, W. B.; Liu, C. S. Uptake of Oleoyl-Chitosan Nanoparticles by A549 Cells Nanomedicine 2008, 4, 208-214
34. Ye, Y. Q.; Yang, F. L.; Hu, F. Q.; Du, Y. Z.; Yuan, H.; Yu, H. Y. Core-Modified Chitosan-Based Polymeric Micelles for Controlled Release of Doxorubicin Int. J. Pharmaceutics 2008, 352, 294-301
35. Hashimoto, M.; Morimoto, M.; Saimoto, H.; Shigemasa, Y.; Sato, T. Lactosylated Chitosan for DNA Delivery into Hepatocytes: The Effect of Lactosylation on the Physicochemical Properties and Intracellular Trafficking of pDNA/Chitosan Complexes Bioconjugate Chem. 2006, 17, 309-316
36. Nam, H. Y.; Kwon, S. M.; Chung, H.; Lee, S. Y.; Kwon, S. H.; Jeon, H.; Kim, Y.; Park, J. H.; Kim, J.; Her, S.; Oh, Y. K.; Kwon, I. C.; Kim, K.; Jeong, S. Y. Cellular Uptake Mechanism and Intracellular Fate of Hydrophobically Modified Glycol Chitosan Nanoparticles J. Controlled Release 2009, 135, 259-267
37. Yang, J.; Liu, Y.; Wang, H.; Liu, L.; Wang, W.; Wang, C.; Wang, Q.; Liu, W. The Biocompatibility of Fatty Acid Modified Dextran-Agmatine Bioconjugate Gene Delivery Vector Biomaterials 2012, 33, 604-613
38. Kainthan, R. K.; Gnanamani, M.; Ganguli, M.; Ghosh, T.; Brooks, D. E.; Maiti, S.; Kizhakkedathu, J. N. Blood Compatibility of Water Soluble Hyperbranched Polyglycerol-Based Multivalent Cationic Polymers and Their Interaction with DNA Biomaterials 2006, 27, 5377-5390
39. Amin, K.; Dannenfelser, R. M. In vitro hemolysis: guidance for the pharmaceutical scientist J. Pharm. Sci. 2006, 95, 1173-1176
40. Zauner, W.; Ogris, M.; Wagner, E. Polylysine-Based Transfection Systems Utilizing Receptor-Mediated Delivery Adv. Drug Delivery Rev. 1998, 30, 97-113
41. Katayose, S.; Kataoka, K. Remarkable Increase in Nuclease Resistance of Plasmid DNA through Supramolecular Assembly with Poly (ethylene glycol)-poly (l-lysine) Block Copolymer J. Pharm. Sci. 1998, 87, 160-163
42. Mao, H. Q.; Roy, K.; Troung-Le, V. L.; Janes, K. A.; Lin, K. Y.; Wang, Y.; August, J. T.; Leong, K. W. Chitosan-DNA Nanoparticles as Gene Carriers: Synthesis, Characterization and Transfection Efficiency J. Controlled Release 2001, 70, 399-421
43. Schaffer, D. V.; Fidelman, N. A.; Dan, N.; Lauffenburger, D. A. Vector Unpacking as a Potential Barrier for Receptor-Mediated Polyplex Gene Delivery Biotechnol. Bioeng. 2000, 67, 598-606
44. Pack, D. W.; Hoffman, A. S.; Pun, S.; Stayton, P. S. Design and Development of Polymers for Gene Delivery Nat. Rev. Drug Discovery 2005, 4, 581-593
45. Banaszczyk, M. G.; Lollo, C. P.; Kwoh, D. Y.; Phillips, A. T.; Amini, A.; Wu, D. P.; Mullen, P. M.; Coffin, C. C.; Brostoff, S. W.; Carlo, D. J. Poly-L-Lysine-Graft-PEG-Comb-Type Polycation Copolymers for Gene Delivery J. Macromol. Sci., Pure Appl. Chem. 1999, 36, 1061-1084
46. Douglas, K. L.; Piccirillo, C. A.; Tabrizian, M. Cell Line-Dependent Internalization Pathways and Intracellular Trafficking Determine Transfection Efficiency of Nanoparticle Vectors Eur. J. Pharm. Biopharm. 2008, 68, 676-687