Cyclen-based lipidic oligomers as potential gene delivery vehicles

Acta Biomaterialia

Volumn 10, Issue 3, 2014, Pages 1412-1422

  Yi, Wen Jing ^a   Zhang, Qin Fang ^a   Zhang, Ji ^a   Liu, Qiang ^a   Ren, Laifeng ^b   Chen, Qian Ming ^b   Guo, Liandi ^b   Yu, Xiao Qi ^a  

^a Sichuan University   (China)

^b SICHUAN UNIVERSITY   (China)

Author keywords

Cyclen; Gene delivery; Lipopolymer; Non viral vector; Structure activity relationship

Indexed keywords

BIOCOMPATIBILITY; CHAINS; DNA; EFFICIENCY; FLUORESCENCE; GENE EXPRESSION; HYDROPHOBICITY; LINOLEIC ACID; MOLECULAR BIOLOGY; OLIGOMERS;

CYCLEN; DEGREE OF SUBSTITUTION; DNA BINDING ABILITY; GENE DELIVERY; HYDROPHOBICS; LIPO-POLYMER; LONG CHAINS; NONVIRAL VECTORS; STRUCTURE-ACTIVITY RELATIONSHIPS; TRANSFECTION EFFICIENCY;

GENE TRANSFER;

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; CYCLEN BASED LIPIDIC OLIGOMER; ETHIDIUM BROMIDE; LINOLEIC ACID; OLIGOMER; PLASMID DNA; POLYETHYLENEIMINE; UNCLASSIFIED DRUG; BIOMATERIAL; CYCLEN; DNA; HETEROCYCLIC COMPOUND; LIPID; LUCIFERASE;

ARTICLE; BIOCOMPATIBILITY; CELLULAR DISTRIBUTION; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; DNA TRANSFECTION; FLOW CYTOMETRY; GENE EXPRESSION; GENE VECTOR; GENETIC TRANSFECTION; HEMOLYSIS; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO GENE TRANSFER; IN VITRO STUDY; NONVIRAL GENE DELIVERY SYSTEM; PARTICLE SIZE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL; AGAR GEL ELECTROPHORESIS; ANIMAL; CELL DEATH; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECTS; ENDOCYTOSIS; FLUORESCENCE; GENE TRANSFER; GENETICS; HEK293 CELL LINE; INTRACELLULAR SPACE; METABOLISM; PLASMID; RABBIT; STATIC ELECTRICITY; TUMOR CELL LINE; ULTRASTRUCTURE;

ANIMALS; BIOCOMPATIBLE MATERIALS; CELL DEATH; CELL LINE, TUMOR; DNA; ELECTROPHORESIS, AGAR GEL; ENDOCYTOSIS; FLOW CYTOMETRY; FLUORESCENCE; GENE EXPRESSION; GENE TRANSFER TECHNIQUES; HEK293 CELLS; HEMOLYSIS; HETEROCYCLIC COMPOUNDS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INTRACELLULAR SPACE; LINOLEIC ACID; LIPIDS; LUCIFERASES; PARTICLE SIZE; PLASMIDS; RABBITS; STATIC ELECTRICITY; TRANSFECTION;

EID: 84895072266     PISSN: 17427061     EISSN: 18787568     Source Type: Journal    
DOI: 10.1016/j.actbio.2013.12.010     Document Type: Article

References (37)

1. J.L. Santos, H. Oliveira, D. Pandita, J. Rodrigues, A.P. Pêgo, and P.L. Granja et al. Functionalization of poly (amidoamine) dendrimers with hydrophobic chains for improved gene delivery in mesenchymal stem cells J Control Release 144 2010 55 64
2. M.A. Mintzer, and E.E. Simanek Nonviral vectors for gene delivery Chem Rev 109 2009 259 302
3. V. Russ, M. Günther, A. Halama, M. Ogris, and E. Wagner Oligoethylenimine-grafted polypropylenimine dendrimers as degradable and biocompatible synthetic vectors for gene delivery J Control Release 132 2008 131 140
4. O.M. Merkel, A. Beyerle, D. Librizzi, A. Pfestroff, T.M. Behr, and B. Sproat et al. Nonviral siRNA delivery to the lung: investigation of PEG-PEI polyplexes and their in vivo performance Mol Pharmacol 6 2009 1246 1260
5. K. Kogure, R. Moriguchi, K. Sasaki, M. Ueno, S. Futaki, and H. Harashima Development of a non-viral multifunctional envelope-type nano device by a novel lipid film hydration method J Control Release 98 2004 317 323
6. M.N. Ravi Kumar, M. Sameti, S.S. Mohapatra, X. Kong, R.F. Lockey, and U. Bakowsky et al. Cationic silica nanoparticles as gene carriers: synthesis, characterization and transfection efficiency in vitro and in vivo J Nanosci Nanotechnol 4 2004 876 881
7. M.N. Kumar, S.S. Mohapatra, X. Kong, P.K. Jena, U. Bakowsky, and C.M. Lehr Cationic poly (lactide-co-glycolide) nanoparticles as efficient in vivo gene transfection agents J Nanosci Nanotechnol 4 2004 990 994
8. M.L. Forrest, G.E. Meister, J.T. Koerber, and D.W. Pack Partial acetylation of polyethylenimine enhances in vitro gene delivery Pharm Res 21 2004 365 371
9. M. Ogris, P. Steinlein, M. Kursa, K. Mechtler, R. Kircheis, and E. Wagner The size of DNA/transferrin-PEI complexes is an important factor for gene expression in cultured cells Gene Ther 5 1998 1425 1433
10. M. Neu, D. Fischer, and T. Kissel Recent advances in rational gene transfer vector design based on poly (ethylene imine) and its derivatives J Gene Med 7 2005 992 1009
11. S. Nimesh, A. Aggarwal, P. Kumar, Y. Singh, K.C. Gupta, and R. Chandra Influence of acyl chain length on transfection mediated by acylated PEI nanoparticles Int J Pharm 337 2007 265 274
12. Y. Nie, M. Günther, Z. Gu, and E. Wagner Pyridylhydrazone-based PEGylation for pH-reversible lipopolyplex shielding Biomaterials 32 2011 858 869
13. O. Gusachenko Simonova, Y. Kravchuk, D. Konevets, V. Silnikov, V.V. Vlassov, and M.A. Zenkova Transfection efficiency of 25-kDa PEI-cholesterol conjugates with different levels of modification J Biomater Sci Polym Ed 20 2009 1091 1110
14. A. Dehshahri, R.K. Oskuee, W.T. Shier, A. Hatefi, and M. Ramezani Gene transfer efficiency of high primary amine content, hydrophobic, alkyl-oligoamine derivatives of polyethylenimine Biomaterials 30 2009 4187 4194
15. D. Wakebayashi, N. Nishiyama, Y. Yamasaki, K. Itaka, N. Kanayama, and A. Harada et al. Lactose-conjugated polyion complex micelles incorporating plasmid DNA as a targetable gene vector system: their preparation and gene transfecting efficiency against cultured HepG2 cells J Control Release 95 2004 653 664
16. V. Incani, A. Lavasanifar, and H. UludaÇ Lipid and hydrophobic modification of cationic carriers on route to superior gene vectors Soft Matter 6 2010 2124 2138
17. W.G. Liu, X. Zhang, S.J. Sun, G.J. Sun, K.D. Yao, and D.C. Liang et al. N-alkylated chitosan as a potential nonviral vector for gene transfection Bioconjug Chem 14 2003 782 789
18. A. Neamnark, O. Suwantong, K.C.R. Bahadur, C.Y.M. Hsu, P. Supaphol, and H. Uludaǧ Aliphatic lipid substitution on 2 kDa polyethylenimine improves plasmid delivery and transgene expression Mol Pharm 6 2009 1798 1815
19. V. Incani, E. Tunis, B.A. Clements, C. Olson, C. Kucharski, and A. Lavasanifar et al. Palmitic acid substitution on cationic polymers for effective delivery of plasmid DNA to bone marrow stromal cells J Biomed Mater Res A 81 2007 493 504
20. T. Le Gall, D. Loizeau, E. Picquet, N. Carmoy, J.J. Yaouanc, and L. Burel-Deschamps et al. A novel cationic lipophosphoramide with diunsaturated lipid chains: synthesis, physicochemical properties, and transfection activities J Med Chem 25 53 2010 1496 1508
21. X. Zhang, S. Ercelen, V.E. Tikhonov, S.Z. Karaeva, A.V. Slita, and V.V. Zarubaev et al. Alkylated chitosans of low molecular weight as non-viral transfection vectors for gene therapy Russ J Gen Chem 78 2008 1093 1102
22. J.H. Jeong, S.W. Kim, and T.G. Park Molecular design of functional polymers for gene therapy Prog Polym Sci 32 2007 1239 1274
23. O.A. Ahmed, C. Pourzand, and I.S. Blagbrough Varying the unsaturation in N4, N9-dioctadecanoyl spermines: nonviral lipopolyamine vectors for more efficient plasmid DNA formulation Pharm Res 23 2006 31 40
24. Z.H. Liu, Z.Y. Zhang, C.R. Zhou, and Y.P. Jiao Hydrophobic modifications of cationic polymers for gene delivery Prog Polym Sci 35 2010 1144 1162
25. B. Wang, C. He, C. Tang, and C. Yin Effects of hydrophobic and hydrophilic modifications on gene delivery of amphiphilic chitosan based nanocarriers Biomaterials 32 2011 4630 4638
26. A.M. Doody, J.N. Korley, K.P. Dang, P.N. Zawaneh, and D. Putnam Characterizing the structure/function parameter space of hydrocarbon-conjugated branched polyethylenimine for DNA delivery in vitro J Control Release 116 2006 227 237
27. W.J. Yi, Z.H. Feng, Q.F. Zhang, J. Zhang, L.D. Li, and W. Zhu et al. Diol glycidyl ether-bridged cyclens: preparation and their applications in gene delivery Org Biomol Chem 9 2011 2413 2421
28. Y.Z. Xiang, Z.H. Feng, J. Zhang, Y.L. Liao, C.J. Yu, and W.J. Yi et al. Linear cyclen-based polyamine as a novel and efficient reagent in gene delivery Org Biomol Chem 8 2010 640 647
29. S. Li, Y. Wang, S. Wang, J. Zhang, S.F. Wu, and B.L. Wang et al. Biodegradable cyclen-based linear and cross-linked polymers as non-viral gene vectors Bioorg Med Chem 20 2012 1380 1387
30. L.M. De León-Rodríguez, Z. Kovacs, A.C. Esqueda-Oliva, and A.D. Miranda-Olvera Highly regioselective N-trans symmetrical diprotection of cyclen Tetrahedron Lett 47 2006 6937 6940
31. W. Peng, P.Y. Liu, N. Jiang, H.H. Lin, G.L. Zhang, and Y. Liu et al. Dinuclear macrocyclic polyamine zinc(II) complexes linked with flexible spacers: Synthesis, characterization, and DNA cleavage Bioorg Chem 33 2005 374 385
32. J. Yang, Y. Liu, H. Wang, L. Liu, W. Wang, and C. Wang et al. The biocompatibility of fatty acid modified dextran-agmatine bioconjugate gene delivery vector Biomaterials 33 2012 604 613
33. P.S. Kuhn, Y. Levin, and M.C. Barbosa Charge inversion in DNA-amphiphile complexes: possible application to gene therapy Phys A 274 1999 8 18
34. H.F. Wang, X.H. Luo, C.W. Liu, J. Feng, X.Z. Zhang, and R.X. Zhuo A smart micellar system with an amine-containing polycarbonate shell Acta Biomater 8 2012 589 598
35. C.Y. Hsu, M. Hendzel, and H. UludaÇ Improved transfection efficiency of an aliphatic lipid substituted 2 kDa polyethylenimine is attributed to enhanced nuclear association and uptake in rat bone marrow stromal cell J Gene Med 13 2011 46 59
36. C.Y. Hsu, and H. Uludaǧ Cellular uptake pathways of lipid-modified cationic polymers in gene delivery to primary cells Biomaterials 33 2012 7834 7848
37. L.J. van der Aa, P. Vader, G. Storm, R.M. Schiffelers, and J.F. Engbersen Optimization of poly(amido amine)s as vectors for siRNA delivery J Control Release 150 2011 177 186