Novel cationic lipids possessing protonated cyclen and imidazolium salt for gene delivery

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 78, Issue 3, 2011, Pages 326-335

  Huang, Qing Dong ^a   Ou, Wen Jing ^a   Chen, Hong ^a,b   Feng, Zhi Hua ^a   Wang, Jing Yi ^a   Zhang, Ji ^a   Zhu, Wen ^a   Yu, Xiao Qi ^a  

^a China   (China)

^b SOUTHWEST UNIVERSITY   (China)

Author keywords

Calcium ion; Cationic liposome; Cyclen; Gene delivery; Gene therapy; Imidazolium salt

Indexed keywords

AMPHOPHILE; CALCIUM ION; DIOLEOYLPHOSPHATIDYLGLYCEROL; ETHIDIUM BROMIDE; IMIDAZOLE DERIVATIVE;

ARTICLE; CELL STRAIN HEK293; CYTOTOXICITY; GENE TARGETING; GENE VECTOR; GENETIC TRANSFECTION; POLYMERIZATION;

CATIONS; DNA; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; GENE THERAPY; GENETIC VECTORS; HEK293 CELLS; HETEROCYCLIC COMPOUNDS; HUMANS; IMIDAZOLES; LIPIDS; LIPOSOMES; NANOPARTICLES; TRANSFECTION;

EID: 79960589933     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2011.03.017     Document Type: Article

References (33)

1. M. Cavazzana-Calvo, S. Hacein-Bey, C.D. Basile, F. Gross, E. Yvon, P. Nusbaum, F. Selz, C. Hue, S. Certain, J.L. Casanova, P. Bousso, F. Le Deist, and A. Fischer Gene therapy of human severe combined immunodeficiency (SCID)-X1 disease Science 288 2000 669 672 (Pubitemid 30241569)
2. M.A. Mintzer, and E.E. Simanek Nonviral vectors for gene delivery Chem. Rev. 109 2009 259 302
3. S. Yla-Herttuala, and J.F. Martin Cardiovascular gene therapy Lancet 355 2000 213 222 (Pubitemid 30068227)
4. E. Check Harmful potential of viral vectors fuels doubts over gene therapy Nature 423 2003 573 574 (Pubitemid 36713190)
5. S. Bhattacharya, and A. Bajaj Advances in gene delivery through molecular design of cationic lipids Chem. Commun. 2009 4632 4656
6. D. Schaffert, and E. Wagner Gene therapy progress and prospects: synthetic polymer-based systems Gene Ther. 15 2008 1131 1138
7. J.H. Park, S. Lee, J.H. Kim, K. Park, K. Kim, and I.C. Kwon Polymeric nanomedicine for cancer therapy Prog. Polym. Sci. 33 2008 113 137 (Pubitemid 350278530)
8. R. Duncan, and L. Izzo Dendrimer biocompatibility and toxicity Adv. Drug Deliv. Rev. 57 2005 2215 2237 (Pubitemid 41759394)
9. M. Rajesh, J. Sen, M. Srujan, K. Mukherjee, B. Sreedhar, and A. Chaudhuri Dramatic influence of the orientation of linker between hydrophilic and hydrophobic lipid moiety in liposomal gene delivery J. Am. Chem. Soc. 129 2007 11408 11420 (Pubitemid 47555560)
10. C.A.H. Prata, Y.X. Zhao, P. Barthelemy, Y.G. Li, D. Luo, T.J. McIntosh, S.J. Lee, and M.W. Grinstaff Charge-reversal amphiphiles for gene delivery J. Am. Chem. Soc. 126 2004 12196 12197 (Pubitemid 39304865)
11. P.L. Felgner, T.R. Gadek, M. Holm, R. Roman, H.W. Chan, M. Wenz, J.P. Northrop, G.M. Ringold, and M. Danielsen Lipofection: a highly efficient, lipid-mediated DNA-transfection procedure Proc. Natl. Acad. Sci. USA 84 1987 7413 7417
12. A. Liberska, A. Unciti-Broceta, and M. Bradley Very long-chain fatty tails for enhanced transfection Org. Biomol. Chem. 7 2009 61 68
13. A. Ahmad, H.M. Evans, K. Ewert, C.X. George, C.E. Samuel, and C.R. Safinya New multivalent cationic lipids reveal bell curve for transfection efficiency versus membrane charge density: lipid-DNA complexes for gene delivery J. Gene Med. 7 2005 739 748 (Pubitemid 40872860)
14. K.K. Ewert, H.M. Evans, A. Zidovska, N.F. Bouxsein, A. Ahmad, and C.R. Safinya A columnar phase of dendritic lipid-based cationic liposome-DNA complexes for gene delivery: hexagonally ordered cylindrical micelles embedded in a DNA honeycomb lattice J. Am. Chem. Soc. 128 2006 3998 4006
15. T. Fujiwara, S. Hasegawa, N. Hirashima, M. Nakanishi, and T. Ohwada Gene transfection activities of amphiphilic steroid-polyamine conjugates BBA - Biomembranes 1468 2000 396 402
16. A. Aissaoui, B. Martin, E. Kan, N. Oudrhiri, M. Hauchecorne, J.P. Vigneron, J.M. Lehn, and P. Lehn Novel cationic lipids incorporating an acid-sensitive acylhydrazone linker: synthesis and transfection properties J. Med. Chem. 47 2004 5210 5223 (Pubitemid 39314918)
17. I.A. Petukhov, M.A. Maslov, N.G. Morozova, and G.A. Serebrennikova Synthesis of polycationic lipids based on cholesterol and spermine Russ. Chem. B 59 2010 260 268
18. K. Ewert, A. Ahmad, H.M. Evans, H.W. Schmidt, and C.R. Safinya Efficient synthesis and cell-transfection properties of a new multivalent cationic lipid for nonviral gene delivery J. Med. Chem. 45 2002 5023 5029 (Pubitemid 35278697)
19. W. Dobbs, B. Heinrich, C. Bourgogne, B. Donnio, E. Terazzi, M.E. Bonnet, F. Stock, P. Erbacher, A.L. Bolcato-Bellemin, and L. Douce Mesomorphic imidazolium salts: new vectors for efficient siRNA transfection J. Am. Chem. Soc. 131 2009 13338 13346
20. S.B. Zhang, B. Zhao, H.M. Jiang, B. Wang, and B.C. Ma Cationic lipids and polymers mediated vectors for delivery of siRNA J. Control. Release 123 2007 1 10 (Pubitemid 47444388)
21. Q.D. Huang, H. Chen, L.H. Zhou, J. Huang, J. Wu, and X.Q. Yu A novel macrocyclic polyamine cationic lipid containing an imidazolium salt group: synthesis, characterization and its transfection activity as a gene delivery vector Chem. Biol. Drug Des. 71 2008 224 229 (Pubitemid 351208197)
22. D.F. Zhi, S.B. Zhang, B. Wang, Y.N. Zhao, B.L. Yang, and S.J. Yu Transfection efficiency of cationic lipids with different hydrophobic domains in gene delivery Bioconjugate Chem. 21 2010 563 577
23. S. Walker, M.J. Sofia, R. Kakarla, N.A. Kogan, L. Wierichs, C.B. Longley, K. Bruker, H.R. Axelrod, S. Midha, S. Babu, and D. Kahne Cationic facial amphiphiles: a promising class of transfection agents Proc. Natl. Acad. Sci. USA 93 1996 1585 1590 (Pubitemid 26075169)
24. A. Kichler, C. Leborgne, P.B. Savage, and O. Danos Cationic steroid antibiotics demonstrate DNA delivery properties J. Control. Release 107 2005 174 182 (Pubitemid 41253712)
25. L.M. Deck, M.L. Baca, S.L. Salas, L.A. Hunsaker, and D.L. Vander Jagt 3-Alkyl-6-Chloro-2-pyrones: selective inhibitors of pancreatic cholesterol esterase J. Med. Chem. 42 1999 4250 4256 (Pubitemid 29483042)
26. E. Kimura, M. Kikuchi, H. Kitamura, and T. Koike Selective and efficient recognition of thymidylylthymidine (TpT) by Bis(Zn-II-cyclen) and thymidylylthymidylylthymidine (TpTpT) by tris(Zn-II-cyclen) at neutral pH in aqueous solution Chem. Eur. J. 5 1999 3113 3123 (Pubitemid 129611757)
27. R. Koynova, B. Tenchov, L. Wang, and R.C. MacDonald Hydrophobic moiety of cationic lipids strongly modulates their transfection activity Mol. Pharm. 6 2009 951 958
28. B.C. Baguley, and M.L. Bret Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron-transfer effect Biochemistry 23 1984 937 943 (Pubitemid 14168073)
29. C. Kawaura, A. Noguchi, T. Furuno, and M. Nakanishi Atomic force microscopy for studying gene transfection mediated by cationic liposomes with a cationic cholesterol derivative FEBS Lett. 421 1998 69 72 (Pubitemid 28068821)
30. T. Fujita, M. Furuhata, Y. Hattori, H. Kawakami, K. Toma, and Y. Maitani Calcium enhanced delivery of tetraarginine-PEG-lipid-coated DNA/protamine complexes Int. J. Pharm. 368 2009 186 192
31. M.R. Mozafari, and A. Omri Importance of divalent cations in nanolipoplex gene delivery Int. J. Pharm. 96 2007 1955 1966 (Pubitemid 47280093)
32. M. Mevel, N. Kamaly, S. Carmona, M.H. Oliver, M.R. Jorgensen, C. Crowther, F.H. Salazar, P.L. Marion, M. Fujino, Y. Natori, M. Thanou, P. Arbuthnot, J.J. Yaouanc, P.A. Jaffres, and A.D. Miller DODAG; a versatile new cationic lipid that mediates efficient delivery of pDNA and siRNA J. Control. Release 143 2010 222 232
33. D.A. Medvedeva, M.A. Maslov, R.N. Serikov, N.G. Morozova, G.A. Serebrenikova, D.V. Sheglov, A.V. Latyshev, V.V. Vlassov, and M.A. Zenkova Novel cholesterol-based cationic lipids for gene delivery J. Med. Chem. 52 2009 6558 6568