Effect of the headgroup variation on the gene transfer properties of cholesterol based cationic lipids possessing ether linkage

Biochimica et Biophysica Acta - Biomembranes

Volumn 1778, Issue 5, 2008, Pages 1222-1236

  Bajaj, Avinash ^a   Mishra, Santosh K ^a   Kondaiah, Paturu ^a   Bhattacharya, Santanu ^a,b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

Cationic lipid; Gene transfection; Liposome; Serum

Indexed keywords

1,2 DIOLEOYL ALPHA GLYCERO 3 PHOSPHATIDYLETHANOLAMINE; 4 N,N' DIMETHYLAMINOPYRIDINE; CHOLESTEROL DERIVATIVE; ETHIDIUM BROMIDE; LIPOSOME; PYRIDINE DERIVATIVE; WATER;

ARTICLE; CELL CULTURE; CELL VIABILITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; CULTURE MEDIUM; CYTOTOXICITY; DNA BINDING; DRUG FORMULATION; GEL ELECTROPHORESIS; GENE TRANSFER; HELA CELL; HUMAN; HUMAN CELL; LIPOSOMAL GENE DELIVERY SYSTEM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SERUM; SUSPENSION; SYNTHESIS; TOXICITY TESTING;

BLOOD; CATIONS; CELL SEPARATION; CHOLESTEROL; ELECTROPHORESIS, AGAR GEL; ETHERS; FLOW CYTOMETRY; HELA CELLS; HUMANS; LIPIDS; LIPOSOMES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; SCATTERING, RADIATION; TRANSFECTION;

EID: 43049149346     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2007.12.010     Document Type: Article

References (65)

1. Miller A.D. Human gene therapy comes of age. Nature 357 (1992) 455-460
2. Friedmann T. Human gene therapy - an immature genie, but certainly out of the bottle. Nat. Med. 2 (1996) 144-147
3. Anderson W.F. Human gene therapy. Nature 392 (1998) 25-30
4. Knowles M.R., Hohneker K.W., Zhou Z., Olsen J.C., Noah T.L., Hu P.C., Leigh M.W., Engelhardt J.F., Edwards L.J., and Jones K.R. A controlled study of adenoviral-vector-mediated gene transfer in the nasal epithelium of patients with cystic fibrosis. New Engl. J. Med. 333 (1995) 823-831
5. Crystal R.G., McElvaney N.G., Rosenfeld M.A., Chu C.-S., Mastrangeli A., Hay J.G., Brody S.L., Jaffe H.A., Eissa N.T., and Danel C. Administration of an adenovirus containing the human CFTR cDNA to the respiratory tract of individuals with cystic fibrosis. Nat. Genet. 8 (1994) 42-51
6. Yang Y., Nunes F.A., Berencsi K., Furth E.E., Gonczol E., and Wilson J.M. Cellular immunity to viral antigens limits E1-deleted adenoviruses for gene therapy. Proc. Natl. Acad. Sci. U. S. A. 91 (1994) 4407-4411
7. Yang Y., Nunes F.A., Berencsi K., Goenczoel E., Engelhardt J.F., and Wilson J.M. Inactivation of E2a in recombinant adenoviruses improves the prospect for gene therapy in cystic fibrosis. Nat. Genet. 7 (1994) 362-369
8. Miller A. Cationic liposomes in gene therapy. Angew. Chem., Int. Ed. 37 (1998) 1768-1785
9. Boussif O., Lezoualc'h F., Zanta M.A., Mergny M.D., Scherman D., Demeneix B., and Behr J.-P. A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: polyethylenimine. Proc. Natl. Acad. Sci. U. S. A. 92 (1995) 7297-7301
10. Han S.-o., Mahato R.I., and Kim S.W. Water-soluble lipopolymer for gene delivery. Bioconjug. Chem. 12 (2001) 337-345
11. Mahato R.I., Lee M., Maheswari A., and Kim S.W. Intratumoral delivery of p2CMVmIL-12 using water-soluble lipopolymers. Molecular Ther. 4 (2001) 130-138
12. Wang D.-A., Narang A.S., Kotb M., Gaber O.A., Miller D.D., Kim S.W., and Mahato R.I. Novel branched poly(ethylenimine)-cholesterol water-soluble lipopolymers for gene delivery. Biomacromolecules 3 (2002) 1197-1207
13. Furgeson D.Y., Chan W.S., Yockman J.W., and Kim S.W. Modified linear polyethylenimine-cholesterol conjugates for DNA complexation. Bioconjugate Chem. 14 (2003) 840-847
14. Kirby A.J., Camilleri P., Engberts J.B.F.N., Feiters M.C., Nolte R.J.M., Soderman O., Bergsma M., Bell P.C., Fielden M.L., Garcia Rodriguez C.L., Guedat P., Kremer A., McGregor C., Perrin C., Ronsin G., and van Eijk M.C.P. Gemini surfactants: new synthetic vectors for gene transfection. Angew. Chem., Int. Ed. 42 (2003) 1448-1457
15. Bombelli C., Faggioli F., Luciani P., Mancini G., and Sacco M.G. Efficient transfection of DNA by liposomes formulated with cationic gemini amphiphiles. J. Med. Chem. 48 (2005) 5378-5382
16. Chien P.-Y., Wang J., Carbonaro D., Lei S., Miller B., Sheikh S., Ali S.M., Ahmad M.U., and Ahmad I. Novel cationic cardiolipin analog-based liposome for efficient DNA and small interfering RNA delivery in vitro and in vivo. Cancer Gene Ther. 12 (2005) 321-328
17. Bajaj A., Kondaiah P., and Bhattacharya S. Synthesis and gene transfer activities of novel serum compatible cholesterol based gemini lipids possessing oxy-ethylene type spacers. Bioconjugate Chem. 18 (2007) 1537-1546
18. Hulst R., Muizebelt I., Oosting P., Van der Pol C., Wagenaar A., Smisterova J., Bulten E., Driessen C., Hoekstra D., and Engberts J.B.F.N. Sunfish amphiphiles: conceptually new carriers for DNA delivery. Eur. J. Org. Chem. (2004) 835-849
19. Ilies M.A., Seitz W.A., Ghiviriga I., Johnson B.H., Miller A., Thompson E.B., and Balaban A.T. Pyridinium cationic lipids in gene delivery: a structure-activity correlation study. J. Med. Chem. 47 (2004) 3744-3754
20. Prata C.A.H., Zhao Y., Barthelemy P., Li Y., Luo D., McIntosh T.J., Lee S.J., and Grinstaff M.W. Charge-reversal amphiphiles for gene delivery. J. Am. Chem. Soc. 126 (2004) 12196-12197
21. Bombelli C., Borocci S., Diociaiuti M., Faggioli G., Galantini L., Luciani P., Mancini G., and Sacco M.G. Role of the spacer of cationic gemini amphiphiles in the condensation of DNA. Langmuir 21 (2005) 10271-10274
22. Chittimalla C., Zammut-Italiano L., Zuber G., and Behr J.-P. Monomolecular DNA nanoparticles for intravenous delivery of genes. J. Am. Chem. Soc. 127 (2005) 11436-11441
23. Kasireddy K., Ali S.M., Ahmad M.U., Choudhury S., Chien P.-Y., Sheikh S., and Ahmad I. Synthesis of cationic cardiolipin analogs. Bioorg. Chem. 33 (2005) 345-362
24. Koiwai K., Tokuhisa K., Karinaga R., Kudo Y., Kusuki S., Takeda Y., and Sakurai K. Transition from a normal to inverted cylinder for an amidine-bearing lipid/pDNA complex and its excellent transfection. Bioconjugate Chem. 16 (2005) 1349-1351
25. Sen J., and Chaudhuri A. Design, syntheses, and transfection biology of novel non-cholesterol-based guanidinylated cationic lipids. J. Med. Chem. 48 (2005) 812-820
26. Chabaud P., Camplo M., Payet D., Serin G., Molreau L., Barthelemy P., and Grinstaff M.W. Cationic nucleoside lipids for gene delivery. Bioconjugate Chem. 17 (2006) 466-472
27. Jewell C.M., Hays M.E., Kondo Y., Abbott N.L., and Lynn D.M. Ferrocene-containing cationic lipids for the delivery of DNA: oxidation state determines transfection activity. J. Controlled Release 112 (2006) 129-138
28. Duzgunes N., Ilarduya C.T., Simoes S., Zhdanoc r.I., Konopka K., and Lima M.C.P.d. Cationic liposomes for gene therapy: novel cationic lipids and enhancement by proteins and peptides. Curr. Med. Chem. 10 (2003) 1213-1220
29. Hirko A., Tang F., and Hughes J.A. Cationic lipid vectors for plasmid gene delivery. Curr. Med. Chem. 10 (2003) 1185-1193
30. Kumar V.V., Singh R.S., and Chaudhuri A. Cationic transfection lipids in gene therapy: successes, set-backs, challenges and promises. Curr. Med. Chem. 10 (2003) 1297-1306
31. Felgner P.L., Gadek T.R., Holm M., Roman R., Chan H.W., Wenz M., Northrop J.P., Ringold G.M., and Danielsen M. Lipofection: a highly efficient, lipid-mediated DNA-transfection procedure. Proc. Natl. Acad. Sci. U. S. A. 84 (1987) 7413-7417
32. Gao X., and Huang L. A novel cationic liposome reagent for efficient transfection of mammalian cells. Biochem. Biophys. Res. Commun. 179 (1991) 280-285
33. Lima M.C.P.d., Neves S., Filipe A., Duzgunes N., and Simoes S. Cationic liposomes for gene delivery: from biophysic to biological applications. Curr. Med. Chem. 10 (2003) 1221-1231
34. Liu D., Ren T., and Gao X. Cationic transfection lipids. Curr. Med. Chem. 10 (2003) 1307-1315
35. Miller A.D. The problem with cationic liposome/micelle-based non-viral vector systems for gene therapy. Curr. Med. Chem. 10 (2003) 1195-1211
36. Nakanishi M. New strategy in gene transfection by cationic transfection lipids with a cationic cholesterol. Curr. Med. Chem. 10 (2003) 1289-1296
37. Bhattacharya S., and Haldar S. Synthesis, thermotropic behavior, and permeability properties of vesicular membranes composed of cationic mixed-chain surfactants. Langmuir 11 (1995) 4748-4757
38. Bhattacharya S., Subramanian M., and Hiremath U.S. Surfactant lipids containing aromatic units produce vesicular membranes with high thermal stability. Chem. Phys. Lipids 78 (1995) 177-188
39. m spacers: pronounced m-value dependence of thermal properties, vesicle fusion, and cholesterol complexation. Chem. Eur. J. 5 (1999) 2335-2347
40. Bhattacharya S., De S., and George S.K. Synthesis and vesicle formation from novel pseudoglyceryl dimeric lipids. Evidence of formation of widely different membrane organizations with exceptional thermotropic properties. Chem. Commun. (1997) 2287-2288
41. Bhattacharya S., and Dileep P.V. Membrane-forming properties of cationic lipids bearing oxyethylene-based linkages. J. Phys. Chem., B 107 (2003) 3719-3725
42. Bhattacharya S., and Dileep P.V. Cationic oxyethylene lipids. Synthesis, aggregation, and transfection properties. Bioconjugate Chem. 15 (2004) 508-519
43. Bhattacharya S., and Krishnan-Ghosh Y. Vesicle formation from oligo(oxyethylene)-bearing cholesteryl amphiphiles: site-selective effects of oxyethylene units on the membrane order and thickness. Langmuir 17 (2001) 2067-2075
44. Bhattacharya S., and Haldar S. Interactions between cholesterol and lipids in bilayer membranes. Role of lipid headgroup and hydrocarbon chain-backbone linkage. Biochim. Biophys. Acta, Biomembr. 1467 (2000) 39-53
45. Bhattacharya S., and Bajaj A. Membrane forming properties of aromatic derived gemini lipids possessing polymethtlene spacers. J. Phys. Chem., B 111 (2007) 13511-13519
46. Bajaj A., Kondiah P., and Bhattacharya S. Design, synthesis and in vitro gene transfection efficacies of cholesterol based gemini lipids and their serum compatibility: a structure activity relationship. J. Med. Chem. 50 (2007) 2432-2442
47. Bhattacharya S., and Bajaj A. Thermotropic and hydration studies of membranes formed from gemini pseudoglyceryl lipids possessing polymethylene spacers. Langmuir 23 (2007) 8988-8994
48. Felgner J.H., Kumar R., Sridhar C.J., Wheeler Y.J., Tsai R., Border P., Ramsey M., Martin C.N., and Felgner P.L. Enhanced gene delivery and mechanism studies with a novel series of cationic lipid formulations. J. Biol. Chem. 269 (1994) 2550-2561
49. Song Y.K., Liu F., Chu S., and Liu D. Characterization of cationic liposome-mediated gene transfer in vivo by intravenous administration. Hum. Gene Ther. 8 (1997) 1585-1594
50. Gao H., and Hui K.M. Synthesis of a novel series of cationic lipids that can act as efficient gene delivery vehicles through systematic heterocyclic substitution of cholesterol derivatives. Gene Ther. 8 (2001) 855-863
51. Zhu M.-Z., Wu Q.-H., Zhang G., Ren T., Liu D., and Guo Q.-X. Synthesis and evaluation of cationic lipids bearing cholesteryl groups for gene delivery in vitro. Bull. Chem. Soc. Jpn. 75 (2002) 2207-2213
52. Bhattacharya S., and Haldar S. The effects of cholesterol inclusion on the vesicular membranes of cationic lipids. Biochim. Biophys. Acta. 1283 (1996) 21-30
53. Ghosh Y.K., Visweswariah S.S., and Bhattacharya S. Nature of linkage between the cationic headgroup and cholesteryl skeleton controls gene transfection efficiency. FEBS Lett. 473 (2000) 341-344
54. Ghosh Y.K., Visweswariah S.S., and Bhattacharya S. Advantage of the ether linkage between the positive charge and the cholesteryl skeleton in cholesterol-based amphiphiles as vectors for gene delivery. Bioconjugate Chem. 13 (2002) 378-384
55. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65 (1983) 55-63
56. Hansen M.B., Nielsen S.E., and Berg K. Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J. Immunol. Methods 119 (1989) 203-210
57. Choi J.S., Lee E.J., Jang H.S., and Park J.S. New cationic liposomes for gene transfer into mammalian cells with high efficiency and low toxicity. Bioconjugate Chem. 12 (2001) 108-113
58. E. Martz. 2000. http://www.bio.umass.edu/micro/immunology/facs542/facsprin.htm
59. Bhattacharya S., and Snehalatha K. Evidence for the formation of acylated or phosphorylated monoperoxyphthalates in the catalytic esterolytic reactions in cationic surfactant aggregates. J. Org. Chem. 62 (1997) 2198-2204
60. Zabner J., Fasbender A.J., Moninger T., Poellinger K.A., and Welsh M.J. Cellular and molecular barriers to gene transfer by a cationic lipid. J. Biol. Chem. 270 (1995) 18997-19007
61. Xu Y., and Szoka Jr. F.C. Mechanism of DNA release from cationic liposome/DNA complexes used in cell transfection. Biochemistry 35 (1996) 5616-5623
62. Bhattacharya S., and Bajaj A. Membrane forming properties of pseudoglyceryl backbone based gemini lipids possessing oxyethylene spacers. J. Phys. Chem., B 111 (2007) 2463-2472
63. Farhood H., Bottega R., Epand R.M., and Huang L. Effect of cationic cholesterol derivatives on gene transfer and protein kinase C activity. Biochim. Biophys. Acta, Biomembr. 1111 (1992) 239-246
64. Bhattacharya S., and Mandal S.S. Interaction of surfactants with DNA. Role of hydrophobicity and surface charge on intercalation and DNA melting. Biochim. Biophys. Acta, Biomembr. 1323 (1997) 29-44
65. Bhattacharya S., and Mandal S.S. Evidence of inter-lipidic ion-pairing in anion-induced DNA release from cationic amphiphile-DNA complexes. Mechanistic implications in transfection. Biochemistry 37 (1998) 7764-7777