Structural and transfection properties of amine-substituted gemini surfactant-based nanoparticles

Journal of Gene Medicine

Volumn 9, Issue 8, 2007, Pages 649-658

  Wettig, Shawn D ^c   Badea, Ildiko ^b   Donkuru, McDonald ^a   Verrall, Ronald E ^a   Foldvari, Marianna ^c  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

^c UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Circular dichroism; DNA transfection; Dynamic light scattering; Gemini surfactant; Small angle X ray scattering

Indexed keywords

1,9 BIS(DODECYL) 1,1,9,9 TETRAMETHYL 5 IMINO 1,9 NONANEDIAMMONIUM DIBROMIDE; AMINE; BROMINE DERIVATIVE; GEMINI SURFACTANT; HETEROCYCLIC COMPOUND; IMINO ACID; LIPID; LUCIFERASE; NANOPARTICLE; PLASMID DNA; SURFACTANT; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL STRAIN COS7; CHEMICAL MODIFICATION; CIRCULAR DICHROISM; COMPLEX FORMATION; CONTROLLED STUDY; DNA TRANSFECTION; GENETIC TRANSFECTION; MEMBRANE FUSION; NONHUMAN; NONVIRAL GENE DELIVERY SYSTEM; PARTICLE SIZE; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; ZETA POTENTIAL;

AMINES; ANIMALS; CERCOPITHECUS AETHIOPS; COS CELLS; LIPIDS; LUCIFERASES; NANOPARTICLES; PLASMIDS; SURFACE TENSION; SURFACE-ACTIVE AGENTS; TRANSFECTION;

EID: 34548071905     PISSN: 1099498X     EISSN: 15212254     Source Type: Journal    
DOI: 10.1002/jgm.1060     Document Type: Article

References (48)

1. Pearson S, Jia HP, Kandachi K. China approves first gene therapy. Nat Biotechnol 2004; 22: 3-4.
2. Branca MA. Gene therapy: cursed or inching towards credibility? Nat Biotechnol 2005; 23: 519-521.
3. Gardlik R, Palffy R, Hodosy J, et al. Vectors and delivery systems in gene therapy. Med Sci Monit 2005; 11: RA110-121.
4. Patil SD, Rhodes DG, Burgess DJ. DNA-based therapeutics and DNA delivery systems: a comprehensive review. AAPS J 2005; 7: E61-77.
5. Goncalves MA. A concise peer into the background, initial thoughts and practices of human gene therapy. Bioessays 2005; 27: 506-517.
6. Smyth Templeton N. Cationic liposomes as in vivo delivery vehicles. Curr Med Chem 2003; 10: 1279-1287.
7. Hulst R, Muizebelt I, Oosting P, et al. Sunfish amphiphiles: conceptually new carriers for DNA delivery. Eur J Org Chem 2004; 835-849.
8. Niculescu-Duvaz D, Heyes J, Springer CJ. Structure-activity relationship in cationic lipid mediated gene transfection. Curr Med Chem 2003; 10: 1233-1261.
9. McGregor C, Perrin C, Monck M, et al. Rational approaches to the design of cationic gemini surfactants for gene delivery. J Am Chem Soc 2001; 123: 6215-6220.
10. Bombelli C, Faggioli F, Luciani P, et al. Efficient transfection of DNA by liposomes formulated with cationic gemini amphiphiles. J Med Chem 2005; 48: 5378-5382.
11. Badea I, Verrall R, Baca-Estrada M, et al. In vivo cutaneous interferon-gamma gene delivery using novel dicationic (gemini) surfactant-plasmid complexes. J Gene Med 2005; 7: 1200-1214.
12. Rosenzweig HS, Rakhmanova. VA, MacDonald RC. Diquaternary ammonium compounds as transfection agents. Bioconjugate Chem 2001; 12: 258-263.
13. Kirby AJ, Camilleri P, Engberts JBFN, et al. Gemini surfactants: new synthetic vectors for gene transfection. Angew Chem Int Edn 2003; 42: 1448-1457.
14. Bell PC, Bergsma M, Dolbnya IP, et al. Transfection mediated by gemini surfactants: engineered escape from the endosomal compartment. J Am Chem Soc 2003; 125: 1551-1558.
15. Bergsma M, Fielden ML, Engberts JBFN. pH-dependent aggregation behavior of a sugar-amine gemini surfactant in water: vesicles, micelles, and monolayers of hexane-1,6-bis(hexadecyl-1′-deoxyglucitylamine). J Colloid Interf Sci 2001; 243: 491-495.
16. Fielden ML, Perrin C, Kremer A, et al. Sugar-based tertiary amino gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediate efficient transfection in vitro. Eur J Biochem 2001; 268: 1269-1279.
17. Johnsson M, Wagenaar A, Stuart MCA, et al. Sugar-based gemini surfactants with pH-dependent aggregation behavior: vesicle-to-micelle transition, critical micelle concentration, and vesicle surface charge reversal. Langmuir 2003; 19: 4609-4618.
18. Johnsson M, Wagenaar A, Engberts JBFN. Sugar-based gemini surfactant with a vesicle-to-micelle transition at acidic pH and a reversible vesicle flocculation near neutral PH. J Am Chem Soc 2003; 125: 757-760.
19. Johnsson M, Engberts JBFN. Novel sugar-based gemini surfactants: aggregation properties on aqueous solution. J Phys Org Chem 2004; 17: 934-944.
20. Yoshimura T, Ishihara K, Esumi K. Sugar-based gemini surfactants with peptide bonds-synthesis, adsorption, micellization, and biodegradability. Langmuir 2005; 21: 10409-10415.
21. Vijayanathan V, Thomas T, Antony T, et al. Formation of DNA nanoparticles in the presence of novel polyamine analogues: a laser light scattering and atomic force microscopic study. Nucleic Acids Res 2004; 32: 127-134.
22. Vijayanathan V, Thomas T, Shirahata A, et al. DNA condensation by polyamines: A laser light scattering study of structural effects. Biochemistry 2001; 40: 13644-13651.
23. Wilson RW, Bloomfield VA. Counter-ion-induced condensation of deoxyribonucleic-acid - light-scattering study. Biochemistry 1979; 18: 2192-2196.
24. Wettig SD, Wang C, Verrall R, et al. Thermodynamic and aggregation properties of aza- and imino-substituted gemini surfactants designed for gene delivery. Phys Chem Chem Phys 2007; 9: 871-877.
25. Wettig SD, Verrall RE. Thermodynamic studies of aqueous m-s-m gemini surfactant systems. J Colloid Interf Sci 2001; 235: 310-316.
26. Balendiran K, Rao ST, Sekharudu CY, et al. X-ray structures of the B-DNA dodecamer d(CGCGTTAACGCG) with an inverted central tetranucleotide and its netropsin complex. Acta Crystallogr D Biol Crystallogr 1995; 51: 190-198.
27. Dass CR. Biochemical and biophysical characteristics of lipoplexes pertinent to solid tumour gene therapy. Int J Pharm 2002; 241: 1-25.
28. Koltover I, Salditt T, Radler JO, et al. An inverted hexagonal phase of cationic liposome-DNA complexes related to DNA release and delivery. Science 1998; 281: 78-81.
29. Radler JO, Koltover I, Salditt T, et al. Structure of DNA-cationic liposome complexes: DNA intercalation in multilamellar membranes in distinct interhelical packing regimes. Science 1997; 275: 810-814.
30. Ewert K, Slack NL, Ahmad A, et al. Cationic lipid-DNA complexes for gene therapy: understanding the relationship between complex structure and gene delivery pathways at the molecular level. Curr Med Chem 2004; 11: 133-149.
31. Chesnoy S, Huang L. Structure and function of lipid-DNA complexes for gene delivery. Annu Rev Biophys Biomol Struct 2000; 29: 27-47.
32. Hirsch-Lerner D, Zhang M, Eliyahu H, et al. Effect of "helper lipid" on lipoplex electrostatics. Biochim Biophys Acta - Biomembranes 2005; 1714: 71-84.
33. Simberg D, Danino D, Talmon Y, et al. Phase behavior, DNA ordering, and size instability of cationic lipoplexes. Relevance to optimal transfection activity. J Biol Chem 2001; 276: 47453-47459.
34. Zuidam NJ, Barenholz Y, Minsky A. Chiral DNA packaging in DNA-cationic liposome assemblies. FEBS Lett 1999; 457: 419-422.
35. Braun CS, Jas GS, Choosakoonkriang S, et al. The structure of DNA within cationic lipid/DNA complexes. Biophys J 2003; 84: 1114-1123.
36. Saenger W. Principles of Nucleic Acid Structure, Springer-Verlag: New York, 1984.
37. Ruiz-Chica J, Medina MA, Sanchez-Jimenez F, et al. Fourier transform Raman study of the structural specificities on the interaction between DNA and biogenic polyamines. Biophys J 2001; 80: 443-454.
38. Ouameur AA, Tajmir-Riahi HA. Structural analysis of DNA interactions with biogenic polyamines and cobalt(III)hexamine studied by Fourier transform infrared and capillary electrophoresis. J Biol Chem 2004; 279: 42041-42054.
39. Tycko B, Maxfield FR. Rapid acidification of endocytic vesicles containing alpha 2-macroglobulin. Cell 1982; 28: 643-651.
40. Pitard B. Supramolecular assemblies of DNA delivery systems. Somat Cell Mol Genet 2002; 27: 5-15.
41. Lin AJ, Slack NL, Ahmad A, et al. Structure and structure-function studies of lipid/plasmid DNA complexes. J Drug Target 2000; 8: 13-27.
42. Kreiss P, Cameron B, Rangara R, et al. Plasmid DNA size does not affect the physicochemical properties of lipoplexes but modulates gene transfer efficiency. Nucleic Acids Res 1999; 27: 3792-3798.
43. Zhou S, Liang D, Burger C, et al. Nanostructures of complexes formed by calf thymus DNA interacting with cationic surfactants. Biomacromolecules 2004; 5: 1256-1261.
44. Lin AJ, Slack NL, Ahmad A, et al. Three-dimensional imaging of lipid gene-carriers: membrane charge density controls universal transfection behavior in lamellar cationic liposome-DNA complexes. Biophys J 2003; 84: 3307-3316.
45. Rosenzweig HS, Rakhmanova VA, McIntosh TJ, et al. O-Alkyl dioleoylphosphatidylcholinium compounds: the effect of varying alkyl chain length on their physical properties and in vitro DNA transfection activity. Bioconjugate Chem 2000; 11: 306-313.
46. Foldvari M, Badea I, Wettig S, et al. Dicationic gemini surfactant gene delivery complexes contain cubic-lamellar mixed polymorphic phase. NSTI Nanotech 2006, NSTI Nanotechnology Conference and Trade Show, Boston, May 7-11, 2006; 2: 400-403.
47. Foldvari M, Badea I, Wettig SD, et al. Structural characterization of novel micro- and nano-scale non-viral DNA delivery systems for cutaneous gene therapy. J Exp Nanosci 2006; 1: 165-176.
48. Angelov B, Ollivon M, Angelova A. X-ray diffraction study of the effect of the detergent octyl glucoside on the structure of lamellar and nonlamellar lipid/water phases of use for membrane protein reconstitution. Langmuir 1999; 15: 8225-8234.