Varying the unsaturation in N4,N9-dioctadecanoyl spermines: Nonviral lipopolyamine vectors for more efficient plasmid DNA formulation

Pharmaceutical Research

Volumn 23, Issue 1, 2006, Pages 31-40

  Ahmed, Osama A A ^a   Pourzand, Charareh ^a   Blagbrough, Ian S ^a  

^a University of Bath   (United Kingdom)

Author keywords

FCP; FEK4; gene delivery; HtTA; lipopolyamine; N4,N 9 dilinoleoyl spermine; N4,N9 dioleoyl spermine; N4,N9 distearoyl spermine; Primary skin cells; Transfection

Indexed keywords

AMMONIA; CARBON; CIRCULAR DNA; DIOCTADECYLAMIDOGLYCYL SPERMINE; ETHIDIUM BROMIDE; GREEN FLUORESCENT PROTEIN; LIPID; N4,N9 DILINOLEOYL SPERMINE; N4,N9 DIOLEOYL SPERMINE; N4,N9 DISTEAROYL SPERMINE; NANOPARTICLE; PHOSPHATE; PLASMID DNA; POLYAMINE DERIVATIVE; SPERMINE DERIVATIVE; TRANSFECTAM; UNCLASSIFIED DRUG; DIOCTADECYLAMIDOGLYCYLSPERMINE; DNA; DRUG CARRIER; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FATTY ACID; GLYCINE; NANOMATERIAL; SPERMINE; TETRAZOLIUM; THIAZOLE DERIVATIVE; THIAZOLYL BLUE;

ARTICLE; CANCER CELL CULTURE; CELL CULTURE; CELL IMMORTALIZATION; COMPARATIVE STUDY; CONTROLLED STUDY; DNA TRANSFECTION; DRUG EFFICACY; DRUG FORMULATION; DRUG SYNTHESIS; FLUORESCENCE; HUMAN; HUMAN CELL; NONVIRAL GENE DELIVERY SYSTEM; PHOTOCHEMICAL QUENCHING; POLYMERIZATION; PRIORITY JOURNAL; SKIN CELL; CELL LINE; CELL SURVIVAL; CHEMISTRY; CYTOLOGY; ELECTROCHEMISTRY; GENETIC TRANSFECTION; GENETICS; PARTICLE SIZE; PLASMID; SKIN; SYNTHESIS; TUMOR CELL LINE;

CELL LINE; CELL LINE, TUMOR; CELL SURVIVAL; CELLS, CULTURED; CHEMISTRY, PHARMACEUTICAL; DNA; DRUG CARRIERS; ELECTROCHEMISTRY; FATTY ACIDS; GLYCINE; HUMANS; INDICATORS AND REAGENTS; NANOSTRUCTURES; PARTICLE SIZE; PLASMIDS; SKIN; SPERMINE; TETRAZOLIUM SALTS; THIAZOLES; TRANSFECTION;

EID: 32244431760     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11095-005-8717-3     Document Type: Article

References (65)

1. N. Somia I. M. Verma 2000 Gene therapy: trials and tribulations Nat. Rev., Genet. 1 91 99
2. H. Nakai E. Montini S. Fuess T. A. Storm M. Grompe M. A. Kay 2003 AAV serotype 2 vectors preferentially integrate into active genes in mice Nat. Genet. 34 297 302
3. E. Check 2003 Harmful potential of viral vectors fuels doubts over gene therapy Nature 423 573 574
4. A. J. Geall M. A. W. Eaton T. Baker C. Catterall I. S. Blagbrough 1999 The regiochemical distribution of positive charges along cholesterol polyamine carbamates plays significant roles in modulating DNA binding affinity and lipofection FEBS Lett. 459 337 342
5. I. S. Blagbrough D. Al-Hadithi A. J. Geall 2000 Cheno-, urso- and deoxycholic acid spermine conjugates: relative binding affinities for calf thymus DNA Tetrahedron 56 3439 3447
6. A. J. Geall R. J. Taylor M. E. Earll M. A. W. Eaton I. S. Blagbrough 2000 Synthesis of cholesteryl polyamine carbamates: pK(a) studies and condensation of calf thymus DNA Bioconjug. Chem. 11 314 326
7. A. J. Geall D. Al-Hadithi I. S. Blagbrough 2002 Efficient calf thymus DNA condensation upon binding with novel bile acid polyamine amides Bioconjug. Chem. 13 481 490
8. I. S. Blagbrough A. J. Geall A. P. Neal 2003 Polyamines and novel polyamine conjugates interact with DNA in ways that can be exploited in non-viral gene therapy Biochem. Soc. Trans. 31 397 406
9. A. J. Geall I. S. Blagbrough 2000 Homologation of polyamines in the rapid synthesis of lipospermine conjugates and related lipoplexes Tetrahedron 56 2449 2460
10. I. S. Blagbrough N. Adjimatera O. A. A. Ahmed A. P. Neal C. Pourzand 2004 Spermine and lipopolyamines as gene delivery agents. In D. J. Beadle, I. R. Mellor, and P. N. R. Usherwood (eds.), D. J. Beadle I. R. Mellor P. N. R. Usherwood Neurotox '03: Neurotoxicological targets from Functional Genomics and Proteomics SCI London 147 159
11. 9-dioleoyl spermine is a novel nonviral lipopolyamine vector for plasmid DNA formulation Pharm. Res. 22 972 980
12. V. W. Y. Lui Y. K. He L. Falo L. Huang 2002 Systemic administration of naked DNA encoding interleukin 12 for the treatment of human papillomavirus DNA-positive tumor Hum. Gene Ther. 13 177 185
13. T. Kitagawa T. Iwazawa P. D. Robbins M. T. Lotze H. Tahara 2003 Advantages and limitations of particle-mediated transfection (gene gun) in cancer immuno-gene therapy using IL-10, IL-12 or B7-1 in murine tumor models J. Gene Med. 5 958 965
14. M. Thomas A. M. Klibanov 2003 Conjugation to gold nanoparticles enhances polyethylenimine's transfer of plasmid DNA into mammalian cells Proc. Natl. Acad. Sci. USA 100 9138 9143
15. A. L. Coulberson N. V. Hud J. M. Ledoux I. D. Vilfan M. R. Prausnitz 2003 Gene packaging with lipids, peptides and viruses inhibits transfection by electroporation in vitro J. Control. Release 86 361 370
16. A. Noguchi N. Hirashima M. Nakanishi 2002 Cationic cholesterol promotes gene transfection using the nuclear localization signal in protamine Pharm. Res. 19 933 938
17. K. Fabio J. Gaucheron C. Di Giorgio P. Vierling 2003 Novel galactosylated polyamine bolaamphiphiles for gene delivery Bioconjug. Chem. 14 358 367
18. S. A. Cryan C. M. O'Driscoll 2003 Mechanistic studies on nonviral gene delivery to the intestine using in vitro differentiated cell culture models and an in vivo rat intestinal loop Pharm. Res. 20 569 575
19. E. Wagner 2004 Strategies to improve DNA polyplexes for in vivo gene transfer: will "artificial viruses" be the answer? Pharm. Res. 21 8 14
20. M. Thomas Q. Ge J. J. Lu J. Z. Chen A. M. Klibanov 2005 Cross-linked small polyethylenimines: while still nontoxic, deliver DNA efficiently to mammalian cells in vitro and in vivo Pharm. Res. 22 373 380
21. G. Zuber E. Dauty M. Nothisen P. Belguise J. P. Behr 2001 Towards synthetic viruses Adv. Drug Deliv. Rev. 52 245 253
22. T. Niidome L. Huang 2002 Gene therapy progress and prospects: nonviral vectors Gene Ther. 9 1647 1652
23. M. Thomas A. M. Klibanov 2003 Non-viral gene therapy: polycation-mediated DNA delivery Appl. Microbiol. Biotechnol. 62 27 34
24. J. B. Rothbard T. C. Jessop P. A. Wender 2005 Adaptive translocation: the role of hydrogen bonding and membrane potential in the uptake of guanidinium-rich transporters into cells Adv. Drug Deliv. Rev. 57 495 504
25. S. Mehier-Humbert R. H. Guy 2005 Physical methods for gene transfer: improving the kinetics of gene delivery into cells Adv. Drug Deliv. Rev. 57 733 753
26. V. A. Bloomfield 1991 Condensation of DNA by multivalent cations-considerations on mechanism Biopolymers 31 1471 1481
27. O. Rosella A. Sinclair P. R. Gibson 2000 Polyunsaturated fatty acids reduce non-receptor-mediated transcellular permeation of protein across a model of intestinal epithelium in vitro J. Gastroenterol. Hepatol. 15 626 631
28. Z. Siprashvili F. A. Scholl S. F. Oliver A. Adams C. H. Contag P. A. Wender P. A. Khavari 2003 Gene transfer via reversible plasmid condensation with cysteine-flanked, internally spaced arginine-rich peptides Hum. Gene Ther. 14 1225 1233
29. J. Rothbard P. Robbins S. Sheu S. Oliver J. Goodnough P. Wender P. Khavari 2001 Molecular transporters facilitate topical protein transduction into the skin J. Invest. Dermatol. 117 955
30. J. B. Rothbard T. C. Jessop R. S. Lewis B. A. Murray P. A. Wender 2004 Role of membrane potential and hydrogen bonding in the mechanism of translocation of guanidinium-rich peptides into cells J. Am. Chem. Soc. 126 9506 9507
31. B. Razani M. P. Lisanti 2001 Caveolins and caveolae: molecular and functional relationships Exp. Cell Res. 271 36 44
32. Y. Xu F. C. Szoka Jr 1996 Mechanism of DNA release from cationic liposome/DNA complexes used in cell transfection Biochemistry 35 5616 5623
33. A. Roosjen J. Smisterova C. Driessen J. T. Anders A. Wagenaar D. Hoekstra R. Hulst J. B. F. N. Engberts 2002 Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery Eur. J. Org. Chem. 7 1271 1277
34. J. P. Behr B. Demeneix J. P. Loeffler J. P. Mutul 1989 Efficient gene-transfer into mammalian primary endocrine-cells with lipopolyamine-coated DNA Proc. Natl. Acad. Sci. USA 86 6982 6986
35. J. S. Remy C. Sirlin P. Vierling J. P. Behr 1994 Gene-transfer with a series of lipophilic DNA-binding molecules Bioconjug. Chem. 5 647 654
36. P. L. Felgner Y. Barenholz J. P. Behr S. H. Cheng P. Cullis L. Huang J. A. Jessee L. Seymour F. Szoka A. R. Thierry E. Wagner G. Wu 1997 Nomenclature for synthetic gene delivery systems Hum. Gene Ther. 8 511 512
37. G. Ronsin C. Perrin P. Guedat A. Kremer P. Camilleri A. J. Kirby 2001 Novel spermine-based cationic gemini surfactants for gene delivery Chem. Commun. 21 2234 2235
38. R. M. Tyrrell M. Pidoux 1986 Quantitative differences in host cell reactivation of ultraviolet-damaged virus in human skin fibroblasts and epidermal keratinocytes cultured from the same foreskin biopsy Cancer Res. 46 2665 2669
39. J. L. Zhong A. Yiakouvaki P. Holley R. M. Tyrrell C. Pourzand 2004 Susceptibility of skin cells to UVA-induced necrotic cell death reflects the intracellular level of labile iron J. Invest. Dermatol. 123 771 780
40. D. Fischer T. Bieber Y. X. Li H. P. Elsasser T. Kissel 1999 A novel non-viral vector for DNA delivery based on low molecular weight, branched polyethylenimine: effect of molecular weight on transfection efficiency and cytotoxicity Pharm. Res. 16 1273 1279
41. V. A. Bloomfield 1997 DNA condensation by multivalent cations Biopolymers 44 269 282
42. B. Sternberg F. L. Sorgi L. Huang 1994 New structures in complex formation between DNA and cationic liposomes visualized by freeze-fracture electron microscopy FEBS Lett. 356 361 366
43. S. Feng G. Huang 2001 Effects of emulsifiers on the controlled release of paclitaxel (Taxol) from nanospheres of biodegradable polymers J. Control. Release 71 53 69
44. L. Ciani S. Ristori L. Calamai G. Martini 2004 DOTAP/DOPE and DC-Chol/DOPE lipoplexes for gene delivery: zeta potential measurements and electron spin resonance spectra Biochim. Biophys. Acta, Biomembr. 1664 70 79
45. B. A. Lobo A. Davis G. Koe J. G. Smith C. R. Middaugh 2001 Isothermal titration calorimetric analysis of the interaction between cationic lipids and plasmid DNA Arch. Biochem. Biophys. 386 95 105
46. C. M. Wiethoff J. G. Koe G. S. Koe C. R. Middaugh 2004 Compositional effects of cationic lipid/DNA delivery systems on transgene expression in cell culture J. Pharm. Sci. 93 108 123
47. T. Mosmann 1983 Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 55 63
48. C. F. Hung T. L. Hwang C. C. Chang J. Y. Fang 2005 Physicochemical characterization and gene transfection efficiency of lipid emulsions with various co-emulsifiers Int. J. Pharm. 289 197 208
49. D. G. Anderson A. Akinc N. Hossain R. Langer 2005 Structure/property studies of polymeric gene delivery using a library of poly(beta-amino esters) Molec. Ther. 11 426 434
50. K. Romoren A. Aaberge G. Smistad B. J. Thu O. Evensen 2004 Long-term stability of chitosan-based polyplexes Pharm. Res. 21 2340 2346
51. X. Gao L. Huang 1996 Potentiation of cationic liposome-mediated gene delivery by polycations Biochemistry 35 1027 1036
52. S. C. De Smedt J. Demeester W. E. Hennink 2000 Cationic polymer based gene delivery systems Pharm. Res. 17 113 126
53. J. Panyam V. Labhasetwar 2003 Biodegradable nanoparticles for drug and gene delivery to cells and tissue Adv. Drug Deliv. Rev. 55 329 347
54. S. Mansouri P. Lavigne K. Corsi M. Benderdour E. Beaumont J. C. Fernandes 2004 Chitosan-DNA nanoparticles as non-viral vectors in gene therapy: strategies to improve transfection efficacy Eur. J. Pharm. Biopharm. 57 1 8
55. J. Rejman V. Oberle I. S. Zuhorn D. Hoekstra 2004 Size-dependent internalization of particles via the pathways of clathrin- and caveolae-mediated endocytosis Biochem. J. 377 159 169
56. M. Ogris P. Steinlein M. Kursa K. Mechtler R. Kircheis E. Wagner 1998 The size of DNA/transferrin-PEI complexes is an important factor for gene expression in cultured cells Gene Ther. 5 1425 1433
57. E. Wagner M. Cotten R. Foisner M. L. Birnstiel 1991 Transferrin- polycation-DNA complexes: the effect of polycations on the structure of the complex and DNA delivery to cells Proc. Natl. Acad. Sci. USA 88 4255 4259
58. G. Byk C. Dubertret V. Escriou M. Frederic G. Jaslin R. Rangara B. Pitard J. Crouzet P. Wils B. Schwartz D. Scherman 1998 Synthesis, activity, and structure-activity relationship studies of novel cationic lipids for DNA transfer J. Med. Chem. 41 224 235
59. B. G. Feuerstein L. D. Williams H. S. Basu L. J. Marton 1991 Implications and concepts of polyamine-nucleic acid interactions J. Cell. Biochem. 46 37 47
60. H. Farhood N. Serbina L. Huang 1995 The role of dioleoyl phosphatidylethanolamine in cationic liposome-mediated gene-transfer Biochim. Biophys. Acta, Biomembr. 1235 289 295
61. B. Buchberger E. Fernholz H. v. d. Eltz M. Hinzepeter 1996 DOSPER liposomal transfection reagent: a reagent with unique transfection properties Biochem. Inform. 98 27 29
62. J. Monkkonen A. Urtti 1998 Lipid fusion in oligonucleotide and gene delivery with cationic lipids Adv. Drug Deliv. Rev. 34 37 49
63. D. C. Litzinger L. Huang 1992 Phosphatidylethanolamine liposomes-drug delivery, gene-transfer and immunodiagnostic applications Biochim. Biophys. Acta 1113 201 227
64. J. Gaucheron C. Santaella P. Vierling 2001 Highly fluorinated lipospermines for gene transfer: synthesis and evaluation of their in vitro transfection efficiency Bioconjug. Chem. 12 114 128
65. P. Vierling C. Santaella J. G. Riess 1995 Fluorinated liposomes F. Puisieux P. Courveur J. Delattre J. P. Devissaguet Liposomes: New Systems and New Trends in Their Application Edition de Sante Paris 293 318