Gemini surfactant based carriers in gene and drug delivery

Current Medicinal Chemistry

Volumn 16, Issue 2, 2009, Pages 171-183

  Bombelli, C ^a   Giansanti, L ^a   Luciani, P ^a   Mancini, Giovanna ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Drug delivery; Gemini surfactants; Gene therapy; Liposomes; Structure activity correlation; Transfection

Indexed keywords

AMPHOPHILE; ARGININE; AROMATIC COMPOUND; CARDIOLIPIN; CHOLESTEROL; CYSTEINE; GEMINI SURFACTANT; LIPOSOME; QUATERNARY AMMONIUM DERIVATIVE; SPERMINE; SUGAR; SURFACTANT; UNCLASSIFIED DRUG; ALKANE; CATION; DRUG CARRIER; POLYSACCHARIDE; QUATERNARY BISAMMONIUM SALT;

BIOCOMPATIBILITY; BIODEGRADABILITY; CHEMICAL STRUCTURE; DNA TRANSFECTION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STABILITY; GENE EXPRESSION; GENETIC TRANSFECTION; HUMAN; LIPOSOMAL GENE DELIVERY SYSTEM; NONHUMAN; NONVIRAL GENE THERAPY; PHYSICAL CHEMISTRY; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; CHEMISTRY; GENE THERAPY; GENE TRANSFER; SYNTHESIS;

ALKANES; CARDIOLIPINS; CATIONS; CHOLESTEROL; DRUG CARRIERS; GENE THERAPY; GENE TRANSFER TECHNIQUES; HUMANS; LIPOSOMES; POLYSACCHARIDES; QUATERNARY AMMONIUM COMPOUNDS; SURFACE-ACTIVE AGENTS;

EID: 62349128166     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986709787002808     Document Type: Review

References (70)

1. Lasic, D.D. In Vesicles; Morton Rosoff, Ed.; Marcel Dekker: New York, 1996: Pp. 447-476.
2. Papahadjopoulos, D.; Ed. Liposomes and Their Uses in Biology and Medicine. Ann. NY Acad. Sci., 1978, 308, The New York Academy of Sciences, New York.
3. Knight, C.G. Liposomes, from Physical Structure to Therapeutic Applications, Elsevier/North Holland: Amsterdam, 1981.
4. Ostro, M. J. Liposomes: From Biophysics to Therapeutics, Marcel Dekker: New York, 1987.
5. Gregoriadis, G. Liposomes as Drug Carriers: Recent Trends and Progress, John Wiley & Sons: New York, 1988.
6. Templeton, N.S. Cationic liposomes as in vivo delivery vehicles. Curr. Med. Chem., 2003, 10, 1279-1287.
7. Pedroso de Lima, M.C; Neves, S.; Filipe, A.; Duzgunes, S.; Simoes, S. Cationic liposomes for gene delivery: From biophysics to biological applications. Curr. Med. Chem., 2003, 10, 1221-1231.
8. Menger, F.M.; Littau, C.A. Gemini Surfactants: Synthesis and Properties. J. Am. Chem. Soc., 1991, 113, 1451-1452.
9. Menger, F.M.; Littau, C.A. Gemini surfactants: A new class of self-assembling molecules. J. Am. Chem. Soc., 1993, 115, 10083-10090.
10. Menger, F.M.; Keiper, J. S. Gemini surfactants. Angew. Chem. Int. Ed., 2000, 39, 1906-1920.
11. Menger, F.M.; Peresypkin, A. V. Strings of vesicles: Flow behavior in a unusual type of aqueous gel. J. Am. Chem. Soc., 2003, 125, 5340-5345.
12. Zana, R. Dimeric (Gemini) Surfactants: Effect of the spacer group on the association behavior in aqueous solution. J. Colloid Interface Sci., 2002, 248, 203-220.
13. Danino, D.; Talmon, Y.; Zana, R. Alkanediyl-α, ω-bis (dimethylalkylammonium bromide) surfactants (dimeric surfactants) 5. Aggregation and microstructure in aqueous solutions. Langmuir, 1995, 11, 1448-1456.
14. Yaroslavov, A.A.; Udalykh, O.Y.; Melik-Nubarov, S.; Kabanov, V.A.; Ermakov, Y.A.; Azov, V.A.; Menger, F.M. Conventional and gemini surfactants embedded within bilayer membranes: Contrasting behavior. Chem. Eur. J., 2001, 4835-4843.
15. Zuhorn, I.S.; Kalicharan, R.; Hoekstra, D. Lipoplex-mediated transfection of mammalian cells occurs through the cholesterol-dependent clathrin-mediated pathway of endocytosis. J. Biol. Chem., 2002, 277, 18021-18028.
16. Chicco, A.J.; Sparagna, G.C. Role of cardiolipin alterations in mitochondrial dysfunction and disease. Am. J. Physiol. Cell Physiol., 2007, 292, C33-C44.
17. Matsumoto, K.; Kusaka, J.; Nishibori, A.; Hara, H. Lipid domains in bacterial membranes Mol. Microbiol., 2006, 61, 1110-1117.
18. Kasireddy, K.; Ahmad, M. U.; Ali, S.M.; Ahmad, I. Synthesis of novel cationic cardiolipin analogues for the optimal delivery of therapeutic agents. Tetrahedron Lett., 2004, 45, 2743-2746
19. Kasireddy, K.; Ali, S.M.; Ahmad, M.U.; Choudhury, S.; Chien, P.Y.; Sheikh, S.; Ahmad, I. Synthesis of cationic cardiolipin analogues. Bioorg. Chem., 2005, 33, 345-362.
20. Song, Y.K.; Liu, F.; Chu, S.; Liu, D. Characterisation of cationicliposome mediated gene transfer in vivo by intravenous administration. Hum. Gene Ther., 1997, 8, 1585-1594.
21. Chien, P.Y.; Wang, J.; Carbonaro, D.; Lei, S.; Milerr, B.; Sheikh, S.; Ali, S.M.; Ahmad, M.U.; Ahmad, I. Novel cationic cardiolipin analogue-based liposome for efficient DNA and small interfering RNA delivery in vitro and in vivo. Cancer Gene Ther., 2005, 12, 321-328.
22. Rosenzweig, H.S.; Rakhmanova, V.A.; MacDonald, C. Diquaternary ammonium compounds as transfection agents. Bioconjug. Chem., 2001, 12, 258-263.
23. Badea, I.; Verrall, R.; Baca-Estrada, M.; Tikoo, S.; Rosenberg, A.; Kumar, P.; Foldvari, M. In vivo cutaneous interferon-γ gene delivery using novel dicationic (gemini) surfactant-plasmid complexes. J. Gene Med., 2005, 7, 1200-1214.
24. Badea, I.; Wettig, S.; Verrall, R.; Foldvari, M. Ene delivery using gemini nanoparticles in interferon-γ-deficient mice. Eur. J. Pharm. Biopharm., 2007, 65, 414-422.
25. Fisicaro, E.; Compari, C.; Duce, E.; Donofrio, G.; Rózycka-Roszak B.; Wozniak, E. Biologically active bisquaternary ammonium chlorides: Physico-chemical properties of long chain amphiphiles and their evaluation as non-viral vectors for gene delivery. Biochim. Biophys. Acta, 2005, 1722, 224-233.
26. Bello, C.; Bombelli, C.; Borocci, S.; di Profio, P.; Mancini, G. Role of the spacer stereochemistry on the aggregation properties of cationic gemini surfactants. Langmuir, 2006, 22, 9333-9338
27. Bombelli, C.; Caracciolo, G.; di Profio, P.; Diociaiuti, M.; Luciani, P.; Mancini. G.; Mazzuca, C.; Marra, M.; Molinari, A.; Monti, D.; Toccacieli, L.; Venanzi, M. Inclusion of a photosensitizer in liposomes formed by DMPC/gemini surfactant: Correlation between physicochemical and biological features of the complexes. J. Med. Chem., 2005, 48, 4882-4891.
28. Molinari, A.; Bombelli, C.; Mannino, S.; Stringaro, A.; Toccacieli, L.; Calcabrini, A.; Colone, M.; Mangiola, A.; Maira, G.; Luciani, P.; Mancini, G.; Arancia, G. m-THPC-mediated photodynamic therapy of malignant gliomas: Assessment of a new transfection strategy. Int. J. Cancer, 2007, 121, 1149-1155.
29. Bombelli, C.; Faggioli, F.; Luciani, P.; Mancini, G.; Sacco, M.G. Efficient transfection of DNA by liposomes formulated with cationic gemini amphiphiles. J. Med. Chem., 2005, 48, 5378-5382.
30. Keller, D.; Bustamante, C. Theory of the interaction of light with large inhomogeneous molecular aggregates. I. Absorption. J. Chem. Phys., 1986, 84, 2961-2971.
31. Bombelli, C.; Faggioli, F.; Luciani, P.; Mancini, G.; Sacco, M.G. PEGylated lipoplex: Preparation protocols affecting DNA condensation and cell transfection efficiency. J. Med. Chem., 2007, 50, 6274-6278.
32. Bajaj, A.; Kondaiah, P.; Bhattacharya, S. Synthesis and gene transfer activities of novel serum compatible cholesterol-based gemini lipids possesing oxyethylene-type spacers. Bioconjug. Chem., 2007, 18, 1537-1546.
33. Bajaj, A.; Kondaiah, P.; Bhattacharya, S. Design, synthesis, and in vitro gene delivery efficacies of novel cholesterol-based gemini cationic lipids and their serum compatibility: A structure-activity investigation. J. Med. Chem., 2007, 50, 2432-2442
34. Bajaj, A.; Kondaiah, P.; Bhattacharya, S. Effect of the nature of the spacer on gene transfer efficacies of novel thiocholesterol derived gemini lipids in different cell lines: A structure-activity investigation. J. Med. Chem., 2008, 51, 2533-2540
35. Dalkara, D.; Chandrashekhar, C.; Zuber, G. Intracellular protein delivery with a dimerizable amphiphile for improved complex stability and prolonged protein release in the cytoplasm of adherent cell lines. J. Control. Release, 2006, 116, 353-359.
36. Felgner, J.H.; Kumar, R.; Sridar, C.J.; Wheeler, Y.J.; Tsai, R.; Border, P.; Ramsey, M.; Martin, C.N.; Felgner, P.L. Enhanced gene delivery and mechanism studies with a novel series of cationic lipid formulations. J. Biol. Chem., 1994, 269, 2550-2561.
37. Bajaj, A.; Kondaiah, P.; Bhattacharya, S. Gene transfection efficacies of novel cationic gemini lipids possessing aromatic backbone and oxyethylene spacers. Biomacromolecules, 2008, 9, 991-999.
38. Bajaj, A.; Kondaiah, P.; Bhattacharya, S. Effect of the hydrocarbon chain and polymethylene spacer lenght on gene transfection efficacies of gemini lipids based on aromatic backbone. Bioconjugate Chem., 2007, 18, 2144-2158.
39. Ilies, M.A.; Seitz, W.A.; Johnson, B.H.; Ezel, E.L.; Miller, A.L.; Thompson, E.B.; Balaban, A.T. Pyridinium cationic lipids in gene delivery: A structure-activity correlation study. J. Med. Chem., 2006, 49, 3872-3887.
40. Van der Woude, I.; Wagenaar, A.; Meekel, A.A.P.; ter Beest, M.B.A.; Ruiters, M.H.J.; Engberts, J.B.F.N.; Hoekstra, D. Novel pyridinium surfactants for efficient, nontoxic in vitro gene delivery. Proc. Natl. Acad. Sci. USA, 1997, 94, 1160-1165.
41. Castro, M.J.L.; Kovensky, J.; Fernandez Cirelli, A. New dimeric surfactants from alkyl glucosides. Tetrahedron, 1999, 55, 12711-12722.
42. Kitagawa, M.; Suzuki, M.; Yamamoto, S.; Sogabe, A.; Kitamoto, H.; Morita, T.; Fukuoka, T. Preparation of triacyl glycolipid with biosurfactant-producing microorganism. Jpn. Kokai Tokkyo Koho 2008, 18pp., JP 2008043210.
43. β1cer). Langmuir, 1999, 15, 6163-6169.
44. Kaieda, S.; Tomi, C.; Oki, S.; Yamamura, T.; Miyake, S. Activation of invariant natural killer T cells by synthetic glycolipid ligands suppresses autoantibody-induced arthritis. Arthritis & Rheumatism, 2007 56, 1836-1845.
45. Lu, X.; Song, L.; Metelitsa, L.S.; Bittman, R. Synthesis and evaluation of an α-C-galactosylceramide analogue that induces Th1-biased responses in human natural killer T cells. ChemBioChem, 2006, 7, 1750-1756.
46. Du, W.; Kulkarni, S.S.; Gervay-Hague, J. Efficient, one-pot syntheses of biologically active. α-linked glycolipids. J. Chem. Soc., Chem. Comm., 2007, 2336-2338.
47. Blanzat, M.; Perez, E.; Rico-Lattes, Lattes, A.; Gulik, A. Correlation between structure, aggregation behaviour and cellular toxicity of anti-HIV catanionic analogues of galactosylceramide. J. Chem. Soc., Chem. Comm., 2003, 244-245.
48. Brard, M.; Laine, C.; Rethore, G.; Laurent, I.; Neveu, C.; Lemiegre, L.; Benvegnu, T. Synthesis of archaeal bipolar lipid analogues: A way to versatile drug/gene delivery systems. J. Org. Chem., 2007, 72 8267-8279.
49. Falconer, R.A.; Toth, I. Design, synthesis and biological evaluation of novel lipoamino acid-based glycolipids for oral drug delivery. Bioorg. Med. Chem., 2007, 15, 7012-7020.
50. Perouzel, E.; Jorgensen, M.R.; Keller, M.; Miller, A.D. Synthesis and formulation of neoglycolipids for the functionalization of liposomes and lipoplexes. Bioconjug. Chem., 2003, 14, 884-898
51. Menger, F.M.; Mdadugha, B.N. Gemini surfactants with a disaccharide spacer. J. Am. Chem. Soc., 2001, 123, 875-885.
52. Shibata, A.; Kamiyama, H.; Kuraishi, T.; Kukita, K.; Katori, T. 6,6′-Bis(acylamino)-6,6′-dideoxy-x,x′-trehalose analogs as antitumor agents. 1986, 9pp JP 61130298.
53. Soussan, E.; Blanzat, M.; Rico-Lattes, I.; Brun, A.; Teixeira, C.V.; Brezesinski, G.; Al-Ali, F.; Banu, A.; Tanaka, M. Physical study of the arrangment of pure catanionic glycolipids and interaction with phospholipids, in support of the optimisation of anti-HIV therapies. Colloids and Surfaces A: Physicochem. Eng. Aspects, 2007, 303, 55-72.
54. Johnsson, M.; Wagenaar, A.; Stuart, M.C.A.; Engberts, J.B.N.F. 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.
55. Johnsson, M.; Engberts, J.B.N.F. Novel sugar-based gemini surfactants: aggregation properties in aqueous solution. J. Phys. Org. Chem., 2004, 17, 934-944.
56. Johnsson, M.; Wagenaar, A.; Engberts, J.B.N.F. 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.
57. Wasungu, L.; Scarzello, M.; van Dam, G.; Molema, G.; Wagennar, A.; Engberts, J.B.N.F.; Hoekstra, D. Transfection mediated by pH-sensitive sugar-based gemini surfactants; potential for in vivo gene therapy applications. J. Mol. Med., 2006, 84, 774-784.
58. Ellens, H.; Siegel, D.P.; Alford, D.; Yeagle, P.L.; Boni, L.; Lis, L.J.; Quinn, P.J.; Bentz, J. Membrane fusion and inverted phases. Biochemistry, 1989, 28, 3692-3703.
59. Siegel, D.P.; Epand, R.M. The mechanism of lamellar-to-inverted hexagonal phase transitions in phosphatidylethanolamine: Implications for membrane fusion mechanisms. Biophys. J., 1997, 73, 3089-3111.
60. Audouy, S.; Hoekstra, D. Cationic lipid-mediated transfection in vitro and in vivo. Mol. Membr. Biol., 2001, 18, 129-143.
61. Oberle, V.; Zuhorn, I.; Audouy, S.; Bakowsky, U.; Sÿmisterova', J.; Engberts, J.B.F.N.; Hoekstra, D. In Targeting of Drugs; Gregoriadis, G., McCormack, B., Eds.; Plenum Press: New York, 2000; pp 146-155.
62. Wasungu, L.; Stuart, M.C.A.; Scarzello, M.; Engberts, J.B.N.F.; Hoekstra, D. Lipoplex formed from sugar-based gemini surfactants undergo a lamellar-to-micellar phase transition at acidic pH. Evidence for a non inverted membrane-destabilizing hexagonal phase of lipoplex. Biochim. Biophys. Acta, 2006, 1758, 1677-1684.
63. Fielden, M.L.; Perrin, C.; Kremer, A.; Bergsma, M.; Stuart, M.C.; Camilleri, P.; Engberts, J.B.F.N. 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.
64. Hashida, M.; Nishikawa, M.; Yamashita, F.; Takakura, Y. Cell-specific delivery of genes with glycosylated carriers. Adv. Drug Deliv. Rev., 2001, 52, 187-196.
65. Asokan, A.; Cho, M.J. Cytosolic delivery of macromolecules 3. Synthesis and characterization of acid-sensitive bis-detergents-Bioconjug. Chem., 2004, 15, 1166-1173.
66. Pérez, L.; Torres, J.L.; Manresa, A.; Solans, C.; Infante, M.R. Synthesis, aggregation, and biological properties of a new class of gemini cationic amphiphilic compounds from arginine, bis(Args). Langmuir, 1996, 12, 5296-5301.
67. McGregor, C.; Perrin, C.; Monck, M.; Camilleri, P.; Kirby, A.J. Rational approaches to the design of cationic gemini surfactants for gene delivery. J. Am. Chem. Soc., 2001, 123, 6215-6220
68. Dauty, E.; Remy, J.-S.; Blessing, T.; Behr, J.-P. Dimerizable cationic detergents with low cmc condense plasmid DNA into nanometric particles and transfect cells in culture. J. Am. Chem. Soc., 2001, 123, 9227-9234.
69. Ronsin, G.; Perrin, C.; Guédat, P.; Kremer, A.; Camilleri, P.; Kirby, A.J. Novel spermine-based cationic gemini surfactants for gene delivery. J. Chem. Soc. Chem. Commun., 2001, 2234-2235.
70. Bruijnster, P.J.J.A.; Garcia Rodriguez, C.L.; Willighagen, E.L.; Sommerdijk, N.A.J.M.; Kremer, A.; Camilleri, P.; Feiters, M.C.; Nolte, R.J.M.; Zwanenburg, B. Cationic gemini surfactants based on tartaric acid: Synthesis, aggregation, monolayer behaviour, and interaction with DNA. Eur. J. Org. Chem., 2002, 1397-1406.