Synthesis and characterization of a series of carbamate-linked cationic lipids for gene delivery

Felgner, P.L., Gadek, T.R., Holm, M., Roman, R., Chan, H.W., Wenz, M., Northrop, J.P., Ringold, G.M., and Danielsen, M. (1987) Lipofection: A Highly Efficient, Lipid-Mediated DNA-Transfection Procedure, Proc. Natl. Acad. Sci. USA 84, 7413–7417. Miller, A.D. (1998) Cationic Liposomes for Gene Therapy, Angew. Chem. Int. Ed. 37, 1768–1785. Zhang, S.B., Xu, Y.M., Wang, B., Qiao, W.H., Liu, D.L., and Li, Z.S. (2004) Cationic Compounds Used in Lipoplexes and Polyplexes for Gene Delivery, J. Controlled Release 100, 165–180. Leventis, R., and Silvius, J.R. (1990) Interactions of Mammalian Cells with Lipid Dispersions Containing Novel Metabolizable Cationic Amphiphiles, Biochim. Biophys. Acta 1023, 124–132. Bennett, M.J., Malone, R.W., and Nantz, M.H. (1995) A Flexible Approach to Synthetic Lipid Ammonium Salts for Polynucleotide Transfection, Tetrahedron Lett. 36, 2207–2210. Kikuchi, I.S., and Carmona-Ribeiro, A.M. (2000) Interactions Between DNA and Synthetic Cationic Liposomes, J. Phys. Chem. B 104, 2829–2835. Kim, A., Lee, E.H., Choi, S.H., and Kim, C.K. (2004) In vitro and in vivo Transfection Efficiency of a Novel Ultradeformable Cationic Liposome, Biomaterials 25, 305–313. Gao, X., and Huang, L. (1991) A Novel Cationic Liposome Reagent for Efficient Transfection of Mammalian Cells, Biochem. Biophys. Res. Commun. 179, 280–285. Bottega, R., and Epand, R.M. (1992) Inhibition of Protein Kinase C by Cationic Amphiphiles, Biochemistry 31, 9025–9030. Walker, S., Sofia, M.J., Kakarla, R., Kogan, N.A., Wierichs, L., Longley, C.B., Bruker, K., Axelrod, H.R., Midha, S., Babu, S., and Kahne, D. (1996) Cationic Facial Amphiphiles: A Promising Class of Transfection Agents, Proc. Natl. Acad. Sci. USA 93, 1585–1590. Smith, A.E. (1995) Viral Vectors in Gene Therapy, Annu. Rev. Microbiol. 4, 807–838. Smith, L.C., Duguid, J., Wadhwa, M.S., Logan, M.J., Tung, C.H., Edwards, V., and Sparrow, J.T. (1998) Synthetic Peptidebased DNA Complexes for Nonviral Gene Delivery, Adv. Drug Deliv. Rev. 30, 115–131. Rittner, K., Benavente, A., Bompard-Sorlet, A., Heitz, F., Divita, G., Brasseur, R., and Jacobs, E. (2002) New Basic, Membrane-Destabilizing Peptides for Plasmid-based Gene Delivery in vitro and in vivo, Mol. Ther. 5, 104–114. El-Aneed, A. (2004) An Overview of Current Delivery Systems in Cancer Gene Therapy, J. Controlled Release 94, 1–14. Boussif, O., Lezoualc’h, F., Zanta, M.A., Mergny, M.D., Scherman, D., Demeneix, B., and Behr, J.P. (1995) A Novel, Versatile Vector for Gene and Oligonucleotide Transfer into Cells in Culture and in vivo: Polyethylenimine, Proc. Natl. Acad. Sci. USA 92, 7297–7301. Lampela, P., Elomaa, M., Ruponen, M., Urtti, A., Männistö, P.T., and Raasmaja, A. (2003) Different Synergistic Roles of Small Polyethylenimine and Dosper in Gene Delivery, J. Controlled Release 88, 173–183. Wu, G.Y., and Wu, C.H. (1987) Receptor Mediated in vitro Gene Transformation by a Soluble DNA Carrier System, J. Biol. Chem. 262, 4429–4432. Ward, C.M., Pechar, M., Oupicky, D., Ulbrich, K., and Seymour, L.W. (2002) Modification of pLL/DNA Complexes with a Multivalent Hydrophilic Polymer Permits Folate-Mediated Targeting in vitro and Prolonged Plasma Circulation in vivo, J. Gene Med. 4, 536–547. Hood, J.D., Bednarski, M., Frausto, R., Guccione, S., Reisfeld, R.A., Xiang, R., and Cheresh, D.A. (2002) Tumor Regression by Targeted Gene Delivery to the Neovasculature, Science 296, 2404–2407. Cavazzana-Calvo, M., Thrasher, A., and Mavilio, F. (2004) The Future of Gene Therapy, Nature 427, 779–781. Liu, D.L., Hu, J.J., Qiao, W.H., Li, Z.S., Zhang, S.B., and Cheng, L.B. (2005) Synthesis of Carbamate-Linked Lipids for Gene Delivery, Bioorg. Med. chem. Lett. 15, 3147–3150. Kokotos, G., Verger, R., and Chiou, A. (2000) Synthesis of 2-Oxo Amide Triacylglycerol Analogues and Study of Their Inhibition Effect on Pancreatic and Gastric Lipases, Chem. Eur. J. 6, 4211–4217. Boomer, J.A., and Thompson, D.H. (1999) Synthesis of Acid-Labile Diplasmenyl Lipids for Drug and Gene Delivery Applications, Chem. Phys. Lipids 99, 145–153. Boomer, J.A., Thompson, D.H., and Sullivan, S.M. (2002) Formation of Plasmid-based Transfection Complexes with an Acid-Labile Cationic Lipid: Characterization of in vitro and in vivo Gene Transfer, Pharm. Res. 19, 1292–1301. Bangham, A.D., Standish, M.M., and Watkins, J.C. (1965) Diffusion of Univalent Ions Across the Lamellae of Swollen Phospholipids, J. Mol. Biol. 13, 238–253. Rider, T.H., and Hill, A.J. (1930) Studies of Glycidol. I. Preparation from Glycerol Monochlorohydrin, J. Am. Chem. Soc. 52, 1521–1527. National Institute of Advanced Industrial Science and Technology (AIST), Spectral Database for Organic Compounds, SDBS, http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng (accessed July, 2005). Ruth, J.M., and Philippe, R.J. (1966) Mass Spectra of Isocyanates, Anal. Chem. 38, 720–723. Alquist, F.N., and Slagh, H.R. (1939) Manufacture of 1-Dimethylamino-2,3-propanediol, U.S. Patent 2,147,226. Chinese Statistics Society (1985) Orthogonal Test and Thrice Design, pp. 1–100, Science Press, Beijing (in Chinese). Chen, Y. (1981) Organic Analysis, pp. 713–716, Higher Education Press, Beijing (in Chinese). Cotarca, L., Delogu, P., Nardelli, A., and Šunjić, V. (1996) Bis(trichloromethyl) Carbonate in Organic Synthesis, Synthesis 5, 553–576. Wang, X.Z., Li, X.Q., Shao, X.B., Zhao, X., Deng, P., Jiang, X.K., Li, Z.T., and Chen, Y.Q. (2003) Selective Rearrangements of Quadruply Hydrogen-Bonded Dimer Driven by Donor-Acceptor Interaction, Chem. Eur. J. 9, 2904–2913. Moniruzzaman, M., Goodbrand, B., and Sundararajan, P.R (2003) Morphology and Thermal Behavior of Self-Assembling Carbamates, J. Phys. Chem. B 107, 8416–8423. Feitosa, E., Barreleiro, P.C.A., and Olofsson, G. (2000) Phase Transition in Dioctadecyldimethylammonium Bromide and Chloride Vesicles Prepared by Different Methods, Chem. Phys. Lipids 105, 201–213. Feitosa, E., and Brown, W. (1997) Fragment and Vesicle Structures in Sonicated Dispersions of Dioctadecyldimethylammonium Bromide, Langmuir 13, 4810–4816. Cuccovia, I.M., Sesso, A., Abuin, E.B., Okino, P.F., Tavares, P.G., Campos, J.F.S., Florenzano, F.H., and Chaimovich, H. (1997) Characterization of Dioctadecyldimethylammonium Chloride Vesicles Prepared by Membrane Extrusion and Dichloromethane Injection, J. Mol. Liq. 72, 323–336. Uchegbu, I.F., and Vyas, S.P. (1998) Non-ionic Surfactant based Vesicles (niosomes) in Drug Delivery, Int. J. Pharm. 172, 33–70. Basu, R., De, S., and Nandy, P. (1998) Effect of n-Decane on Lecithin Phase Transition Temperatures: A Microscopic Study, Colloids Surf. B: Biointerfaces 11, 29–31. Hata, T., Matsuki, H., and Kaneshina, S. (2000) Effect of Local Anesthetics on the Phase Transition Temperatures of Ether- and Ester-Linked Phospholipid Bilayer Membranes, Colloids Surf. B: Biointerfaces 18, 41–50. Uchegbu, I.F., Schätzlein, A., and Florence, A.T. (1996) Nonionic Surfactant Vesicle (niosome) Phase Transitions, Eur. J. Pharm. Sci. 4 (Suppl. 1), S138. Uchegbu, I.F., and Florence, A.T. (1995) Non-ionic Surfactant Vesicles (niosomes): Physical and Pharmaceutical Chemistry, Adv. Colloid Interface Sci. 58, 1–55. Harris, J.R., Roos, C., Djalali, R., Rheingans, O., Maskos, M., and Schmidt, M. (1999) Micron 30, 289–298.