Синтез и изучение свойств положительно заряженных гидрофобных производных циклических и ациклических полиолов
Диссертация
Вторым этапом трансфекции является взаимодействие геносом с мембраной клеток с последующим их проникновением и распределением во внутриклеточном пространстве. На данном этапе катионный липид обеспечивает остаточный положительный заряд геносомы, что позволяет ему взаимодействовать с отрицательно заряженной клеточной мембраной. Агрегированные на клеточной поверхности комплексы в дальнейшем могут… Читать ещё >
Список литературы
- D. D. Lasic, Liposomes in gene delivery, CRC Press, N.-Y., 1997.
- A. D. Miller, Cationic liposomes for gene therapy// Angew. Chem. Int. Ed., 1998, 37, 1768.
- И. Д. Константинова, Г. А. Серебренникова, Положительно заряженные липиды: структура синтез применение// Успехи химии, 1996, 65, 581 Russ. Chem. Rev., 1996, 65, 537 (Engl. Transl.).
- P. L. Feigner, T. R. Gadek, M. Holm, R. Roman, H. W. Chan, M. Wenz, J. P. Northop, G. M. Ringold and M. Danielsen, Lipofection: a hghly efficient lipid-mediated DNA transfection procedure// Proc. Natl. Acad. Sci. USA, 1987, 84, 7413.
- R. Leventis and J. R. Silvius, Interaction of mammalian cells with lipid dispersions containing novel metabolizable cationic amphiphiles// Biochim. Biophys. Acta, 1990, 1023, 124.
- J. H. Feigner, R. Kumar, C. N. Sridhar, C. J. Wheeler, Y. J. Tsai, R. Border, P. Ramsey, M. Martin and P. L. Feigner, Enhanced gene delivery and mechanism studies with novel series of cationic lipid formulations// J. Biol. Chem., 1994, 269, 2550.
- M. J. Bennett, R. W. Malone and M. H. Nantz, A flexible approach to synthetic lipid ammonium salts for polinucleotide transfection// Tetrahedron Lett., 1995, 36, 2207.
- M. J. Bennett, A. M. Aberle, R. P. Balasubramaniam, J. G. Malone, R. W. Malone and M. H. Nantz, Cationic lipid-mediated gene delivery to murine lung: correlation of lipid hydration with in vivo transfection activity// J. Med. Chem., 1997, 40, 4067.
- R. W. Malon, P. L. Feigner and I. M. Verma, Cationic liposome-mediated RNA transfection// Proc. Natl. Acad. Sci. USA, 1989, 86, 6077.
- P. L. Feigner and G. M. Ringold, Cationic liposome-mediated transfection// Nature, 1989, 337, 387.
- H. Gershon, R. Ghirlando, S. B. Guttman and A. Minsky, Mode of formation and structural featurees of DNA-cationic liposome complexes used for transfection// Biochemistry, 1993, 32, 7143
- S. May and A. Ben-Shaul, DNA-lipid complexes: stability of honeycomb-like and spaghetti-like structures// Biophys. J., 1997, 73, 2427.
- K. W. Mok and P. R. Cullis, Structural and fusogenic properties of cationic liposomes in the presence of plasmid DNAII Biophys. J., 1997, 73, 2534.
- R. B. Arenas, A. Fichera, P. Mok, M.C. Blanco and F. Michelassi, Introduction of human adenomatous polyposis gene into min mice via cationic liposomes// Surgery, 1996,120, 712.
- F. Lui, H. Qi, L. Huang and D. Liu, Factors controlling the efficiency of cationic lipid-mediated transfection in vivo via intraenous administration// Gene Ther., 1997, 4, 517
- J. O. Radier, I. Koltover, T. Salditt and C. R. Safinya, Structure of DNA-cationic liposome complexes: DNA intercalation in multilamellar memranes in distinct interhelical packing regimes// Science, 1997, 275, 810.
- N. S. Templeton, D. D. Lais, P. M. Frederik, H. H. Strey, D. D. Roberts and G. N. Pavlakis, Improved DNA-liposome comlexes for increased systemic delivery and gene expression// Nature Biotechnol., 1997, 15, 647.
- N. J. Zuidam, Y. Barenholz and A. Minsky, Chiral DNA paking in DNA-cationic liposome assemblies// FEBS Lett., 1999, 457, 419.
- G. Gregoriadis, R. Saffie and B. de Souza, Liposome-mediated DNA vaccination//FEBS Lett., 1997, 402, 107.
- J. Zabner, A.J. Fasbender, T. Moninger, K. A. Poellinger and M. J. Welsh, Cellular and molecular barriers to gene transfer by cationic lipids// J. Biol. Chem., 1995, 270, 18 997.
- T. Ochiya, Y. Takahama, H. Baba-Toriyama, M. Tsukamoto, Y. Yasuda, H. Kikuchi and M. Terada, Evalution of cationic liposome suitable for gene transfer into pregnant animals// Biochem. Biophys. Res. Commun., 1999, 258, 358.
- P. И. Жданов, О. В. Подобед, Н. Г. Куценко, О. А. Бунеева, Т. А. Цветкова, С. О. Гурьев, Г. А. Серебренникова, И. Д. Константинова, М. А. Маслов, Новые катионные липосомы для трансфекции эукариотических клеток// Док. Акад. Наук, 1998, 362, 557.
- Y. Kaneko and A. Tsukamoto, Structural characteristics of cationic liposomes with potent enhancing effect on retroviral transduction into human hepatoma cells// Cancer Lett., 1996, 105, 39.
- V. Budken, V. Gurevich, J. Hagstrom, F. Bortsov and J. Wolff, pH Sensitive cationic liposomes: a new synthetic virus-like vector// Nat. Biotech., 1996, 14, 760.
- EP 0747 351 A2, C07C 381/12.
- I. Solodin, C. S. Brown and T. D. Heath, Synthesis of phosphotriester cationic phospholipids// Synlett., 1996, 5, 457.
- R. C. MacDonald, V. A. Rakhmanova, K. L. Choi, H. S. Rosenzweig and M. K. Lahiri, O-ethylphosphat: A metabolizable cationic phospholipid which is a serum-compatible DNA transfection agent// J. Pharm. Sci., 1999, 88, 896.
- C. M. Gorman, M. Aikawa, B. Fox, E. Fox, C. Lapuz, B. Michaud, H. Nguyen, E. Roche, T. Sawa and J. P. Wiener-Kronish, Gene Ther., 1997, 4, 983.
- G. Le Bolch, N. Le Bris, J. -J. Yaouanc, J. -C. Clement and H. des Abbays, Cationic phosphonolipid as non viral vectors for DNAa transfection// Tetrahedron Lett., 1995, 36, 6681.
- H. Farhood, R. Bottega, R. M. Epand and L. Huang, Effect of cholesterol derivatives on gene transfer and protein kinase C activity// Biochim. Biophys. Acta, 1992, 1111,239.
- X. Gao and L. Huang, A novel cationic liposome reagent for efficient transfection// Biochem. Biophys. Res. Commun., 1991, 179, 280.
- R. Okayama, M. Noji and M. Nakanishi, Cationic cholesterol with a hydroxyethylamino head group promotes significantly liposome-mediated gene transfection// FEBS Lett., 1997, 408, 232.
- A. Singal and L. Huang, Gene transfer in mammalian cells using liposomes as carriers// in Gene Therapeutics: Methods and Application of Direct Gene Transfer (Ed. Wolf J. A.), Birkhauser, Boston, 1994, 118.
- H. Farhood, N. Serbina and L. Huang, The role of dioleoylphoshpatidylethanolamine in cationic liposome formulations for in vivo gene transfer// Biochim. Biophys. Acta, 1995,1235, 289.
- A. McQuillin, K. D. Murray, C. J. Etheridge, L. Stewart, R. G. Cooper, P. M. Brett, A. D. Miller and H. M. D. Gurling, Optimization of liposome mediated transfection of neuronal cell line// NeuroReport, 1997, 8, 1481.
- K. Yang, X. S. Mu, R. L. Hayers, Y. H. Qiu, F. L. Sorgi, L. Huang, G. L. Clifton and L. Vivian, DC-Choi liposome-mediated gene transfer in rat spinal cord// NeuroReport, 1997, 8, 2355.
- B. Sternberg, F. L. Sorgi and L. Huang, New structures in complex formation between DNA and cationic liposomes visualized by freeze-fructure electron microscopy// FEBS Lett., 1994, 356, 361.
- K. M. Hui, P. T. Ang, L. Huang and S. K. Tay, Phase I study of immunotherapy of cutaneous metastases of human carcinoma using allogenic and xenogenic MHC of DNA-liposome complexes// Gene Ther., 1997, 4, 783.
- R. G. Cooper, C. J. Etheridge, L. Stewart, J. Marshall, S. Rudginsky, S. H. Cheng and A. D. Miller, Chem. Eur. J., 1998, 4, 137.
- D. Moradpour, J. I. Shauer, V. R. Zurdwski, J. R. Wands and R. H. Boutin, Efficient gene transfer into mammalian cells with cholesteryl-spermidine// Biochem. Biophys. Res. Commun., 1996, 221, 82.
- N. Ouderhiri, J. P. Vigneron, M. Peuchmar T., Leclerc, J. M. Lehn and P. Lehn, Gene transfer by guanidinium-cholesterol cationic lipids into airway epithelial cells in vitro and in vivo! I Proc. Natl. Acad. Sci. USA, 1997, 94, 1651.
- J. P. Bher, DNA strongly binds to micelles and vesicles containing lipopolyamines or lipointercalants// Tetrahedron Lett., 1986, 27, 5861
- J. P. Bher, B. Demeneix, J. P. Loeffler and J. Perez-Mutul, Efficient gene transfer into mammalian primari endocrine cells with lipopolyamine-coated DNA// Proc. Natl. Acad. Sci. USA, 1989, 86, 6982
- P. Hawley-Nelson, V. Ciccarone, G. Geleyehu, J. Jesse and P. L. Feigner, Focus, 1993, 15, 73.
- J. P. Behr, Gene transfer with synthetic cationic amphiphiles: prospects for gene therapy// Bioconj. Chem., 1994, 5, 382.
- K. Lappalainen, R. Miettinen, J. Kellokoski, I. Jaaskelainen and S. Syrjanen, Intracellular distribution of oligonucleotides delivered by cationic lipids: light and electron microscopic study// J. Histochem. Cytochem., 1997, 45, 265.
- T. Boukhnikachvili, O. Ageurre-Chariol, M. Airau, S. Lesieur, M. Ollivon and J. Vacus, Structure of in-serum transfecting DNA-cationic lipid complexes// FEBS Lett., 1997, 409, 188.
- D. D. Dunlap, A. Maggi, M. R. Soria and L. Monaco, Nanoscopic structure of DNA condensed for gene delivery// Nucl. Acids Res., 1997, 25, 3095.
- M. Tsukamoto, T. Ochiya, S. Yoshida, T. Sugimura and M. Terada, Gene transfer and expression in pogeny alter intravenous DNA injection into pregnant mice// Nature Genet., 1995, 9, 243.
- A. R. Thierry, Y. Lunardi-lskandar, J. L. Bryant, P. Rabinovitch, R. C. Gallo and L. C. Mahan, Systemic gene therapy: biodistribution and long-term expression of a trasgene in mice// Proc. Natl. Acad. Sci. USA, 1995, 92, 9742
- K. Lappalainen, L. Pirila, I. Jaaskelainen, K. Syrjanen and S. Syrjanen, Effect of liposomal antisense oligonucleotides on mRNA and protein levels of the HPV 16 E7 oncogene// Anticancer Res., 1996,16, 2485.
- B. A. Demeneix, D. Goula, C. Benoist, J. S. Remy and J. P. Behr, Theory and practicce of using policationic amphiphiles and polymers for in vitro and in vivo gene transfer// in Gene Therapy (Ed. K.G. Xanthopoulos), Springer, 1998, 195.
- B. A. Demeneix, O. Boussif, M. A. Zanta, J. C. Remy and J. P. Behr, Delivery of polynucleotides with polyamine lipids and polymers// Nucleos. Nucleot, 1997, 16,1121.
- B. Abdallah, L. Sachs and B. A. Demeneix, Non-viral gene transfer: application in developmental biology and gene therapy// Biol. Cell, 1995, 85, 1.
- X. Zhou, A. L. Klibanov and L. Huang, Lipophilic polylysines mediate efficient DNA transfection in mammalian cells// Biochim. Biophys. Acta, 1991, 1065, 8.
- X. Zhou and L. Huang, DNA transfection mediated by cationic liposomes containing lipopolysine: characterization and mechanism of action// Biochim. Biophys. Acta, 1994, 1189, 195.
- V. Budker, J. E. Hagstrom, 0. Lapina, D. Eifrig and J. Fritz, Protein-amphipathic polyamine complexes enable highly efficient transfection with minimal toxicity// Biotechniques, 1997, 23, 139.
- A. Nazih, Y. Cordier, R. Bischoff, H. V. J. Kolbe, D. Heissler, Synthesis and stability stydy of the new pentaammonio lipid pcTG90, a gene transfer agent// Teterahedron Lett, 1999, 40, 8089.
- F. H. Cameron, M. J. Moghaddam, V. J. Bender, R. G. Whittaker, M. Mott and T. J. Lockett, A transfection compound series based on versatile Tris linkage// Biochem. Biophys. Acta, 1999, 1417, 37.
- A. Ito, R. Miyazoe, J. Mitoma, T. Akao, T. Osaki and T. Kunitake, Synthetic cationic amphiphiles for liposome-mediated DNA transfection// Biochem. Int., 1990, 22, 235.
- T. Akao, T. Fukumoto, H. Ihara and A. Ito, Conformational change in DNA induced by cationic bilayer membranes// FEBS Lett., 1996, 391, 215.
- T. Koshizaka, Y. Hayashi and K. Yagi, Novel liposomes for efficient transfection of beta-galactosidase gene into COS-1 cells// J. Clin. Biochem. Nutr., 1989, 7, 185.
- D. D. Zhao, S. Watarai, Y. T. Lee, S. Kouchi, H. Ohmori and T. Yasuda, Gene transfection by cationic liposomes: comparison of the transfection efficiency of liposomes prepared from various positively charged lipids// Acta Medica Okayama, 1997, 51, 149.
- H. Arima, Y. Aramaki and S. Tsuchiya, Effects of oligonucleotides on the physicochemical characteristics and cellular uptake of liposomes// J. Pharm. Sci., 1997, 86, 438.
- T. Tana, S. Watarai, M. Onuma, K. Ochiai, H. Kakidani and T. Yasuda, In vivo antitumor effect of cationic liposomes containing diphteria toxin A-chain gene on cells infected with bovine leukemia virus// J. Vet. Med. Sci., 1997, 59, 617.
- M. Yanase, M. Shinkai, H. Honda, T. Wakabayashi, J. Yoshida and T. Kobayashi, Antitumor immunity induction by intracellular Hyperthermia using magnetite cationic liposomes// Jpn. J. Cancer Res., 1998, 89, 463, 775.
- T. Kato, K. Iwamoto, H. Ando, N. Asakawa, I. Tanaka, J. Kiruchi and Y. Murakami, Synthetic cationic amphiphiles for liposome-mediated DNA transfection woth less cytotoxicity// Biol. Pharm. Bull., 1996,19, 860
- J. K. Wang, X. Guo, Y. H. Xu, L. Barron and F.C. Szoka, Synthesis and characterization of long chain alky acyl carnitine esters. Potentially biodegradable cationic lipids for use in gene delivery// J. Med. Chem., 1998, 41, 2207.
- F. Tang and J.A. Hughes, Introduction of a disulfide bond into a cationic lipid enhances transgene expression of plasmid DNAII Biochem. Biophys. Res. Commun., 1998, 242, 141.
- P. S. Ajmani, F. Tang, S. Krishnaswami, E. M. Meyer, C. Sumners and J. A. Hughes, Enhanced transgene expression in rat brain cell cultures with a disulfide-containing cationic lipid// Neuroscience Lett., 1999, 277, 141.
- J. M. Ruysschaert, A. E. Ouanabi, V. Willeaume, G. Huez, R Fuks, M. Vandenbranden and P. Di Stefano, A novel cationic amphiphile for transfection of mammalian cells// Biochem. Biophys. Res. Comm., 1994, 203, 1622.
- A. E. Ouhabi, V. Pector, R. Fuks and M. Vandenbranden, Double long chain amidine liposome-mediated self replicating RNA transfection// FEBS Lett., 1996,380,108.
- A. E. Ouhabi, M. Thiry, V. Pector, R. Fuks, J. M. Ruysschaert and M. Vandenbranden, The role of endosome destabilizing activity in the gene transfer process mediated by cationic lipids// FEBS Lett., 1997, 414, 187.
- I Martin, and J. M. Ruysschaert, Comparison of lipidd vesicle fusion induced by the putative fusion peptide of fertilin (a protein active in sperm-egg fusion) and the NH2-terminal domain of the HIV2 gp41// FEBS Lett., 1997, 405, 351.
- G. Zhang, V. Gurtu, T. H. Smith, P. Nelson and S. R. Kain, A cationic lipid for rapid and efficient delivery of plasmid DNA into mammalian cells// Biochem. Biophys. Res. Commun., 1997, 236, 126.
- I. Solodin, C. S. Brown, M. S. Bruno, C. -Y. Chow, E. -H. Jang, R. J. Debs and T. D. Heath, A novel series of amphiphilic imidazolinium compound for in vitro and in vivo gene delivery// Biochemystry, 1995, 34, 13 537.
- J. W. McLean, E. A. Fox, P. Baluc, P. B. Bolton, A. Haskell, R. Pearlman, G. Thurston, E. Y. Umemoto and D. M. McDonald, Organ-specific endothelial cell uptake of cationic liposome-DNA complexes in mice// Am. J. Physiol., 1997, 273, 387.
- Y. Liu, L. C. Mounkes, H. D. Liggitt, C. S. Brown, I Solodin, T. D. Health and R. J. Debs, Factors influencing the efficiency of cationic liposome-mediated intravenous gene delivery// Nature Biotechnol., 1997,15, 167.
- J. A. Hughes, A. I. Aronsohn, A. V. Avrutskaya and R. L. Juliano, Evaluation of adjuvants that enhance the effectiveness of antisense oligonucleotides// Pharm. Res., 1996, 13, 404.
- E. Liang and J. A. Hughes, Characterization of a pH-sensitive surfactant, dodecyl-2-(1'-imidazolyi|propionate (DIP) and preliminary studies in liposome-mediated gene transfer// Biochem. Biophys. Acta, 1998,1369, 39.
- I. Van der Woude, A. Wagenaar, A. A. P. Meekel, M.B. A. ter Beest, M. H. J. Ruiters, J. B. F. N. Engberts and D. Hoekstra, Novel pyridinium sursactants for efficient, nontoxic in vitro gene delivery// Proc. Natl. Acad. Sci. USA, 1997, 94, 1160.
- P. Pinnaduwage, L. Schmitt and L. Huang, Use of quaternary ammonium detergent in liposome mediated DNA transfection of mous L-cells// Biochim. Biophys. Acta, 1989, 985, 33.
- J. K. Rose, L. Buonocore and M. A. Whitt, A new cationic liposome reagent mediating nearly quantitative transfection of animal cells// Biotechniques, 1991, 10, 520.
- N. Ballas, N. Zakai, I. Sela and A. Loyter, Biochim. Biophys. Acta, 1988, 939, 8.
- PCT Int. Appl. WO 96/10 390 A61K 9/127.
- S. Bhattacharya and S. S. Mandal, Evidence of interlipidic ion-rairing in anion-induced DNA release from cationic amphiphile-DNA complexes. Mechanistic implications in transfection// Biochemistry, 1998, 37, 7765.
- T. Kunitake, N. Nakayama, M. Shimomura, Y. Okahaata, K. Kano and T. Ogawa, Unique properties of chromophore-containing bilayer aggregates: enhanced chirality and photochemically induced morphological change// J. Amer. Chem. Soc., 1980, 102, 6642.
- K. Han, An efficient DDAB-mediated transfection of drosophila S2 cells// Nucl. Acids Res., 1996, 24, 4362.
- D. L. Reimer, S. Kong and M. B. Bally, Analysis of cationic liposome-mediated interactions of plasmid DNA witj murine and human melanoma cells in vitroll J. Biol. Chem., 1997, 272, 19 480.
- P. Wielbo, N. Shi and C. Sernia, Antisense inhibition of angiotensinogen in hepatoma cell culture is enhanced by cationic liposome delivery// Biochem. Biophys. Res. Commun., 1997, 232, 794.
- F. M. P. Wong, D. L. Reimer and M.B. Bally, Cationic lipid binding to DNA: characterization of complex formation// Biochemistry, 1996, 35, 5756.
- D. D. Lasic, H. Strey, M. C. A. Stuart, R. Podgornik and P. M. Frederik, The structure of DNA-liposomes complexes// J. Amer. Chem. Soc., 1997, 119, 832.
- A. M. Aberle, F. Tablin, J. Zhu, N. J. Walker, D. C. Gruenert and M. H. Nantz, A novel tetraester construct that reduces cationic lipid-associated cytotoxity. Implication for the onsrt of cytotoxicity// Biochemistry, 1998, 37, 6533.
- T. Ren and D. Liu, Synthesis of cationic lipids from 1,2,4-butanetriol// Tetrahedron Lett., 1999, 40, 209.
- T. Ren and D. Liu, Synthesis of diether-linked cationic lipids for gene transfer// Bioorg. Med. Chem. Lett., 1999, 9, 1247.
- K. I. Takeuchi, M. Ishihara, C. Kawaura, M. Noji, T. Furuno and M. Nakanishi, Effect of zeta potential of cationic liposomes containing cationic cholesterol derivatives on gene transfection// FEBS Lett., 1996, 397, 207.
- C. Kawaura, A. Nogucki, T. Furuno and M. Nakonishi, Atomic force microscopy for studing gene transfection mediated by cationic liposomes with a cationic cholesterol derivatives// FEBS Lett., 1998, 421, 69.
- J. Bentz, H. Ellens, M. Z. Lai and F. C. Szoka, On the correlation between hexagonal II phase and the contact-induced destabilization of phosphatidyethanolamine containing membranes// Proc. Natl. Acad. Sci. USA, 1985, 82, 5742.
- A. M. Aberle, M. J. Bennett, R. W. Malon and M. H. Hantz, The counterion influence on cationic lipid-mediated transfection of plasmid DNA// Biochim. Biophys. Acta, 1996, 1299, 281.
- S. Obiika, A. Shimoyama, T. Uneda, K. Miyashita, T. Doi and T. Imanishi, A symmetrical and biodegradable cationic lipid. Synthesis and application for efficient gene trnsfectionII Bioorg. Med. Chem. Lett., 1997, 7, 1817.
- L. Huang, H. Farhood, N. Serbina, and A.G. Teepl, Endosomolytic activity of cationic liposomes enhances the delivery of human immunodeficiecy virus-1 transactivator protein (tat) to mammalian cells// Biochem. ahd Biophys. Res. Commun., 1995, 217, 761.
- А. П. Каплун, Ле Банг Шон, Ю. М. Краснопольский, В. И. Швец, Липосомы и другие наночастицы как средство доставки лекарственных веществ// Вопросы мед. химии, 1999, 54, 3.
- S. Kawakami, F. Yamashita, M. Nashikawa, Y. Takakura and M. Hashida, Asialoglycoprotein receptor-mediated gene transfer using novel galactosylated cationic liposomes// Biochem. Biophys. Res. Commun., 1998, 252, 78.
- H. Kamata, H. Yagisawa, S. Takahashi and H. Hirata, Amphiphilic peptides enhance the efficiency of liposome-mediated DNA transfection// Nucleic Acids Res., 1994, 22, 536.
- A. Subramanian, P. Ranganathan and S. L. Diamond, Nuclear targeting peptide scaffolds for lipofection of non diving mammalian cells// Nature Biotechnol., 1999, 17, 873.
- H. Mizuguchi, T. Nakagawa, M. Nakanishi, S. Imasu, S. Nakagawa and T. Mayumi, Efficient gene transfer into mammalian cells using fusogenic liposome// Biochem. Biophys. Res. Commun., 1996, 218, 402.
- C. Meunier-Durmot, N. Ferry, B. Hainque, J. Delattre and C. Forest, Efficient transfer of regulated genes in adipocytes and hepatoma cells by combination of liposomes and replication-deficient adenovirus// Eur. J. Biochem., 1997, 237, 660.
- R. Cazzola, P. Viani, P. Allevi, G. Cighetti and B. Cestaro, pH Sensitivity and plasma stability of liposomes containing N-stearoylcysteamine// Biochim. Biophys. Acta, 1997, 1329, 291.
- K. Hong, W. Zheng, A. Baker and D. Papahadjopoulos, Stabilization of cationic liposome-plasmid DNA complexes by polyamines and poly (ethylen glycol)-phospholipid conjugates for efficient in vivo gene delivery// FEBS Lett., 1997, 400, 233
- J. J. Wheeler, L. Palmer, M. Ossanlou, I. MacLachlan, R. Graham, P. Scherrer, M. J. Hope and P. R. Cullis, Stabilized plasmid-lipid particles: construction and characterization// Gene Ther., 1999, 6, 271.
- K. W. С. Мок, A. M. I. Lam and P. R. Cullis, Stabilized plasmid-lipid particles: factors influencing plasmid entrapment and transfection properties// Biochim. Biophys. Acta, 1999, 1419, 137.
- M. В. Аникин, И. П. Ушакова, Г. А. Серебренникова, Р. П. Евстигнеева, Депонированная статья, ВИНИТИ, 1987, № 915-ХП 87.7.
- В. Nasser, S. Morpain, В. Laude, and N. Latruffe, Synthesis and characterization of chemical intermediates of acyl and alkyl phospholipids// Can. J. Chem., 1992, 70, 2319.
- Общая органическая химия, под ред. Д. Бартона, В. Д. Оллиса, Химия, Москва, 1985, 8, 81.
- М. A. Maslov, N. G. Morozova, and G. A. Serebrennikova, Convenient synthesis of cationic glycerolipids via methylthiomethyl ethers// Mendeleev Commun., 2000, 65.
- P. M. Pojer and S. J. Angyal, Methylthiomethyl ethers: general synthesis and mild cleavage. Protection of hydroxyl group// Tetrahedron Lett., 1976, 26, 3067.
- E. J. Corey and M. G. Bock, Protection of primary hydroxyl groups as methylthiomethyl ethers// Tetrahedron Lett., 1975, 25, 3269.
- К. Yamado, К. Kato, and N. Nagase, Protection of tertiary hydroxyl group as methylthiomethyl ethers// Tetrahedron Lett., 1976, 26, 65.
- P. M. Pojer and S. J. Angyal, Methylthiomethyl ethers: their use in the protection and methylation of hydroxyl group// Aust. J. Chem., 1978, 31, 1031.
- K. Suzuki, J. Inanaga, and M. Yamaguchi, A mild and convenient method for the preparation of methylthiomethyl ethers: protection of hydroxyl groups// Chem. Lett., 1979, 29, 1277.
- L. G. Wade, J. M. Gerdes, and R. P. Wirth, Protection of carboxylic acids as methythiomethyl esters// Tetrahedron Lett., 1978, 28, 731.
- M. А. Саблина, И. П. Ушакова, Г. А. Серебренникова, Липиды с простой эфирной связью в онкологии// Хим.-фарм. Журнал, 1993, 27, 3.
- М. А. Саблина, И. П. Ушакова, Г. А. Серебренникова, Аналоги и антагонисты фактора активации тромбоцитов// Хим.-фарм. Журнал, 1994, 28, 9.
- N. Murahashi, and A. Sasaki, In vivo behavior of liposomes modified with novel galactosyllipid derivative// Biol. Pharm. Bull., 1996, 19, 418.
- S. Figueroa-Perez, and U. Verez-Bencomo, Synthesis of neoglycolipids containing oligosaccharides based on 3,6-branched-a-D-mannopiranosides as the carbohydrate moieties// J. Carbohyd. Chem., 1998,17, 851.
- G. Gastaldi, B. Focher, M. Guerrini, and D. Alonso, Synthesis of octyl p-D-glucopyranoside-aminobutiric (GABA) and aminohydroxybutiric (GABOB) conjugates// J. Carbohyd. Chem., 1994,13, 1009.
- P. Beraud, A. Bourhim, S. Czernecki, and P. Krausz, Modification selective de mono- et di-saccarides non proteges par I’intermeiaire de liaison ester et ether// Tetrahedron Lett., 1989, 30, 325.
- A. Bourhim, S. Czernecki, and P. Krausz, Selective monoesterification of unprotected mono- and disaccarides// J. Carbohyd. Chem., 1993, 12, 853.
- M. Varasi, К. A. M. Walker, and M. L. Maddox, A revised mechanism for the Mitsunobu reaction// J. Organ. Chem., 1987, 52, 4235.
- А. А. Гершкович, и В. К. Кибирев, Химический синтез пептидов, Наукова Думка, Киев, 1992, 144.
- И. Д. Константинова, И. П. Ушакова, и Г. А Серебренникова, Синтез положительно заряженных липидов с простой эфирной связью// Биоорг. химия, 1993, 19, 844.
- О. Ю. Абакумова, Современные методы в биохимии, Медицина, Москва, 1977, 285.
- Т. Mossman, Application of MTT-test in cell toxicity assays// J. Immunol. Methods, 1983, 89, 271
- F. M. Ausubel, and R Breut, in Current protocols in molecular biology, Wiley, New York, 1991, unit 9.4.1.13.
- N. Du^ne|, and P. L. Feigner, // Meth. Enzymol., 1993, 221, 361.
- И. Д. Константинова, И. H. Зайцева, И. П. Ушакова, и Г. А Серебренникова, Синтез катионных липидов алкильного типа с короткоцепными заместителями при С (2) атоме глицеринового скелета// Изв. АН, Сер. хим., 1994, 10, 1826.
- Р. Досон, Д. Эллиот, У. Эллиот, К. Джонс, Справочник биохимика, Мир, Москва, 1991, 383.
- И. Д. Константинова, И. П. Ушакова, и Г. А Серебренникова, Синтез положительно заряженных липидов с простой эфирной связью// Биоорг. химия, 1993, 19, 844.