Синтез и изучение свойств липодипептидов для самоорганизующихся систем доставки функциональных генов тема диссертации и автореферата по ВАК РФ 02.00.10, кандидат химических наук Буданова, Ульяна Александровна

  • Буданова, Ульяна Александровна
  • кандидат химических науккандидат химических наук
  • 2008, Москва
  • Специальность ВАК РФ02.00.10
  • Количество страниц 110
Буданова, Ульяна Александровна. Синтез и изучение свойств липодипептидов для самоорганизующихся систем доставки функциональных генов: дис. кандидат химических наук: 02.00.10 - Биоорганическая химия. Москва. 2008. 110 с.

Оглавление диссертации кандидат химических наук Буданова, Ульяна Александровна

СПИСОК ПРИНЯТЫХ В РАБОТЕ СОКРАЩЕНИЙ.

ВВЕДЕНИЕ.

ЛИТЕРАТУРНЫЙ ОБЗОР.

Компоненты катионных липосом.

Комплекс амфифил/ДНК.

Средства для модификации липосом.

Включение в липосомы векторов активного нацеливания на клетку-мишень.

Контролируемое высвобождение содержимого липосом.

РЕЗУЛЬТАТЫ РАБОТЫ И ИХ ОБСУЖДЕНИЕ.

Синтез липодипептидов на основе эфиров /,-глутаминовой кислоты и /,-глутамина.

Исследование свойств агрегатов, формируемых полученными соединениями в водной среде.

Изучение свойств комплексов катионные липодипептиды/ДНК.

Определение эффективности трансфекции полученных соединений.

ВЫВОДЫ.

ЭКСПЕРИМЕНТАЛЬНАЯ ЧАСТЬ.

Рекомендованный список диссертаций по специальности «Биоорганическая химия», 02.00.10 шифр ВАК

Список литературы диссертационного исследования кандидат химических наук Буданова, Ульяна Александровна, 2008 год

1.Warrens A.N., Heaton Т., Sid S., Lombardi G., Lecheler R.1. Transfected murine cells expressing HLA class II can be used to generate alloreactive human T cell clones // J. of immunological methods. - 1994. -V. 169. № 1. - P. 25-33.

2. Wurm F.M. Production of recombinant protein therapeutics in cultivated mammalian cells // Nature Biotechnol. 2004. - V. 22. - P. 1393-1398.

3. Grimm S. The art and design of genctic screens: mammalian culture cells // Nature Rev. Gen. -2004.-V. 5.-P. 179-189.

4. Raymond L.A., Moshaver A., Tingley W.G., Shalaby I., Huganir R.L. Glutamate receptor ion channel properties predict vulnerability to cytotoxicity in a transfected nonneuronal cell line // Mol. and Cell. Neurosci. 1996. - V. 7. - №. 2. - P. 102-115.

5. Glover D.J., Lipps H.J., Jans D.A. Towards safe, non-viral therapeutic gene expression in humans // Nature Rev. Gen. 2005. - V. 6. - P. 299-310.

6. Breakefield X., Pechan P., Johnston K., Jacoby D. Herpes virus vectors // Stemcell Biology and Gene Therapy / Eds P. Quesenberry et al. San Diego.- 1997.

7. Жданов Р.И., Хусаинов P.С., Иваницкий Г.Р., Борисенко А.С. Невирусные векторы в генной терапии. Новый подход в липофекции // Вопросы биологии, медицинской и фармацевтич. химии.- 2000.- № 1.- С. 10-17.

8. Mahato R.I., Rolland A., Tomlinson Е. Cationic Lipid-Based Gene Delivery Systems: Pharmaceutical Perspectives // Pharm. Res. 1997.- V. 14, №. 7.- P 853-859.

9. Tomlinson E, Rolland A. Controllable gene therapy: Pharmaceutics of non-viral gene delivery systems // J. Control. Rel.- 1996.- V 39: 357-372.

10. Anderson W. Human gene therapy. // Science.- 1992.- V. 256,- P. 808-812.

11. Xiujuan Z., Godbey W. T. Viral vectors for gene delivery in tissue engineering // Adv. drug del. rev. 2006. - V. 58. № 4. P. 515-534.

12. Strauss M., Baringer J. Consepts in Gene Therape. // Berlin.- 1997.

13. Ferber D. Gene therapy: safer and virus-free? И Science. 2001. - V. 294. - P. 1638- 1642.

14. Pietersz G.A., Tang C.-K., Apostolopoulos V. Structure and Design of Polycationic Carriers For Gene Delivery // Mini Rev. in Med. Chem. 2006. - V. 6. № 12. - P. 1285-1298.

15. Жданов Р.И., Куценко Н.Г., Федченко В.И. Невирусные методы переноса генов в генной терапии. //Вопр. мед. химии.- 1997.- Т. 1, С. 3-10.

16. Edelstein, М. L., Abedi, М. R., Wixon, J. and Edelstein, R. M. Gene therapy clinical trials worldwide 1989-2004 an overview // J. Gene Med. 2004. V. 6. P. 597-602.

17. Gascon A.R., Pedraz J. L. Cationic lipids as gene transfer agents: a patent review // Expert Opin. on Tlier. Patents. 2008. - V. 18. - № 5. - P. 515-524.

18. Wasungu L., Hoekstra D. Cationic lipids, lipoplexes and intracellular delivery of genes // J. of Control. Rel. 2006. V. 116. P. 255-264.

19. Lasic D.D., Templeton N.S. Liposomes in gene therapy // Adv. Drug Deliv. Rev. 1996. - V.20. P. 221-266.

20. Audouy S.A.L., de Leij L.F.M.H., Hoekstra D., Molema G. In Vivo Characteristics of Cationic Liposomes as Delivery Vectors for Gene Therapy // Pharm. Res. 2002. - V. 19. № 11. P. 15991605.

21. U'Ren L., Kedl R., Dow S. Vaccination with liposome-DNA complexes elicits enhanced antitumor immunity // Cancer Gene Ther. 2006. V. 13. - P. 1033-1044.

22. Opanasopit P., Nishikawa M., Hashida M. Factors affecting drug and gene delivery: effects of interaction with blood components // Crit. Rev. Ther, Drug Carr. Syst. 2002. - V. 19. - P.191-233.

23. Labat-Moleur F., Steffan A.-M., Brisson C. et al. An electron microscopy study into the mechanism of gene transfer with lipopoliamines // Gene Ther. 1996. - V. 3. - P. 1010-1017.

24. Hoekstra D., Rejman J., Wasungu L., Shi and F., Zuhorn I. Gene delivery by cationic lipids: in and out of ail endosome // Biochem. Soc. Transact. 2007. - V. 35. - P. 68-71.

25. Li S., Huang L. Lipidic supramolecular assemblies for gene transfer // J. Liposome Res. 1996. - V. 6. - P. 589-608.

26. Briane D., Lesage D., Cao A., Coudert R., Lievre N., Salzmann J.L., Taillandier E. Cellular Pathway of Plasmids Vectorized by Cholesterol-based Cationic Liposomes // J. of Histochem. and Cytochem. 2002. - V. 50. - P. 983-992.

27. Gao X. and Huang L. Cytoplasmic expression of a reporter gene by co-delivery of T7-RNA-polymerase and T7-promotor sequence with cationic liposomes // Nucleic Acids Res. 1993. - V. 21. - P. 2867-2872.

28. Baraldo K., Leforestier N., Bureau M., et al. Sphingosine-based liposome as DNA vector for intramuscular gene delivery // Pharm. Res. 2002. - V. 19. - P. 1143-1148.

29. Boussif O., Gaucheron J., Santaella Hanno C., Kolbe V.J., Vierling P. Enhanced in vitro and in vivo cationic lipid-mediated gene delivery with a fluorinated glycerophosphoethanolamine helper lipid//J. Gene Med. 2001. -V. 3. - P. 109-114.

30. Kikuchi I.S., Carmona-Ribeiro A.M. Interactions between DNA and synthetic cationic liposomes // J. Phys. Chem. 2000. - V. 104. - P. 2829-2835.

31. Hasegawa S., Hirashima N, Nakanishi M. Comparative study of transfection efficiency of cationic cholesterols mediated by liposomes-based gene delivery. // Bioorg Med Chem Lett 2002. -V. 12. -№9. P. 1299-1302.

32. Константинова И.Д., Ушакова И.П., Серебренникова Г.А. Синтез положительно заряженных липидов с простой эфирной связью. // Биоорганич. химия. 1993. - Т. 19. - № 8. С. 844-848.

33. Kim A., Lee Е.Н., Choi S.H., Kim С.К. In vitro and in vivo transfection efficiency of a novel ultradeformable cationic liposome // Biomaterials. 2004. - V. 25. - P. 305-313.

34. Sen J., Chaudhuri A. Gene transfer efficacies of novel cationic amphiphiles with alanine, beta-alanine, and serine headgroups: a structure-activity investigation // Bioconjug. Chem. 2005. - V. 16. - P. 903-12.

35. Obika S.i, Yu W., Shimoyama A., Uneda Т., Miyashita K., Doi Т., Imanishi T. Symmetrical cationic triglycerides: an efficient synthesis and application to gene transfer // Bioorg. Med. Chem. -2001.-V. 9.-P. 245-254.

36. Herscovici J., Egron M., Quenot A., et al. Synthesis of new cationic lipids from an unsaturated glycoside scaffold // Org. Lett. 2001. - V. 3. - P. 1893-1896.

37. Tranchant I., Thompson В., Nicolazzi C. et al. Physicochemical optimization of plasmid delivery by cationic lipids // J. Gene Med. 2004. - V. 6. - P. 24-35.

38. Niculescu-Duvaz D., Heyes J., Springer C. Structure-activity relationship in cationic lipid mediated gene transfection // Curr. Med. Chem. 2003. - V. 10. - P. 1233-1261.

39. Martin B.,M.Sainlos M., Aissaoui A. The design of cationic lipids for gene delivery. Current pharmaceutical design. 2005.- V. 11.- P. 375-394.

40. Floch V., Loisel S., Guenin E., et al. Cation substitution in cationic phosphonolipids: a new concept to improve transfection activity and decrease cellular toxicity // J. Med. Chem. 2000. -V. 43.-P. 4617-4628.

41. Heyes J. A., Niculescu-Duvaz D., Cooper R. G., et al. Synthesis of novel cationic lipids: Effect of structural modification on the efficiency of gene transfer // J. Med. Chem. 2002. - V. 49. -P. 99-114.

42. Thomas M., Klibanov A. M. Non-viral gene therapy: polication-mediated DNA delivery // Appl. Microbiol. Biotechnol. 2003. - V. 62. - P. 27-34.

43. Fortunati E., Bout A., Antonia Zanta M., Valerio D., Scarpa M. In vitro and in vivo gene transfer to pulmonary cells mediated by cationic liposomes // BBA. 1996. V. 1306. - P. 55-62.

44. Imaoka T., Date I., Ohmoto T., Yasuda T., Tsuda M. In vivo gene transfer into the adult mammalian central nervous system by continuous injection of plasmid DNA-cationic liposome complex // Brain Res. 1998. V. 780. - P. 119- 128.

45. Ewert K., Ahmad A., Evans H. M., Scmidt H.-W. and Safinya C. R. Efficient Synthesis and Cell-Transfection Properties of a New Multivalent Cationic Lipid for Non-viral Gene Delivery // J. Med. Chem. 2002. - V. 45. - P. 5023-5029.

46. Lleres D., Dauty E., Behr J., Mely Y., Duportail G. DNA condensation by an oxidizable cationic detergent. Interactions with lipid vesicles // Chem. Phys. Lipids. 2001. - V. 111. - P. 59-71.

47. Vigneron M. J.-P., Oudrhirt N., Fauquet M., et al. Guanidinum-cholesterol cationic lipids: Efficient vectors for the transfection of eukaryotic cells // Proc. Natl. Acad. Sci. USA. 1996. - V. 93.-P. 9682-9686.

48. Frederic M., Schennan D., Byk G. Introduction of cyclic guanidines into cationic lipids for non-viral gene delivery // Tetrahedron Lett. 2000. V. 41. P. 675- 679.

49. Perez L. Pinazo A., Vinardell P., et al. Synthesis and biological properties of dicationic arginine-diglycerides //New J. Chem. 2002. - V. 26. - P. 1221-1227.

50. Noguchi A., Furuno T., Kawaura C., Nakanishi M. Membrane fusion plays an important role in gene transfection mediated by cationic liposomes // FEBS Lett. 1998. - 433. - P. 169-173.

51. Heyes J. A., Niculescu-Duvaz D., Cooper R. G., et al. Synthesis of novel cationic lipids: Effect of structural modification on the efficiency of gene transfer // J. Med. Chem. 2002. - V. 49. - P. 99-114.

52. Maitani Y., Igarashi S., Sato M., Hattori Y. Cationic liposome (DC-Chol/DOPE = 1:2) and a modified ethanol injection method to prepare liposomes, increased gene expression // Int. J. of Pharm. 2007. - V. 342 - № 1. - P. 33-39.

53. Read M.L., Singh S. Ahmed Z. A versatile reducible polycation-based system for efficient delivery of a broad range of nucleic acids // Nucleic Acids Res. 2005. V. 33:

54. Wyman B., Nicol F., Zelphati O., Scaria P.V., Plank C., Szoka F.C. Jr. Design, synthesis, and characterization of a cationic peptide that binds to nucleic acids and perméabilités bilayers // Biochem. 1997. - V. 36. - 3008-3017.

55. Smith L.C., Duguid J., Wadhwa M.S., Logan M.J., Tung C.H., Edwards V., Sparrow J. T. Synthetic peptide based DNA complexes for non-viral gene delivery // Adv. Drug Deliv. Rev. -1998. V. 30.-P. 115-131.

56. Kim H.H., Lee W.S., Yang J.M., Shin S. Basic peptide system for efficient delivery of foreign genes//BBA. -2003. V. 1640.-P. 129- 136.

57. K. Rittner, A. Benavente, A. Bompard-Sorlet, F. Heitz, G. Divita, R. Brasseur, E. Jacobs, New basic membranedestabilizing peptides for plasmid-based gene delivery in vitro and in vivo II Molec. Ther. 2002. - V. 5. - P. 104- 114.

58. Tokunaga M., Hazemoto N., Yotsuyanagi T. Effect of oligopeptides on gene expression: comparison of DNA/peptide and DNA/peptide/Iiposome complexes // Int. J. Pharm. 2004. - V. 269.-P. 71-80.

59. Ewert, K. K., Ahmad, A., Evans, H. M., Safinya, C. R. Cationic lipid-DNA complexes for non-viral gene therapy: relating supramolecular structures to cellular pathways // Expert Opin. Biol. Ther. 2005. - V. 5.-P. 33-53.

60. Miguel M.G., Pais A., Dias R.S., Leal C., Rosa M., Lindman B. DNA-cationic amphiphile interactions // Colloids and Surfaces A: Physicochem. Eng. Aspects. 2003. - V. 228. - P. 43-55.

61. Chesnoy S., Huang L. Structure and function of lipid-DNA complexes for gene delivery // Annu. Rev. Biophys. Biomol. Struct. 2000. V. 29. P. 27-47.

62. Dunlap D., Maggi A., Soria R., Monaco L. Nanoscopic structure of DNA condensed for gene delivery//Nucleic Acids Res. 1997. -V. 12.- P. 3095-3101.

63. Thomson N. H., Collin I., Davies M.C. et al. Atomic Force Microscopy of Cationic Liposomes II Langmuir. 2000. V. 16. P. 4813-4818.

64. Elouahabi A., Ruysschaert J. Formation and intracellular trafficking of lipoplexes and polyplexes // Molecular therapy.- 2005. V. 11.- №3.- P. 336-347.

65. Zuliorn I. S., Visser W. II., Bakowsky U. et al. Interference of serum with lipoplex-cell interaction: modulation of intracellular processing // Biochimica et Biophysica Acta. 2002. - V. 1560. - P. 25-36.

66. Choosakoonkriang S., Wiethoff C. M., Anchordoquy T. J., et al. Infrared Spectroscopic Characterization of the Interaction of Cationic Lipids with Plasmid DNA // J. Biol. Chem. 2001. -V. 276.-№. 11.-P. 8037-8043.

67. Pohle W., Selle C. Gauger D. R. FTIR spectroscopic characterization of a cationic lipid-DNA complex and its components // Phys. Chem. Chem. Phys. 2000. - V. 2. - P. 4642-4650.

68. Farago O., Ewert K., Ahmad A., Evans H.M., Grunbech-Jensen N., Safinya C.R. Transitions between Distinct Compaction Regimes in Complexes of Multivalent Cationic Lipids and DNA // Biophys. J. 2008. - V. 95. - P. 836-846.

69. Li S., Huang L. In vivo gene transfer via intravenous administration of cationic lipid-protamine-DNA (LPD) complexes // Gene Ther.- 1997,- V. 4.- P. 891-900.

70. Plane C., Mechtler K., Szoka F. C., et al. Activation of the complement system by synthetic DNA complexes: A potential barrier for intravenous gene delivery // Hum. Gene Ther.- 1996,- V. 7,- P. 1437-1446.

71. Andresen T.L.,. Jensen S.S, Jorgensen K. Advanced strategies in liposomal cancer therapy: Problems and prospects of active and tumor specific drug release // Progress in Lipid Res. 2005. -V. 44. - P. 68-97.

72. Kostarelos K. Rational design and engineering of delivery systems for therapeutics: biomedical exercises in colloid and surface science // Adv. in Colloid and Interface Sci. 2003. - V. 106. - P. 147-168.

73. Vlerken L.E., Vyas T.K., Amiji M.M. Poly(ethylene glycol)-modified nanocarriers for tumor-targeted and intracellular delivery // Pharm. Res. 2007. - V. 24. - № 8. P. 1405-1414.

74. Heyes J., Hall K., Tailor V., Lenz R., MacLachlan I. Synthesis and characterization of novel poly(ethylene glycol)-lipid conjugates suitable for use in drug delivery // J. of Controll. Release. -2006.-V. 112. P. 280-290.

75. Hashizaki K., Taguchi H., Sakai H., Abe M., Saito Y., Ogawa N. Carboxyfluorescein leakage from poly(ethylene glycol)-grafted liposomes induced by the interaction with serum II Chem. Pharm. Bull. (Tokyo). 2006. V. 54. - № 1. - P. 80-4.

76. Judge A.D., McClintock K. Shaw J.R., MacLachlan I. Hypersensitivity and loss of disease site targeting caused by antibody responses to pegylated liposomes // Mol. Ther. 2006. - V. 13. - P. 328-337.

77. Maruyama K., Okuizumi S., Ishida O. Phosphatidyl polyglycerols prolong liposomes circulation in vivo. Int. J. of Pharmaceutics. 1994. V. - 111. - P. 103-107.

78. Gregoriadis, G., McCormack, B., Wang, Z., and Lifely, R. Polysialic acids: potential in drug delivery // FEBS Lett. 1993. - V. 315. - P. 271-276.

79. Rooijen. N., Bakekr J., Sander. A. Transient suppression of macrophage function by liposomes-encapsulated drugs // Trends Biotechnol. 1997. - V. 15. - P. 178-185.

80. Sapra P, Allen T.M. Ligand-target liposomal anticancer drugs // Prog. Lipid. Res. 2003. - V. 42. - P. 439-62.

81. Cavalli S., Tipton A.R., Overhand M., Kros A. The chemical modification of liposome surfaces via a copper-mediated 3 + 2. azide-alkyne cycloaddition monitored by a colorimetric assay // Chem. Commun. 2006. - P. 3193-3195.

82. Kok R.J., Schraa A. J., Bos E.J., et al. Preparation and Functional Evolution of RGD-Modified Proteins as Integrin Directed Therapeutics // Bioconjugate Chem. 2002.- V. 13.- P. 128-135.

83. Gabizon A., Shmeeda H., Horowitz A.T., Zalipsky S. Tumor cell targeting of liposome-entrapped drugs with phospholipid-anchored folic acid-PEG conjugates // Adv. Drug Del. Rev. -2004.-V. 56-P. 1177- 1192

84. Saul J. M., Annapragada A., Natarajan J. V., Bellamkonda Ravi V. Controlled targeting of liposomal doxorubicin via the folate receptor in vitro II J. of Control. Release. 2003. - V. 92. - P. 49-67.

85. Leamon C.P., Cooper S.R., Hardee G.E. Folate-liposome-mediated antisense oligodeoxynucleotide targeting to cancer cells: Evaluation in vitro and in vivo 11 Bioconjugate Chem. 2003. - V. 14. - P. 738-47.

86. Pan X.Q., Wang H.Q., Lee R.J. Antitumor Activity of Folate Receptor-Targeted Liposomal Doxorubicin in a KB Oral Carcinoma Murine Xenograft Model // Pharm. Res. 2003. - V. 20. - P. 417-22.

87. Reddy J.A., Abburi C., Hofland H. Howard S.J., Vlahov I., Wils P., Leamon C.P. Folate-targeted, cationic liposome-mediated gene transfer into disseminated peritoneal tumors // Gene Ther. 2002. - V. 9. - P. 1542-1550.

88. Gabizon A., Shmeeda H., Horowitz A.T., Zalipsky S. Liposomes as targeted drug delivery systems in the treatment of breast cancer // Adv. Drug Del. Rev. 2004. - V. 56. - P. 1177-92.

89. Faivre V., de Lourdes Costa M., Boullanger P., Baszkin A., Rosilio V. Specific interaction of lectins with liposomes and monolayers bearing neoglycolipids // Chem. and Phys. of Lipids. 2003. - V. 125. - 147-159

90. Hisayasu S., Miyauchi M., Akiyama K., Gotoh T., Satoh S. and Shimada T. In vivo targeted gene transfer into liver cells mediated by a novel galactosyl-D-lysine/D-serine copolymer // Gene Ther. 1999. - V. 6. - №. 4. - P. 689-693.

91. Walton C.M., Wu C.H., Wu G.Y. A DNA delivery system containing listeriolysin O results in enhanced hepatocyte-directed gene expression // World J. of Gastroenterology. 1999. - V. 5. № 6. V. 465-469.

92. Wang S., Deng Y., Xu H., Wu H., Qiu Y., Chen D. Synthesis of a novel galactosylated lipid and its application to the hepatocyte-selective targeting of liposomal doxorubicin // Eur. J. of Pharm, and Biopharmaceutics. 2006. - V. 62. - P. 32-38.

93. Zhu J., Yan F., Guo Z., Marchant R.E. Surface modification of liposomes by saccharides: Vesicle size and stability of lactosyl liposomes studied by photon correlation spectroscopy // J. of Colloid and Interface Sei. 2005. - V. 289. - P. 542-550.

94. Tang C.K., Lodding J., Minigo G. Pouniotis D.S., Plebanski M., Scholzen A., McKenzie I., Pietersz G.A., Apostolopoulos V. Mannan-mediated gene delivery for canccr immunotherapy // Immunology. 2007. - V. 120. - P. 325-335.

95. Bhattacharya S. Bajaj A. Recent advances in lipid molecular design // Curr. Opin. in Chem.l Biol. 2005. - V. 9. P. 647-655.

96. Drummond D.C., Zignani M. Leroux J. Current status of pH-sensitive liposomes in drug delivery // Prog. Lipid Res. 2000. - V. 39. - P. 409-60.

97. Sakaguchi N., Kojima C., Harada A., Koiwai K., Emi N., Kono K. Effect of Transferrin As a Ligand of pH-Sensitive Fusogenic Liposomc-Lipoplex Hybrid Complexes // Bioconjug. Chem. -2008. -V. 19. P. 1588-1595.

98. Guo X., MacKay J.A., Szoka F.C. Mechanism of pH-Triggered Collapse of Phosphatidylethanolamine Liposomes Stabilized by an Ortho Ester Polyethyleneglycol // Lipid Biophys. J. 2003. - V. 84. - P. 1784-95.

99. Spratt T., Bondurant B., O'Brien D.F. Rapid release of liposomal contents upon photo initiated destabilization with UV exposure // BBA. 2003. - V. 1611. - P. 35-43.

100. Drummond D.C,. Noble C. O , Hayes M. E., Park J.W., Kirpotin D.B. Pharmacokinetics and in vivo drug release rates in liposomal nanocarrier development // J.of Pharm. Sei. 2008. - V. 97. -№11. - P. 4696 - 4740.

101. Bisby RH, Mead C, Morgan CG. Active-uptake of drugs into photosensitive liposomes and rapid release on UV photolysis. // Photochem. Photobiol. 2000. - V. 72. - P. 57-61.

102. Meers P. Enzyme-activated targeting of liposomes // Adv. Drug. Del. Rev. 2001. - V. 53. -№ 3. P. 265-72.

103. Foged C., Nielsen H.M., Frokjae S. Phospholipase A2 Sensitive Liposomes for Delivery of Small Interfering RNA (siRNA) // J. of Liposome Res. 2007. - V. 17. - P. 191 - 196.

104. Millan J.8L., Fishman W.H. Biology of human alkaline phosphatases with special reference to cancer// Crit. Rev. Clin. Lab. Sci. 1995. - V. 32. - P. 1-39.

105. Себякин Ю.Л. Буданова У.А. «рН-Чувствительные катионные липопептиды для создания транспортных систем медицинского назначения» // Биоорган, химия. 2006. - Т. 32. №5. -С. 453-458.

106. Себякин Ю.Л., Федякова И.Л, Рунова Т.Л. Синтез алифатических производных L-серина//Биоорган. химия.-1994.-Т.20.-№10.-С. 1101-1106.

107. Позднев В.Ф., Подгорнова H. Н., Зенцова Е. К., Ауконе Г. И., Калей У. О. // Химия природных соединений.- 1979.- № 4,- С. 543-548.

108. Позднев В.Ф. N", N', Л;; -трп-/»/;е?/»-бутилоксипирокарбониларгинин новое производное аргинина для пептидного синтеза// Биоорган, химия.- 1986.- Т. 12.- № 8.- С. 1013-1022.

109. Anderson G.W., Zimmerman J.E. Callahan F.M. The use of esters of vV-hydroxysuccinimide in peptide synthesis // J. Amer. Chem. Soc. 1964. - V. 86. - P. 1839-1842.

110. Себякин Ю.Л., Буданова У.А., Гурьева Л.Ю. «Структурно-функциональное разнообразие искусственных мембран на основе катионных липопептидов» // Биологии, мембраны. 2007. - Т. 24. №3. - С. 273-279.

111. Yurii L. Sebyakin, Uliyana A. Budanova and Lyudmila Yu. Gur'eva «Self-organising aggregates of lipodipeptides in aqueous medium and their complexes with DNA» // Mendeleev Comm. 2007. -V. 17. - P. 188-189.

112. Tanhuanpaa K., Virtanen J., Somerharju P. Fluorescence imaging of pyrene-labeled lipids in living cells // BBA. 2000. - V. 1497. - № 3. - P. 308-320.

113. Boissonnas R. A., Guttmann St., Jaquenoud P.-A., Waller J.-P., Cherbuliez E., Stoll A. Une nouvelle synthèse de l'oxytocine // Helv. Chim. Acta. 1955. - V. 38. - P. 1491-1501.

Обратите внимание, представленные выше научные тексты размещены для ознакомления и получены посредством распознавания оригинальных текстов диссертаций (OCR). В связи с чем, в них могут содержаться ошибки, связанные с несовершенством алгоритмов распознавания. В PDF файлах диссертаций и авторефератов, которые мы доставляем, подобных ошибок нет.