Дизайн, синтез и свойства лактозосодержащих неогликолипидов как компонентов адресных систем доставки биологически активных соединений

1. Fuente J., Penades S. Glyconanoparticles: Types, synthesis and applications in glycoscience, biomedicine and material science // Biochim Biophys Acta. — 2006. — 1760. — P. 636−651.

2. Goldstein I., Hugues R., Monsigny M., Osawa Т., Sharon N. What should be called a lectin? // Nature. — 1980. — 285. — P. 66.

3. Lindhorst T. Artificial multivalent sugar ligands to understand and manipulate carbohydrate-protein interactions // Top. Curr. Chem. — 2002. — 218. — P. 201−235.

4. Monsigny M., Roche A., Midoux P., Mayer R. Glycoconjugates as carriers for specific delivery of therapeutic drugs and genes // Adv Drug Del Rev. — 1994. —14. — P. 1−24.

5. Ashwell G., Harford J., Harford J. Carbohydrate-specific receptors on the Hver // Rev.Biochem. 1982. — 51. — P. 531−554.

6. Roy R., Tropper F., Morrison Т., Boratynski J. Syntheses and transformations of glycohydrolase substrates into protein conjugates based on Michael additions // J. Chem. Soc., Chem. Commun. — 1991. — P. 536−537.

7. Paz J.L., Ojeda R., Barrientes A.G., Penades S., Martin-Lomas M. Synthesis of a Ley neoglycoconjugate and Ley-functionalized gold glyconanoparticles // Tetr. Asym. — 2005. — 16.P. 149−158.

8. Rojo J., Diaz V., Fuente J. M, Segura I., Barrientes A.G., Riese H.H., Bernad A., Penades S. Gold glyconanoparticles as new tools in antiadhesive therapy // Chem. Bio. Chem. 2004. — 5(3). — P.291−297.

9. Fuente J., Fandel M., Berry C., Riehle M., Cronin L., Aitchison G., Curtis A. Quantum dots protected with tiopronin: a new fluorescent system for cell-biology studies // Chem. Bio. Chem. — 2005. — 6. — P. 989−991.

10. Sutherland A. Quantum dots as luminescent probes in biological systems // Curr. Opin. Solid State Mater. Sci. — 2002. — 6. — P. 365−370.

11. Robinson A., Fang J., Chou P., Liao K., Chu R., Lee S. Probing lectin and sperm with carbohydrate-modified quantum dots // Chem. Bio. Chem. — 2005. — 6. — P. 1899−1905.

12. Huwiler A., Kolter Т., Pteilschifter J., Sandhoft K. Phisiology and pathophysiology of sphingolipid metabolism and signaling // Biochim. Biophi. Acta. — 2000: —1485. — P. 63−99.

13. Alexander C., Rietschel E. Bacterial lipopolysaccharides and innate immunity // J. Endotoxin Res. — 2001. — 7. — P. 167−202.

14. Tamai R., Asai Y., Hashimoto M., Fukase K., Kusumoto S., Ishida H., Kiso M., Ogawa T. Cell activation by monosaccharide lipid A analogues utilizing Toll-like receptor 4 // Immunology.2003. —110. — P. 66−72.

15. Baldridge J., McGowan P., Evans J., Cluff C., Mossman S., Johnson D., Persing D. Taking a Toll on human disease: Toll-like receptor 4 agonists as vaccine adjuvants and monotherapeutic agents // Expert Opin. Biol Ther. — 2004. — 4. — P. 1129−1138.

16. Jensen K.J., Brask J. Carbohydrates in Peptide and Protein Design // Inc. Biopolymers (Pept Sci). — 2005. — 80. — P. 747−761.

17. Fuente J., Berry C., Tat peptide as an efficient molecule to translocate gold nanoparticles into the cell nucleus // Bioconj. Chem. — 2005. —16. — P. 1176−1180.

18. Marikanos S., Anderson M., Ryan J., Martin L., Feldheim P. Encapsulation, permeability, and cellular uptake characteristics of hollow nanometer-sized conductive polymer capsules // J. Phys. Chem. — 2001. —105. — P. 8872−8876.

19. Liu Y., Mounkes L.C., Liggitt H.D., Brown C.S., Solodin I., Heath T.D., Debs R.J. Factors influencing the efficiency of cationic liposome-mediated intravenous gene delivery // Nat. Biotechnol.1997. —15. — P. 167−173.

20. Rosenthal S., Tomlinson I., Adkins E., Schroeter S., Adams S., Swafford L., McBride J., Wang Y., DeFelice L., Blakely R. Targeting cell surface receptors with ligand-conjugated nanocrystals // J. Am. Chem. Soc. — 2002. —124. — P. 4586−4594.

21. Westenhoff S., Kotou N. Quantum dot on a rope // J. Am. Chem. Soc. — 2002. — 124. — P.2448−2449.

22. Potapova I., Mrak R., Preht S., Zentel R., Basche T., Mews A., Semiconductor nanocrystals with multifunctional polymer ligands // J. Am. Chem. Soc. — 2003. —125. — P. 320−321.

23. Asian К., Zhang J., Lakowicz J., Geddes C. Saccharide sensing using gold and silver nanoparticles—A review II J. Fluoresc. — 2004. —14. — P. 391−400.

24. Chen Y., Chen S., Chien Y., Chang Y., Liao H., Chang C., Jan M., Wang K., Lin C., Carbohydrate-encapsulated gold nanoparticles for rapid target-protein indentification and bindingepitope mapping // Chem. Bio. Chem. — 2005. — 6. — P. 1169−1173.

25. Игнатов В. В. Углеводузнающие белки лектины // Соросовский образовательный журнал. — 1997. — 2. — Р. 14−20.

26. Lehmann F., Tiralongob Е., Tiralongo J. Sialic acid-specific lectins: occurrence, specificity and function // Cell. Mol. Life Sci. 2006. — 63. — P. 1331−1354.

27. Brito-Arias M. Synthesis and Characterization of Glycosides. Springer, US — 2007. — 352 p.

28. Daniel K., Fu-Tong Liu. Regulation of cellular homeostasis by galectins // Glycoconjugate Journal. — 2004. —19. — P. 507−515.

29. Leffler H., Carlsson S., Hedlund M., Qian Y., Poirier F. Introduction to galectins // Glycoconjugate Journal. — 2004. —19. — P. 433¹⁴⁰.

30. Grancelli A., Morros A., Domenech O., Vazquez J., Vinas M., Hernandez-Borrell J. Interaction of 6-fluoroquinolones with dipalmitoylphosphatidylcholine monolayers and liposomes // Langmuir. — 2002. —18. — P. 9177−9182.

31. Niidome Т., Hung L. Gene Therapy Progress and Prospects: Nonviral Vectors // Gene Therapy. — 2002. — 9(24). — P. 1647−1652.

32. Gref R., Domb A., Quellec P., Blunk Т., Muller R. H., Verbavatz J. M., et al. The controlled intravenous delivery of drugs using PEG-coated sterically stabilized nanospheres // Adv. Drug Deliv. Rev. — 1999. —16. — P. 215−233.

33. Owens D. E., Peppas N. A. Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles // Int. J. Pharm. — 2006. — 307. — P. 93—102.

34. Hamidi M., Azadi A., Rafiei P. Pharmacokinetic consequences of pegylation I I Drug Deliv. — 2006. —13. — P. 399−409.

35. Immordino M. L., Brusa P., Arpicco S., et al. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing docetaxel // J. Control. Release. — 2003. — 91. — P. 29−417.

36. Gaucheron J., Santaella C., Verlung P. In Vitro Gene Transfer with a novel galactosylated spermine bolaamphiphile // Bioconjugate Chem. — 2001. —12. — P. 569−575.

37. Barthelemy P., Tomao V., Selb J., Chaudier Y., Pucci B. Fluorocarbon Hydrocarbon nonionic surfactants mixtures: A study of their miscibility // Langmuir. — 2002. —18. — P. 25 572 563.

38. Perrino S., Contino-Pepin A., Jasseron S., Rapp M., Maurizis J., Pucci B. Design, synthesis and preliminary biological evaluations of novel amphiphilic drug carriers // Bioorg Med Chem Lett.2006. —16. — P. Ill 1−1114.

39. Engel A., Chatterjee S.K., Al-Arifi A., Nulin P. Influence of spacer length on the agglutination of glycolipid-incorporated liposomes by ConA as model membrane // J. Pharm. Sci.2003. — 92(11). — P. 2229−2235.

40. Dizhe E., Akifiev B., Missul B., Orlov S., Kidgotko O., Sukonina V. Receptor-mediated transfer of DNA: galactosylated poIy-L-lysine complexes into mammalian cells in vitro and in vivo // Biochemistry. — 2001. — 66. — P. 55−61.

41. Midoux P., Mendes C., Legrand A., Raimond J., Mayer R., Monsigny M. Specific gene transfer mediated by lactosylated poly-L-lysine into hepatoma cells // Nucleic Acids Res. — 1993.21. — P. 871−878.

42. Diebold S., Kursa M., Wagner E., Cotten M., Zenke M. Mannose polyethylenimine conjugates for targeted DNA delivery into dendritic cells // J. Biol. Chem. — 1999. — 274. — P. 19 087−19 094.

43. Bettinger T., Remy J., Erbacher P. Size reduction of galactosylated PEI/DNA complexes improves lectin-mediated gene transfer into hepatocytes // Bioconjug. Chem. — 1999. — 10. — P. 558−561.

44. Gotoha Y., Niimib S., Hayakawab T., Miyashita T. Preparation of lactose-silk fibroin conjugates and their application as a scaffold for hepatocyte attachment // Biomaterials. — 2004. — 25. — P. 1131−1140.

45. Angenendt P. Progress in protein and antibody microarray technology // Drug. Discov. Today. — 2005. —10. — P. 503−511.

46. Kersten B., Wanker E.E., Hoheisel J.D., Angenendt P. Multiplex approaches in protein microarray technology // Expert. Rev. Proteomics. — 2005. — 2. — P. 499−510.

47. De Paz J.L., Seeberger P.H. Recent advances in carbohydrate microarrays // Osar. Comb. Sc. — 2006. — 25. — P. 1027−1032.

48. Uzawa H., Ito H., Izumi M., Tokuhisa H., Taguchi K., Minoura N. Synthesis of polyanionic glycopolymers for the facile assembly of glycosyl arrays // Tetrahedr. — 2005. — 61. — P. 58 955 905.

49. Disney M.D., Seeberger P.H. The use of carbohydrate microarrays to study carbohydrate-cell interactions and to detect pathogens // Chem. Biol. — 2004. —11. — P. 1701−1707.

50. Chen J.R., Miao Y.Q., He N.Y., Wu X.H., Li S.J. Nanotechnology «and biosensors // Biotechnology Advances. — 2004. — 22. — P. 505−518.

51. Jeng E.S., Moll A.E., Roy A.C., Gastala J.B., Strano M.S. Detection of DNA hybridization using the near-infrared band-gap fluorescence of single-walled carbon nanotubes // Nano. Letters.2006. — 6. — P. 371−375.

52. Gu L.R., Elkin T., Jiang X.P., Li H.P., Lin Y., Qu L.W., Tzeng TR.J., Joseph R, Sun Y.P. Single-walled carbon nanotubes displaying multivalent ligands for capturing pathogens // Chem. Commun. — 2005. — P. 874−876.

53. Wang H.F., Gu L.R., Lin Y., Lu F.S., Meziani M.J., Luo PG.J., Wang W., Cao L., Sun Y.P. Unique aggregation of anthrax (Bacillus anthracis) spores by sugar-coated single-walled carbon nanotubes II J. Am. Chem. Soc. — 2006. —128. — P. 13 364−13 365.

54. Disney M.D., Zheng J., Swager T.M., Seeberger P.H. Detection of bacteria with carbohydrate-functionalized fluorescent polymers // J. Am. Chem. Soc. — 2004. — 126. — P. 13 343−13 346.

55. Baek M.G., Stevens R.C., Charych D.H. Design and synthesis of novel glycopolythiophene assemblies for colorimetric detection of influenza virus and E. coli // Bioconjug. Chem. — 2000. — 11. — P. 777−788.

56. Xue C.H., Jog S.P., Murthy P., Liu H.Y. Synthesis of highly water-soluble fluorescent conjugated glycopoly (p-phenylene)s for lectin and Escherichia coli // Biomacromolec. — 2006. — 7,—P. 2470−2474.

57. Reichert A., Nagy J.O., Spevak W., Charych D. Polydiacetylene liposomes functionalized with sialic acid bind and colorimetrically detect influenza virus // J. Am. Chem. Soc. — 1995. — 117. — P. 829−830.

58. Johannes F.G., Vliegenthart J. Carbohydrate based vaccines // FEBS Letter. — 2006. — 580(12). — P. 2945−2950.

59. Francis Jr.T., Tillett W.S. Cutaneous reactions in pneumonia. The development of antibodies following the intradermal injection of type-specific polysaccharide // J. Exp. Med. — 1999. — 52.P. 573−585.

60. Penades S., de la Fuentel J., Barrientos A., Clavell C., Martinez-Evilal O., Alcantara D. Nanomaterials for Application in Medicine and Biology. Springer. — 2008. — 204p.

61. Soussan E., Mille C., Blanzat M., Bordat P., Rico-Lattes I. Sugar-derived tricatenar catanionic surfactant: synthesis, self-assembly properties, and hydrophilic probe encapsulation by vesicles // Langmiur. — 2008. — 24(6). — P. 2326−2330.

62. Vautrin C., Dubois M., Zemb T., Schmolzer S., Hoffmann H., Gradzielski M. Colloids Surf. Chain melting in swollen catanionic bilayers // Colloids Surf. A Physicochem. Eng. Asp. — 2003.217. — P. 165−170.

63. 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 Colloid Interface Sci. — 2005. — 289. — P. 542−550.

64. Tomita K., Fukuda M., Kawasaki K. Mechanism of arbutin inhibitory effect on melanogenesis and effect on the human skin with cosmetic use // Fragrance J. — 1990. — 6. — P. 72−77.

65. Fiume L., Di Stefano G., Busi C., Mattioli A., Bonino F., Torrani-Cerenzia M. Liver targeting of antiviral nucleoside analogues through the asialoglycoprotein receptor // J. Viral.Hepat. — 1997. — 4. — P. 363−370.

66. Rochea A., Fajacb I., Grosseb S., Frisona N., Rondaninoa C., Mayera R., Monsigny M. Glycofection: facilitated gene transfer by cationic glycopolymers // Cell. Mol. Life Sci. — 2003. — 60. — P. 288−297.

67. Frese J., Wu C., Wu G. Targeting of genes to the liver with glycoprotein carriers // Adv. Drug Delivery Rev. — 1994. —14. — P. 137−152.

68. Leeuwenburgh M., Marel G., Overkleeft H. Olefin metathesis in glycobiology: new routes towards diverse neoglycoconjugates // Cur Opin Chem Bio. — 2003. — 7. — P. 757−765.

69. Dominique R., Liu B., Das S., Roy R. Synthesis of «molecular asterisks» via sequential cross-metathesis, Sonogashira and cyclotrimerization reactions // Synthesis. — 2000. — P: 862−868.

70. Fiume L., Busi C., Preti P., Spinosa G. Conjugate of ara-AMP with lactosaminated serum albumin: a study on their immunogenicity in mouse and rat // Cancer Drug Deliv. — 1987. — 4. — P. 145−150.

71. Huwe C., Woltering T., Jiricek J., Weitz-Schmidt G., Wong C. Design, synthesis and biological evaluation of aryl-substituted sialyl Lewis X mimetics prepared via cross-metathesis of C-fucopeptides // Bioorg. Med. Chem. — 1999. — 7. — P. 773−788.

72. Duncan R. The dawning era of polymer therapeutics //Nut. Rev. Drug. Discov. — 2003.2. — P. 347−360.

73. Peppas N. Hydrogels and drug delivery // Curr. Opin. Colloid. Interface Sci. — 1997. — 2.P. 531−537.

74. Wolthius van Dijk W., Hoogeboom J., Steenbergen van M., Tsang S., Hennink W. Degradation and release behavior of dextran-based hydrogels // Macromolec. — 1997. — 30. — P. 4639−45.

75. Zhou W., Kurth M., Hsieh Y., Krochta J. Synthesis and thermal properties of a novel lactose-containing poly (Nisopropylacrylamide-co-acrylamidolactamine) hydrogel // J. Polym. Sci, Part A: Polym. Chem. — 1999. —37. — P. 1393−402.

76. Shantha K., Harding D. Synthesis, characterisation and evaluation of polyflactose acrylate-N-vinyl-2-pyrrolidinone. hydrogels for drug delivery // Eur Pol J. — 2003. — 39. — P. 63−68.

77. Osaki F., Kanamori T., Sando S., Sera T., Aoyama Y., A quantum dot conjugated sugar ball and its cellular uptake. On the size effects of endocytosis in the subviral region // J. Am. Chem. Soc.2004. —126. — P. 6520−6521.

78. Gaucheron J., Santaella C., Vierling P. In vitro gene transfer with a novel galactosylated spermine bolaamphiphile //Bioconjug. Chem. — 2001. —12. — P. 569−575.

79. Erbacher P., Roche A., Monsigny M., Midoux P. The reduction of the positive charges of polylysine by partial gluconoylation increases the transfection efficiency of DNA/polylysine complexes // Biochim. Biophys. Acta. — 1997. —1324. — P. 27−36.

80. Aoyama Y. Macrocyclic glycoclusters. From amphiphile through nanoparticles to glycoviruses // Chem. Eur. J. — 2004. —10. — P. 588−593.

81. Aoyama Y., Kanamori T., Nakai T., Sasaki T., Horiuchi S., Sando S., Niidome T. Artificial viruses and their application to gene delivery. Sizecontrolled gene coating with glycocluster nanoparticles // J. Am. Chem. Soc. — 2003. —125. — P. 3455−3457.

82. Boutin V., Legrand A., Mayer R., Nachtigal M., Monsigny M., Midoux P. Glycofection: the ubiquitous roles of sugar bound on glycoplexes // Drug Delivery. — 1999. — 6. — P. 45−50.

83. Smedt S., Demeester J., Hennink W. Cationic polymer based gene delivery systems // Pharm. Res. — 2000. — 77. — P. 113−126.

84. Mornet S., Vasseur S., Grasset F., Duguet E., Magnetic nanoparticles design for medical diagnosis and therapy // J. Mater. Chem. — 2004. —14. — P. 2161−2175.

85. Pankhurst Q., Connolly J., Jones S., Dobson J., Applications of magnetic nanoparticles in biomedicine // D. Appl. Phys. — 2003 .—36. — P. 167−181.

86. Tartaj P., Morales M., Veintemillas-Verdaguer S., Gonzalez-Carreno T., Serna C. The preparation of magnetic nanoparticles for applications in biomedicine // J. Phys. D. Appl. Phys. — 2003. — 36. — P. 182−197.

87. Lopez-Cartes C., Rojas T., Litran R., Martinez-Martinez D., Fuente J., Penades S., Fernandez A. Gold nanoparticles with different capping systems: an electronic and structural XAS analysis II J. Phys. Chem. — 2005. —109. — P. 8761−8766.

88. Kolb H. C., Finn M. G., Sharpless K. B. Click chemistry: diverse chemical function from a few good reactions II Angew. Chem. Int. Ed. Engl. — 2001. — 40. — P. 2004;2021.

89. Kolb H. C., Sharpless K. B. The growing impact of click chemistry on drug discovery // DrugDiscov. Today. — 2003. — 8. —P. 1128−1137.

90. Bock V. D., Hiemstra H., Maarseveen J. H.-V. Cul-Catalyzed alkyne-azide «click» cycloadditions from a mechanistic and synthetic perspective II Eur. J. Org. Chem. — 2006. — P. 51−68.

91. Chinchilla R., Najera C. The sonogashira reaction: a booming methodology in synthetic organic chemistry // Chem. Rev. — 2007. —107. — P. 874−922.

92. Home W. S., Stout C. D., Ghadiri M. R. A heterocyclic polymer nanotube //J. Am. Chem. Soc. — 2003. —125. — P. 9372−9376.

93. Malkoch M., Schleicher K., Drockenmuller E., Hawker C.J., Russell T.P., Wu P., Fokin V.V. Structurally diverse dendritic libraries: A highly efficient functionalization approach using Click chemistry II Macromolecul. — 2005. — 38. — P. 3663−3678.

94. Giguere D., Patnam R., Bellefleur M.A., St-Pierre C., Sato S., Roy R. For recent references on the biological activity of 1,2,3-triazoles // Chem. Commun. — 2006. — P. 2379−2381.

95. Hotha S., Kashyap S. «Click chemistry» inspired synthesis of pseudo-oligosaccharides and amino acid glycoconjugates II J. Org. Chem. — 2006. — 71. — P. 364−367.

96. Hassane S. F., Frisch B., Schuber F. Targeted liposomes: convenient coupling of ligands to preformed vesicles using «click chemistry» // Bioconjugate Chem. — 2006. —17. — P. 849−854.

97. 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.

98. Cao S., Tropper D., Roy R. Stereoselective phase transfer catalyzed syntheses of glycosyloxysuccinimides and their transformations into glycoprobes // Tetrahedr. — 2000. — 51.P. 6679−6686.

99. Dahnren J., Freid Т., Magnusson G., Noori G. Synthesys of some divalent Oand S-Glycosides of galabiose and globotriose // Carbohydr. Res. — 1982. — 111. —P. 1−4.

100. Гурьева Л. Ю., Северьянова А. А., Себякин Ю. Л. Активные производные £>-галактозы и /)-лактозы в синтезе неогликоконъюгатов // Вестник МИТХТ. — 2006. — 1 (4). — С. 33−38.

101. Reineke Т.М., Davis М.Е. Carbohydrate Size and Its Distance from Charge Centers Bioconjugate Chemistry // Bioconjugate Chem. — 2003. —14. — P. 247−254.

102. Heyes J., Niculescu-Duvaz D., Cooper R.G., Springer C.J. Synthesis of novel cationic lipids: effect of structural modification on the efficiency of gene transfer // J. Med. Chem. — 2002. — 45.P. 99−114.

103. Hyvonen Z., Ruponen M., Ronkko S., Suhonen P., Urtti A. Extracellular and intracellular factors influencing gene transfection mediated by 1,4-dihydropyridine amphiphiles // Eur. J. Pharm. Sci. — 2002. —15. — P. 449−460.

104. Regelin A.E., Fankhaenel S., Gurtesch L., Prinz C., von Kiedrowski G., Massing U. Biophysical and lipofection studies of DOTAP analogs // Biochim. Biophys. Acta. — 2000. — 1464(1). — P. 151−164.

105. Ren Т., Zhang G., Song Y.K., Liu D. Synthesis and characterization of aromatic ring-based cationic lipids for gene delivery in vitro and in vivo II J. Drug Target. — 1999. — 7. — P. 285−292.

106. Guan L.P., Zhao D. H, Xiu J.H., Sui X., Piao H.R., Quan Z.S. Synthesis and Anticonvulsant Activity of N-(2-Hydroxyethyl) amide Derivatives // Arch. Pharm. Chem. Life Sci. — 2009. — P. 342. 34−40.

107. Себякин Ю. Л., Федякова Н. Л., Рунова E.A. Синтез амфифильных производных Z-серина И Биоорг. хим. — 1994. — 20. — С. 1101−1114.

108. Immordino M. L., Brusa P., Arpicco S., et al. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing docetaxel // J. Control. Release. — 2003. — 91. — P. 29−417.

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

110. Svetlakov N.V., Nikitin V.G., Orekhova A.O. Oxidation of Diethylene Glycol with Nitric Acid // Zh. Org. Khim. — 2002. — 38. No. 5. — P. 789.

111. BogatskiA.V., Luk’yanenko N.G., Kirichenko T.I. // Zh. Org. Khim. 1980.16. 1301.

112. Huisgen, R. In «1.3-Dipolar Cycloadditional Chemistry"/ R. Huisgen. NY: Wiley. — 1984. —176 p.

113. Tornoe C.W., Christensen С., Meldal M. Peptidotriazoles on Solid Phase: 1.2.3.-Triazoles by Regiospecific Copper (I)-Catalyzed 1.3-Dipolar Cycloadditions of Terminal Alkynes to Azides H J. Org. Chem. — 2002. — 67. — P. 3057−3062.

114. Гурьева Л. Ю., Буданова У. А., Себякин Ю. Л. Исследования в области синтеза неогликолипидов на основе £)-лактозы // Журнал органической химии.—2009.—Т. 45 № 2.— Р. 186−190.

115. Себякин Ю. Л., Буданова У. А., Гурьева Л. Ю. Структурно функциональное разнообразие искусственных мембран на основе катионных липодипептидов // Биологичсекие мембраны. —2007. —24. № 3. — С. 273—279.

116. Dulaney J.T. Binding interactions of glycoproteins with lectins // Mol. Cell. Biochem. — 1979. — 21. № 1. — P. 43−63.

117. Кочетков H.K. Методы химии углеводов // М.: Мир. — 1967. — 428с.

118. Лурье A.A. Хроматографические материалы, М. Химия — 1978. — 122с.

119. Гурьева Л. Ю., Северьянова А. А., Себякин Ю. Л. Активные производные £>-галактозы и D-лактозы в синтезе неогликоконъюгатов // Вестник МИТХТ.—2006.—Т. 1 № 4.—Р. 33−38.

120. Буданова У. А., Себякин ЮЛ., Гурьева Л. Ю. Структурно-функциональное разнообразие искусственных мембран на основе катионных липопептидов // Биологические мембраны,—2007.—'Г. 24 № 3.—Р. 273−279.

121. Гурьева Л. Ю., Буданова У .А., Себякин Ю. Л. Исследования в области синтеза неогликолипидов на основе .D-лактозы // Журнал органической химии.—2009.—Т. 45 № 2.— Р. 186−190.

122. Гурьева Л. Ю., Болыпебородова А. К., Себякин Ю. Л. Синтез углеводсодержащих компонентов липидных транспортных систем направленного действия методом «click-chemistry» // Вестник МИТХТ.—2009.—'Г. 4 № 6.—Р. 61−66.

123. Гурьева Л. Ю., Буданова У. А., Себякин Ю. Л. Синтез новых углеводсодержащих липидов на основе D-лактозы.// 18-й Менделеевский съезд по общей и прикладной химии.— 2007.—Москва,—Т. 4,—Р. 527.

124. Гурьева Л. Ю., Северьянова А. А., Себякин Ю. Л. Технологии получения и свойства модифицированных гликолипидов.// XII Международная научно-техническая конференция «Наукоемкие химические технологии 2008». —2008.—Волгоград.—Р. 127.

125. Болыпебородова А. К., Гурьева Л. Ю., Себякин Ю. Л. Структурная модификация липосомальных транспортных систем углеводсодержащими компонентами // IX Ежегодной международной молодежной конференции «Биохимическая физика» ИБХФ РАН-ВУЗы.—2009—Москва,—Р. 32−34.