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Neoglycoconjugates for the delivery of nucleic acids into eucaryotic cells

Abstract

А development of stable and safety non-viral transport systems for delivery of therapeutic nucleic acids (NA) into the target cells is one of the problem of gene therapy. Cationic liposomes are promising delivery systems capable to transfer various kind of NA. However, the wide application of cationic liposomes for gene therapy purposes is limited by their low efficiency and unspecific NA delivery into cells. These drawbacks are related to the presence of different biological barriers for lipoplexes: the instability in biological fluids, the interaction with blood serum proteins, plasmatic and nucleic membranes and endosomal degradation. Modular gene delivery systems introduced ten years ago consist of different lipophilic modules that mediate environmental and cellular receptors interactions as well as intracellular trafficking. Modular systems containing synthetic neoglycolipids are widely used for development of targeted gene delivery based on specific carbohydrate-lectin interactions (glycotargeting). This review combines examples of neoglycolipids used as active components of cationic liposomes. Targeted delivery of plasmid DNA, mRNA, oligonucleotides and small interfering RNA into hepatocytes, Kupffer cells and dendritic cells are discussed.

About the Authors

M. A. Maslov
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


N. G. Morozova
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


References

1. Templeton N.S. Optimization of nonviral gene therapeutics / In: Gene and Cell Therapy: Therapeutic Mechanisms and Strategies, 3 ed. / Ed. N.S. Templeton. Воса Raton: CRC Press, 2009. 1120 p.

2. Blau H.M., Springer M.L. // N. Engl. J. Med. 1995. V. 333. P. 1204-1207.

3. Verma I.M., Weitzman M.D. // Ann. Rev. Biochem. 2005. V. 74. P. 711-738.

4. Huang L. Non-viral vectors for gene therapy. 2nd ed. Part 1. / Huang L., Hung M.C., Wagner E. / Advances in Genetics. Amsterdam: Elsevier Academic Press, 2005. V. 53. 400 p.

5. Lv H.T., Zhang S.B., Wang B., Cui S.H., Yan J. // J. Control. Release. 2006. V. 114. P. 100-109.

6. Morille M., Passirani C., Vonarbourg A., Clavreul A., Benoit J.-P. // Biomaterials. 2008. V. 29. P. 3477-3496.

7. Karmali P.P., Chaudhuri A. // Med. Res. Rev. 2007. V. 27. P. 696-722.

8. Non-Viral Gene Therapy / Ed. X. Yuan. Rijeka: InTech, 2011. 696 p.

9. Mahato R.I. // Adv. Drug Del. Rev. 2005. V. 57. P. 699-712.

10. Tseng Y.-C., Mozumdar S., Huang L. // Adv. Drug Deliv. Rev. 2009. V. 61. P. 721-731.

11. Spack E.G., Sorgi F.L. // Drug Discov. Today. 2001. V. 6. P. 186-197.

12. Wasungu L., Hoekstra D. // J. Control. Release. 2006. V. 116. P. 255-264.

13. Zuhorn I.S., Engberts J.B.F.N., Hoekstra D. // Eur. Biophys. J. 2007. V. 36. P. 349-362.

14. El Ouahabi A., Ruysschaert J.M. // Molecular Therapy. 2005. V. 11. P. 336-347.

15. Conner S.D., Schmid S.L. // Nature. 2003. V. 422. P. 37-44.

16. Fang J., Nakamura H., Maeda H. // Adv. Drug Deliv. Rev. 2011. V. 63. P 136-151.

17. De Laporte L., Cruz Rea J., Shea L.D. // Biomaterials. 2006. V. 27. P. 947-954.

18. Kostarelos K., Miller A.D. // Chem. Soc. Rev. 2005. V. 34. P. 970-994.

19. Серебренникова Г.А., Маслов М.А., Морозова Н.Г. // Вестник МИТХТ. 2011. T. 6 № 5. C. 72-86.

20. Srinivas R., Samanta S., Chaudhuri A. // Chem. Soc. Rev. 2009. V. 38. P. 3326-3338.

21. Martin B., Sainlos M., Aissaoui A., Oudrhiri N., Hauchecorne M., Vigneron J.-P., Lehn J.-M., Lehn P. // Curr. Pharm. Design. 2005. V. 11. P. 375-394.

22. Mintzer M.A., Simanek E.E. // Chem. Rev. 2009. V. 109. P. 259-302.

23. Maslov M.A., Zenkova М.A. Non-viral gene delivery systems based on cholesterol cationic lipids: Structure-activity relationships / In: Non-Viral Gene Therapy / Ed. X. Yuan. Rijeka: InTech, 2011. P. 349-380.

24. Hui S.W., Langner M., Zhao Y.L., Hurley E., Chan K. // Biophys. J. 1996. V. 71. P. 590-599.

25. Mok K.W.C., Cullis P.R. // Biophys. J. 1997. V. 73. P. 2534-2545.

26. Kerner M., Meyuhas O., Hirsch-Lerner D., Rosen L.J., Min Z., Barenholz Y. // Biochim. Biophys. Acta. 2001. V. 1532. P. 128-136.

27. Zuidam N.J., Barenholz Y. // Biochim. Biophys. Acta. 1998. V. 1368. P. 115-128.

28. Zuidam N.J., Hirsch-Lerner D., Margulies S., Barenholz Y. // Biochim. Biophys. Acta. 1999. V. 1419. P. 207-220.

29. Liu Y., Mounkes L.C., Liggitt H.D. Brown C.S., Solodin I., Heath T.D., Debs R.J. // Nat. Biotech. 1997. V. 15. P. 167-173.

30. Sternberg B., Hong K., Zheng W., Papahadjopoulos D. // Biochim. Biophys. Acta. 1998. V. 1375. P. 23-35.

31. Simberg D., Weisman S., Talmon Y., Faerman A., Shoshani T., Barenholz Y. // J. Biol. Chem. 2003. V.278. P. 39858-39865.

32. Romberg B., Hennink W.E., Storm G. // Pharm. Res. 2008. V. 25. P. 55-71.

33. Martin-Herranz A., Ahmad A., Evans H.M., Ewert K., Schulze U., Safinya C.R. // Biophys. J. 2004. V. 86. P. 1160-1168.

34. Song L.Y., Ahkong Q.F., Rong Q., Wang Z., Ansell S., Hope M.J., Mui B. // Biochim. Biophys. Acta. 2002. V. 1558. P. 1-13.

35. Masson C., Garinot M., Mignet N., Wetzer B., Mailhe P., Scherman D., Bessodes M. // J. Control. Release. 2004. V. 99. P. 423-434.

36. Sapra P., Allen T.M. // Cancer Res. 2002. V. 62. P. 7190-7194.

37. Molas M., Gómez-Valadés A.G., Vidal-Alabró A., Miguel-Turu M., Bermudez J., Bartrons R., Perales J.C. // Curr. Gene Ther. 2003. V. 3. P. 468-485.

38. Brown J., Hunt R. // Internal. Rev. Cytol. 1978. V. 52. P. 277-349.

39. Nicolson G., Irimura Т. // Biology of the Cell. 1984. V. 51. P. 157-164.

40. Biesa C., Lehra C.-M., John F. // Adv. Drug Deliver. Rev. 2004. V. 56. P. 425-435.

41. Aneed A.E. // Pharm. Technol. 2003. V. 27. P. 58-62.

42. Ashwell G., Harford J. // Annu. Rev. Biochem. 1982. V. 51. P. 531-554.

43. Spiess M. // Biochemistry. 1990. V. 29. P. 10009-10018.

44. Zhang Y., Rong X., Gao Q., Maitani Y., Nagai T. // J. Control. Release. 2007. V. 117. P. 281-290.

45. Salvador F., Alin O., Benet M., Dasi´ F., Crespo J. // Method. Enzymol. 2003. V. 373. P. 6876-6879.

46. Erbacher P., Roche A.C., Monsigny M., Midoux P. // Bioconjugate Chem. 1995. V. 6. P. 401-410.

47. Barbro N.M., Leonie B., Dirk K., Meijer F., Poelstra K. Cell specific delivery of anti-inflammatory drugs to hepatic endothelial and Kupffer cells for the treatment of inflammatory liver diseases / In: Drug Targeting: Organ-Specific Strategies / Eds. G. Molema, D.K.F. Meijer. Wiley-VCH, 2001. V. 12. 381 p.

48. Kawakami S., Munakata C., Fumoto S., Yamashita F., Hashida M. // J. Pharm. Sci. 2001. V. 90. P. 105-113.

49. Kawakami S., Yamashita F., Nishikawa M., Takakura Y., Hashida M. // Biochem Biophys. Res. Commun. 1998. V. 252. P. 78-83.

50. Shigeta K., Kawakami S., Higuchi Y., Okuda T., Yagi H., Yamashita F., Hashida M. // J. Control. Release. 2007. V. 118. P. 262-270.

51. Lu Y., Kawakami S., Yamashita F., Hashida M. // Biomaterials. 2007. V. 28. P. 3255-3262.

52. Yeeprae W., Kawakami S., Higuchi Y., Yamashita F., Hashida M. // J. Drug Target. 2005. V. 13. P. 479-487.

53. Yeeprae W., Kawakami S., Yamashita F., Hashida M. // J. Control. Release. 2006. V. 114. P. 193-201.

54. Higuchi Y., Kawakami S., Yamashita F., Hashida M. // Biomaterials. 2007. V. 28. P. 532-539.

55. Mukthavarama R., Marepallya S., Venkataa M.Y., Vegi G.N., Sistlab R., Chaudhuria A. // Biomaterials. 2009. V. 30. P. 2369-2384.

56. Fabio K., Gaucheron J., Di Giorgio C., Vierling P. // Bioconjugate Chem. 2003. V. 14. P. 358-367.

57. Ren T., Zhang G., Liu D. // Bioorg. Med. Chem. 2001. V. 9. P. 2969-2978.

58. Maslov M.A., Medvedeva D.A., Rapoport D.A., Serikov R.N., Morozova N.G., Serebrennikova G.A., Vlassov V.V., Zenkova М.A. // Bioorg. Med. Chem. Lett. 2011. V. 21. P. 2937-2940.

59. Mahon E., Aastrup T., Barboiu M. // Chem. Commun. 2010. V. 46. P. 5491-5493.

60. Lindhorst T.K. Artificial multivalent sugar ligands to understand and manipulate carbohydrateprotein interactions / In: Host-Guest Chemistry: Mimetic Approaches to Study Carbohydrate Recognition / Ed. S. Penadés. Springer Berlin Heidelberg, 2002. P. 201-235.

61. Lee Y.C., Lee R.T. // Accounts Chem. Res. 1995. V. 28. P. 321-327.

62. Connolly D.T., Townsend R.R., Kawaguchi K., Bell W.R., Lee Y.C. // J. Biol. Chem. 1982. V. 257. P. 939-945.

63. Lee Y.C., Townsend R.R., Hardy M.R., Lönngren J., Arnarp J., Haraldsson M., Lönn H. // J. Biol. Chem. 1983. V. 258. P. 199-202.

64. Lee Y.C., Lee R.T. / In: Carbohydrates in Chemistry and Biology / Eds. B. Ernst, G.W. Hart, P. Sinaÿ. Weinheim: Wiley-WCH, 2000. V. 4. P. 549-561.

65. Lee R.T., Lin P., Lee Y.C. // Biochemistry. 1984. V. 23. P. 4255-4261.

66. Biessen E.A.L., Noorman F., van Teijlingen M.E., Kuiper J., Barrett-Bergshoeff M., Bijsterbosch M.K., Rijken D.C., van Berkel T.J.C. // J. Biol. Chem. 1996. V. 271. P. 28024-28030.

67. Schierholt A., Hartmann M., Lindhorst T.K. // Carbohyd. Res. 2011. V. 346. P. 1519-1526.

68. Page D., Aravind S., Roy R. // Chem. Commun. 1996. V. 16. P. 1913-1914.

69. Vrasidas I., André S., Valentini P., Böck C., Lensch M., Kaltner H., Liskamp R.M.J., Gabius H. J., Pieters R.J. // Org. Biomol. Chem. 2003. V. 1. P. 803-810.

70. Dubber M., Patel A., Sadalapure K., Aumüller I., Lindhorst T.K. // Eur. J. Org. Chem. 2006. V. 16. P. 5357-5366.

71. Patel A., Lindhorst T.K. // J. Org. Chem. 2001. V. 66. P. 2674-2680.

72. Biessen E.A., Vietsch H., van Berkel T.J. // Circulation. 1995. V. 91. P. 1847-1854.

73. Sliedregt L.A., Rensen P.C., Rump E.T., van Santbrink P.J., Bijsterbosch M.K., Valentijn A.R., van der Marel G.A., van Boom J.H., van Berkel T.J., Biessen E.A. // J. Med. Chem. 1999. V. 42. P. 609-618.

74. Rensen P.C.N., van Leeuwen S.H., Sliedregt L.A.J.M., van Berkel T.J.C., Biessen E.A.L. // J. Med. Chem. 2004. V. 47. P. 5798-5808.

75. Carrière M., V. Escriou, Jollet A., Scherman D. // Drug Delivery. 2004. V. 11. P. 351-363.

76. Murahashi N., Ishihara H., Sasaki A., Sakagami M., Hamana H. // Biol. Pharm. Bull. 1997.V . 20. P. 259-266.

77. Frisch B., Carrière M., Largeau C., Mathey F., Masson C., Schuber F., Scherman D., Escriou V. // Bioconjugate Chem. 2004. V. 15. P. 754-764.

78. Ivanova E.A., Maslov M.A., Morozova N.G., Serebrennikova G.A., Chupin V.V. // RSC Adv. 2012. V. 2. P. 4600-4602.

79. Maslov M.A., Ivanova E.A., Morozova N.G., Filatov A.V., Zenkova M.A. // Book of Abstracts of 18th Eur. Carbohydrate Symposium. Moscow, Russia, August 2-6, 2015. P. 52.

80. Watanabe T., Umehara T., Yasui F., Nakagawa S.- I., Yano J., Ohgi T., Sonoke S. Satoh K., Inoue K., Yoshiba M., Kohara M. // J. Hepatol. 2007. V. 47. P. 744-750.

81. Horiuchi S., Aoyama Y. // J. Control. Release. 2006. V. 116. P. 107-114.

82. Guermonprez P., Valladeau J., Zitvogel L., Thery C., Amigorena S. // A. Rev. Immunol. 2002. V. 20. P. 621-667.

83. Gogolák P., Réthi B., Hajas G., Rajnavölgyi E. // J. Mol. Recognit. 2003. V. 16. P. 299-317.

84. Ribas A., Butterfield L.H., Glaspy J.A., Economou J.S. // J. Clin. Oncol. 2003. V. 21. P. 2415-2432.

85. Ribas A. // Curr. Gene Ther. 2005. V. 5. P. 619-628.

86. Altin J.G. Liposomes and other nanoparticles as cancer vaccines and immunotherapeutics / In: Innovation in Vaccinology / Ed. S. Baschieri. Springer Netherlands, 2012. P. 135-178.

87. Mukhopadhyay A., Basu S.K. // Adv. Biochem. Eng. Biotechnol. 2003. V. 84. P. 183-209.

88. Carrillo-Conde B., Song E.H., ChavezSantoscoy A., Phanse Y., Ramer-Tait A.E., Pohl N.L., Wannemuehler M.J., Bellaire B.H., Narasimhan B. // Mol. Pharm. 2011. V. 8. P. 1877-1886.

89. Mével M., Breuzard G., Yaouanc J.J., Clément J.C., Lehn P., Pichon C., Jaffrès P.A., Midoux P. // Chembiochem. 2008. V. 9. P. 1462-1471.

90. Pichon C., Midoux P. // Methods. Mol. Biol. 2013. V. 969. P. 247-274.

91. Markov O.V., Mironova N.L., Shmendel E.V., Serikov R.N., Morozova N.G., Maslov M.A., Vlassov V.V., Zenkova M.A. // J. Control. Release. 2015. V. 213. P. 45-56.

92. Sato A., Takagi M., Shimamoto A., Kawakami S., Hashida M. // Biomaterials. 2007. V. 28. P. 1434-1442.

93. White K., Rades T., Kearns P., Toth I., Hook S. // Pharm. Res. 2006. V. 23. P. 1473-1481.

94. Copland M.J., Baird M.A., Rades T., McKenzie J.L., Becker B., Reck F., Tyler P.C., Davies N.M. // Vaccine. 2003. V. 21. P. 883-890.

95. Proudfoot O., Apostolopoulos V., Pietersz G.A. // Mol. Pharm. 2007. V. 4. P. 58-72.

96. Cui L., Cohen J.A., Broaders K.E., Beaudette T.T., Fréchet J.M. // Bioconjug. Chem. 2011. V. 22. P. 949-957.


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Maslov M.A., Morozova N.G. Neoglycoconjugates for the delivery of nucleic acids into eucaryotic cells. Fine Chemical Technologies. 2015;10(4):5-21. (In Russ.)

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