Neoglycoconjugates for the delivery of nucleic acids into eucaryotic cells
Abstract
About the Authors
M. A. MaslovRussian Federation
N. G. Morozova
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.
Review
For citations:
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.)