Synthesis of lipid-oligonucleotide conjugates for RNA interference studies

Chemistry and Biodiversity

Volumn 8, Issue 2, 2011, Pages 287-299

  Grijalvo, Santiago ^a   Ocampo, Sandra M ^a   Perales, José C ^b   Eritja, Ramon ^a  

^a BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Lipid oligonucleotide conjutages; Oligonucleotides; RNA

Indexed keywords

DNA; LIPID; LIPOFECTAMINE; OLIGODEOXYNUCLEOTIDE; OLIGONUCLEOTIDE; PHOSPHORAMIDOUS ACID DERIVATIVE; RNA; SMALL INTERFERING RNA; TUMOR NECROSIS FACTOR;

ARTICLE; CONJUGATE; GENE EXPRESSION; GENE SILENCING; GENETIC TRANSFECTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPOGENESIS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; RNA INTERFERENCE; RNA SYNTHESIS;

ANIMALS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME-LINKED IMMUNOSORBENT ASSAY; GENE EXPRESSION; HELA CELLS; HUMANS; LIPIDS; MICE; MOLECULAR TARGETED THERAPY; OLIGONUCLEOTIDES; RECOMBINANT PROTEINS; RNA INTERFERENCE; RNA, SMALL INTERFERING; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TRANSFECTION; TUMOR NECROSIS FACTOR-ALPHA;

EID: 79951886164     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.201000274     Document Type: Article

References (45)

1. T. Aboul-Fadl, Curr. Med. Chem. 2005, 12, 2193.
2. J. H. P. Chan, S. Lim, W. S. F. Wong, Clin. Exper. Pharmacol. Physiol. 2006, 33, 533.
3. C. Wilson, A. D. Keefe, Curr. Opin. Chem. Biol. 2006, 10, 607.
4. T. Tuschl, ChemBioChem 2001, 2, 239.
5. E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543.
6. D. Bumcrot, M. Manoharan, V. Koteliansky, D. W. Y. Sah, Nat. Chem. Biol. 2006, 2, 711.
7. A. de Fougerolles, M. Manoharan, R. Meyers, H.-P. Vornlocher, Methods Enzymol. 2005, 392, 278.
8. M. A. Mintzer, E. E. Simanek, Chem. Rev. 2009, 109, 259.
9. E. Urban, C. R. Noe, Farmaco 2003, 58, 243.
10. C. X. Li, A. Parker, E. Menocal, S. Xiang, L. Borodyansky, J. H. Fruehauf, Cell Cycle 2006, 5, 2103.
11. T. M. Rana, Nat. Rev. Mol. Cell. Biol. 2007, 8, 23.
12. R. S. Geary, Expert Opin. Drug. Metab. Toxicol. 2009, 5, 381.
13. P. S. Miller, Nat. Biotechnol. 1991, 9, 358.
14. S. M. Gryaznov, Chem. Biodiversity 2010, 7, 477.
15. R. N. Veedu, J. Wengel, Chem. Biodiversity 2010, 7, 536.
16. P. E. Nielsen, Curr. Opin. Mol. Ther. 2010, 12, 184.
17. H. de Martimprey, C. Vauthier, C. Malvy, P. Couvreur, Eur. J. Pharm. Biopharm. 2009, 3, 490.
18. G. Godeau, C. Staedel, P. Barthélémy, J. Med. Chem. 2008, 51, 4374.
19. F. Said Hassane, A. F. Saleh, R. Abes, M. J. Gait, B. Lebleu, Cell. Mol. Life Sci. 2010, 67, 715.
20. N. Li, T. Larson, H. H. Nguyen, K. V. Sokolov, A. D. Ellington, Chem. Commun. 2010, 46, 392.
21. R. Eritja, A. Pons, M. Escarceller, E. Giralt, F. Albericio, Tetrahedron 1991, 47, 4113.
22. Y.-L. Chiu, A. Ali, C.-Y. Chu, H. Cao, T. M. Rana, Chem. Biol. 2004, 11, 1165.
23. A. Detzer, M. Overhoff, W. Wünsche, M. Rompf, J. J. Turner, G. D. Ivanova, M. J. Gait, G. Sczakiel, RNA 2009, 15, 627.
24. S.-S. Kim, C. Ye, P. Kumar, I. Chiu, S. Subramanya, H. Wu, P. Shankar, N. Manjunath, Mol. Ther. 2010, 18, 993.
25. A. Pathak, S. Patnaik, K. C. Gupta, Biotechnol. J. 2009, 4, 1559.
26. K. A. Whitehead, R. Langer, D. G. Anderson, Nat. Rev. Drug Discovery 2009, 8, 129.
27. J. K. Watts, D. R. Corey, Bioorg. Med. Chem. Lett. 2010, 20, 3203.
28. A. de Fougerolles, H. P. Vornlocher, J. Maraganore, J. Lieberman, Nat. Rev. Drug Discovery 2007, 7, 443.
29. J. Soutschek, A. Akinc, B. Bramlage, K. Charisse, R. Constien, M. Donoghue, S. Elbashir, A. Geick, P. Hadwiger, J. Harborth, M. John, V. Kesavan, G. Lavine, R. K. Pandey, T. Racie, K. G. Rajeev, I. Röhl, I. Toudjarska, G. Wang, S. Wuschko, D. Bumcrot, V. Koteliansky, S. Limmer, M. Manoharan, H.-P. Vornlocher, Nature 2004, 432, 173.
30. C. Lorenz, P. Hadwiger, M. John, H.-P. Vornlocher, C. Unverzagt, Bioorg. Med. Chem. Lett. 2004, 14, 4975.
31. Y. Ueno, K. Kawada, T. Naito, A. Shibata, K. Yoshikawa, H.-S. Kim, Y. Wataya, Y. Kitade, Bioorg. Med. Chem. 2008, 16, 7698.
32. C. Wolfrum, S. Shi, K. N. Jayaprakash, M. Jayaraman, G. Wang, R. K. Pandey, K. G. Rajeev, T. Nakayama, K. Charisse, E. M. Ndungo, T. Zimmermann, V. Koteliansky, M. Manoharan, M. Stoffel, Nat. Biotechnol. 2007, 25, 1149.
33. A. Aviñõ, S. M. Ocampo, C. Caminal, J. C. Perales, R. Eritja, Mol. Diversity 2009, 13, 287.
34. S. Grijalvo, M. Terrazas, A. Aviñõ, R. Eritja, Bioorg. Med. Chem. Lett. 2010, 20, 2144.
35. A. D. Judge, V. Sood, J. R. Shaw, D. Fang, K. McClintock, I. MacLachlan, Nat. Biotechnol. 2005, 23, 457.
36. J. Heyes, L. Palmer, K. Bremner, I. MacLachlan, J. Controlled Release 2005, 107, 276.
37. T. S. Zimmermann, A. C. H. Lee, A. Akinc, B. Bramlage, D. Bumcrot, M. N. Fedoruk, J. Harborth, J. A. Heyes, L. B. Jeffs, M. John, A. D. Judge, K. Lam, K. McClintock, L. V. Nechev, L. R. Palmer, T. Racie, I. Röhl, S. Seiffert, S. Shanmugam, V. Sood, J. Soutschek, I. Toudjarska, A. J. Wheat, E. Yaworski, W. Zedallis, V. Koteliansky, M. Manoharan, H.-P. Vornlocher, I. MacLachlan, Nature 2006, 441, 111.
38. T. W. Geisberg, L. E. Hensley, E. Kagan, E. Z. Yu, J. B. Geisberg, K. Daddano-DiCaprio, E. A. Fritz, P. B. Jahrling, K. McClintock, J. R. Phelps, A. C. H. Lee, A. Judge, L. B. Jeffs, I. MacLachlan, J. Infect. Dis. 2006, 193, 1650.
39. A. Rait, K. Pirollo, D. W. Will, A. Peyman, W. Rait, E. Uhlmann, E. H. Chang, Bioconjugate Chem. 2000, 11, 153.
40. R. T. Pon, in 'Methods in Molecular Biology Vol. 20: Protocols for Oligonucleotides and Analogs', Ed. S. Agrawal, Humana Press Inc., Totowa, New Jersey, 1993, p. 465.
41. K. C. Gupta, P. Kumar, D. Bhatia, A. K. Sharma, Nucleosides, Nucleotides Nucleic Acids 1995, 14, 829.
42. R. A. Moss, W. Jiang, Langmuir 1995, 11, 4217.
43. D. R. Sørensen, M. Leirdal, M. Sioud, J. Mol. Biol. 2003, 327, 761.
44. M. Manoharan, Biochim. Biophys. Acta, Gene Struct. Express. 1999, 1489, 117
45. E. Rozners, J. Moulder, Nucleic Acids Res. 2004, 32, 248.