Oligonucleotide mimics for antisense therapeutics: Solution phase and automated solid-support synthesis of MMI linked oligomers

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 255-256

  Morvan, François ^a   Sanghvi, Yogesh S ^a   Perbost, Michel ^a   Vasseur, Jean Jacques ^a   Bellon, Laurent ^a  

^a ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030053079     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9533959     Document Type: Article

References (32)

1. Selected books and reviews published in 1995: (a) Therapeutic Applications of Oligonucleotides; Crooke, S. T., Ed.; R. G. Landes Co.:. Austin. TX, 1995. (b) Carbohydrate Modifications in Anlisense Research; Sanghvi, Y. S., Cook, P D., Eds.: ACS Symposium Series 580; American Chemical Society: Washington, DC. 1995. (c) Crooke, S. T. Hematol. Pathol. 1995, 9, 59. (d) Crooke, S. T. In Burger's Medicinal Chemistry and Drug Discovery. Vol 1; Wolff, M. E., Ed.; John Wiley: New York. 1995: p 863. (e) Mesmaeker, A. D.; Haner. R.; Martin, P.; Moser, H. E.; Acc. Chem. Res. 1995, 28, 366.
2. Selected books and reviews published in 1995: (a) Therapeutic Applications of Oligonucleotides; Crooke, S. T., Ed.; R. G. Landes Co.:. Austin. TX, 1995. (b) Carbohydrate Modifications in Anlisense Research; Sanghvi, Y. S., Cook, P D., Eds.: ACS Symposium Series 580; American Chemical Society: Washington, DC. 1995. (c) Crooke, S. T. Hematol. Pathol. 1995, 9, 59. (d) Crooke, S. T. In Burger's Medicinal Chemistry and Drug Discovery. Vol 1; Wolff, M. E., Ed.; John Wiley: New York. 1995: p 863. (e) Mesmaeker, A. D.; Haner. R.; Martin, P.; Moser, H. E.; Acc. Chem. Res. 1995, 28, 366.
3. Selected books and reviews published in 1995: (a) Therapeutic Applications of Oligonucleotides; Crooke, S. T., Ed.; R. G. Landes Co.:. Austin. TX, 1995. (b) Carbohydrate Modifications in Anlisense Research; Sanghvi, Y. S., Cook, P D., Eds.: ACS Symposium Series 580; American Chemical Society: Washington, DC. 1995. (c) Crooke, S. T. Hematol. Pathol. 1995, 9, 59. (d) Crooke, S. T. In Burger's Medicinal Chemistry and Drug Discovery. Vol 1; Wolff, M. E., Ed.; John Wiley: New York. 1995: p 863. (e) Mesmaeker, A. D.; Haner. R.; Martin, P.; Moser, H. E.; Acc. Chem. Res. 1995, 28, 366.
4. Selected books and reviews published in 1995: (a) Therapeutic Applications of Oligonucleotides; Crooke, S. T., Ed.; R. G. Landes Co.:. Austin. TX, 1995. (b) Carbohydrate Modifications in Anlisense Research; Sanghvi, Y. S., Cook, P D., Eds.: ACS Symposium Series 580; American Chemical Society: Washington, DC. 1995. (c) Crooke, S. T. Hematol. Pathol. 1995, 9, 59. (d) Crooke, S. T. In Burger's Medicinal Chemistry and Drug Discovery. Vol 1; Wolff, M. E., Ed.; John Wiley: New York. 1995: p 863. (e) Mesmaeker, A. D.; Haner. R.; Martin, P.; Moser, H. E.; Acc. Chem. Res. 1995, 28, 366.
5. Selected books and reviews published in 1995: (a) Therapeutic Applications of Oligonucleotides; Crooke, S. T., Ed.; R. G. Landes Co.:. Austin. TX, 1995. (b) Carbohydrate Modifications in Anlisense Research; Sanghvi, Y. S., Cook, P D., Eds.: ACS Symposium Series 580; American Chemical Society: Washington, DC. 1995. (c) Crooke, S. T. Hematol. Pathol. 1995, 9, 59. (d) Crooke, S. T. In Burger's Medicinal Chemistry and Drug Discovery. Vol 1; Wolff, M. E., Ed.; John Wiley: New York. 1995: p 863. (e) Mesmaeker, A. D.; Haner. R.; Martin, P.; Moser, H. E.; Acc. Chem. Res. 1995, 28, 366.
6. Sanghvi, Y S., Cook, P. D. In ref 1b; Chapter 1, p 1, Mesmaeker, A. D.; Altman, K.-H.; Waldner, A.; Wendeborn, S. Curr. Opin. Struct. Biol. 1995, 5, 343.
7. Sanghvi, Y. S.; Cook, P. D. In Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York. 1993; p 311.
8. Vasseur, J.-J.; Debart, F.; Sanghvi, Y. S.; Cook, P. D. J. Am. Chem. Soc. 1992, 114, 4006.
9. (a) Mohan, V.; Griffey, R H.; Davis D. R. Tetrahedron 1995, 51, 8655.
10. 2 group reduces the ring gauche effects and may enhance conformational stability. See: Roushton, A. L.; Portmann, S.; Benner, S A.: Esli, M. J. Am. Chem. Soc. 1995, 117, 7249.
11. Sanghvi, Y. S., Bellon, L.; Morvan, F.; Hoshiko, T.; Swayze, E.; Cummins, L., Freier, S.: Dean, N.; Monia, B.; Griffey, R.; Cook, P. D. Nucleosides Nucleotides 1995, 14, 1087.
12. (a) We refer to modified oligonucleotides that lack the phosphorus atom in the backbone linkage as oligonucleosides.
13. (b) Chimeric AOs are oligomers that contain more than one type of modifications to create a gap for RNase H activity.
14. Perbost, M.; Hoshiko, T.; Morvan, F.; Swayze, E.; Griffey, R. H.; Sanghvi, Y.S. J. Org. Chem. 1995, 60, 5150.
15. Pon, R. T. In Protocols for Oligonucleotides and Analogs; Agraval, S., Ed.; Humana Press: Totowa, NJ, 1993; p 465.
16. (a) Hughes, D. L. In Organic Reactions; Raquette, L, A., Ed.; John Wiley: New York. 1992; Vol. 42. p 335.
17. (b) Rano, T.A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789.
18. (a) Sanghvi, Y. S.; Ross, B.; Bharadwaj, R.; Vasseur, J.-J. Tetrahedron Lett 1994, 35, 4697.
19. (b) Sanghvi, Y. S.; Bharadwaj, R.; Debart, F.; Mesmaeker, A. D. Synthesis 1994, 1163.
20. (a) Mitsunobu, O. Synthesis 1981, 1.
21. (b) Debart, F.; Vasseur, J.-J.; Sanghvi, Y. S.; Cook, P. D. Tetrahedron Lett. 1992, 33, 2645.
22. (a) Divakar, R. J.; Reese, C. B. J. Chem. Soc., Perkin Trans, 1 1982, 1171.
23. (b) Perbost, M.; Sanghvi, Y. S. J. Chem. Soc., Perkin Trans, 1 1994. 2051.
24. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223.
25. Cook, P. D.; Sanghvi, Y. S.; Morvan, F. PCT Int. Appl. WO 95/ 18136. July 6, 1995
26. In addition to the pyrimidine olisonuclesides, we have also synthesized several purine-containing dimers (A*T, T*A, G*A, G*T) according to the SS methodology.
27. For a sulfonate backbone, see: Huang, J.: McELroy, E. B.; Widlanski, T. S. J. Org. Chem. 1994, 59, 3520. For a silyl backbone, see: Cormier, J. F.; Ogilvie, K. K. Nucleic Acids Res 1988, 16, 4583. For an extensive list, see ref 2.
28. For a sulfonate backbone, see: Huang, J.: McELroy, E. B.; Widlanski, T. S. J. Org. Chem. 1994, 59, 3520. For a silyl backbone, see: Cormier, J. F.; Ogilvie, K. K. Nucleic Acids Res 1988, 16, 4583. For an extensive list, see ref 2.
29. Dean, N M.; McKay, R.; Condon, T. P.; Bennert, C. F. J. Biol. Chem. 1994, 269, 16416.
30. White, M. A. In Solid Supports Catalysts in Organic Synthesis; Smith, K., Ed., Horwood: Chichester, U.K., 1992; p 225.
31. For experimental conditions, see: Cummins, L.; Owens, S. R.; Risen, L. M.; Lesnik, E. A., Freier, S. M.; McGee, D.; Guinosso, C. J.; Cook, P. D. Nucleic Acids Res. 1995, 23, 2019.
32. Cook, P. D.; Sanshvi, Y. S.; Kung, P.-P. PCT Int. Appl. WO 95/ 18623, July 13, 1995