Amino acid nucleic acids: Synthesis and hybridization properties of a novel class of antisense oligonucleotides

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 15, 1996, Pages 1799-1804

  Ramasamy, Kanda S ^a   Seifert, Wilfried ^a  

^a Valeant Pharmaceuticals International   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE;

ARTICLE; DRUG STABILITY; DRUG SYNTHESIS; HYBRIDIZATION;

EID: 0030572482     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00320-4     Document Type: Article

References (31)

1. 1. (a) Zamecnik, P. C.; Stephenson, M. L. Proc. Natl. Acad. Sci. U. S. A. 1978, 75, 280.
2. (b) Goodchild, J. Bioconjugate Chem. 1990, 1, 165.
3. 2. Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 544.
4. 3. Marcus-Sekura, C. J.; Woerner, A. M.; Shinozuka, K.; Zon, G.; Quinnan, G. V. Nucleic Acids Res. 1987, 15, 5749.
5. 4. Gryaznov, S.; Chen, K-J. J. Am. Chem. Soc. 1994,116, 3143.
6. 5. Loschner, T.; Engels, J. W. Nucleosides Nucleotides 1988, 7, 729.
7. 6. (a) Stec, W. J.; Zon, G.; Egan, W.; Stec, B. J. Am. Chem. Soc. 1984, 106, 6077.
8. (b) Connolly, B. A.; Potter, B. V. L.; Eckstein, F.; Pingoud, A.; Grothjahn, L. Biochemistry 1984, 23, 3443.
9. 7. Nielsen, J.; Brill, W. K.; Caruthers, M. H. Tetrahedron Lett. 1988, 29, 2911.
10. 8. Sood, A.; Shaw, B. R.; Spielvogel, B. F. J. Am. Chem. Soc. 1990, 112, 9000.
11. 9. (a) Matteucci, M. Tetrahedron Lett. 1990, 31, 2385.
12. (b) ACS Symposium series: Carbohydrate modifications in Antisense Research; Shanghvi, Y. S.; Cook, P. D., Eds.; 1994, pp 1-65.
13. 10. (a) Coull, J. M.; Carlson, D. V.; Weith, H. L. Tetrahedron Lett. 1987, 28, 745.
14. (b) Stirchak, E. P.; Summerton, J. E.; Weller, D. D. J. Org. Chem. 1987, 52, 4202.
15. 11. Cormier, J. F.; Ogilvie, K. K. Nucleic Acids Res. 1988, 16, 4583.
16. 12. (a) Huang, Z.; Schneider, K. C.; Benner, S. A. J. Org. Chem. 1991, 56, 3869.
17. (b) Schneider, K. C.; Benner, S. A. Tetrahedron Lett. 1990, 31, 335.
18. 13. Lebreton, J.; Waldner, A.; Lesueur, C.; De Mesmaeker, A. Synlett. 1994, 137.
19. 14. Saha, A. K.; Schairer, W.; Waychunas, C.; Prasad, C. V. C.; Sardaro, M.; Upson, D. A.; Kruse, L. Tetrahedron Lett. 1993, 34, 6017.
20. 15. Vasseur, J-J.; Bebart, F.; Sanghvi, Y. S.; Cook, P. D. J. Am. Chem. Soc. 1992, 114, 4006.
21. 16. Egholm, M.; Buchardt, O.; Nielsen, P. E.; Berg, R. H. J. Am. Chem. Soc. 1992, 114, 1895.
22. 17. We refer to nucleobases attached to serinol via acetamide linker. See Fig. 1 and structure (2).
23. 18. We thank one of the refree for suggesting such a name for neutralization of the phosphodiester backbone negative charge via intramolecular hydrogen bonding.
24. 19. Ramasamy, K.; Olsen, R. K.; Emery, T. Synthesis 1982, 42.
25. 1HNMR and elemental analysis.
26. 21. Schaller, H.; Weimann, G.; Lerch, B.; Khorana, H. G. J. Am. Chem. Soc. 1963, 85, 3821.
27. 22. Karpyshev, N. N. Russ. Chem. Rev. 1988, 57, 886.
28. 23. Freier, S. M.; Albergo, D. D.; Turner, D. H. Biopolymers 1982, 22, 1107.
29. 24. Atkinson, T.; Smith, M. in Oligonucleotide Synthesis: A practical Approach; Gait, M. J., Ed.; IRL: Oxford; 1984; pp 35-81.
30. 25. Oligonucleotides were digested with a mixture of spleen phosphodiesterase, snake venom phosphodiesterase, and bacterial alkaline phosphatase to provide individual nucleosides which were analyzed by HPLC.
31. 26. The enzymatic stability of the AANA modified oligonucleotides were tested against snake venom phosphodiesterase (SV PDE, 3'-exonuclease). The increase in absorbance at 260 nm was followed during digestion with SV PDE. For experimental procedure see: Svendsen, M. L.; Wengel, J. Tetrahedron 1993, 49, 11341.