Antisense oligonucleotides: Efficient synthesis of 2′-O-methoxyethyl phosphorothioate oligonucleotides using 4,5-dicyanoimidazole. Are these oligonucleotides comparable to those synthesized using 1H-tetrazole as coupling activator?

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 14, 2006, Pages 5049-5060

  Wang, Zhiwei ^a   Siwkowski, Andy ^a   Lima, Walt F ^a   Olsen, Phil ^a   Ravikumar, Vasulinga T ^a  

^a ISIS PHARMACEUTICALS   (United States)

Author keywords

1H Tetrazole; Activator; Antisense; Dicyanoimidazole; Oligonucleotide synthesis; Phosphorothioate

Indexed keywords

1H TETRAZOLE; 2' O METHOXYETHYL PHOSPHOROTHIOATE OLIGONUCLEOTIDE DERIVATIVE; 4,5 DICYANOIMIDAZOLE; ANTISENSE OLIGONUCLEOTIDE; IMIDAZOLE; OLIGONUCLEOTIDE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; IN VIVO STUDY; MASS SPECTROMETRY; NONHUMAN; SEQUENCE ANALYSIS;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, LIQUID; IMIDAZOLES; INDICATORS AND REAGENTS; KIDNEY; LIVER; MALE; MASS SPECTROMETRY; MICE; MICE, INBRED BALB C; OLIGONUCLEOTIDES, ANTISENSE; SAFETY; TETRAZOLES; THERAPEUTIC EQUIVALENCY;

EID: 33646791810     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.03.005     Document Type: Article

References (36)

1. Crooke S.T. Curr. Mol. Med. 4 (2004) 465-487
2. Crooke S.T. Annu. Rev. Med. 55 (2004) 61-95
3. Crooke S.T. Progress in Antisense Technology. In: Brown D.M. (Ed). Drug Delivery Systems in Cancer Therapy (2004), Humana Press, Totowa, NJ
4. Crooke S.T., and Twain M. Antisense Therapy. In: Thomson A.W., and Lotze M.T. (Eds). Cytokine Handbook. 4th ed. (2003), Elsevier Sciences, London, UK
5. Dias N., and Stein C.A. Mol. Cancer Ther. 1 (2002) 347-355
6. Bennett C.F. Antisense Nucleic Acid Drug Dev. 12 (2002) 215-224
7. Altmann K.-H., Dean N.M., Fabbro D., Freier S.M., Geiger T., Haner R., Husken D., Martin P., Monia B.P., Muller M., Natt F., Nicklin P., Phillips J., Pieles U., Sasmor H., and Moser H.E. Chimia 50 (1996) 168-176
8. A number of second-generation phosphorothioate oligonucleotides are in various stages of pre-clinical and clinical trials against APOB-100, PTP-1B, VLA4, TRPM2, survivin, STAT-3. eIF-eE, etc. for the treatment of a variety of diseases such as cancer, psoriasis, diabetes, asthma, arthritis, multiple sclerosis, etc.
9. Moore M.N., Andrade M., Scozzari A.N., and Krotz A.H. Org. Proc. Res. Dev. 8 (2004) 271-274
10. Krotz A.H., Rentel C., Gorman D., Olsen P., Gaus H.J., McArdle J.V., and Scozzari A.N. Nucleosides Nucleotides Nucleic Acids 23 (2004) 767-775
11. Krotz A.H., Cole D.L., and Ravikumar V.T. Nucleosides Nucleotides Nucleic Acids 22 (2003) 129-134
12. Krotz A.H., McElroy B., Scozzari A.N., Cole D.L., and Ravikumar V.T. Org. Proc. Res. Dev. 7 (2003) 47-52
13. Ravikumar V.T., Kumar R.K., Capaldi D.C., Turney B., Rentel C., and Cole D.L. Org. Proc. Res. Dev. 7 (2003) 259-266
14. Krotz A.H., Gaus H.J., Ravikumar V.T., and Cole D.L. Bioorg. Med. Chem. Lett. 11 (2001) 1863-1867
15. Zhang Z., and Tang J.-Y. Curr. Opin. Drug Discovery Dev. 1 (1998) 304-313 and references cited therein
16. Vargeese C., Carter J., Yegge J., Krivjansky S., Settle A., Kropp E., Peterson K., and Pieken W. Nucleic Acids Res. 26 (1998) 1046-1050
17. Hayakawa Y., Iwase T., Nurminen E.J., Tsukamoto M., and Kataoka M. Tetrahedron 61 (2005) 2203-2209
18. Eleuteri A., Capaldi D.C., Krotz A.H., Cole D.L., and Ravikumar V.T. Org. Proc. Res. Dev. 4 (2000) 182-189 Work comparing novel activators with 1H-tetrazole reported by many laboratories is cited in this reference
19. Krotz A.H., Klopchin P., Cole D.L., and Ravikumar V.T. Bioorg. Med. Chem. Lett. 7 (1997) 73-78
20. Krotz A.H., Klopchin P., Cole D.L., and Ravikumar V.T. Nucleosides Nucleotides 16 (1997) 1637-1640
21. Experience has taught us that yields expressed in terms of weight/micromole of support are more reliable than those expressed in terms of optical density/micromole.
22. Ausubel F.M., Brent R., Kingston R.E., Moore D.D., Seidman J.G., Smith J.A., and Struhl K. Current Protocols in Molecular Biology (1989), John Wiley, New York
23. Sambrook J., Fritsch E.F., and Maniatis T. Molecular Cloning: A Laboratory Manual. 2nd ed. (1989), Cold Spring Harbor Laboratory, Plainview, NY
24. Crooke S.T., Lemonidis K.M., Neilson L., Griffey R., Lesnik E.A., and Monia B.P. Biochem. J. 312 (1995) 599-608
25. Lima W.F., and Crooke S.T. Biochemistry 36 (1997) 390-398
26. Ravikumar V.T., and Cole D.L. Org. Proc. Res. Dev. 6 (2002) 798-806
27. Krishna Kumar, R.; Olsen, P.; Ravikumar, V. T. J. Org. Chem., submitted for publication.
28. Krotz A.H., Cole D.L., and Ravikumar V.T. Bioorg. Med. Chem. 7 (1999) 435-439
29. Krotz A.H., Cart R.L., Moore M.N., Scozzari A.N., Cole D.L., and Ravikumar V.T. Green Chem. (1999) 277-281
30. Krotz A.H., Carty R.L., Scozzari A.N., Cole D.L., and Ravikumar V.T. Org. Proc. Res. Dev. 4 (2000) 190-193
31. Capaldi D.C., Scozzari A.N., Cole D.L., and Ravikumar V.T. Org. Proc. Res. Dev. 3 (1999) 485-487
32. Hayakawa Y., Hirata A., Sugimoto J., Kawai R., Sakakura A., and Kataoka M. Tetrahedron (2001) 8823-8826
33. Cheruvallath Z.S., Wheeler P.D., Cole D.L., and Ravikumar V.T. Nucleosides Nucleotides 18 (1999) 485-492
34. Cheruvallath Z.S., Carty R.L., Moore M.N., Capaldi D.C., Krotz A.H., Wheeler P.D., Turney B.J., Craig S.R., Gaus H.J., Scozzari A.N., Cole D.L., and Ravikumar V.T. Org. Proc. Res. Dev. 4 (2000) 199-204
35. Krotz A.H., Gorman D., Mataruse P., Foster C., Godbout J.D., Coffin C.C., and Scozzari A.N. Org. Proc. Res. Dev. 8 (2004) 852-858
36. Capaldi D.C., Gaus H., Krotz A.H., Arnold J., Carty R.L., Moore M.N., Scozzari A.N., Lowery K., Cole D.L., and Ravikumar V.T. Org. Proc. Res. Dev. 7 (2003) 832-838