Synthesis, Characterization, and Biological Properties of 8-Azido- and 8-Amino-Substituted 2′,5′-Oligoadenylates

Journal of Medicinal Chemistry

Volumn 46, Issue 23, 2003, Pages 4926-4932

  Sawai, Hiroaki ^a   Hirano, Atushi ^a,c   Mori, Hiroyuki ^a,d   Shinozuka, Kazuo ^a   Dong, Beihua ^b   Silverman, Robert H ^b  

^a GUNMA UNIVERSITY   (Japan)

^b LERNER RESEARCH INSTITUTE   (United States)

^c TAIHO PHARMACEUTICAL CO LTD   (Japan)

^d J F E Chemical Co   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8 AMINOADENOSINE 5' PHOSPHORIMIDAZOLIDE; 8 AZIDOADENOSINE 5' PHOSPHORIMIDAZOLIDE; ADENOSINE DERIVATIVE; ALKALINE PHOSPHATASE; GLYCOSIDE; PHOSPHODIESTERASE; RIBONUCLEASE; SNAKE VENOM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DEPHOSPHORYLATION; DRUG DETERMINATION; DRUG SYNTHESIS; ENZYME ACTIVATION; ENZYME BINDING; ENZYME DEGRADATION; PHOTOAFFINITY LABELING; POLYMERIZATION;

EID: 0242362298     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030035k     Document Type: Article

References (28)

1. Kerr, I. M.; Brown, R. E. pppA2′p5′A2′p5′A: an inhibitor of protein synthesis synthesized with an enzyme fraction from interferon-treated cell. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 256-260.
2. Lengyel, P. Biochemistry of interferons and their actions. Annu. Rev. Biochem. 1982, 51, 251-282.
3. Johnston, M. I.; Torrence, P. F. The role of interferon-induced proteins, double-stranded RNA and 2′,5′-oligoadenylate in the interferon-mediated inhibition of viral translation. In Interferon; Friedman, R. M., Ed. Elsevier: Amsterdam/New York, 1985; Vol. 3, pp 189-298.
4. Torrence, P. F.; Xiao, W.; Li, G.; Khamnei, S. Development of 2′,5′-oligonucleotides as potential therapeutic agent. Curr. Med. Chem. 1994, 1, 176-191.
5. Stark, G. R.; Kerr, I. M.; Williams, B. R. G.; Silverman, R. H.; Schreiber, R. D. How cells respond to interferons. Annu. Rev. Biochem. 1998, 67 227-264.
6. Justesen, J.; Hartmann, R.; Kjeldgaard, N. O. Gene Structure and function of the 2′-5′-oligoadenylate synthetase family. CMLS Cell. Mol. Life Sci. 2000, 57, 1593-1612.
7. Lesiak, K.; Torrence, P. F. Synthesis and Biological Activities of Oligo(8-bromoadenylates) as Analogues of 5′-O-Triphospho-adenylyl(2′ -5′)adenylyl(2′-5′)adenosine. J. Med. Chem. 1986, 29, 1015-1022.
8. Lesiak, K.; Torrence, P. F. Purine 8-Bromination Modulates the Ribonuclease L Binding and Activation Abilities of 2′,5′ -Oligoadenylates. J. Biol. Chem. 1987, 262, 1961-1965.
9. Kanou, M.; Ohomori, H.; Takaku, H.; Yokoyama, S.; Kawai, G.; Suhaldonik, R. J.; Sobol, R W., Jr. Chemical synthesis and biological activities of analogues of 2′,5′-oligoadenylates containing 8-substittued adenosine derivatives. Nucleic Acids Res. 1990, 18, 4439-4446.
10. Suhaldonik, R. J.; Kariko, K.; Sobol, R. W., Jr.; Li, S. W.; Reichenbach, N. L. Haley, B. E. 2- and 8-Azido Photoaffinity Probes. Enzymatic Synthesis, Characterization, and Biological Properties of 2- and 8-Azido Photoprobes of 2-5A and Photo-labeling of 2-5A Binding Protein. Biochemistry 1988, 27, 8840-8846.
11. 8A. Helv. Chim. Acta 1989, 72, 1354-1361.
12. Kitade, Y.; Nakata, Y.; Hirota, K.; Maki, Y.; Pabuccuoglu, A.; Torrence, P. F. 8-Methyladenosien-substitued analogues of 2-5A: synthesis and their biological activities. Nucleic Acid Res. 1991, 15, 4103-4108.
13. Nagai, K.; Kanbara, K.; Nakashima, H.; Yamamoto, N.; Torrence, P. F.; Suhalodonik, R. J.; Takaku, H. Characterization and biological activity of 8-substituted analogs of 2′,5′-oligoadenylates. Biochim. Biophys. Acta 1993, 1156, 321-326.
14. van den Hoogen, Y. T.; Hilgerson, C. M. A.; Brozda, D.; Lesiak, K.; Torrence, P. F.; Altona, C. Conformational analysis of brominated pA2′-5′A2′-5′A analogs An NMR and model-building study. Eur. J. Biochem. 1989, 182, 629-637.
15. Shetzline, S. E.; Suhaldonik, R. J. Characterization of a 2′,5′-Oligoadenylate (2-5A)-dependent 37-kDa RNase L. J. Biol. Chem. 2001, 276, 23707-23711.
16. 2+ ion Catalyst. Tetrahedron 1981, 37, 481-485.
17. Cramer, F.; Schatter, H.; Staab, A. Darstellung von imidazoliden der phosphorsaure. Chem. Ber. 1961, 94, 1612-1616.
18. Sawai, H.; Kuroda, K.; Hojo, T. Uranyl Ion as a Highly Effective Catalyst for Internucleotide Bond Formation. Bull. Chem. Soc. Jpn. 1989, 62, 2018-2023.
19. Sawai, H.; Kuroda, K.; Seki, J.; Ozaki, H. Conformational and Stacking Properties of 3′-5′ and 2′-5′ Linked Oligoribonucleotides Studied by CD. Biopolymers 1996, 39, 173-182.
20. Sawai, H.; Taira, H.; Ishibashi, K.; Itoh, M. Synthesis and Biological Activities of β-Alanyltyrosine Derivative of 2′,5′ -Oligoadenylate, and Its Use in Radiobinding Assay for 2′,5′ -Oligoadenylate. J. Biochem. 1987, 101, 339-346.
21. Dong, B.; Xu, L.; Zhou, A.; Hassel, B. A.; Lee, X.; Torrence, P. F.; Silverman, R. H. Intrinsic molecular activities of the interferon-induced 2-5A-dependent RNase. J. Biol. Chem. 1994, 269, 14153-14158.
22. Dong, B.; Silverman, R. H. A bipartite model of 2-5A-dependent RNase L. J. Biol. Chem. 1997, 272, 22236-22242.
23. Carroll, S. S.; Chen, E.; Viscount, T.; Geib, J.; Sardana, M. K.; Gehman, J.; Kuo, L.C. Cleavage of oligoribonucleotides by the 2′,5′ -oligoadenylate-dependent ribonuclease L. J. Biol. Chem. 1996, 271, 4988-4992.
24. Wreschner, D. H.; McCauley, J. W.; Skehel, J. J.; Kerr, I. M. Interferon action-sequence specificity of the ppp(A2′p)nA-dependent ribonuclease. Nature 1981, 289, 414-417.
25. Floyd-Smith, G.; Slattery, E.; Lengyel, P. Interferon action: RNA cleavage pattern of a (2′-5′)oligoadenylate-dependent endonuclease. Science 1981, 212, 1020-1032.
26. Saenger, W. Syn-anti conformation. In Principles in Nucleic Acid Structure; Springer-Verlag: New York, 1984; pp 69-78.
27. Abdallah, M. A.; Biellmann, J. F.; Nordstroem, B.; Braenden, C. I. The conformation of adenosine diphosphoribose and 8-bromoadenosine diphosphoribose when bound to liver alcohol dehydrogenase. Eur. J. Biochem. 1975, 50, 475-481.
28. Freist, W.; Cramer, F. Synthesis of AMP and ATP analogues. In Nucleic Acid Chemistry, Part 2; Townsend, L. W., Tipson, R. S., Eds.; John Wiley & Sons: New York, 1978; pp 827-841.