Synthesis of 7-deaza-8-bromo cyclic adenosine 5′-diphosphate ribose: the first hydrolysis resistant antagonist at the cADPR receptor

(Note: The full text of this document is currently only available in the PDF Version )

Victoria C. Bailey, Jaswinder K. Sethi, Antony Galione and Barry V. L. Potter


Abstract

7-Deaza-8-bromo cyclic adenosine 5′-diphosphate ribose is synthesised from 7-deazaadenosine via 7-deaza-8-bromo nicotinamide adenine dinucleotide; it is both a more potent antagonist than the 8-bromo derivative and has the advantage of chemical and enzymatic hydrolytic stability.


References

  1. H. C. Lee and R. Aarhus, Cell Reg., 1991, 2, 203 Search PubMed.
  2. S. Takasawa, K. Nata, H. Yonekura and H. Okamoto, Science, 1993, 259, 370 CrossRef CAS.
  3. A. H. Guse, C. P. DaSilva, F. Emmrich, G. A. Ashamu, B. V. L. Potter and G. W. Mayr, J. Immunol., 1995, 155, 3353 Search PubMed.
  4. A. Galione, Trends Pharmacol. Sci., 1992, 13, 304 CrossRef CAS.
  5. N. J. Willmott, J. K. Sethi, T. F. Walseth, H. C. Lee, A. M. White and A. Galione, J. Biol. Chem., 1996, 271, 3699 CrossRef CAS.
  6. H. C. Lee, R. Aarhus, R. M. Graeff, M. E. Gurnack and T. F. Walseth, Nature, 1994, 370, 307 CrossRef CAS.
  7. T. F. Walseth and H. C. Lee, Biochim. Biophys. Acta, 1993, 1178, 235 CrossRef CAS.
  8. S. Rakovic, A. Galione, G. A. Ashamu, B. V. L. Potter and D. A. Terrar, Curr. Biol., 1996, 6, 989 CrossRef CAS.
  9. V. C. Bailey, J. K. Sethi, S. M. Fortt, A. Galione and B. V. L. Potter, Chem. Biol., 1997, 4, 51 CrossRef CAS.
  10. S. Yamada, Q.-M. Gu and C. J. Sih, J. Am. Chem. Soc., 1994, 116, 10 787 CrossRef CAS.
  11. G. A. Ashamu, A. Galione and B. V. L. Potter, J. Chem. Soc., Chem. Commun., 1995, 1359; 1929 RSC.
  12. H. C. Lee and R. Aarhus, Cell Reg., 1991, 2, 203 Search PubMed.
  13. V. C. Bailey, S. M. Fortt, R. J. Summerhill, A. Galione and B. V. L. Potter, FEBS Lett., 1996, 379, 227 CrossRef CAS.
  14. D. E. Bergstrom and A. Brattesani, Nucleic Acids Res., 1980, 8, 6213 CAS.
  15. M. Yoshikawa, T. Kato and T. Takenishi, Bull. Chem. Soc. Jpn., 1969, 42, 3505 CAS.
  16. N. H. Hughes, G. W. Kenner and A. Todd, J. Chem. Soc., 1957, 3733 RSC.
  17. A. Briggs, J. Biol. Chem., 1922, 53, 13 CAS.
  18. D. L. Clapper, T. F. Walseth, P. J. Dargie and H. C. Lee, J. Biol. Chem., 1987, 262, 9561 CAS.
  19. J. E. Pike, L. Slechta and P. F. Weley, J. Heterocycl. Chem., 1964, 1, 159 CAS.
  20. L. Ji, N. A. Corfu and H. Sigel, J. Chem. Soc., Dalton Trans., 1991, 1367 RSC.
  21. E. R. Garrett and P. J. Mehta, J. Am. Chem. Soc., 1972, 94, 8532 CrossRef CAS.
  22. C. M. Perez-Terzic, E. N. Chini, S. S. Shen, T. D. Dousa and D. E. Clapham, Biochem. J., 1995, 312, 955 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.