Cyclic aristeromycin diphosphate ribose: a potent and poorly hydrolysable Ca(2+)-mobilising mimic of cyclic adenosine diphosphate ribose

FEBS Lett. 1996 Feb 5;379(3):227-30. doi: 10.1016/0014-5793(95)01515-9.

Abstract

Cyclic aristeromycin diphosphate ribose, a carbocyclic analogue of cyclic adenosine diphosphate ribose, was synthesised using a chemo-enzymatic route involving activation of aristeromycin 5'-phosphate by diphenyl phosphochloridate. The calcium-releasing properties of this novel analogue were investigated in sea urchin egg homogenates. While cyclic aristeromycin diphosphate ribose has a calcium release profile similar to that of cyclic adenosine diphosphate ribose (EC50 values are 80 nM and 30 nM, respectively), it is degraded significantly more slowly (t1/2 values are 170 min and 15 min, respectively) and may, therefore, be a useful tool to investigate the activities of cyclic adenosine diphosphate ribose.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives
  • Adenosine / chemistry
  • Adenosine Diphosphate Ribose / analogs & derivatives*
  • Adenosine Diphosphate Ribose / chemistry
  • Adenosine Diphosphate Ribose / metabolism
  • Animals
  • Calcium / metabolism*
  • Cyclic ADP-Ribose
  • Hydrolysis
  • Ovum / metabolism*
  • Phosphorylation
  • Sea Urchins

Substances

  • cyclic aristeromycin diphosphate ribose
  • Cyclic ADP-Ribose
  • aristeromycin
  • Adenosine Diphosphate Ribose
  • Adenosine
  • Calcium