Synthesis and biological activity of cyclic ADP-carbocyclic-ribose analogs: structure-activity relationship and conformational analysis of N-1-carbocyclic-ribose moiety

Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):655-8. doi: 10.1081/ncn-200060167.

Abstract

Several cyclic ADP-carbocyclic-ribose analogs 3-10 modified in the N-1-carbocyclic-ribose moiety were synthesized. Their Ca2+-releasing activity was estimated in sea urchin eggs to show that the 3"-deoxy analog 6 shows 5 times more potent activity than cADPcR, but the 2",3"-didieoxy-2",3"-unsunsaturated analog 3 has very weak activity. We also calculated their stable conformation and found that 3 and 6 were significantly different in their stable conformation.

MeSH terms

  • Adenosine Diphosphate / chemistry
  • Animals
  • Calcium / metabolism
  • Cyclic ADP-Ribose / analogs & derivatives*
  • Cyclic ADP-Ribose / chemistry
  • Cyclic ADP-Ribose / pharmacology
  • Dose-Response Relationship, Drug
  • Models, Chemical
  • Models, Molecular
  • Molecular Biology / methods
  • Molecular Conformation
  • Protein Conformation
  • Ribose / chemistry*
  • Sea Urchins
  • Structure-Activity Relationship

Substances

  • cyclic ADP-carbocyclic-ribose
  • Cyclic ADP-Ribose
  • Adenosine Diphosphate
  • Ribose
  • Calcium