Synthesis of cyclic ADP-carbocylcic-xylose and its 3"-O-methyl analogue as stable and potent Ca2+ -mobilizing agents

Nucleosides Nucleotides Nucleic Acids. 2006;25(4-6):583-99. doi: 10.1080/15257770600685867.

Abstract

We previously showed that 3"-deoxy-cyclic ADP-carbocyclic-ribose (3"-deoxy-cADPcR, 3) is a stable and highly potent analogue of cyclic ADP-ribose (cADPR, 1), a Ca2+ -mobilizing second messenger. From these results, we newly designed another 3"-modified analogues of cADPcR and identified the N1-"xylo"-type carbocyclic analogue, i.e., cADPcX (4), as one of the most potent cADPR-related compounds reported so far.

MeSH terms

  • Animals
  • Biomimetic Materials / chemical synthesis
  • Biomimetic Materials / chemistry
  • Biomimetic Materials / pharmacology
  • Calcium / metabolism*
  • Cyclic ADP-Ribose / analogs & derivatives*
  • Cyclic ADP-Ribose / chemical synthesis
  • Cyclic ADP-Ribose / chemistry
  • Cyclic ADP-Ribose / pharmacology
  • Molecular Structure
  • Ovum / drug effects
  • Ovum / metabolism
  • Sea Urchins
  • Xylose / chemical synthesis*
  • Xylose / chemistry
  • Xylose / pharmacology*

Substances

  • 3''-deoxy-cyclic ADP-carbocyclic-ribose
  • cyclic ADP-carbocyclic-ribose
  • cyclic ADP-carbocyclic-xylose
  • Cyclic ADP-Ribose
  • Xylose
  • Calcium