Liquid-phase synthesis of a pegylated adenosine-oligoarginine conjugate, cell-permeable inhibitor of cAMP-dependent protein kinase

Bioorg Med Chem Lett. 2003 Sep 15;13(18):3035-9. doi: 10.1016/s0960-894x(03)00641-3.

Abstract

An adenosine-oligoarginine conjugate (ARC) was assembled in a stepwise manner on a poly(ethylene glycol) carrier. The pegylated conjugate inhibited cAMP-dependent protein kinase with IC(50)=460 nM and the cellular uptake of its BODIPY FL derivative was demonstrated and compared to that of free ARC with fluorescence microscopy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / chemistry
  • Cell Membrane Permeability
  • Cyclic AMP-Dependent Protein Kinases / antagonists & inhibitors*
  • Drug Carriers / chemical synthesis*
  • Drug Carriers / pharmacokinetics
  • Drug Design
  • Drug Stability
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacokinetics
  • HeLa Cells
  • Humans
  • Inhibitory Concentration 50
  • Microscopy, Fluorescence
  • Molecular Structure
  • Peptides / chemistry*
  • Polyethylene Glycols / chemistry*
  • Structure-Activity Relationship

Substances

  • Drug Carriers
  • Enzyme Inhibitors
  • Peptides
  • polyarginine
  • Polyethylene Glycols
  • Cyclic AMP-Dependent Protein Kinases
  • Adenosine