Toward a PKB inhibitor: modification of a selective PKA inhibitor by rational design

Biochemistry. 2002 Aug 13;41(32):10304-14. doi: 10.1021/bi0202530.

Abstract

Protein kinase B/Akt (PKB) is an anti-apoptotic protein kinase that has strongly elevated activity in human malignancies. We therefore initiated a program to develop PKB inhibitors, "Aktstatins". We screened about 500 compounds for PKB inhibitors, using a radioactive assay and an ELISA assay that we established for this purpose. These compounds were produced as combinatorial libraries, designed using the structure of the selective PKA inhibitor H-89 as a starting point. We have identified a successful lead compound, which inhibits PKB activity in vitro and in cells overexpressing active PKB. The new compound shows reversed selectivity to H-89: In contrast to H-89, which inhibits PKA 70 times better than PKB, the new compound, NL-71-101, inhibits PKB 2.4-fold better than PKA. The new compound, but not H-89, induces apoptosis in tumor cells in which PKB is amplified. We have identified structural features in NL-71-101 that are significant for the specificity and that can be used for future development and optimization of PKB inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3 Cells
  • Adenosine Triphosphate / chemistry
  • Animals
  • Apoptosis
  • Binding, Competitive
  • Calcium-Calmodulin-Dependent Protein Kinases / antagonists & inhibitors
  • Calcium-Calmodulin-Dependent Protein Kinases / chemistry
  • Cell Line
  • Combinatorial Chemistry Techniques / methods
  • Cyclic AMP-Dependent Protein Kinases / antagonists & inhibitors*
  • Cyclic AMP-Dependent Protein Kinases / chemistry
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Glycogen Synthase Kinase 3
  • Humans
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Mice
  • Phosphorylation
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Protein Serine-Threonine Kinases / chemistry
  • Proto-Oncogene Proteins / antagonists & inhibitors*
  • Proto-Oncogene Proteins / chemistry
  • Proto-Oncogene Proteins c-akt
  • Structure-Activity Relationship
  • Substrate Specificity
  • Sulfonamides*
  • Tumor Cells, Cultured / enzymology
  • Tumor Cells, Cultured / pathology

Substances

  • Enzyme Inhibitors
  • Isoquinolines
  • NL-71-101
  • Proto-Oncogene Proteins
  • Sulfonamides
  • Adenosine Triphosphate
  • AKT1 protein, human
  • Protein Serine-Threonine Kinases
  • Proto-Oncogene Proteins c-akt
  • Cyclic AMP-Dependent Protein Kinases
  • Calcium-Calmodulin-Dependent Protein Kinases
  • Glycogen Synthase Kinase 3
  • N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide
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