Glycogen synthase kinase-3β inhibition of 6-(methylsulfinyl)hexyl isothiocyanate derived from wasabi (Wasabia japonica Matsum)

Biosci Biotechnol Biochem. 2011;75(1):136-9. doi: 10.1271/bbb.100507. Epub 2011 Jan 7.

Abstract

A new biological activity of 6-(methylsulfinyl)hexyl isothiocyanate derived from Wasabia japonica was discovered as an inhibitor of glycogen synthase kinase-3β. The most potent isothiocyanate, 9-(methylsulfinyl)hexyl isothiocyanate, inhibited glycogen synthase kinase-3β at a K(i) value of 10.5 µM and showed ATP competitive inhibition. The structure-activity relationship revealed an inhibitory potency of methylsulfinyl isothiocyanate dependent on the alkyl chain length and the sulfoxide, sulfone, and/or the isothiocyanate moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycogen Synthase Kinase 3 / antagonists & inhibitors*
  • Glycogen Synthase Kinase 3 beta
  • Humans
  • Inhibitory Concentration 50
  • Isothiocyanates / chemistry*
  • Isothiocyanates / pharmacology*
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacology*
  • Wasabia / chemistry*

Substances

  • 6-methylsulfinylhexyl isothiocyanate
  • Isothiocyanates
  • Protein Kinase Inhibitors
  • GSK3B protein, human
  • Glycogen Synthase Kinase 3 beta
  • Glycogen Synthase Kinase 3