Design and synthesis of biotin-tagged photoaffinity probes of jasmonates

Bioorg Med Chem. 2010 May 1;18(9):3012-9. doi: 10.1016/j.bmc.2010.03.059. Epub 2010 Mar 27.

Abstract

Jasmonates (JAs) are a class of oxylipin compounds that play diverse roles in plant defense and development. The F-box protein coronatine insensitive 1 (COI1) plays a crucial role in the JA signaling pathway. To determine whether COI1 binds directly to jasmonates, three biotin-tagged photoaffinity probes for JAs, a jasmonic acid photoaffinity probe (PAJA), a JAIle photoaffinity probe (PAJAIle), and a coronatine photoaffinity probe (PACOR), were designed and synthesized based on analysis of JA structure-activity relationships and molecular modeling of the interaction between COI1 and JAs. Among them, PACOR exhibited the most significant biological activity in inhibiting root growth, promoting accumulation of JA-responsive proteins, and triggering COI1-JAZ1 interaction in Arabidopsis seedlings. PACOR is an effective tool for elucidating the interaction between COI1 and JA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Amino Acids / metabolism
  • Arabidopsis Proteins / chemistry
  • Arabidopsis Proteins / metabolism
  • Biotin*
  • Cyclopentanes / chemistry*
  • Cyclopentanes / metabolism
  • Drug Design*
  • Indenes / chemistry
  • Indenes / metabolism
  • Light*
  • Models, Molecular
  • Molecular Structure
  • Oxylipins / chemistry*
  • Oxylipins / metabolism
  • Photoaffinity Labels* / chemical synthesis
  • Photoaffinity Labels* / chemistry
  • Photochemistry
  • Signal Transduction
  • Structure-Activity Relationship

Substances

  • Amino Acids
  • Arabidopsis Proteins
  • COI1 protein, Arabidopsis
  • Cyclopentanes
  • Indenes
  • Oxylipins
  • Photoaffinity Labels
  • coronatine
  • jasmonic acid
  • Biotin