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(S)-(-)-5-Fluorowillardiine

Fluoro-willardiine, (S)-(−)-α-Amino-5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid
A Highly Potent and Selective Agonist of AMPA Receptors
  • New
Cat #: F-205
  • Lyophilized Powder
  • Bioassay Tested
  • Shipped at Room Temp.
    • Source Synthetic
    MW: 217.16
    Purity: >97%
    Effective concentration 10 nM – 1 µM.
    Structure
    Chemical name (2S)-2-amino-3-(5-fluoro-2,4-dioxopyrimidin-1-yl)propanoic acid.
    Molecular formula C7H8FN3O4.
    CAS No.: 140187-23-1
    Activity (S)-(-)-5-Fluorowillardiine is a potent and selective AMPA receptor agonist (Ki values of 14.7 nM and 25.1 nM, on hGluR1 and hGluR2, respectively), selective over kainate receptors (Ki of 1.82 µM on hGluR5). More potent and selective than AMPA1-2.
    Storage before reconstitution Store at room temperature.
    Reconstitution Soluble up to 50 mM in 1.1eq NaOH, with gentle heating. Centrifuge all products before handling (10000 x g 5 min).
    Storage after reconstitution Store at -20°C. It is recommended to aliquot stock solutions to prevent repeated thawing and freezing.
    Our bioassay
    Alomone Labs (S)-(-)-5-Fluorowillardiine activates AMPA receptors expressed in Xenopus oocytes.
    Representative time course of GluA1 channel current activation by a continuous application of 50 nM and 500 nM (S)-(-)-5-Fluorowillardiine (#F-205), duration indicated by bars (bottom left), compared to activation by 5 µM (S)-AMPA (#A-267), at a holding potential of -80 mV.
    References
    1. Jane, D.E. et al. (1997) J. Med. Chem. 40, 3645.
    2. Patneau, D.K. et al. (1992) J. Neurosci. 12, 595.
    3. Chizh, B.A. et al. (1994) Br. J. Pharmacol. 112, 843.
    4. Perrais, D. et al. (2009) Neuropharmacology 56, 131.
    Scientific background

    (S)-(-)-5-Fluorowillardiine is a highly potent and selective AMPA receptor agonist. 5-Fluorowillardiine is synthesized as two distinct isomers: R and S. (S)-(-)-5-Fluorowillardiine is selective over kainate receptors and is more potent and selective than AMPA itself; at equilibrium, (S)-(-)-5-Fluorowillardiine is seven times more potent than AMPA and 30 times more potent than willardiine. (S)-(-)-5-Fluorowillardiine demonstrates an EC50 value of 1.5 µm1,2.

    The ionotropic glutamate AMPA receptors (AMPARs) are the primary receptors mediating fast excitatory synaptic transmission in the mammalian brain. This function is essential for synaptic plasticity and learning and memory3,4.

    Target AMPA receptors
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    Last update: 20/09/2018

    (S)-(-)-5-Fluorowillardiine (#F-205) is a highly pure, synthetic, and biologically active compound.

    For research purposes only, not for human use
    Citations
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