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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

Cat #: F-205
Alternative Name Fluoro-willardiine, (S)-(−)-α-Amino-5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid
Lyophilized Powder yes
  • Bioassay Tested
    • 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
    PubChem CID 126569
    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.
    References-Activity
    1. Jane, D.E. et al. (1997) J. Med. Chem. 40, 3645.
    2. Patneau, D.K. et al. (1992) J. Neurosci. 12, 595.
    Shipping and storage Shipped at room temperature. Product as supplied can be stored intact at room temperature for several weeks. For longer periods, it should be stored at -20°C.
    Solubility Soluble up to 50 mM in 1.1eq NaOH, with gentle heating. Centrifuge all products before handling (10000 x g 5 min).
    Storage of solutions 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.
      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 - Scientific background
    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
    Lyophilized Powder
    Last update: 12/08/2021

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

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    For research purposes only, not for human use
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