(S)-(-)-5-Fluorowillardiine (hydrochloride)  (Synonyms: (5S)-Fluorowillardiine hydrochloride; (S)-5-Fluorowillardiine hydrochloride)

(S)-(-)-5-Fluorowillardiine ((5S)-Fluorowillardiine; (S)-5-Fluorowillardiine) hydrochloride is a potent, highly selective non-NMDA ionotropic glutamate receptor (iGluR, AMPA/Kainate receptor) agonist. (S)-(-)-5-Fluorowillardiine hydrochloride activates high-affinity AMPA-preferring receptors (EC₅₀ = 0.70 μM) and low-affinity kainate-preferring receptors (EC₅₀ = 170 μM), thereby inducing biphasic dose-dependent neurotoxicity/excitotoxicity. (S)-(-)-5-Fluorowillardiine hydrochloride is applicable to research related to schizophrenia, temporal lobe epilepsy, and bipolar disorder^[1][2][3].

(S)-(-)-5-Fluorowillardiine (10-100 μM; 24 h) hydrochloride induces > 90% neurotoxicity in primary cultured murine cortical neurones via a biphasic mechanism, with high-affinity component activity at AMPA receptors (EC₅₀ = 0.70 μM) and low-affinity component activity at kainate receptors (EC₅₀ = 170 μM)^[1].
(S)-(-)-5-Fluorowillardiine (200 nM-60 μM) hydrochloride potently activates AMPA/kainate receptors on primary dissociated cultures of mouse embryonic hippocampal neurons with an equilibrium EC₅₀ of 1.47 μM, induces strong desensitization (92.5%), exhibits cross-desensitization with other willardiine derivatives, and produces a prolonged inward tail current following agonist removal^[2].
(S)-(-)-5-Fluorowillardiine (0.1 nM-1 mM; 2 h) hydrochloride binds to mouse GluK5 kainate receptor subunits expressed in Sf9 cell membranes with a K_i of 1.79 μM, and exhibits similar affinity for GluK5 and GluK1 subunits^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

253.62

C₇H₉ClFN₃O₄

1321546-70-6

Solid

White to off-white

OC([C@@H](N)CN1C=C(F)C(NC1=O)=O)=O.[H]Cl

Room temperature in continental US; may vary elsewhere.

4°C, sealed storage, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

• [1]. Larm JA, et al. (S)-5-fluorowillardiine-mediated neurotoxicity in cultured murine cortical neurones occurs via AMPA and kainate receptors. Eur J Pharmacol. 1996;314(1-2):249-254.  [Content Brief]

  [2]. Patneau DK, et al. Activation and desensitization of AMPA/kainate receptors by novel derivatives of willardiine. J Neurosci. 1992;12(2):595-606.  [Content Brief]

  [3]. Møllerud S, et al. A pharmacological profile of the high-affinity GluK5 kainate receptor. Eur J Pharmacol. 2016;788:315-320.  [Content Brief]