(S)-(-)-5-Fluorowillardiine
(S)-(-)-5-Fluorowillardiine ((5S)-Fluorowillardiine; (S)-5-Fluorowillardiine) is a potent, highly selective non-NMDA ionotropic glutamate receptor (iGluR, AMPA/Kainate receptor) agonist. (S)-(-)-5-Fluorowillardiine 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 is applicable to research related to schizophrenia, temporal lobe epilepsy, and bipolar disorder.
For research use only. We do not sell to patients.
- CAS No.: 140187-23-1
- Formula: C7H8FN3O4
- Molecular Weight:217.15
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
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Biological Activity
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AMPA Receptor |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| Oocyte | EC50 |
0.38 μM
Compound: (S)-2b
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Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR1 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method
Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR1 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method
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[PMID: 18811139] |
| Oocyte | EC50 |
0.38 μM
Compound: (S)-F-Willardiine
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Agonist activity at recombinant GluA1 receptor expressed in Xenopus oocytes
Agonist activity at recombinant GluA1 receptor expressed in Xenopus oocytes
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[PMID: 20096591] |
| Oocyte | EC50 |
0.382 μM
Compound: (S)-F-Willardiine
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Agonist activity at recombinant GluA1 receptor flip isoform expressed in Xenopus oocytes
Agonist activity at recombinant GluA1 receptor flip isoform expressed in Xenopus oocytes
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[PMID: 20096591] |
| Oocyte | EC50 |
0.46 μM
Compound: (S)-2b
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Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR2(Q) expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method
Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR2(Q) expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method
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[PMID: 18811139] |
| Oocyte | EC50 |
0.463 μM
Compound: (S)-F-Willardiine
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Agonist activity at recombinant GluA2 receptor flip isoform expressed in Xenopus oocytes
Agonist activity at recombinant GluA2 receptor flip isoform expressed in Xenopus oocytes
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[PMID: 20096591] |
| Oocyte | EC50 |
11.9 μM
Compound: (S)-2b
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Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR4 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method
Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR4 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method
|
[PMID: 18811139] |
| Oocyte | EC50 |
11.9 μM
Compound: (S)-F-Willardiine
|
Agonist activity at recombinant GluA4 receptor flip isoform expressed in Xenopus oocytes
Agonist activity at recombinant GluA4 receptor flip isoform expressed in Xenopus oocytes
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[PMID: 20096591] |
| Oocyte | EC50 |
20.9 μM
Compound: (S)-2b
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Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR3 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method
Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR3 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method
|
[PMID: 18811139] |
| Oocyte | EC50 |
20.9 μM
Compound: (S)-F-Willardiine
|
Agonist activity at recombinant GluA3 receptor expressed in Xenopus oocytes
Agonist activity at recombinant GluA3 receptor expressed in Xenopus oocytes
|
[PMID: 20096591] |
| Oocyte | EC50 |
20.9 μM
Compound: (S)-F-Willardiine
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Agonist activity at recombinant GluA3 receptor flip isoform expressed in Xenopus oocytes
Agonist activity at recombinant GluA3 receptor flip isoform expressed in Xenopus oocytes
|
[PMID: 20096591] |
(S)-(-)-5-Fluorowillardiine (10-100 μM; 24 h) 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) 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) binds to mouse GluK5 kainate receptor subunits expressed in Sf9 cell membranes with a Ki 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.
Chemical Information
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CAS No. 140187-23-1
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Molecular Weight 217.15
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Formula C7H8FN3O4
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SMILES
OC([C@@H](N)CN1C=C(F)C(NC1=O)=O)=O
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Synonyms
(5S)-Fluorowillardiine; (S)-5-Fluorowillardiine
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[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]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
(S)-(-)-5-Fluorowillardiine Related Classifications
HY-16713 Related Classifications
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- (S)-(-)-5-Fluorowillardiine
- 140187-23-1
- (5S)-Fluorowillardiine
- (S)-5-Fluorowillardiine
- iGluR
- GluK1 kainate receptors
- AMPA-preferring receptors
- schizophrenia
- AMPA/kainate receptor
- murine cortical neurones
- bipolar disorder
- kainate-preferring receptors
- temporal lobe epilepsy
- GluK5 kainate receptors
- mouse embryonic hippocampal neurons
- Inhibitor
- inhibitor
- inhibit