5-Fluorowillardiine
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5-Fluorowillardiine
| 5-Fluorowillardiine | |
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Other names
2-Amino-3-(5-fluoro-2,4-dioxopyrimidin-1-yl)propanoic acid[citation needed] |
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| Identifiers | |
| CAS number | 140187-23-1 (S)  |
| PubChem | 1299, 126569 (S) |
| ChemSpider | 1259  , 112461 (S) |
| DrugBank | DB02966 |
| MeSH | 5-Fluorowillardiine |
| ChEBI | CHEBI:42549 |
| ChEMBL | CHEMBL123132 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C7H8FN3O4 |
| Molar mass | 217.15 g mol−1 |
| log P | -1.168 |
| Acidity (pKa) | 2.118 |
| Basicity (pKb) | 11.879 |
| Isoelectric point | 4.28 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
5-Fluorowillardiine is a selective agonist for the AMPA receptor,[1][2][3] with only limited effects at the kainate receptor.[4] It is an excitotoxic neurotoxin when used in vivo and so is rarely used in intact animals, but it is widely used to selectively stimulate AMPA receptors in vitro.[5][6][7]
5-Fluorowillardiine exists as two distinct isomers:
- (2R) or D
- (2S) or L
References
- ^ Patneau, DK; Mayer, ML; Jane, DE; Watkins, JC (1992). "Activation and desensitization of AMPA/kainate receptors by novel derivatives of willardiine". Journal of Neuroscience 12 (2): 595–606. PMID 1371315.
- ^ Hawkins, LM; Beaver, KM; Jane, DE; Taylor, PM; Sunter, DC; Roberts, PJ (1995). "Characterization of the pharmacology and regional distribution of (S)-3H-5-fluorowillardiine binding in rat brain". British Journal of Pharmacology 116 (3): 2033–9. PMC 1908955. PMID 8640342. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1908955.
- ^ Lunn, ML; Ganakas, AM; Mercer, LD; Lawrence, AJ; Beart, PM (1996). "Localisation and properties of AMPA-insensitive kainate sites: receptor autoradiography and gene expression in rat brain". Neuroscience letters 204 (1–2): 121–4. doi:10.1016/0304-3940(96)12335-1. PMID 8929993.
- ^ Larm, JA; Cheung, NS; Beart, PM (1996). "(S)-5-fluorowillardiine-mediated neurotoxicity in cultured murine cortical neurones occurs via AMPA and kainate receptors". European Journal of Pharmacology 314 (1–2): 249–54. doi:10.1016/S0014-2999(96)00633-4. PMID 8957243.
- ^ Jensen, RJ (1999). "Responses of directionally selective retinal ganglion cells to activation of AMPA glutamate receptors". Visual neuroscience 16 (2): 205–19. PMID 10367956.
- ^ Olivera, S; Rodriguez-Ithurralde, D; Henley, JM (2001). "Regional localization and developmental profile of acetylcholinesterase-evoked increases in 3H-5-fluorowillardiine binding to AMPA receptors in rat brain". British Journal of Pharmacology 133 (7): 1055–62. doi:10.1038/sj.bjp.0704167. PMC 1572873. PMID 11487516. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1572873.
- ^ Kessler, M; Arai, AC (2006). "Use of 3Hfluorowillardiine to study properties of AMPA receptor allosteric modulators". Brain Research 1076 (1): 25–41. doi:10.1016/j.brainres.2005.09.024. PMID 16256076.
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