5-Fluorowillardiine

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5-Fluorowillardiine
Stereo, Kekulé, skeletal formula of a minor 5-fluorowillardiine ((2S)-2-amino)
Names
Other names
2-Amino-3-(5-fluoro-2,4-dioxopyrimidin-1-yl)propanoic acid[citation needed]
Identifiers
140187-23-1 (S) N
3D model (Jmol) Interactive image
ChEBI CHEBI:42549 N
ChEMBL ChEMBL123132 N
ChemSpider 1259 YesY
112461 (S) YesY
DrugBank DB02966 N
ECHA InfoCard 100.162.280
MeSH 5-Fluorowillardiine
PubChem 1299
126569 (S)
Properties
C7H8FN3O4
Molar mass 217.16 g·mol−1
log P -1.168
Acidity (pKa) 2.118
Basicity (pKb) 11.879
Isoelectric point 4.28
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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[edit]

  1. ^ Patneau, DK; Mayer, ML; Jane, DE; Watkins, JC (1992). "Activation and Desensitization of AMPA / Kainate Receptors by Novel Derivatives of Willardiine" (PDF). Journal of Neuroscience. 12 (2): 595–606. PMID 1371315. 
  2. ^ 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. doi:10.1111/j.1476-5381.1995.tb16408.x. PMC 1908955Freely accessible. PMID 8640342. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ Jensen, RJ (1999). "Responses of directionally selective retinal ganglion cells to activation of AMPA glutamate receptors". Visual Neuroscience. 16 (2): 205–19. doi:10.1017/s0952523899162023. PMID 10367956. 
  6. ^ 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 1572873Freely accessible. PMID 11487516. 
  7. ^ Kessler, M; Arai, AC (2006). "Use of 3H fluorowillardiine 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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