5-Fluorowillardiine

5-Fluorowillardiine
Other names

2-Amino-3-(5-fluoro-2,4-dioxopyrimidin-1-yl)propanoic acid
Identifiers
CAS number 140187-23-1 (S) N
PubChem 1299, 126569 (S)
ChemSpider 1259 Y, 112461 (S) Y
DrugBank DB02966
MeSH 5-Fluorowillardiine
ChEBI CHEBI:299497 N
ChEMBL CHEMBL123132 N
Jmol-3D images Image 1
Properties
Molecular formula C7H8FN3O4
Molar mass 217.15 g mol−1
Exact mass 217.049883964 g mol-1
log P -1.168
Acidity (pKa) 2.118
Basicity (pKb) 11.879
Isoelectric point 4.28
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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:

References

  1. ^ 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. 
  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. PMC 1908955. PMID 8640342. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1908955. 
  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. 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 1572873. PMID 11487516. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1572873. 
  7. ^ 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.