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Open Access Articles- Top Results for 5-Fluorowillardiine

5-Fluorowillardiine

5-Fluorowillardiine
Stereo, Kekulé, skeletal formula of a minor 5-fluorowillardiine ((2S)-2-amino)
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Other names
2-Amino-3-(5-fluoro-2,4-dioxopyrimidin-1-yl)propanoic acid[citation needed]
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140187-23-1 (S) 7pxN
ChEBI CHEBI:42549 7pxN
ChEMBL ChEMBL123132 7pxN
ChemSpider 1259 7pxY
112461 (S) 7pxY
DrugBank DB02966 7pxN
Jmol-3D images Image
MeSH 5-Fluorowillardiine
PubChem Template:Chembox PubChem/formatTemplate:Chembox PubChem/format
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C7H8FN3O4
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). 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).
 14pxN verify (what is10pxY/10pxN?)
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

  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. PMC 1908955. PMID 8640342. doi:10.1111/j.1476-5381.1995.tb16408.x. 
  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. PMID 8929993. doi:10.1016/0304-3940(96)12335-1. 
  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. PMID 8957243. doi:10.1016/S0014-2999(96)00633-4. 
  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. doi:10.1017/s0952523899162023. 
  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. PMC 1572873. PMID 11487516. doi:10.1038/sj.bjp.0704167. 
  7. Kessler, M; Arai, AC (2006). "Use of 3H fluorowillardiine to study properties of AMPA receptor allosteric modulators". Brain Research 1076 (1): 25–41. PMID 16256076. doi:10.1016/j.brainres.2005.09.024. 

Template:Glutamate receptor ligands

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