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5-Iodowillardiine

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5-Iodowillardiine
Names
IUPAC name (2S)-2-Amino-3-(5-iodo-2,4-dioxopyrimidin-1-yl)propanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
IUPHAR/BPS
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H8IN3O4/c8-3-1-11(2-4(9)6(13)14)7(15)10-5(3)12/h1,4H,2,9H2,(H,13,14)(H,10,12,15)/t4-/m0/s1Key: AXXYLTBQIQBTES-BYPYZUCNSA-N
  • InChI=1/C7H8IN3O4/c8-3-1-11(2-4(9)6(13)14)7(15)10-5(3)12/h1,4H,2,9H2,(H,13,14)(H,10,12,15)/t4-/m0/s1Key: AXXYLTBQIQBTES-BYPYZUCNBL
SMILES
  • C1=C(C(=O)NC(=O)N1C(C(=O)O)N)I
  • O=C(O)(N)CN1/C=C(/I)C(=O)NC1=O
Properties
Chemical formula C7H8IN3O4
Molar mass 325.061 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

5-Iodowillardiine is a selective agonist for the kainate receptor, with only limited effects at the AMPA receptor. It is selective for kainate receptors composed of GluR5 subunits. It is an excitotoxic neurotoxin in vivo, but has proved highly useful for characterising the subtypes and function of the various kainate receptors in the brain and spinal cord.

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. doi:10.1523/jneurosci.12-02-00595.1992. PMC 6575614. PMID 1371315.
  2. Swanson, GT; Green, T; Heinemann, SF (1998). "Kainate receptors exhibit differential sensitivities to (S)-5-iodowillardiine". Molecular Pharmacology. 53 (5): 942–9. PMID 9584222.
  3. Cui, C; Mayer, ML (1999). "Heteromeric kainate receptors formed by the coassembly of GluR5, GluR6, and GluR7". Journal of Neuroscience. 19 (19): 8281–91. doi:10.1523/JNEUROSCI.19-19-08281.1999. PMC 6782997. PMID 10493729.
  4. Moldrich, RX; Cheung, NS; Pascoe, CJ; Beart, PM (1999). "Excitotoxic injury profiles of low-affinity kainate receptor agonists in cortical neuronal cultures". European Journal of Pharmacology. 378 (2): R1–3. doi:10.1016/S0014-2999(99)00456-2. PMID 10478637.
  5. Moldrich, RX; Beart, PM; Pascoe, CJ; Cheung, NS (2000). "Low-affinity kainate receptor agonists induce insult-dependent apoptosis and necrosis in cultured murine cortical neurons". Journal of Neuroscience Research. 59 (6): 788–96. doi:10.1002/(SICI)1097-4547(20000315)59:6<788::AID-JNR11>3.0.CO;2-K. PMID 10700016. S2CID 21898801.
  6. Mascias, P; Scheede, M; Bloms-Funke, P; Chizh, B (2002). "Modulation of spinal nociception by GluR5 kainate receptor ligands in acute and hyperalgesic states and the role of gabaergic mechanisms". Neuropharmacology. 43 (3): 327–39. doi:10.1016/S0028-3908(02)00112-0. PMID 12243762. S2CID 29126134.
  7. Alt, A; Weiss, B; Ogden, AM; Knauss, JL; Oler, J; Ho, K; Large, TH; Bleakman, D (2004). "Pharmacological characterization of glutamatergic agonists and antagonists at recombinant human homomeric and heteromeric kainate receptors in vitro". Neuropharmacology. 46 (6): 793–806. doi:10.1016/j.neuropharm.2003.11.026. PMID 15033339. S2CID 23514969.
  8. Jane, DE; Lodge, D; Collingridge, GL (2009). "Kainate receptors: pharmacology, function and therapeutic potential". Neuropharmacology. 56 (1): 90–113. doi:10.1016/j.neuropharm.2008.08.023. PMID 18793656. S2CID 25291377.
Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
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