5-Iodowillardiine

Last updated
5-Iodowillardiine
5-Iodowillardiine.svg
Names
IUPAC name
(2S)-2-Amino-3-(5-iodo-2,4-dioxopyrimidin-1-yl)propanoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
PubChem CID
  • 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/s1 Yes check.svgY
    Key: AXXYLTBQIQBTES-BYPYZUCNSA-N Yes check.svgY
  • 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/s1
    Key: AXXYLTBQIQBTES-BYPYZUCNBL
  • C1=C(C(=O)NC(=O)N1C[C@@H](C(=O)O)N)I
  • O=C(O)[C@@H](N)CN1/C=C(/I)C(=O)NC1=O
Properties
C7H8IN3O4
Molar mass 325.061 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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5-Iodowillardiine is a selective agonist for some kainate receptor subunits with only limited effects at AMPA receptors. [1] It activates kainate receptors containing GluK1 (GluR5) or GluK5 (KA2) subunits, but it does not act on GluK2 (GluR6) subunits. [2] [3] [4] [5] It is an excitotoxic neurotoxin in vivo, [6] [7] but has proved highly useful for characterising the subtypes and function of the various kainate receptors in the brain and spinal cord. [8] [9] [10]

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. doi:10.1016/S0026-895X(24)13262-2. 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. ↑ Alt, A.; Weiss, B.; Ogden, A.M.; Knauss, J.L.; Oler, J.; Ho, K.; Large, T.H.; 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.
  5. ↑ Pollok, S.; Reiner, A. (2020). "Subunit-selective iGluR antagonists can potentiate heteromeric receptor responses by blocking desensitization". Proceedings of the National Academy of Sciences. 117 (41): 25851–25858. Bibcode:2020PNAS..11725851P. doi: 10.1073/pnas.2007471117 . PMC   7568280 . PMID   32999066.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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.
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