5-Iodowillardiine

5-Iodowillardiine

Names
IUPAC name (2S)-2-Amino-3-(5-iodo-2,4-dioxopyrimidin-1-yl)propanoic acid
Identifiers
CAS Number	140187-25-3
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL121915
ChemSpider	394358
DrugBank	DB02818
IUPHAR/BPS	4071
PubChem	447196
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/s1 Key: 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/s1 Key: AXXYLTBQIQBTES-BYPYZUCNBL
SMILES 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
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 [77 °F], 100 kPa).
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Infobox references

5-Iodowillardiine is a selective agonist for the kainate receptor, with only limited effects at the AMPA receptor.^[1] It is selective for kainate receptors composed of GluR5 subunits.^[2][3] It is an excitotoxic neurotoxin in vivo,^[4][5] but has proved highly useful for characterising the subtypes and function of the various kainate receptors in the brain and spinal cord.^[6][7][8]

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. 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. 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.
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.
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.
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.