5-Iodowillardiine

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477224748

| ImageFile = 5-Iodowillardiine.svg

| ImageSize = 200px

| IUPACName = (2S)-2-Amino-3-(5-iodo-2,4-dioxopyrimidin-1-yl)propanoic acid

| OtherNames =

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4071

| 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

| InChIKey = AXXYLTBQIQBTES-BYPYZUCNBL

| SMILES1 = O=C(O)[C@@H](N)CN1/C=C(/I)C(=O)NC1=O

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 121915

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = AXXYLTBQIQBTES-BYPYZUCNSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 140187-25-3

| PubChem = 447196

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB02818

| SMILES = C1=C(C(=O)NC(=O)N1C[C@@H](C(=O)O)N)I

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 394358

| MeSHName =

}}

|Section2={{Chembox Properties

| C=7 | H=8 | I=1 | N=3 | O=4

| MolarMass = 325.061 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

5-Iodowillardiine is a selective agonist for some kainate receptor subunits with only limited effects at AMPA receptors.{{cite journal | last1 = Patneau | first1 = DK | last2 = Mayer | first2 = ML | last3 = Jane | first3 = DE | last4 = Watkins | first4 = JC | title = Activation and desensitization of AMPA/kainate receptors by novel derivatives of willardiine | journal = Journal of Neuroscience | volume = 12 | issue = 2 | pages = 595–606 | year = 1992 | pmid = 1371315 | doi = 10.1523/jneurosci.12-02-00595.1992 | pmc = 6575614 | doi-access = free }} It activates kainate receptors containing GluK1 (GluR5) or GluK5 (KA2) subunits, but it does not act on GluK2 (GluR6) subunits.{{cite journal | last1 = Swanson | first1 = GT | last2 = Green | first2 = T | last3 = Heinemann | first3 = SF | title = Kainate receptors exhibit differential sensitivities to (S)-5-iodowillardiine | journal = Molecular Pharmacology | volume = 53 | issue = 5 | pages = 942–9 | year = 1998 | pmid = 9584222 }}{{cite journal | last1 = Cui | first1 = C | last2 = Mayer | first2 = ML | title = Heteromeric kainate receptors formed by the coassembly of GluR5, GluR6, and GluR7 | journal = Journal of Neuroscience | volume = 19 | issue = 19 | pages = 8281–91 | year = 1999 | pmid = 10493729 | doi = 10.1523/JNEUROSCI.19-19-08281.1999 | pmc = 6782997 | doi-access = free }}{{Cite journal |last=Alt |first=A. |last2=Weiss |first2=B. |last3=Ogden |first3=A.M. |last4=Knauss |first4=J.L. |last5=Oler |first5=J. |last6=Ho |first6=K. |last7=Large |first7=T.H. |last8=Bleakman |first8=D. |date=2004 |title=Pharmacological characterization of glutamatergic agonists and antagonists at recombinant human homomeric and heteromeric kainate receptors in vitro |url=https://linkinghub.elsevier.com/retrieve/pii/S0028390803004623 |journal=Neuropharmacology |language=en |volume=46 |issue=6 |pages=793–806 |doi=}}{{Cite journal |last=Pollok |first=S. |last2=Reiner |first2=A. |date=2020 |title=Subunit-selective iGluR antagonists can potentiate heteromeric receptor responses by blocking desensitization |url=https://www.pnas.org/doi/full/10.1073/pnas.2007471117 |journal=Proceedings of the National Academy of Sciences |volume=117 |issue=41 |pages=25851–25858 |doi=10.1073/pnas.2007471117 |pmc=7568280 |pmid=32999066}} It is an excitotoxic neurotoxin in vivo,{{cite journal | last1 = Moldrich | first1 = RX | last2 = Cheung | first2 = NS | last3 = Pascoe | first3 = CJ | last4 = Beart | first4 = PM | title = Excitotoxic injury profiles of low-affinity kainate receptor agonists in cortical neuronal cultures | journal = European Journal of Pharmacology | volume = 378 | issue = 2 | pages = R1–3 | year = 1999 | pmid = 10478637 | doi=10.1016/S0014-2999(99)00456-2}}{{cite journal | last1 = Moldrich | first1 = RX | last2 = Beart | first2 = PM | last3 = Pascoe | first3 = CJ | last4 = Cheung | first4 = NS | title = Low-affinity kainate receptor agonists induce insult-dependent apoptosis and necrosis in cultured murine cortical neurons | journal = Journal of Neuroscience Research | volume = 59 | issue = 6 | pages = 788–96 | year = 2000 | pmid = 10700016 | doi = 10.1002/(SICI)1097-4547(20000315)59:6<788::AID-JNR11>3.0.CO;2-K | s2cid = 21898801 }} but has proved highly useful for characterising the subtypes and function of the various kainate receptors in the brain and spinal cord.{{cite journal | last1 = Mascias | first1 = P | last2 = Scheede | first2 = M | last3 = Bloms-Funke | first3 = P | last4 = Chizh | first4 = B | title = Modulation of spinal nociception by GluR5 kainate receptor ligands in acute and hyperalgesic states and the role of gabaergic mechanisms | journal = Neuropharmacology | volume = 43 | issue = 3 | pages = 327–39 | year = 2002 | pmid = 12243762 | doi=10.1016/S0028-3908(02)00112-0| s2cid = 29126134 }}{{cite journal | last1 = Alt | first1 = A | last2 = Weiss | first2 = B | last3 = Ogden | first3 = AM | last4 = Knauss | first4 = JL | last5 = Oler | first5 = J | last6 = Ho | first6 = K | last7 = Large | first7 = TH | last8 = Bleakman | first8 = D | title = Pharmacological characterization of glutamatergic agonists and antagonists at recombinant human homomeric and heteromeric kainate receptors in vitro | journal = Neuropharmacology | volume = 46 | issue = 6 | pages = 793–806 | year = 2004 | pmid = 15033339 | doi = 10.1016/j.neuropharm.2003.11.026 | s2cid = 23514969 }}{{cite journal | last1 = Jane | first1 = DE | last2 = Lodge | first2 = D | last3 = Collingridge | first3 = GL | title = Kainate receptors: pharmacology, function and therapeutic potential | journal = Neuropharmacology | volume = 56 | issue = 1 | pages = 90–113 | year = 2009 | pmid = 18793656 | doi = 10.1016/j.neuropharm.2008.08.023 | s2cid = 25291377 }}