| Revision as of 19:32, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 445028219 of page AG_489 for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 00:05, 25 July 2024 edit AnomieBOT (talk | contribs)Bots6,588,874 editsm Dating maintenance tags: {{Unclear-section}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 399347458 |
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| verifiedrevid = 477235479 |
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|ImageFile=Agatoxin-489.png |
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| ImageFile=Agatoxin 489.svg |
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|ImageSize=350 px |
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| ImageSize=300px |
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|IUPACName=N- propylamino]propyl-hydroxyamino] propyl]-2-(1H-indol-3-yl)acetamide |
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| PIN=''N''-(20-Amino-4-hydroxy-4,8,12,17-tetraazaicosan-1-yl)-2-(9''H''-purin-3-yl)acetamide |
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|OtherNames=Agatoxin 489 |
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| OtherNames=Agatoxin 489 |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| IUPHAR_ligand = 2484 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 115840 |
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| ChemSpiderID = 115840 |
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| InChI = 1/C26H47N7O2/c27-11-5-14-28-12-3-4-13-29-15-6-16-30-17-7-19-33(35)20-8-18-31-26(34)21-23-22-32-25-10-2-1-9-24(23)25/h1-2,9-10,22,28-30,32,35H,3-8,11-21,27H2,(H,31,34) |
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| InChI = 1/C26H47N7O2/c27-11-5-14-28-12-3-4-13-29-15-6-16-30-17-7-19-33(35)20-8-18-31-26(34)21-23-22-32-25-10-2-1-9-24(23)25/h1-2,9-10,22,28-30,32,35H,3-8,11-21,27H2,(H,31,34) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LIURIBSBVUMOJS-UHFFFAOYSA-N |
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| StdInChIKey = LIURIBSBVUMOJS-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 128549-96-2 --> |
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| CASNo=128549-96-2 |
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| PubChem=131007 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = O=C(NCCCN(O)CCCNCCCNCCCCNCCCN)Cc2c1ccccc1nc2 |
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| UNII = 4Q64GNZ7KX |
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| PubChem=131007 |
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| SMILES = O=C(NCCCN(O)CCCNCCCNCCCCNCCCN)Cc2c1ccccc1c2 |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 26 | H = 47 | N = 7 | O = 2 |
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| Formula=C<sub>26</sub>H<sub>47</sub>N<sub>7</sub>O<sub>2</sub> |
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| MolarMass=489.69708 |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''AG 489''' (or '''agatoxin 489''') is a component of the ] produced by '']'',<ref name="pmid1519789">{{cite journal | vauthors = Herold EE, Yaksh TL | title = Anesthesia and muscle relaxation with intrathecal injections of AR636 and AG489, two acylpolyamine spider toxins, in rat | journal = Anesthesiology | volume = 77 | issue = 3 | pages = 507–12 | date = September 1992 | pmid = 1519789 | doi = 10.1097/00000542-199209000-00016 }}</ref> a North American funnel web spider. It inhibits the ] ] through a pore blocking mechanism.<ref name="pmid16300403">{{cite journal | vauthors = Kitaguchi T, Swartz KJ | title = An inhibitor of TRPV1 channels isolated from funnel Web spider venom | journal = Biochemistry | volume = 44 | issue = 47 | pages = 15544–9 | date = November 2005 | pmid = 16300403 | doi = 10.1021/bi051494l }}</ref> |
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==Discovery== |
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{{unclear-section|date=July 2024}} |
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To identify new inhibitors, capsaicin receptor channels (TRPV<sub>1</sub>) were screened with a venom library for activity against these channels. In result, the robust inhibitory activity was found in the venom. Venom fractionation using ] ] allowed the purification of two acylpolyamine toxins, AG489 and AG505.<ref name="pmid16300403" /> |
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:]{{clear-left}} |
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Both of these inhibit the TRPV<sub>1</sub> channels<ref>{{cite journal | vauthors = Kaneko Y, Szallasi A | title = Transient receptor potential (TRP) channels: a clinical perspective | journal = British Journal of Pharmacology | volume = 171 | issue = 10 | pages = 2474–507 | date = May 2014 | pmid = 24102319 | pmc = 4008995 | doi = 10.1111/bph.12414 }}</ref> from the extracellular membrane side. From the pore blocking mechanism, the pore mutations that change toxic affinity were identified. As a result, the four mutants decreased toxic affinity and several mutants increased it. Therefore, this was consistent with the scanned TM5-TM6 linker region<ref>{{cite journal | vauthors = Winter Z, Buhala A, Ötvös F, Jósvay K, Vizler C, Dombi G, Szakonyi G, Oláh Z | display-authors = 6 | title = Functionally important amino acid residues in the transient receptor potential vanilloid 1 (TRPV1) ion channel--an overview of the current mutational data | journal = Molecular Pain | volume = 9 | pages = 30 | date = June 2013 | pmid = 23800232 | pmc = 3707783 | doi = 10.1186/1744-8069-9-30 | doi-access = free }}</ref> being the outer vestibule of the channels and further confirming that AG489 is a pore blocker. |
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== See also == |
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* ] |
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== References == |
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{{reflist}} |
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== External links == |
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* {{MeshName|AG+489}} |
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] |
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] |
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] |
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] |