| Revision as of 10:03, 20 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 468556698 of page Stigmatellin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo'). |
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{{cs1 config|name-list-style=vanc}} |
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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 = 450635210 |
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| verifiedrevid = 477859381 |
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|ImageFile=Stigmatellin.svg |
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| ImageFile=Stigmatellin.svg |
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|ImageSize=250px |
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| ImageSize=250px |
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|IUPACName= |
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| PIN=2--8-hydroxy-5,7-dimethoxy-3-methyl-4''H''-1-benzopyran-4-one |
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|OtherNames= |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 91682-96-1 --> |
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| CASNo=91682-96-1 |
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| ChEMBL = 486556 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 32155 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 486556 |
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| PubChem=447884 |
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| PubChem=447884 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 394850 |
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| ChemSpiderID = 394850 |
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| SMILES = O=C\1c2c(O/C(=C/1C)CC(C)(OC)(C)(OC)\C=C\C=C\C(=C\C)C)c(O)c(OC)cc2OC |
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| SMILES = O=C\1c2c(O/C(=C/1C)CC(C)(OC)(C)(OC)\C=C\C=C\C(=C\C)C)c(O)c(OC)cc2OC |
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| InChI = 1/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1 |
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| InChI = 1/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1 |
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| InChIKey = UZHDGDDPOPDJGM-CVOZLMQJBZ |
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| InChIKey = UZHDGDDPOPDJGM-CVOZLMQJBZ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1 |
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| StdInChI = 1S/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UZHDGDDPOPDJGM-CVOZLMQJSA-N |
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| StdInChIKey = UZHDGDDPOPDJGM-CVOZLMQJSA-N |
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| MeSHName=Stigmatellin |
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| MeSHName=Stigmatellin |
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}} |
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|Section2= {{Chembox Properties |
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| Formula=C<sub>30</sub>H<sub>42</sub>O<sub>7</sub> |
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| MolarMass=514.65 g/mol |
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|Section3= {{Chembox Hazards |
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|Section2={{Chembox Properties |
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| Formula=C<sub>30</sub>H<sub>42</sub>O<sub>7</sub> |
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| MolarMass=514.65 g/mol |
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}} |
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'''Stigmatellin''' is a potent ] of the quinol oxidation (Qo) site of the ] complex in ]<ref>{{cite journal | vauthors = von Jagow G, Ohnishi T | title = The chromone inhibitor stigmatellin--binding to the ubiquinol oxidation center at the C-side of the mitochondrial membrane | journal = FEBS Letters | volume = 185 | issue = 2 | pages = 311–5 | date = June 1985 | pmid = 2987042 | doi = 10.1016/0014-5793(85)80929-7 | doi-access = | bibcode = 1985FEBSL.185..311V | s2cid = 37956153 }}</ref> and the ] complex of ] ]s. At higher concentrations, stigmatellin also inhibits ], as a "Class B" inhibitor of that enzyme.<ref>{{cite journal | vauthors = Fato R, Bergamini C, Bortolus M, Maniero AL, Leoni S, Ohnishi T, Lenaz G | title = Differential effects of mitochondrial Complex I inhibitors on production of reactive oxygen species | journal = Biochimica et Biophysica Acta (BBA) - Bioenergetics | volume = 1787 | issue = 5 | pages = 384–92 | date = May 2009 | pmid = 19059197 | pmc = 2724837 | doi = 10.1016/j.bbabio.2008.11.003 }}</ref> |
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Stigmatellin is isolated from the myxobacterium '']'', and contains a 5,7-dimethoxy-8-hydroxychromone aromatic headgroup with a ] alkenyl chain in position 2. Crystal structures for stigmatellin-inhibited ] from bovine, avian, yeast ('']'') and bacterial ('']'', '']'', and '']'') sources are available. Stigmatellin binds at the ] Qo site in the '(heme) bl distal' position, and associates with the Rieske ] via a ] to ] residue 181 (His-181), a ligand to the iron-sulfur cluster of this subunit. This association raises the midpoint potential of the iron-sulfur cluster from 290 to 540 mV and restricts movement of the cytoplasmic domain of the ]. |
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== References == |
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{{reflist}} |
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== Further reading == |
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{{refbegin}} |
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* {{cite book | vauthors = von Jagow G, Link TA | chapter = Use of specific inhibitors on the mitochondrial bc1 complex | title = Biomembranes Part N: Transport in Bacteria, Mitochondria, and Chloroplasts: Protonmotive Force | series = Methods in Enzymology | volume = 126 | pages = 253–71 | date = 1986 | pmid = 2856132 | doi = 10.1016/s0076-6879(86)26026-7 | isbn = 978-0-12-182026-8 }} |
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{{refend}} |
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] |
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] |