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Myxothiazol

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Myxothiazol
Names
IUPAC name 7-{2'--4-yl}-3,5-dimethoxy-4-methyl- (2E,4R,5S,6E)-2,6-heptadienamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.151.224 Edit this at Wikidata
MeSH Myxothiazol
PubChem CID
UNII
InChI
  • InChI=1S/C25H33N3O3S2/c1-16(2)9-7-8-10-17(3)24-28-20(15-33-24)25-27-19(14-32-25)11-12-21(30-5)18(4)22(31-6)13-23(26)29/h7-18,21H,1-6H3,(H2,26,29)/b9-7+,10-8+,12-11+,22-13+/t17?,18-,21+/m1/s1Key: XKTFQMCPGMTBMD-YCSHSZEBSA-N
SMILES
  • C((/C=C/c1csc(n1)c2csc(n2)C(C)/C=C/C=C/C(C)C)OC)/C(=C\C(=O)N)/OC
Properties
Chemical formula C25H33N3O3S2
Molar mass 487.68 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Myxothiazol is a chemical compound produced by the myxobacterium Myxococcus fulvus. It is an inhibitor of the mitochondrial cytochrome bc1 complex (coenzyme Q - cytochrome c reductase).

Myxothiazol is a competitive inhibitor of ubiquinol, and binds at the quinol oxidation (Qo) site of the bc1 complex, blocking electron transfer to the Rieske iron-sulfur protein. Binding of myxothiazol induces a red-shift to the visible absorption spectrum of reduced haem bl. In contrast to stigmatellin, myxothiazol does not form a hydrogen bond to the Rieske iron-sulfur protein, binding instead in the 'b-proximal' region of the cytochrome b Qo site. Movement of the cytoplasmic domain of the Rieske protein is therefore unaffected by the binding of this inhibitor.

References

  1. Georg Thierbach, Hans Reichenbach (1981). "Myxothiazol, a new antibiotic interfering with respiration". Antimicrobial Agents and Chemotherapy. 19 (4): 504–507. doi:10.1128/AAC.19.4.504. PMC 181466. PMID 7247372.
  2. Gebhard von Jagow, W. D. Engel (1981). "Complete Inhibition of Electron Transfer from Ubiquinol to Cytochrome by the Combined Action of Antimycin and Myxothiazol". FEBS Letters. 136 (1): 19–24. doi:10.1016/0014-5793(81)81206-9. PMID 7319059.
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