Myxothiazol
Names
IUPAC name
7-{2'-[(1S,2E,4E)-1,6-Dimethyl-2,4-heptadienyl][2,4'-bithiazol]-4-yl}-3,5-dimethoxy-4-methyl- (2E,4R,5S,6E)-2,6-heptadienamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.151.224
MeSH Myxothiazol
UNII
  • 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/s1
    Key: XKTFQMCPGMTBMD-YCSHSZEBSA-N
  • C[C@H]([C@H](/C=C/c1csc(n1)c2csc(n2)C(C)/C=C/C=C/C(C)C)OC)/C(=C\C(=O)N)/OC
Properties
C25H33N3O3S2
Molar mass 487.68 g·mol−1
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

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).[1][2]

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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