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Myxothiazol

SIGMA/T5580 - from Myxococcus fulvus Mx f85, ≥98% (HPLC)

Synonym: Myxothiazol A

CAS Number: 76706-55-3
Empirical Formula (Hill Notation): C25H33N3O3S2
Molecular Weight: 487.68
MDL Number: MFCD00043397
Linear Formula: C25H33N3O3S2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-T5580-1MG 1 mg
 $114.00
1/EA		 Add To Favorites
45-T5580-5MG 5 mg
 $456.00
1/EA		 Add To Favorites

 

antibiotic activity spectrum fungi
assay ≥98% (HPLC)
biological source Myxococcus fulvus Mx f85
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-/m0/s1
InChI key XKTFQMCPGMTBMD-ZDBABOMLSA-N
mode of action enzyme | inhibits
Quality Level 200 
SMILES string CO[C@@H](C=Cc1csc(n1)-c2csc(n2)[C@@H](C)C=CC=CC(C)C)[C@@H](C)C(OC)=CC(N)=O
solubility acetone: soluble
  chloroform: soluble 9.80-10.20 mg/mL, clear, colorless to yellow
  dichloromethane: soluble
  DMSO: soluble
  ethanol: soluble
  ethyl acetate: soluble
  methanol: soluble
storage condition protect from light
  under inert gas
storage temp. −20°C
Application: Myxothiazol has been used as a complex IIIQo inhibitor in C. elegans cultures5. It has also been used to analyze mitochondrial oxygen transport in rat cells6.
Application: Myxothiazol has been used in as a mitochondrial electron transport chain (mETC) inhibitor in P19 murine embryonal carcinoma pluripotent cell line and to treat HeLa cells for integrated stress response activation.
Biochem/physiol Actions: Myxothiazol, an antibiotic with activity against fungi and insects, is a strong inhibitor of mitochondrial cytochrome b/c1-segment of respiratory chain. Myxothiazol binds to the quinol oxidation (Qo) site of the bc1 complex, blocking electron transfer to the Rieske iron-sulfur protein in the mitochondrial respiratory chain. Oxygen consumption blockage leads to a cytostatic effect that could be reversed. Myxothiazol, as other Epothilones, which are known for their anti tumor activity, contains a thiazole ring that is formed by the incorporation of cysteine into the polyketide backbone.
Preparation Note: Myxothiazol dissolves in chloroform at 9.80 - 10.20 mg/ml to yield a clear, colorless to yellow solution. It is also soluble in DMSO, acetone, dichloromethane, ethanol, ethyl acetate and methanol.
Symbol GHS06  GHS06
Signal word Danger
Hazard statements H300
Precautionary statements P264 - P301 + P310
Hazard Codes T+
Risk Statements 28
Safety Statements 28-36/37-45
RIDADR UN 3462 6.1 / PGI
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. −20°C
UNSPSC 51111800

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