T5580

Myxothiazol

from Myxococcus fulvus Mx f85, ≥98% (HPLC), lyophilized solid, antibiotic

• Synonym(s): Myxothiazol A
• Empirical Formula (Hill Notation): C₂₅H₃₃N₃O₃S₂
• CAS Number: 76706-55-3
• Molecular Weight: 487.68
• MDL number: MFCD00043397
• UNSPSC Code: 51111800
• PubChem Substance ID: 329826828
• NACRES: NA.77

Properties

• product name: Myxothiazol, from Myxococcus fulvus Mx f85, ≥98% (HPLC)
• biological source: Myxococcus fulvus Mx f85
• Quality Level: 200
• assay: ≥98% (HPLC)
• storage condition: protect from light; under inert gas
• solubility: chloroform: soluble 9.80-10.20 mg/mL, clear, colorless to yellow; DMSO: soluble; acetone: soluble; dichloromethane: soluble; ethanol: soluble; ethyl acetate: soluble; methanol: soluble
• antibiotic activity spectrum: fungi
• mode of action: enzyme | inhibits
• storage temp.: −20°C
• SMILES string: CO[C@@H](\C=C\c1csc(n1)-c2csc(n2)[C@@H](C)\C=C\C=C\C(C)C)[C@@H](C)\C(OC)=C\C(N)=O
• 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

Description

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.

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable