Merck
All Photos(1)

T5580

Sigma-Aldrich

Myxothiazol

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

Synonym(s):
Anti-CHDSKM
Empirical Formula (Hill Notation):
C25H33N3O3S2
CAS Number:
Molecular Weight:
487.68
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

Myxococcus fulvus Mx f85

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

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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.
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.

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1B - Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More documents

Quotes and Ordering

Andreas Schlotterer et al.
Diabetes, 58(11), 2450-2456 (2009-08-14)
Establishing Caenorhabditis elegans as a model for glucose toxicity-mediated life span reduction. C. elegans were maintained to achieve glucose concentrations resembling the hyperglycemic conditions in diabetic patients. The effects of high glucose on life span, glyoxalase-1 activity, advanced glycation end
Myxothiazol an antibiotic from Myxococcus fuluvus (Myxobacteraies). cultivation, isolation, physico-chemical and biological properties.
Gerth, K., et al.
The Journal of Antibiotics, 33, 1474-1479 (2002)
B Silakowski et al.
The Journal of biological chemistry, 274(52), 37391-37399 (1999-12-22)
The biosynthetic mta gene cluster responsible for myxothiazol formation from the fruiting body forming myxobacterium Stigmatella aurantiaca DW4/3-1 was sequenced and analyzed. Myxothiazol, an inhibitor of the electron transport via the bc(1)-complex of the respiratory chain, is biosynthesized by a
Mitochondrial unfolded protein response controls matrix pre-RNA processing and translation
Munch C and Harper JW
Nature, 534(7609), 710-710 (2016)
Eric Raddatz et al.
American journal of physiology. Heart and circulatory physiology, 300(3), H820-H835 (2011-01-05)
The ability of the developing myocardium to tolerate oxidative stress during early gestation is an important issue with regard to possible detrimental consequences for the fetus. In the embryonic heart, antioxidant defences are low, whereas glycolytic flux is high. The

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