T5580

Myxothiazol

Name: Myxothiazol
Brand: SIGMA

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

Synonym(s):

Myxothiazol A

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About This Item

Empirical Formula (Hill Notation):

C₂₅H₃₃N₃O₃S₂

CAS Number:

76706-55-3

Molecular Weight:

487.68

UNSPSC Code:

51111800

PubChem Substance ID:

329826828

NACRES:

NA.77

MDL number:

MFCD00043397

Product Name

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

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 key

XKTFQMCPGMTBMD-ZDBABOMLSA-N

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

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

Quality Level

200

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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New lessons for combinatorial biosynthesis from myxobacteria. The myxothiazol biosynthetic gene cluster of Stigmatella aurantiaca DW4/3-1.

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)

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)

C. elegans as model for the study of high glucose- mediated life span reduction.

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, a new antibiotic interfering with respiration.

G Thierbach et al.

Antimicrobial agents and chemotherapy, 19(4), 504-507 (1981-04-01)

Myxothiazol, a new antibiotic from the myxobacterium Myxococcus fulvus, inhibited the growth of many yeasts and fungi at concentrations between 0.01 and 3 micrograms/ml. It was generally inactive against bacteria. The inhibitory effect was cytostatic. With Candida albicans, Saccharomyces cerevisiae

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