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T5580

Myxothiazol

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

Synonyme(s) :

Myxothiazol A

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A propos de cet article

Formule empirique (notation de Hill) :
C25H33N3O3S2
Numéro CAS:
76706-55-3
Poids moléculaire :
487.68
UNSPSC Code:
51111800
PubChem Substance ID:
329826828
NACRES:
NA.77
MDL number:
MFCD00043397
Assay:
≥98% (HPLC)
Quality level:
200
Storage condition:
protect from light, under inert gas
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Nom du produit

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

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

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
0000526470
0000526471
0000526470
0000526471
0000524707

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Contenu apparenté

Data Sheet - T5580

Instructions

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
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)
Mitochondrial unfolded protein response controls matrix pre-RNA processing and translation
Munch C and Harper JW
Nature, 534(7609), 710-710 (2016)
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