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Key Documents

T5580

Sigma-Aldrich

Myxothiazol

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

Sinonimo/i:

Myxothiazol A

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About This Item

Formula empirica (notazione di Hill):
C25H33N3O3S2
Numero CAS:
Peso molecolare:
487.68
Numero MDL:
Codice UNSPSC:
51111800
ID PubChem:
NACRES:
NA.77

product name

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

Origine biologica

Myxococcus fulvus Mx f85

Livello qualitativo

Saggio

≥98% (HPLC)

Condizioni di stoccaggio

protect from light
under inert gas

Solubilità

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

Spettro attività antibiotica

fungi

Modalità d’azione

enzyme | inhibits

Temperatura di conservazione

−20°C

Stringa SMILE

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
XKTFQMCPGMTBMD-ZDBABOMLSA-N

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Applicazioni

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.

Azioni biochim/fisiol

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.

Nota sulla preparazione

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.

Pittogrammi

Skull and crossbones

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 2 Oral

Codice della classe di stoccaggio

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


Certificati d'analisi (COA)

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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)
Jelle Vriend et al.
Biological chemistry, 400(10), 1347-1358 (2019-01-18)
Organic anion transporters (OATs) 1 and 3 are, besides being uptake transporters, key in several cellular metabolic pathways. The underlying mechanisms are largely unknown. Hence, we used human conditionally immortalized proximal tubule epithelial cells (ciPTEC) overexpressing OAT1 or OAT3 to

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