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Merck

T5580

Sigma-Aldrich

粘噻唑

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

别名:

Myxothiazol A

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About This Item

经验公式(希尔记法):
C25H33N3O3S2
CAS号:
分子量:
487.68
MDL號碼:
分類程式碼代碼:
51111800
PubChem物質ID:
NACRES:
NA.77

product name

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

生物源

Myxococcus fulvus Mx f85

品質等級

化驗

≥98% (HPLC)

儲存條件

protect from light
under inert gas

溶解度

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

抗生素活性譜

fungi

作用方式

enzyme | inhibits

儲存溫度

−20°C

SMILES 字串

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 密鑰

XKTFQMCPGMTBMD-ZDBABOMLSA-N

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應用

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.

生化/生理作用

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.

準備報告

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.

象形圖

Skull and crossbones

訊號詞

Danger

危險聲明

危險分類

Acute Tox. 2 Oral

儲存類別代碼

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

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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其他客户在看

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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