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安全信息

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:
76706-55-3
分子量:
487.68
MDL编号:
MFCD00043397
UNSPSC代码:
51111800
PubChem化学物质编号:
329826828
NACRES:
NA.77

产品名称

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

生物来源

Myxococcus fulvus Mx f85

质量水平

200

方案

≥98% (HPLC)

储存条件

protect from light
under inert gas

溶解性

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

抗生素抗菌谱

fungi

作用机制

enzyme | inhibits

储存温度

−20°C

SMILES字符串

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 key

XKTFQMCPGMTBMD-ZDBABOMLSA-N

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应用

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.

制备说明

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.

象形图

Skull and crossbones
GHS06

警示用语：

Danger

危险声明

H300

危险分类

Acute Tox. 2 Oral

储存分类代码

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

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number
0000404449
0000338466
0000317543
0000404449
0000317543

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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)
Mitochondrial unfolded protein response controls matrix pre-RNA processing and translation
Munch C and Harper JW
Nature, 534(7609), 710-710 (2016)
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
G Thierbach et al.
Biochimica et biophysica acta, 638(2), 282-289 (1981-12-14)
Myxothiazol inhibited oxygen consumption of beef heart mitochondria in the presence and absence of 2,4-dinitrophenol, as well as NADH oxidation by submitochondrial particles. The doses required for 50% inhibition were 0.58 mol myxothiazol/mol cytochrome b for oxygen consumption of beef
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