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Merck
CN

T5580

Sigma-Aldrich

粘噻唑

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

别名:

Myxothiazol A

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关于此项目

经验公式（希尔记法）:
C25H33N3O3S2
CAS Number:
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

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Product Name

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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相关类别

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

监管及禁止进口产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000445559
0000445578
0000445578
0000445559
0000411478

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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
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)
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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