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Merck
CN

R2146

Radicicol

greener alternative

from Diheterospora chlamydosporia, Tyrosine kinase inhibitor, solid

别名:

[1aS-(1aR*,2Z,4E,14*,15aR*)]-8-氯-1a,14,15,15a-四氢-9,11-二羟基-14-甲基-6H-环氧乙烯并[e][2]苯并氧杂环-6,12(7H)-二酮, 根赤壳菌素

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关于此项目

经验公式（希尔记法）:
C18H17ClO6
化学文摘社编号:
12772-57-5
分子量:
364.78
UNSPSC Code:
51111800
PubChem Substance ID:
24899351
NACRES:
NA.77
MDL number:
MFCD06795865

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产品名称

根赤壳霉素 来源于Diheterospora chlamydosporia, solid

SMILES string

C[C@@H]1C[C@H]2O[C@@H]2C=C\C=C\C(=O)Cc3c(Cl)c(O)cc(O)c3C(=O)O1

InChI

1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2+,5-3-/t9-,14-,15-/m1/s1

InChI key

WYZWZEOGROVVHK-GTMNPGAYSA-N

form

solid

greener alternative product score

old score: 15
new score: 9
Find out more about DOZN™ Scoring

greener alternative product characteristics

Waste Prevention
Atom Economy
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

color

white to yellow-white

solubility

ethanol: 10 mg/mL

antibiotic activity spectrum

fungi

greener alternative category

, Re-engineered

mode of action

enzyme | inhibits

storage temp.

−20°C

Quality Level

200

Gene Information

human ... HSP90AA1(3320), SRC(6714)
rat ... Src(83805)

相关类别

Application

根赤壳菌素（来源于Diheterospora chlamydosporia）作为热休克蛋白90(Hsp90)抑制剂已用于：
  • 研究其对秀丽隐杆线虫寿命延长和健康的影响
  • 研究其对酵母蛋白聚集的影响
  • 研究其对氧杂蒽酮敏化癌细胞的影响

Biochem/physiol Actions

根赤壳菌素是一种抗真菌大环内酯抗生素，存在于Diheterospora chlamydosporia、Chaetomium chiversii和Monosporium bonorden真菌中。它可用作酪氨酸激酶和热休克蛋白90(Hsp90)的抑制剂。根赤壳菌素参与抑制Ras、Mos和Src等各种原癌基因转化。它还可抑制丝裂原诱导型一氧化氮合酶(COX-2)和磷脂酰肌醇依赖性蛋白激酶1(PDK1)的活性。根赤壳菌素参与将细胞周期阻滞在G1-S期。它在体内具有抗癌和抗血管生成活性。

Disclaimer

光敏性

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Carc. 1B - Muta. 1B

存储类别

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000486037
0000486037
0000458784
0000458784
0000320580

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S V Sharma et al.
Oncogene, 16(20), 2639-2645 (1998-06-19)
Radicicol, a macrocyclic anti-fungal antibiotic, has the ability to suppress transformation by diverse oncogenes such as Src, Ras and Mos. Despite this useful property, the mechanism by which radicicol exerts its anti-transformation effects is currently unknown. To understand the transformation-suppressing
Yonghan He et al.
Biochemical and biophysical research communications, 436(2), 169-174 (2013-06-04)
Heat shock protein 90 (Hsp90) is involved in various cellular processes, such as cell proliferation, differentiation and apoptosis. As adipocyte differentiation plays a critical role in obesity development, the present study investigated the effect of an Hsp90 inhibitor radicicol on
Targeting DNA topoisomerases in parasitic protozoa by natural products: Chemical and biological perspectives
Chowdhury S, et al.
Studies in Natural Products Chemistry, 67, 389-410 (2021)
Peter W Piper et al.
Open biology, 2(12), 120138-120138 (2012-12-29)
Heat shock protein 90 (Hsp90) is a promising cancer drug target as a molecular chaperone critical for stabilization and activation of several of the oncoproteins that drive cancer progression. Its actions depend upon its essential ATPase, an activity fortuitously inhibited
Y Shimada et al.
The Journal of antibiotics, 48(8), 824-830 (1995-08-01)
The anti-fungal antibiotic, radicicol, produced in the culture broth of Neocosmospora tenuicristata, was found to induce differentiation of HL-60 cells into macrophages from the following evidence: (1) it caused morphological changes into macrophage-like cells, (2) induced NBT (Nitrobluetetrazolium) reduction activity
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