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R2146

Radicicol

Name: Radicicol
Brand: SIGMA

from Diheterospora chlamydosporia, Tyrosine kinase inhibitor, solid

Synonym(s):

Monorden, [1aS-(1aR*,2Z,4E,14*,15aR*)]-8-Chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-6H-oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₁₇ClO₆

CAS Number:

12772-57-5

Molecular Weight:

364.78

UNSPSC Code:

51111800

PubChem Substance ID:

24899351

NACRES:

NA.77

MDL number:

MFCD06795865

Form:

solid

Quality level:

200

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Properties

Product Name

Radicicol from Diheterospora chlamydosporia, solid

form

solid

Quality Level

200

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

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

Gene Information

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

Description

Application

Radicicol from Diheterospora chlamydosporia has been used as an inhibitor of heat shock protein 90 (Hsp90):

to study its effects on lifespan extension and health in Caenorhabditis elegans
to study its effects on protein aggregation in yeast
to study its effects on xanthone sensitized cancer cells

Biochem/physiol Actions

Radicicol is an antifungal macrolactone antibiotic that is found in Diheterospora chlamydosporia, Chaetomium chiversii, and Monosporium bonorden. It functions as an inhibitor of tyrosine kinase and heat shock protein 90 (Hsp90). Radicicol is involved in the suppression of transformation of various proto-oncogenes such as Ras, Mos, and Src. It also suppresses the activity of mitogen-induced cyclooxygenase-2 (COX-2) and phosphoinositide-dependent kinase 1 (PDK1). Radicicol is involved in arresting the cell cycle at the G1-S phase. It exhibits ant-cancer and anti-angiogenic activity in vivo.

Disclaimer

Photosensitive

pictograms

GHS06,GHS08

signalword

Danger

hcodes

H301,H340,H350

pcodes

P202 - P264 - P280 - P301 + P310 - P405 - P501

Hazard Classifications

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

Storage Class

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

Regulatory Information

涉药品监管产品

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Suppression of RAS and MOS transformation by radicicol.

J F Zhao et al.

Oncogene, 11(1), 161-173 (1995-07-06)

Activated versions of ras and mos oncogenes subvert the signal transduction pathway by mimicking transducers at the plasma membrane and cytosol respectively. Radicicol (UCS1006), an antifungal antibiotic, had the ability to suppress transformation by ras and mos oncogenes in a

Radicicol inhibits tyrosine phosphorylation of the mitotic Src substrate Sam68 and retards subsequent exit from mitosis of Src-transformed cells.

I Pillay et al.

Cell growth & differentiation : the molecular biology journal of the American Association for Cancer Research, 7(11), 1487-1499 (1996-11-01)

Sam68 (Src-associated in mitosis 68 kDa) is a protein that associates with and is tyrosine phosphorylated by Src in a mitosis-specific manner, thereby raising the possibility of a role for Src in the regulation of the cell cycle. This study

Radicicol, a protein tyrosine kinase inhibitor, suppresses the expression of mitogen-inducible cyclooxygenase in macrophages stimulated with lipopolysaccharide and in experimental glomerulonephritis.

P Chanmugam et al.

The Journal of biological chemistry, 270(10), 5418-5426 (1995-03-10)

Two isoforms of cyclooxygenase (COX) have been identified in eukaryotic cells: a constitutively expressed COX-1 and mitogen-inducible COX-2, which is selectively expressed in response to various inflammatory stimuli. Thus, COX-2 instead of COX-1 is implicated to produce prostanoids mediating inflammatory

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Global Trade Item Number

SKU	GTIN
R2146-1MG	04061836694609
R2146-5MG	04061832449647