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Merck

R2146

Radicicol

greener alternative

from Diheterospora chlamydosporia, Tyrosine kinase inhibitor, solid

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C18H17ClO6
Numéro CAS:
12772-57-5
Poids moléculaire :
364.78
UNSPSC Code:
51111800
PubChem Substance ID:
24899351
NACRES:
NA.77
MDL number:
MFCD06795865
Form:
solid
Quality level:
200

Principaux documents

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Nom du produit

Radicicol from 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)

Catégories apparentées

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

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Classe de stockage

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000486037
0000486037
0000458784
0000458784
0000320580

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
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
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
T Oikawa et al.
European journal of pharmacology, 241(2-3), 221-227 (1993-09-14)
Angiogenesis plays a significant role in various pathological states, including the progressive growth of solid tumors, rheumatoid arthritis, psoriasis, and diabetic retinopathy, in addition to its crucial role in embryonic development. Recent studies have revealed that an angiogenesis inhibitor is
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)
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