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R2146

Sigma-Aldrich

Radicicol from Diheterospora chlamydosporia

greener alternative

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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About This Item

Formule empirique (notation de Hill):
C18H17ClO6
Numéro CAS:
12772-57-5
Poids moléculaire :
364.78
Numéro MDL:
MFCD06795865
Code UNSPSC :
51111800
ID de substance PubChem :
24899351
Nomenclature NACRES :
NA.77

Forme

solid

Niveau de qualité

200

Score du produit alternatif plus écologique

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

Caractéristiques du produit alternatif plus écologique

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

sustainability

Greener Alternative Product

Couleur

white to yellow-white

Solubilité

ethanol: 10 mg/mL

Spectre d'activité de l'antibiotique

fungi

Autre catégorie plus écologique

, Re-engineered

Mode d’action

enzyme | inhibits

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

WYZWZEOGROVVHK-GTMNPGAYSA-N

Informations sur le gène

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

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

Actions biochimiques/physiologiques

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.

Attention

Photosensitive

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H340,H350

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
Chizuka Higashi et al.
Biological & pharmaceutical bulletin, 35(5), 725-730 (2012-06-13)
Primary effusion lymphoma (PEL) is an aggressive neoplasm caused by Kaposi's sarcoma-associated herpesvirus (KSHV) in immunosuppressed patients and human immunodeficiency virus (HIV)-infected homosexual males. We evaluated the cytotoxic effects of heat shock protein 90 (HSP90) inhibitors on PEL cells. The
Florian H Schopf et al.
Molecular cell, 74(1), 73-87 (2019-03-17)
The Hsp90 chaperone machinery in eukaryotes comprises a number of distinct accessory factors. Cns1 is one of the few essential co-chaperones in yeast, but its structure and function remained unknown. Here, we report the X-ray structure of the Cns1 fold
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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