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R2146

Sigma-Aldrich

Radicicol from Diheterospora chlamydosporia

greener alternative

solid

Synonym(e):

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

Empirische Formel (Hill-System):
C18H17ClO6
CAS-Nummer:
12772-57-5
Molekulargewicht:
364.78
MDL-Nummer:
MFCD06795865
UNSPSC-Code:
51111800
PubChem Substanz-ID:
24899351
NACRES:
NA.77

Form

solid

Qualitätsniveau

200

Grünere Alternativprodukt-Bewertung

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

Grünere Alternativprodukt-Eigenschaften

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

sustainability

Greener Alternative Product

Farbe

white to yellow-white

Löslichkeit

ethanol: 10 mg/mL

Wirkungsspektrum von Antibiotika

fungi

Grünere Alternativprodukt-Kategorie

, Re-engineered

Wirkungsweise

enzyme | inhibits

Lagertemp.

−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

InChIKey

WYZWZEOGROVVHK-GTMNPGAYSA-N

Angaben zum Gen

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

Anwendung

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. Wirkung

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.

Vorsicht

Photosensitive

Piktogramme

Skull and crossbonesHealth hazard
GHS06,GHS08

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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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