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R2146

Sigma-Aldrich

Radicicol from Diheterospora chlamydosporia

greener alternative

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:
Molecular Weight:
364.78
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

form

solid

Quality Level

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

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

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.

Caution

Photosensitive

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

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


Certificates of Analysis (COA)

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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
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
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
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
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

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