R2146

Radicicol from Diheterospora chlamydosporia

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
• Empirical Formula (Hill Notation): C₁₈H₁₇ClO₆
• CAS Number: 12772-57-5
• Molecular Weight: 364.78
• MDL number: MFCD06795865
• UNSPSC Code: 51111800
• PubChem Substance ID: 24899351
• NACRES: NA.77

Properties

• 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.

Caution

Photosensitive

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301,H340,H350
• Precautionary Statements: P202 - P264 - P280 - P301 + P310 - P405 - P501
• 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