R2146

Radicicol

from Diheterospora chlamydosporia, Tyrosine kinase inhibitor, 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
• UNSPSC Code: 51111800
• PubChem Substance ID: 24899351
• NACRES: NA.77
• MDL number: MFCD06795865

Properties

• Product Name: 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)

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[1]
• to study its effects on protein aggregation in yeast[2]
• to study its effects on xanthone sensitized cancer cells[3]

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).[4] Radicicol is involved in the suppression of transformation of various proto-oncogenes such as Ras, Mos, and Src.[5] It also suppresses the activity of mitogen-induced cyclooxygenase-2 (COX-2) and phosphoinositide-dependent kinase 1 (PDK1).[6][7] Radicicol is involved in arresting the cell cycle at the G1-S phase.[7] It exhibits ant-cancer and anti-angiogenic activity in vivo.[8]

Disclaimer

Photosensitive

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H340,H350
• pcodes: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral - Carc. 1B - Muta. 1B
• Storage Class: 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