553400

Radicicol, Diheterospora chlamydosporia

• Synonym(s): Radicicol, Diheterospora chlamydosporia
• Empirical Formula (Hill Notation): C₁₈H₁₇ClO₆
• CAS Number: 12772-57-5
• Molecular Weight: 364.78
• MDL number: MFCD06795865
• UNSPSC Code: 51111800
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• Quality Level: 100
• form: solid
• potency: 0.27 nM IC₅₀
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: 10 mg/mL; methanol: soluble
• shipped in: ambient
• storage temp.: 2-8°C
• 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+
• InChI key: WYZWZEOGROVVHK-ZUVMSYQZSA-N

Description

General description

A cell-permeable, ATP-site binding, and irreversible antifungal macrocyclic lactone antibiotic that acts as a protein tyrosine kinase inhibitor. Inhibits p60^v-src kinase activity (IC₅₀ = 0.27 nM). Inhibits the expression of COX-2 (IC₅₀ = 27 nM) without affecting COX-1 expression in LPS-stimulated macrophages. Disrupts K-Ras-activated signaling pathways by selectively depleting Raf kinase. Inhibits tyrosine phosphorylation of p53/56^lyn in LPS-stimulated macrophages. Suppresses NIH/3T3 cell transformation by diverse oncogenes such as src, ras, and mos in part by blocking the key signal transduction intermediates such as MAP kinase and GAP-associated p62. Also exhibits anti-angiogenic activity in vivo. Inhibits Wnt-5A expression in dermal papilla cells (IC₅₀ = 190 nM).

A cell-permeable, ATP-site binding, and irreversible antifungal macrocyclic lactone antibiotic that acts as a protein tyrosine kinase inhibitor. Inhibits p60^v-src kinase activity (IC₅₀ = 0.27 µM). Inhibits the expression of COX-2 (IC₅₀ = 27 nM) without affecting COX-1 expression in LPS-stimulated macrophages. Disrupts k-Ras-activated signaling pathway by selectively depleting Raf kinase. Inhibits tyrosine phosphorylation of p53/56^lyn in LPS-stimulated macrophages. Suppresses NIH 3T3 cell transformation by diverse oncogenes, such as src, ras and mos, at least in part by blocking the key signal transduction intermediates, such as MAP kinase and GAP-associated p62. Also exhibits anti-angiogenic activity in vivo. Inhibits Wnt-5A expression in dermal papilla cells (IC₅₀ = 190 nM).

Biochem/physiol Actions

Primary Target
p60^v-src kinase activity

Secondary Target
COX-2 (IC₅₀ = 27 nM)

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful (C)

Other Notes

Shinonaga, H., et al. 2009. Bioorg. Med. Chem.17, In press.
Soga, S., et al. 1998. J. Biol. Chem. 273, 822.
Chanmugam, P., et al. 1995. J. Biol. Chem. 270, 5418.
Shimada, Y., et al. 1995. J. Antibiot. 48, 824.
Zhao, J.F., et al. 1995. Oncogene 11, 161.
Oikawa, T., et al. 1993. Eur. J. Pharmacol. 241, 221.
Kwon, H.J., et al. 1992. Cancer Res. 52, 6926.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• 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