553400

Radicicol, Diheterospora chlamydosporia

• Synonym(e): Radicicol, Diheterospora chlamydosporia
• Empirische Formel (Hill-System): C₁₈H₁₇ClO₆
• CAS-Nummer: 12772-57-5
• Molekulargewicht: 364.78
• UNSPSC Code: 51111800
• NACRES: NA.77
• MDL number: MFCD06795865
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Eigenschaften

• description: Merck USA index - 14, 6253
• Quality Segment: 100
• assay: ≥98% (HPLC)
• 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
• SMILES string: Clc1c2c(c(cc1O)O)C(=O)OC(CC3OC3\C=C\C=C\C(=O)C2)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

Beschreibung

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 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

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

Disclaimer

Toxicity: Harmful (C)

Sicherheitshinweise

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Lagerklasse: 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