317201

DMBO

An oxazine that appears to mimic the pyranosidic moiety of heparin sulfate, and is shown to interact directly with several growth factors and cytokines including VEGF, TNF-α and heparin-binding-EGF in a surface plasmon resonance assay.

• Synonym(s): DMBO, CCDC-272761
• Empirical Formula (Hill Notation): C₂₂H₂₅F₂NO₂
• CAS Number: 951166-09-9
• Molecular Weight: 373.44
• MDL number: MFCD32671854
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥95% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: soluble
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: COC1=CC=C(C2C3(CCCCC3)OC(C4=C(F)C=CC=C4F)NC2)C=C1

Description

General description

An oxazine that appears to mimic the pyranosidic moiety of heparin sulfate, and is shown to interact directly with several growth factors and cytokines including VEGF, TNF-α and heparin-binding-EGF in a surface plasmon resonance assay. At concentrations of 10-80 µM, this compound dose-dependently inhibits the proliferation of VEGF-expressing LM8G7 cells (IC₅₀ = 13 µM), and TNF-α-expressing OVSAHO cells (IC₅₀ = 19 µM). At 195 µM, a 99% reduction in cell growth is observed in HB-EGF-expressing SKOV-3 cultures. This compound inhibits heparanase-mediated degradation of heparin sulfate in LM8G7 cells (IC₅₀ = 65 µM and 104-206 µM, in an enzymatic and a cell based assay, respectively). At 0.5-5 µM, it markedly prevents the migration and invasion of the same culture, in a dose-dependent manner. In addition, it completely suppresses liver metastatic nodules of osteosarcoma mice injected with LM8G7 cells at 0.5 mg/kg without any signs of toxicity in vivo, and demonstrates a synergistic anti-tumor effect when dosed with heparin.

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Basappa, et al. 2010. Cancer Lett.279, 231.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable