B0261

Bufalin

• Synonym(e): 3β,14-Dihydroxy-5β,20(22)-bufadienolide, 5β,20(22)-Bufadienolide-3β,14-diol
• Empirische Formel (Hill-System): C₂₄H₃₄O₄
• CAS-Nummer: 465-21-4
• Molekulargewicht: 386.52
• MDL number: MFCD30207876
• UNSPSC Code: 12352200
• PubChem Substance ID: 24891509
• NACRES: NA.77

Eigenschaften

• SMILES string: O[C@]([C@@](CC[C@@]1([H])[C@@]2(CC[C@H](O)C1)C)([H])[C@]2([H])CC3)(CC[C@@H]4C(C=C5)=COC5=O)[C@]34C
• InChI: 1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
• InChI key: QEEBRPGZBVVINN-BMPKRDENSA-N
• assay: ≥97% (HPLC)
• form: solid
• solubility: DMF: soluble; DMSO: soluble; ethanol: soluble
• storage temp.: 2-8°C
• Quality Level: 200

Beschreibung

Application

Bufalin has been used:

• to test its effect on invasion and activation of nuclear factor kappa- B (NF-κB) cells and tumor necrosis factor-α (TNF-α) stimulated rheumatoid arthritis fibroblast-like synoviocytes (RAFLSs)[1]
• as a nuclear receptor coactivator 3 (NCOA3) inhibitor in chondrocytes[2]
• to test its anti-metastasis effect in lung cancer cells (NCI-H460) resistant to gefitinib[3]

Biochem/physiol Actions

Bufalin is an anti-metastasis drug[3], which elicits anti-tumor functionality by favoring cell cycle arrest and apoptosis in various cancer types including hepatocellular, bladder and osteosarcoma.[1] It also promotes autophagic cell death and possesses anti-inflammatory properties.[4] Bufalin is a steroid receptor coactivator (SRC) inhibitor.[5]

General description

Bufalin is a C-24 steroid with an α-pyrone ring positioned at C-17.[6] It is present in the venom glands and skin of toad, Venenum Bufonis.[1] Bufalin is a cardiotonic steroid[4] and is digoxin-like component of Chan Su.[3]

Sicherheitshinweise

• pictograms: GHS06
• signalword: Danger
• hcodes: H300
• pcodes: P301 + P310 + P330
• Hazard Classifications: Acute Tox. 2 Oral
• Lagerklasse: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges