Bufalin
Synonym(s):3β,14-Dihydroxy-5β,20(22)-bufadienolide;5β, 20(22)-Bufadienolide-3β, 14-diol;5β,20(22)-Bufadienolide-3β,14-diol;Bufalin - CAS 465-21-4 - Calbiochem
- CAS NO.:465-21-4
- Empirical Formula: C24H34O4
- Molecular Weight: 386.53
- MDL number: MFCD30207876
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-08 20:21:46
What is Bufalin?
The Uses of Bufalin
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)
- as a nuclear receptor coactivator 3 (NCOA3) inhibitor in chondrocytes
- to test its anti-metastasis effect in lung cancer cells (NCI-H460) resistant to gefitinib
The Uses of Bufalin
A bufadienolide derivative, cardiac steroid, a component of bufadienolides present in the traditional Chinese medicine Chan'su, used therapeutically for the treatment of heart disease, also has been reported as a protective factor in many tumors.
What are the applications of Application
Bufalin is inducer of apoptosis in human HL-60 and U-937 cell lines
Definition
ChEBI: A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.
General Description
Bufalin is a C-24 steroid with an α-pyrone ring positioned at C-17. It is present in the venom glands and skin of toad, Venenum Bufonis. Bufalin is a cardiotonic steroid and is digoxin-like component of Chan Su.
Hazard
Toxic.
Biochem/physiol Actions
Bufalin is an anti-metastasis drug, which elicits anti-tumor functionality by favoring cell cycle arrest and apoptosis in various cancer types including hepatocellular, bladder and osteosarcoma. It also promotes autophagic cell death and possesses anti-inflammatory properties. Bufalin is a steroid receptor coactivator (SRC) inhibitor.
Enzyme inhibitor
This cardioactive C-24 steroid (FW = 386.52 g/mol; CAS 465-21-4; Solubility: 5 mg/mL chloroform, 25 mg/mL DMSO), also named 3,14- dihydroxybufa-20,22-dienolide;5β,20(22)-bufadienolide-3β,14-diol and 3β,14-dihydroxy-5β,20(22)-bufadienolide, is the major digoxin-like immunoreactive component of Chansu, a traditional Chinese medicine prepared from the skin and venom-containing parotid gland of a poisonous toad. Bufalin increases the doubling time of three prostate cancer cell lines, inducing apoptosis and the caspase-3 activity. Expression of other proapoptoptic factors, such as mitochondrial Bax and cytosolic cytochrome c, were also increased. Bufalin also reduces serum-induced invasiveness of human hepatocellular cancer SK-Hep1 cells, markedly inhibiting MMP-2 and MMP-9 activities. It also attenuates phosphoinisitide-3-kinase (PI3K) and AKT phosphorylation was associated with reduced levels of NF- κB. Bufalin also suppresses protein levels of FAK, Rho A, VEGF, MEKK3, MKK7, and uPA. Such observations indicate that bufalin is as an antiinvasive agent that inhibits MMP-2 and -9 and alters PI3K/AKT and NF- κB signaling pathways.
Properties of Bufalin
Melting point: | 242-243° |
Boiling point: | 556.6±50.0 °C(Predicted) |
alpha | D -20° |
Density | 1.226±0.06 g/cm3(Predicted) |
storage temp. | 2-8°C |
solubility | DMSO:36.0(Max Conc. mg/mL);93.14(Max Conc. mM) DMF:25.0(Max Conc. mg/mL);64.68(Max Conc. mM) Ethanol:27.5(Max Conc. mg/mL);71.15(Max Conc. mM) Ethanol:PBS (pH 7.2) (1:2):0.3(Max Conc. mg/mL);0.78(Max Conc. mM) |
pka | 15.01±0.70(Predicted) |
form | White to off-white solid |
color | White to off-white |
Safety information for Bufalin
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H300:Acute toxicity,oral |
Computed Descriptors for Bufalin
InChIKey | QEEBRPGZBVVINN-ONGIWDLKSA-N |
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