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HomeProduct name listBufalin

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: 2024-11-19 23:02:33
Bufalin Structural

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)
ghs
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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