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Merck

B0261

Sigma-Aldrich

Bufalin

Sinónimos:

3β,14-Dihydroxy-5β,20(22)-bufadienolide, 5β,20(22)-Bufadienolide-3β,14-diol

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About This Item

Fórmula empírica (notación de Hill):
C24H34O4
Número de CAS:
Peso molecular:
386.52
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

Ensayo

≥97% (HPLC)

Nivel de calidad

Formulario

solid

solubilidad

DMF: soluble
DMSO: soluble
ethanol: soluble

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

QEEBRPGZBVVINN-BMPKRDENSA-N

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Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Pictogramas

Skull and crossbones

Palabra de señalización

Danger

Frases de peligro

Consejos de prudencia

Clasificaciones de peligro

Acute Tox. 2 Oral

Código de clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Dong-Ze Qiu et al.
BMC complementary and alternative medicine, 13, 185-185 (2013-07-23)
Hepatocellular carcinoma (HCC) is a common and aggressive cancer, and the treatment options are limited for patients with advanced HCC. Bufalin, the major digoxin-like component of the traditional Chinese medicine Chansu, exhibits significant anti-tumor activities in many tumor cell lines.
Qingfeng Meng et al.
American journal of translational research, 8(11), 4968-4974 (2016-12-03)
Cinobufacini (Huachansu) is a Chinese medicine prepared from the skin of Bufo bufo gargarizans Cantor (Bufonidae), and has long been used in traditional Chinese medicine. In the present study, the anti-retinoblastoma constituent bufalin obtained from Cinobufacini was investigated. Treatment of
Yanlan Li et al.
Anti-cancer drugs, 30(7), e0770-e0770 (2019-03-05)
Breast cancer causes high mortality among females worldwide. Bufalin has recently been shown to trigger tumor cell death, although the mechanism of cytotoxicity remains unclear. The cytotoxicity of bufalin in breast cancer cells was examined using an MTT assay. The
Lingling Tong et al.
Cancer medicine, 8(10), 4782-4791 (2019-06-30)
In the present study, we evaluated the expression and function of human long noncoding RNA (lncRNA) activated by DNA damage (NORAD) in human epithelial ovarian cancer (EOC). NORAD expression was evaluated by qRT-PCR in EOC cell lines and in situ
Peihao Yin et al.
International journal of nanomedicine, 7, 3961-3969 (2012-08-14)
Recent studies have shown that bufalin has a good antitumor effect but has high toxicity, poor water solubility, a short half-life, a narrow therapeutic window, and a toxic dose that is close to the therapeutic dose, which all limit its

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