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Merck

B0261

Bufalin

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C24H34O4
Número CAS:
465-21-4
Peso molecular:
386.52
MDL number:
MFCD30207876
UNSPSC Code:
12352200
PubChem Substance ID:
24891509
NACRES:
NA.77
Assay:
≥97% (HPLC)
Form:
solid
Quality level:
200

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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

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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)
  • 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

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.

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Clase de almacenamiento

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

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Certificados de análisis (COA)

Lot/Batch Number
SLCH1266
SLCG9546
SLCF8874
SLCC0079
SLBZ1480

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Hongyan Zhao et al.
Biology open, 6(10), 1416-1422 (2017-08-26)
Bufalin has been used to treat cancer for several years. However, the molecular mechanisms for its anti-tumor function are not fully understood. This work aimed to investigate the effect of bufalin on the proliferation and apoptosis of human gastric cancer
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.
Ying Wang et al.
Cancer research, 74(5), 1506-1517 (2014-01-07)
Virtually all transcription factors partner with coactivators that recruit chromatin remodeling factors and interact with the basal transcription machinery. Coactivators have been implicated in cancer cell proliferation, invasion, and metastasis, including the p160 steroid receptor coactivator (SRC) family composed of
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
Jiani Yuan et al.
Nanoscale research letters, 12(1), 585-585 (2017-11-11)
Bufalin was reported to show strong pharmacological effects including cardiotonic, antiviral, immune-regulation, and especially antitumor effects. The objective of this study was to determine the characterization, antitumor efficacy, and pharmacokinetics of bufalin-loaded PEGylated liposomes compared with bufalin entity, which were
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