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Merck

B0261

Bufalin

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C24H34O4
Numéro CAS:
465-21-4
Poids moléculaire :
386.52
MDL number:
MFCD30207876
UNSPSC Code:
12352200
PubChem Substance ID:
24891509
NACRES:
NA.77

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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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Cet article
203900PHL89587SMB00428
Bufalin

Sigma-Aldrich

B0261

Bufalin

Bufalin A cardiotonic steroid isolated from toads of Bufo species that potently inhibits ouabain-sensitive Na+,K+-ATPase activity (IC50 = 1.4 nM).

Sigma-Aldrich

203900

Bufalin

Bufalin phyproof® Reference Substance

PHL89587

Bufalin

Resibufogenin ≥98% (HPLC)

Sigma-Aldrich

SMB00428

Resibufogenin

form

solid

form

solid

form

-

form

powder

assay

≥97% (HPLC)

assay

≥98% (HPLC)

assay

≥95.0% (HPLC)

assay

≥98% (HPLC)

Quality Level

200

Quality Level

100

Quality Level

-

Quality Level

200

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMF: soluble, ethanol: soluble, DMSO: soluble

solubility

DMSO: 25 mg/mL, warm ethanol: 25 mg/mL

solubility

-

solubility

-

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]

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Classe de stockage

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

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
SLCP0241
SLCH1266
SLCG9546
SLCF8874
SLCC0079

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Consulter la Bibliothèque de documents

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
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
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
Xia Liu et al.
Journal of ethnopharmacology, 193, 538-545 (2016-10-01)
Bufalin, a cardiotonic steroid isolated from toad venom (bufo gargarizans Cantor or B. melanotictus Schneider), has widely demonstrated antitumor effects and exhibits potential antitumor activity in various human cancer cells lines. The main characteristic of cancers including pancreatic cancer is
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