Bufalin

Names

[ CAS No. ]:
465-21-4

[ Name ]:
Bufalin

[Synonym ]:
3,14-dihydroxybufa-20,22-dienolide
(3β,5β)-3,14-Dihydroxybufa-20,22-dienolide
Bufalin: Bufa-20,22-dienolide, 3,14-dihydroxy-, (3b,5b)-,
Bufa-20,22-dienolide, 3,14-dihydroxy-, (3β,5β)-
5β-Bufa-20,22-dienolide, 3β,14-dihydroxy-
3β,14β-dihydroxy-5β-bufa-20,22-dienolide
(3b,5b)-3,14-Dihydroxybufa-20,22-dienolide
Bufalin
MFCD00056525

Biological Activity

[Description]:

Bufalin a major digoxin-like immunoreactive component of the Chinese medicine Chan Su; has been shown to exert a potential for anticancer activity against various human cancer cell lines in vitro.IC50 value:Target: Anticaner natural compoundin vitro: bufalin remarkably inhibited growth in human gallbladder cancer cells by decreasing cell proliferation, inducing cell cycle arrest and apoptosis in a dose-dependent manner. Bufalin also disrupted the mitochondrial membrane potential (ΔΨm) and regulated the expression of cell cycle and apoptosis regulatory molecules. Activation of caspase-9 and the subsequent activation of caspase-3 indicated that bufalin may be inducing mitochondria apoptosis pathways [1]. bufalin suppressed the protein levels associated with DNA damage and repair, such as a DNA dependent serine/threonine protein kinase (DNA-PK), DNA repair proteins breast cancer 1, early onset (BRCA1), 14-3-3 σ (an important checkpoint keeper of DDR), mediator of DNA damage checkpoint 1 (MDC1), O6-ethylguanine-DNA methyltransferase (MGMT) and p53 (tumor suppressor protein) [2]. TNF-α significantly increased p65 translocation into nucleus (P < 0.01) and enhanced NF-κB DNA-binding activity, which were dose-dependently inhibited by bufalin. Furthermore, bufalin attenuated the TNF-α-induced interleukin-1beta (IL-1β), IL-6, and IL-8 production in RAFLSs in a concentration-dependent manner [3]. bufalin enhanced TRAIL-induced apoptosis in MCF-7 and MDA-MB-231 breast cancer cells by activating the extrinsic apoptotic pathway. Bufalin also promoted the clustering of death receptor 4 (DR4) and DR5 in aggregated lipid rafts [4].in vivo: bufalin (0.3 and 0.6 mg/kg, i.p.) potently decreased carrageenan-induced paw edema. Bufalin down regulated the expression levels of nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) during these treatments [5].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Steroids

[References]

[1]. Jiang L, et al. Bufalin induces cell cycle arrest and apoptosis in gallbladder carcinoma cells. Tumour Biol. 2014 Nov;35(11):10931-41.

[2]. Wu SH, et al. Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways. Am J Chin Med. 2014;42(3):729-42.

[3]. Rong X, et al. Bufalin, a bioactive component of the chinese medicine chansu, inhibits inflammation and invasion of human rheumatoid arthritis fibroblast-like synoviocytes. Inflammation. 2014 Aug;37(4):1050-8.

[4]. Yan S, et al. Bufalin enhances TRAIL-induced apoptosis by redistributing death receptors in lipid rafts in breast cancer cells. Anticancer Drugs. 2014 Jul;25(6):683-9.

[5]. Wen L, et al. Anti-inflammatory and antinociceptive activities of bufalin in rodents. Mediators Inflamm. 2014;2014:171839.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
556.6±50.0 °C at 760 mmHg

[ Melting Point ]:
242 - 243ºC

[ Molecular Formula ]:
C₂₄H₃₄O₄

[ Molecular Weight ]:
386.524

[ Flash Point ]:
189.0±23.6 °C

[ Exact Mass ]:
386.245697

[ PSA ]:
70.67000

[ LogP ]:
3.42

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.594

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EI2962500

CHEMICAL NAME :: 5-beta-Bufa-20,22-dienolide, 3-beta,14-dihydroxy-

CAS REGISTRY NUMBER :: 465-21-4

LAST UPDATED :: 199709

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C24-H34-O4

MOLECULAR WEIGHT :: 386.58

WISWESSER LINE NOTATION :: L E5 B666TJ A1 E1 IQ OQ F- ET6OVJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 740 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - antipsychotic

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 24,1714,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 140 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,189,1963

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 137 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PAHEAA Pharmaceutica Acta Helvetiae. (Schweizerische Apothekerzeitung, Postfach 3006, CH3000 Bern, 7, Switzerland) V.1- 1926- Volume(issue)/page/year: 24,222,1949

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+: Very toxic;

[ Risk Phrases ]:
R28

[ Safety Phrases ]:
28-36/37-45

[ RIDADR ]:
UN 3462

[ WGK Germany ]:
3

[ RTECS ]:
EI2962500

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Articles

Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways.

Am. J. Chin. Med. 42(3) , 729-42, (2014)

Bufalin is a key component of a Chinese medicine (Chan Su) and has been proved effective in killing various cancer cells. Its role in inducing DNA damage and the inhibition of the DNA damage response ...

Hepatitis B virus efficiently infects non-adherent hepatoma cells via human sodium taurocholate cotransporting polypeptide.

Sci. Rep. 5 , 17047, (2015)

Sodium taurocholate cotransporting polypeptide (NTCP) has been reported as a functional receptor for hepatitis B virus (HBV) infection. However, HBV could not efficiently infect HepG2 cells expressing...

Reversal effect of bufalin on multidrug resistance in K562/VCR vincristine-resistant leukemia cell line.

J. Tradit. Chin. Med. 34(6) , 678-83, (2014)

To probe insights into the reversal effect of bufalin on vincristine-acquired multidrug resistance (MDR) in human leukemia cell line K562/VCR.Proliferative inhibition rate and the reversal index (RI) ...

Related Compounds

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