Bufalin

Modify Date: 2024-01-04 13:18:58

Bufalin Structure
Bufalin structure
 Common Name Bufalin
CAS Number 465-21-4 Molecular Weight 386.524
Density 1.2±0.1 g/cm3 Boiling Point 556.6±50.0 °C at 760 mmHg
Molecular Formula C24H34O4 Melting Point 242 - 243ºC
MSDS Chinese USA Flash Point 189.0±23.6 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Bufalin


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].

 Names

Name bufalin
Synonym More Synonyms

 Bufalin 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
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.

 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

 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
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)

 Articles27

More 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) ...

 Synonyms

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
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17008-69-4
Bufalin-3-hydrogen suberate
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4-Bromo-N,3,5-trimethylbenzene-1-sulfonamide
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2-(2,4,5-Trifluorophenyl)propanenitrile
1823853-77-5
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4-(Azetidin-1-yl)thiophene-2-carbaldehyde
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4-(Azetidin-1-yl)-3-fluorobenzaldehyde
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