Cinobufotalin

Names

[ Name ]:
Cinobufotalin

[Synonym ]:
14,15b-Epoxy-3b,5a,16b-trihydroxy-5b,20(22)-bufadienolide 16-acetate
(3b,5b,15b,16b)-16-(Acetyloxy)-14,15-epoxy-3,5-dihydroxybufa-20,22-dienolide
MFCD00055946
Bufa-20,22-dienolide, 16- (acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3β,5β,15β,16β)-
5beta-Hydroxycinobufagin
5β-Bufa-20,22-dienolide, 14,15β-epoxy-3β,5,16β-trihydroxy-, 16-acetate (8CI)
Bufa-20,22-dienolide, 16-(acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3β,5β,15β,16β)-
cinobufotalin venom toad
Cinobufotlin
14,15-Epoxy-14H-cyclopenta[a]phenanthrene,bufa-20,22-dienolide deriv.
Cinobufotalin
CINOBUFOTALIN(RG)
cinobufatolin
(3β,5β,15β,16β)-16-Acetoxy-3,5-dihydroxy-14,15-epoxybufa-20,22-dienolide
14,15b-Epoxy-3b,5,16b-trihydroxy-5b-bufa-20,22-dienolide 16-Acetate

Biological Activity

[Description]:

Cinobufotalin is one of the bufadienolides prepared from toad venom; has anticancer activity.IC50 value:Target:in vitro: Cinobufotalin(CB) caused significant DNA fragmentation, decrease of MMP, and an increase in the intracellular Ca(2+) ion and ROS production. In addition, CB induced upregulation of Fas protein, proteolytic activation of cytochrome c, caspase-2, -3, -8 and -9 together with the activation of Bid and Bax [1]. cinobufotalin displayed considerable cytotoxicity against lung cancer cells (A549, H460 and HTB-58 lines) without inducing significant cell apoptosis. cinobufotalin mainly induces Cyp-D-dependent non-apoptotic death in cultured lung cancer cells [2]. cinobufotalin (at nmol/L) significantly inhibited HCC cell growth and survival while inducing considerable cell apoptosis. Further, cinobufotalin inhibited sphingosine kinase 1 (SphK1) activity and induced pro-apoptotic ceramide production. cinobufotalin inactivated Akt-S6K1 signaling in HepG2 cells, which was again inhibited by ceramide synthase-1 shRNA-depletion [3].in vivo: Using a mice xenograft model, we found that cinobufotalin inhibited A549 lung cancer cell growth in vivo [2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Cancer

[References]

[1]. Kai S, et al. Pre-clinical evaluation of cinobufotalin as a potential anti-lung cancer agent. Biochem Biophys Res Commun. 2014 Sep 26;452(3):768-74.

[2]. Cheng L, et al. Ceramide production mediates cinobufotalin-induced growth inhibition and apoptosis in cultured hepatocellular carcinoma cells. Tumour Biol. 2015 Feb 28.

[3]. Emam H, et al. Apoptotic cell death by the novel natural compound, cinobufotalin. Chem Biol Interact. 2012 Sep 30;199(3):154-60.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
627.3±55.0 °C at 760 mmHg

[ Melting Point ]:
259 - 262ºC

[ Molecular Formula ]:
C₂₆H₃₄O₇

[ Molecular Weight ]:
458.544

[ Flash Point ]:
210.7±25.0 °C

[ Exact Mass ]:
458.230438

[ PSA ]:
109.50000

[ LogP ]:
0.79

[ Vapour Pressure ]:
0.0±4.2 mmHg at 25°C

[ Index of Refraction ]:
1.612

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EI2991000

CHEMICAL NAME :: 5-beta-Bufa-20,22-dienolide, 14,15-beta-epoxy-3-beta,5,16-beta-trihydroxy-, 16-acetate

CAS REGISTRY NUMBER :: 1108-68-5

LAST UPDATED :: 199012

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C26-H34-O

MOLECULAR WEIGHT :: 362.60

WISWESSER LINE NOTATION :: T E6 B6653 1A R AX RO QHTTTT&J EQ GQ J1 N1 POV1 O- ET6O BHJ

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 :: 5150 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 :: 200 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 :: 199 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-H310-H330

[ Precautionary Statements ]:
P260-P264-P280-P284-P302 + P350-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 ]:
R26/27/28

[ Safety Phrases ]:
22-36/37/39-45

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
EI2991000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Pre-clinical evaluation of cinobufotalin as a potential anti-lung cancer agent.

Biochem. Biophys. Res. Commun. 452(3) , 768-74, (2014)

Lung cancer is a major cause of cancer-related mortality in the United States and around the world. Due to the pre-existing or acquired chemo-resistance, the current standard chemotherapy regimens onl...

Ceramide production mediates cinobufotalin-induced growth inhibition and apoptosis in cultured hepatocellular carcinoma cells.

Tumour Biol. 36 , 5763-71, (2015)

Hepatocellular carcinoma (HCC) is a highly aggressive and lethal neoplasm with poor prognosis. The aim of this study is to investigate the anticancer activity of cinobufotalin, a bufadienolide isolate...

Comparative Analysis of the Bufonis Venenum by Using TLC, HPLC, and LC-MS for Different Extraction Methods.

J Pharmacopuncture 15 , 52-65, (2015)

Toad venom, called Chan-Su, is a traditional Oriental medicine secreted from the auricular and the skin glands of the Bufo bufo gargarizanz Cantor or B. melanosticus Schneider and has been widely used...

Related Compounds

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