Gamabufotalin

Names

[ CAS No. ]:
465-11-2

[ Name ]:
Gamabufotalin

[Synonym ]:
(3β,5β,11α)-3,11,14-Trihydroxybufa-20,22-dienolide
Gammabufotalin
3b,11a,14-Trihydroxy-5b-bufa-20,22-dienolide
Bufa-20,22-dienolide, 3,11,14-trihydroxy-, (3β,5β,11α)-
Gamabufotalin
(3b,5b,11a)-3,11,14-Trihydroxybufa-20,22-dienolide
Gamabufagin
Gamabufogenin

Biological Activity

[Description]:

Gamabufotalin (Gamabufagin), a major bufadienolide of Chansu, has been used for cancer therapy due to its desirable metabolic stability and less adverse effect.IC50 value:Target: in vitro: Gamabufotalin (CS-6) strongly suppressed COX-2 expression by inhibiting the phosphorylation of IKKβ via targeting the ATP-binding site, thereby abrogating NF-κB binding and p300 recruitment to COX-2 promoter. In addition, CS-6 induced apoptosis by activating the cytochrome c and caspase-dependent apoptotic pathway [1]. Gamabufotalin significantly potentiated human breast cancer cells with different status of ER-alpha to apoptosis induction of TRAIL, as evidenced by enhanced Annexin V/FITC positive cells (apoptotic cells), cytoplasmic histone-associated-DNA-fragments, membrane permeability transition (MPT), caspases activation and PARP cleavage [2].in vivo: CS-6 markedly down-regulated the protein levels of COX-2 and phosphorylated p65 NF-κB in tumor tissues of the xenograft mice, and inhibited tumor weight and size [1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Steroids

[References]

[1]. Yu Z, et al. Gamabufotalin, a bufadienolide compound from toad venom, suppresses COX-2 expression through targeting IKKβ/NF-κB signaling pathway in lung cancer cells. Mol Cancer. 2014 Aug 31;13:203.

[2]. Dong Y, et al. Bufadienolide compounds sensitize human breast cancer cells to TRAIL-induced apoptosis via inhibition of STAT3/Mcl-1 pathway. Apoptosis. 2011 Apr;16(4):394-403.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
595.8±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₄H₃₄O₅

[ Molecular Weight ]:
402.524

[ Flash Point ]:
203.4±23.6 °C

[ Exact Mass ]:
402.240631

[ PSA ]:
90.90000

[ LogP ]:
1.99

[ Vapour Pressure ]:
0.0±3.8 mmHg at 25°C

[ Index of Refraction ]:
1.612

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EI2996800

CHEMICAL NAME :: 5-beta-Bufa-20,22-dienolide, 3-beta,11-alpha,14-trihydroxy-

CAS REGISTRY NUMBER :: 465-11-2

LAST UPDATED :: 199709

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C24-H34-O5

MOLECULAR WEIGHT :: 402.58

WISWESSER LINE NOTATION :: L E5 B666TJ A1 CQ 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 :: Mammal - cat

DOSE/DURATION :: 100 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: -,191,1963