Gamabufotalin

Modify Date: 2025-08-20 11:53:51

Gamabufotalin Structure
Gamabufotalin structure
 Common Name Gamabufotalin
CAS Number 465-11-2 Molecular Weight 402.524
Density 1.3±0.1 g/cm3 Boiling Point 595.8±50.0 °C at 760 mmHg
Molecular Formula C24H34O5 Melting Point N/A
MSDS N/A Flash Point 203.4±23.6 °C

 Use of Gamabufotalin


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].

 Names

Name 5-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
Synonym More Synonyms

 Gamabufotalin 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
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.

 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
InChIKey FMTLOAVOGWSPEF-KJRPADTMSA-N
SMILES CC12CCC(O)CC1CCC1C2C(O)CC2(C)C(c3ccc(=O)oc3)CCC12O
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

 Synonyms

(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
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