CAS 465-11-2|Gamabufotalin

Introduction：Basic information about CAS 465-11-2|Gamabufotalin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Gamabufotalin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Synonyms

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	/
MSDS	/	Flash Point	203.4±23.6 °C

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 BiologicalActivity

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 >>OthersResearch Areas >>CancerNatural 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.

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 >>OthersResearch Areas >>CancerNatural 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.

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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