CAS 464-74-4|Arenobufagin

Introduction：Basic information about CAS 464-74-4|Arenobufagin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Arenobufagin BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

Common Name	Arenobufagin
CAS Number	464-74-4	Molecular Weight	416.507
Density	1.4±0.1 g/cm3	Boiling Point	637.2±55.0 °C at 760 mmHg
Molecular Formula	C₂₄H₃₂O₆	Melting Point	/
MSDS	/	Flash Point	219.3±25.0 °C

Names

Name	arenobufagin
Synonym	More Synonyms

Arenobufagin BiologicalActivity

Description	Arenobufagin is a natural bufadienolide from toad venom; has potent antineoplastic activity against HCC HepG2 cells as well as corresponding multidrug-resistant HepG2/ADM cells.IC50 value: Target: in vitro: arenobufagin induced mitochondria-mediated apoptosis in HCC cells, with decreasing mitochondrial potential, as well as increasing Bax/Bcl-2 expression ratio, Bax translocation from cytosol to mitochondria. Arenobufagin also induced autophagy in HepG2/ADM cells. Autophagy-specific inhibitors (3-methyladenine, chloroquine and bafilomycin A1) or Beclin1 and Atg 5 small interfering RNAs (siRNAs) enhanced arenobufagin-induced apoptosis, indicating that arenobufagin-mediated autophagy may protect HepG2/ADM cells from undergoing apoptotic cell death [1]. arenobufagin inhibited vascular endothelial growth factor (VEGF)-induced viability, migration, invasion and tube formation in human umbilical vein endothelial cells (HUVECs) in vitro [2]. Arenobufagin blocked the Na+/K+ pump current in a dose-dependent manner with a half-maximal concentration of 0.29 microM and a Hill coefficient of 1.1 [3].in vivo: arenobufagin inhibited the growth of HepG2/ADM xenograft tumors, which were associated with poly (ADP-ribose) polymerase cleavage, light chain 3-II activation and mTOR inhibition [1]. Arenobufagin also suppressed sprouting formation from VEGF-treated aortic rings in an ex vivo model [2].
Related Catalog	Signaling Pathways >>Others >>OthersResearch Areas >>CancerNatural Products >>Steroids
References	[1]. Zhang DM, et al. Arenobufagin, a natural bufadienolide from toad venom, induces apoptosis and autophagy in human hepatocellular carcinoma cells through inhibition of PI3K/Akt/mTOR pathway. Carcinogenesis. 2013 Jun;34(6):1331-42. [2]. Li M, et al. Arenobufagin, a bufadienolide compound from toad venom, inhibits VEGF-mediated angiogenesis through suppression of VEGFR-2 signaling pathway. Biochem Pharmacol. 2012 May 1;83(9):1251-60. [3]. Cruz Jdos S, et al. Arenobufagin, a compound in toad venom, blocks Na(+)-K+ pump current in cardiac myocytes. Eur J Pharmacol. 1993 Aug 3;239(1-3):223-6.

Description

Arenobufagin is a natural bufadienolide from toad venom; has potent antineoplastic activity against HCC HepG2 cells as well as corresponding multidrug-resistant HepG2/ADM cells.IC50 value: Target: in vitro: arenobufagin induced mitochondria-mediated apoptosis in HCC cells, with decreasing mitochondrial potential, as well as increasing Bax/Bcl-2 expression ratio, Bax translocation from cytosol to mitochondria. Arenobufagin also induced autophagy in HepG2/ADM cells. Autophagy-specific inhibitors (3-methyladenine, chloroquine and bafilomycin A1) or Beclin1 and Atg 5 small interfering RNAs (siRNAs) enhanced arenobufagin-induced apoptosis, indicating that arenobufagin-mediated autophagy may protect HepG2/ADM cells from undergoing apoptotic cell death [1]. arenobufagin inhibited vascular endothelial growth factor (VEGF)-induced viability, migration, invasion and tube formation in human umbilical vein endothelial cells (HUVECs) in vitro [2]. Arenobufagin blocked the Na+/K+ pump current in a dose-dependent manner with a half-maximal concentration of 0.29 microM and a Hill coefficient of 1.1 [3].in vivo: arenobufagin inhibited the growth of HepG2/ADM xenograft tumors, which were associated with poly (ADP-ribose) polymerase cleavage, light chain 3-II activation and mTOR inhibition [1]. Arenobufagin also suppressed sprouting formation from VEGF-treated aortic rings in an ex vivo model [2].

Related Catalog

Signaling Pathways >>Others >>OthersResearch Areas >>CancerNatural Products >>Steroids

References

[1]. Zhang DM, et al. Arenobufagin, a natural bufadienolide from toad venom, induces apoptosis and autophagy in human hepatocellular carcinoma cells through inhibition of PI3K/Akt/mTOR pathway. Carcinogenesis. 2013 Jun;34(6):1331-42.

[2]. Li M, et al. Arenobufagin, a bufadienolide compound from toad venom, inhibits VEGF-mediated angiogenesis through suppression of VEGFR-2 signaling pathway. Biochem Pharmacol. 2012 May 1;83(9):1251-60.

[3]. Cruz Jdos S, et al. Arenobufagin, a compound in toad venom, blocks Na(+)-K+ pump current in cardiac myocytes. Eur J Pharmacol. 1993 Aug 3;239(1-3):223-6.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	637.2±55.0 °C at 760 mmHg
Molecular Formula	C₂₄H₃₂O₆
Molecular Weight	416.507
Flash Point	219.3±25.0 °C
Exact Mass	416.219879
PSA	107.97000
LogP	0.80
Vapour Pressure	0.0±4.3 mmHg at 25°C
Index of Refraction	1.622
InChIKey	JGDCRWYOMWSTFC-AZGSIFHYSA-N
SMILES	CC12CCC(O)CC1CCC1C2C(O)C(=O)C2(C)C(c3ccc(=O)oc3)CCC12O
Storage condition	-20°C

Synonyms

Arenobufagin

(3β,5β,11α)-3,11,14-Trihydroxy-12-oxobufa-20,22-dienolide

5β-Bufa-20,22-dienolide, 3β,11α,14-trihydroxy-12-oxo-

ARENOBUFAGIN (REFERENCE GRADE)

Bufa-20,22-dienolide, 3,11,14-trihydroxy-12-oxo-, (3β,5β,11α)-

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