Bufalin
Product Code: AG-CN2-0533
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0533-M010 | 10 mg | £70.00 |
Quantity:
| AG-CN2-0533-M050 | 50 mg | £250.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C
Documents
Further Information
Alternate Names/Synonyms:
(3beta,5beta)-3,14-Dihydroxy-bufa-20,22-dienolide; NSC 89595; BRN 5141601
Appearance:
White to off-white solid.
CAS:
465-21-4
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
Keep cool and dry.Protect from light.
Hazards:
H300
InChi:
InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
InChiKey:
QEEBRPGZBVVINN-BMPKRDENSA-N
Long Description:
Chemical. CAS: 465-21-4. Formula: C24H34O4. MW: 386.5. Isolated from venenum bufonis. Bufalin is a cardiotonic steroid with anaesthetic, blood pressure stimulatory and respiratory activities. It is a potent Na+/K+-ATPase transporter inhibitor (Kd = 42, 45, and 40nM for the alpha1, alpha2, and alpha3 subunits, respectively). Bufalin has anticancer effects in a variety of cancer cell lines both in vitro and in vivo. It inhibits cancer cell proliferation, induces cell cycle arrest, induces apoptosis and autophagy, inhibits angiogenesis and neovascularization, induces cell differentiation, inhibits cancer metastasis and invasion, and enhances chemotherapeutic drug sensitivity through multiple kinase targets and also the Na+/K+-ATPase transporter. It also inhibits proteins of the steroid receptor coactivator family, such as SRC-1 and SRC-3 at 5nM. Bufalin has anti-inflammatory effects by modulating nuclear factor-kappaB (NF-kappaB) signaling and down-regulating inflammatory-related genes such as cyclooxygenases, lipoxygenases, inducible nitric oxide synthase (iNOS), and thereby decrease nitric oxide and prostaglandin E2 (PGE2) production.
MDL:
MFCD00056525
Molecular Formula:
C24H34O4
Molecular Weight:
386.5
Package Type:
Vial
PG:
II
Precautions:
P264-P301+P310
Product Description:
Bufalin is a cardiotonic steroid with anaesthetic, blood pressure stimulatory and respiratory activities. It is a potent Na+/K+-ATPase transporter inhibitor (Kd = 42, 45, and 40nM for the alpha1, alpha2, and alpha3 subunits, respectively). Bufalin has anticancer effects in a variety of cancer cell lines both in vitro and in vivo. It inhibits cancer cell proliferation, induces cell cycle arrest, induces apoptosis and autophagy, inhibits angiogenesis and neovascularization, induces cell differentiation, inhibits cancer metastasis and invasion, and enhances chemotherapeutic drug sensitivity through multiple kinase targets and also the Na+/K+-ATPase transporter. It also inhibits proteins of the steroid receptor coactivator family, such as SRC-1 and SRC-3 at 5nM. Bufalin has anti-inflammatory effects by modulating nuclear factor-kappaB (NF-kappaB) signaling and down-regulating inflammatory-related genes such as cyclooxygenases, lipoxygenases, inducible nitric oxide synthase (iNOS), and thereby decrease nitric oxide and prostaglandin E2 (PGE2) production.
Purity:
>98% (HPLC)
Signal word:
Danger
SMILES:
C[C@@]12[C@@](CC[C@@H]2C3=COC(C=C3)=O)(O)[C@]4([H])CC[C@]5([H])C [C@@H](O)CC[C@]5(C)[C@@]4([H])CC1
Solubility Chemicals:
Soluble in DMSO (5mg/ml), ethanol (15mg/ml) or DMF (20mg/ml).
Source / Host:
Isolated from venenum bufonis.
Transportation:
Excepted Quantity
UN Nummer:
UN 3462
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352211
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Effects of bufalin and related cardiotonic steroids in the neuromuscular junction: S. Yoshida & T. Sakai; Jpn. J. Pharmacol. 23, 859 (1973) | Bufalin as a potent inducer of differentiation of human myeloid leukemia cells: L.S: Zhang, et al.; BBRC 178, 686 (1991) | Chronic blood pressure effects of bufalin, a sodium-potassium ATPase inhibitor, in rats: M.B. Pamnani, et al.; Hypertension 23, I106 (1994) | Bufalin reduces the level of topoisomerase II in human leukemia cells and affects the cytotoxicity of anticancer drugs: S. Hashimoto, et al.; Leuk. Res. 21, 875 (1997) | Selectivity of digitalis glycosides for isoforms of human Na,K-ATPase: A. Katz, et al.; J. Biol. Chem. 285, 19582 (2010) | Bufalin induces autophagy-mediated cell death in human colon cancer cells through reactive oxygen species generation and JNK activation: C.M. Xie, et al.; Free Radic. Biol. Med. 51, 1365 (2011) | Bufalin induces lung cancer cell apoptosis via the inhibition of PI3K/Akt pathway: Z. Zhu, et al.; Int. J. Mol. Sci. 13, 2025 (2012) | Anti-tumor activity and apoptosis-regulation mechanisms of bufalin in various cancers: new hope for cancer patients: P.H. Yin, et al.; Asian Pac. J. Cancer Prev. 13, 5339 (2012) (Review) | Bufalin is a potent small-molecule inhibitor of the steroid receptor coactivators SRC-3 and SRC-1: Y. Wang, et al.; Cancer Res. 74, 1506 (2014) | Anti-inflammatory and antinociceptive activities of bufalin in rodents: L. Wen, et al.; Mediators Inflamm. 2014, 171839 (2014) | Bufalin Inhibits the Inflammatory Effects in Asthmatic Mice through the Suppression of Nuclear Factor-Kappa B Activity: Z. Zhakeer, et al.; Pharmacol. 99, 179 (2017) | Bufalin sensitizes human bladder carcinoma cells to TRAIL-mediated apoptosis: K.H. Kang, et al.; Oncol. Lett. 14, 853 (2017) | Cardiac glycoside bufalin blocks cancer cell growth by inhibition of Aurora A and Aurora B activation via PI3K-Akt pathway: C.M. Xie, et al.; Oncotarget 9, 13783 (2018) | Molecular mechanisms underlying the antimetastatic activity of bufalin: J. Wang, et al.; Mol. Clin. Oncol. 8, 631 (2018) (Review) | A research update on the anticancer effects of bufalin and its derivatives: Y.L. Lan, et al.; Oncol. Lett. 17, 3635 (2019) (Review) | New therapeutic aspects of steroidal cardiac glycosides: the anticancer properties of Huachansu and its main active constituent Bufalin: C.S. Cheng, et al.; Cancer Cell Int. 19, 92 (2019) (Review)