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Pseudobufarenogin

CAS# 17008-69-4

Pseudobufarenogin

2D Structure

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Pseudobufarenogin

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Chemical Properties of Pseudobufarenogin

Cas No. 17008-69-4 SDF Download SDF
PubChem ID 204810 Appearance Powder
Formula C24H32O6 M.Wt 416.51
Type of Compound Steroids Storage Desiccate at -20°C
Synonyms ψ-Bufarenogin
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-10,13-dimethyl-11-oxo-2,3,4,5,6,7,8,9,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
SMILES CC12CCC(CC1CCC3C2C(=O)C(C4(C3(CCC4C5=COC(=O)C=C5)O)C)O)O
Standard InChIKey SOGONHOGEFLVPE-BHZHDSHXSA-N
Standard InChI InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19,21,25,28-29H,4-5,7-11H2,1-2H3/t14-,15+,16-,17-,19-,21+,22+,23+,24+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Pseudobufarenogin

The glandular body of Bufo bufo

Biological Activity of Pseudobufarenogin

Description1. Pseudobufarenogin(ψ-bufarenogin), a novel anti-tumor compound, suppresses liver cancer growth by inhibiting receptor tyrosine kinase-mediated signaling. 2. ψ-Bufarenogin shows inhibition of human kidney Na(+)/K(+)-ATPase activity.
TargetsSodium Channel | ATPase | Potassium Channel | MEK | ERK | PI3K | Akt | EGFR | Raf

Pseudobufarenogin Dilution Calculator

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Pseudobufarenogin Molarity Calculator

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Preparing Stock Solutions of Pseudobufarenogin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4009 mL 12.0045 mL 24.009 mL 48.0181 mL 60.0226 mL
5 mM 0.4802 mL 2.4009 mL 4.8018 mL 9.6036 mL 12.0045 mL
10 mM 0.2401 mL 1.2005 mL 2.4009 mL 4.8018 mL 6.0023 mL
50 mM 0.048 mL 0.2401 mL 0.4802 mL 0.9604 mL 1.2005 mL
100 mM 0.024 mL 0.12 mL 0.2401 mL 0.4802 mL 0.6002 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Pseudobufarenogin

Pseudobufarenogin is a natural compound extracted from toad species with unknown details.

References:
[1]. Jin Ding, et al. ψ-Bufarenogin, a novel anti-tumor compound, suppresses liver cancer growth by inhibiting receptor tyrosine kinase-mediated signaling. Oncotarget. 2015 May 10; 6(13): 11627–11639.

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References on Pseudobufarenogin

Bufadienolides from parotoid gland secretions of Cuban toad Peltophryne fustiger (Bufonidae): Inhibition of human kidney Na(+)/K(+)-ATPase activity.[Pubmed:26615828]

Toxicon. 2016 Feb;110:27-34.

Parotoid gland secretions of toad species are a vast reservoir of bioactive molecules with a wide range of biological properties. Herein, for the first time, it is described the isolation by preparative reversed-phase HPLC and the structure elucidation by NMR spectroscopy and/or mass spectrometry of nine major bufadienolides from parotoid gland secretions of the Cuban endemic toad Peltophryne fustiger: psi-bufarenogin, gamabufotalin, bufarenogin, arenobufagin, 3-(N-suberoylargininyl) marinobufagin, bufotalinin, telocinobufagin, marinobufagin and bufalin. In addition, the secretion was analyzed by UPLC-MS/MS which also allowed the identification of azelayl arginine. The effect of arenobufagin, bufalin and psi-bufarenogin on Na(+)/K(+)-ATPase activity in a human kidney preparation was evaluated. These bufadienolides fully inhibited the Na(+)/K(+)-ATPase in a concentration-dependent manner, although arenobufagin (IC50 = 28.3 nM) and bufalin (IC50 = 28.7 nM) were 100 times more potent than psi-bufarenogin (IC50 = 3020 nM). These results provided evidence about the importance of the hydroxylation at position C-14 in the bufadienolide skeleton for the inhibitory activity on the Na(+)/K(+)-ATPase.

psi-Bufarenogin, a novel anti-tumor compound, suppresses liver cancer growth by inhibiting receptor tyrosine kinase-mediated signaling.[Pubmed:25890498]

Oncotarget. 2015 May 10;6(13):11627-39.

Resistance of hepatocellular carcinoma (HCC) to existing chemotherapeutic agents largely contributes to the poor prognosis of patients, and discovery of novel anti-HCC drug is in an urgent need. Herein we report psi-Bufarenogin, a novel active compound that we isolated from the extract of toad skin, exhibited potent therapeutic effect in xenografted human hepatoma without notable side effects. In vitro, psi-Bufarenogin suppressed HCC cells proliferation through impeding cell cycle progression, and it facilitated cell apoptosis by downregulating Mcl-1 expression. Moreover, psi-Bufarenogin decreased the number of hepatoma stem cells through Sox2 depression and exhibited synergistic effect with conventional chemotherapeutics. Mechanistic study revealed that psi-Bufarenogin impaired the activation of MEK/ERK pathway, which is essential in the proliferation of hepatoma cells. psi-Bufarenogin notably suppressed PI3-K/Akt cascade, which was required in psi-Bufarenogin-mediated reduction of Mcl-1 and Sox2. psi-Bufarenogin inhibited the auto-phosphorylation and activation of epithelial growth factor receptor (EGFR) and hepatocyte growth factor receptor (c-Met), thereafter suppressed their primary downstream cascades Raf/MEK/ERK and PI3-K/Akt signaling. Taken together, psi-Bufarenogin suppressed HCC growth via inhibiting, at least partially, receptor tyrosine kinases-regulated signaling, suggesting that psi-Bufarenogin could be a novel lead compound for anti-HCC drug.

Description

Pseudobufarenogin is a natural compound extracted from toad species with unknown details.

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