Deguelin

Alias: (-)-Deguelin; (-)-cis-Deguelin
Cat No.:V2543 Purity: ≥98%
Deguelin [(-)-Deguelin, (-)-cis-Deguelin], a naturally occurring rotenoid isolated from plants in the Mundulea sericea family, is an Akt inhibitor with anti-tumor effect on several cancers; it acts by decreasing levels of phosphorylated Akt.
Deguelin Chemical Structure CAS No.: 522-17-8
Product category: PI3K
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
50mg
100mg
Other Sizes
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text

 

  • Business Relationship with 5000+ Clients Globally
  • Major Universities, Research Institutions, Biotech & Pharma
  • Citations by Top Journals: Nature, Cell, Science, etc.
Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Deguelin [(-)-Deguelin, (-)-cis-Deguelin], a naturally occurring rotenoid isolated from plants in the Mundulea sericea family, is an Akt inhibitor with anti-tumor effects on various cancers. It works by lowering levels of phosphorylated Akt. When the PI3K/Akt axis is active in leukemia cell lines, deguelin inhibits Akt phosphorylation. Deguelin is effective at preventing Akt phosphorylation at concentrations of 10 or 100 nmol/l. By deguelin, total Akt expression is unaffected. Deguelin also has no impact on the phosphorylation or expression of the p44/42 or p38 MAP kinases in U937 cells.

Biological Activity I Assay Protocols (From Reference)
Targets
PI3K; Akt
ln Vitro
Deguelin downregulates Akt phosphorylation in leukaemia cell lines with an active PI3K/Akt axis. Deguelin is effective at preventing Akt phosphorylation at concentrations of 10 or 100 nmol/l. By deguelin, total Akt expression is unaffected. Deguelin also has no impact on the phosphorylation or expression of the p44/42 or p38 MAP kinases in U937 cells. Deguelin makes human leukemia cells more susceptible to chemotherapy. Deguelin increases cytarabine sensitivity and dephosphorylates Akt in AML blasts, but not in CB CD34+. When used for 24 hours at a concentration of 10 nmol/l, deguelin arrests U937 cells in the S phase and prevents them from progressing to the G2/M phase. Deguelin does not significantly increase the apoptotic rate of U937 cells when used alone for 24 hours at a concentration of 10 nmol/l[1].
ln Vivo
Deguelin inhibits in vivo angiogenesis of chick chorioallantoic membrane (CAM) without cytotoxic effect and significantly reduces laser-induced CNV in a mouse model of AMD without significant retinal toxicity[2]. It demonstrated notable in vitro and in vivo anti-tumorigenesis and anti-proliferative activity in different cancer types. Deguelin significantly decreased the incidence of tumors in pre-clinical studies. Deguelin, when applied topically, significantly reduced the number of skin tumors that were caused by UVB exposure, suggesting that it may have potential as a cancer chemopreventive. In A/J mice exposed to the tobacco-specific carcinogen benzo(a)pyrene (Bap) and other carcinogens, deguelin significantly reduced tumor multiplicity and volume as well as the overall tumor burden with no discernible toxicity. Deguelin is toxic above a certain dose, though, so this should not be disregarded. Parkinson's disease was brought on by the treatment with deguelin, a potential mitochondria complex I inhibitor, which reduced tyrosine hydroxylase-positive neurons. Kim et al shows that deguelin promoted a PD-like syndrome, mainly by Src/STAT signaling, since α-synuclein (a key protein function in the pathogenesis of PD) was phosphorylated by deguelin-activated Src[3].
Enzyme Assay
Caspase 3 activity is determined using Caspase-Glo-3 assays. This assay provides luminogenic substrate in a buffer system optimized for each specific caspase activity. The caspase cleavage of the substrate is followed by generation of a luminescent signal. The signal generated is proportional to the amount of caspase activity present in the sample. Protein (10 µg) from the cell samples is diluted in water to a final volume of 50 µL, then 50 µL of Caspase-Glo-3 reagent is added to a white 96-well microtitre plate. The plate is sealed, gently mixed for 30 seconds at 300-500 rpm, and then incubated for 30 minutes at room temperature. In a microplate reader (TECAN Infinite 200), luminescence is measured.
Cell Assay
Deguelin is incubated with breast cancer cells at increasing concentrations for 24, 48, and 72 hours. The concentrations range from 31 nM to 500 nM. At the conclusion, cells are trypsinized, and cell proliferation is assessed by counting cells using a Z-series Coulter counter. Data are displayed as MeanSE% of control.
Animal Protocol
Female athymic mice (nu/nu), which are six to seven weeks old, are kept in barrier-free housing with 12-hour light/12-hour dark cycles in an environment with a temperature of 24°C and a relative humidity of 50%. Water is available at all times, along with sterile mouse food. The dorsal flank region of the animal is subcutaneously injected with a 23 g hypodermic needle after MDA-MB-231 cells (3.0 million cells/animal) are injected in sterile PBS suspension. A palpable tumor at the injection site is checked daily on the animals. The mice are divided randomly into three groups and given one of the following after the tumor (about 50 mm3) appears: 1) a vehicle as a control. 2) Deguelin therapy at a dose of 2 mg/kg body weight; or 3) Deguelin at a dose of 4 mg/kg body weight. Ten creatures make up each group. For a period of 21 days, vehicle or deguelin is given by i.p. injection. The toxicity of the drugs and vehicles is observed in animals every day, and they are weighed once per week. Every other day, the tumor's growth is observed, and every other day, calipers are used to measure the tumor's size. The widely used equation tumor volume (mm3)=π/6 lengthwidthdepth is used to calculate tumor volume. The information shown in each group's average tumor volume plus SE (mm3). Except when they appear to be moribund or tumors exhibit necrosis, the animals are sacrificed at the appointed time. At termination, the tumor is excised, freed from connective tissue and other organs, a small piece is fixed in 10% buffered formalin, and the remaining tumor is snap-frozen for a future biochemical analysis. The liver, lung, kidney, and spleen are removed and weighed.
References

[1]. Br J Haematol. 2005 Jun;129(5):677-86.

[2]. J Pharmacol Exp Ther. 2008 Feb;324(2):643-7.

[3]. Mol Clin Oncol. 2013 Mar;1(2):215-219.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C23H22O6
Molecular Weight
394.4172
Exact Mass
394.14164
Elemental Analysis
C, 70.04; H, 5.62; O, 24.34
CAS #
522-17-8
Appearance
Solid powder
SMILES
O=C1[C@]2([H])[C@](COC3=CC(OC)=C(OC)C=C32)([H])OC4=C5C=CC(C)(C)OC5=CC=C14
InChi Key
ORDAZKGHSNRHTD-UXHICEINSA-N
InChi Code
InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
Chemical Name
(7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f'''']dichromen-7(7aH)-one.
Synonyms
(-)-Deguelin; (-)-cis-Deguelin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~78 mg/mL (197.8 mM)
Water: <1 mg/mL
Ethanol: 78 mg/mL (197.8 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.5354 mL 12.6768 mL 25.3537 mL
5 mM 0.5071 mL 2.5354 mL 5.0707 mL
10 mM 0.2535 mL 1.2677 mL 2.5354 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Contact Us