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Digitoxose (D-(+)-Digitoxose)

Cat No.:V66886 Purity: ≥98%
Digitoxose (D-(+)-Digitoxose), a naturally occurring compound, specifically and competitively inhibits glucose-stimulated insulin release from islets in lean and obese mice.
Digitoxose (D-(+)-Digitoxose)
Digitoxose (D-(+)-Digitoxose) Chemical Structure CAS No.: 527-52-6
Product category: Biochemical Assay Reagents
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Digitoxose (D-(+)-Digitoxose), a naturally occurring compound, specifically and competitively inhibits glucose-stimulated insulin release from islets in lean and obese mice. Digitoxose may be utilized in diabetes research.
Digitoxose (D-(+)-Digitoxose) is a naturally occurring 2,6-dideoxyhexose sugar with the molecular formula C6H12O4 and a molecular weight of 148.16 g/mol. It is a monosaccharide subunit of the cardiac glycoside digitoxin and plays a crucial role in modulating the solubility and receptor interactions of glycoside molecules.
Biological Activity I Assay Protocols (From Reference)
Targets
Inhibition of glucose-stimulated insulin secretion is a reported target. Specifically, Digitoxose competitively inhibits glucose-stimulated insulin release from pancreatic islets. It also serves as a sugar subunit for cardiac glycosides targeting the Na+/K+-ATPase receptor.
ln Vitro
In vitro, Digitoxose specifically and competitively inhibits glucose-stimulated insulin release from isolated pancreatic islets. It also serves as a model sugar for studying glycosylation reactions and structure-activity relationship (SAR) studies in medicinal chemistry.
ln Vivo
There is no specific in vivo activity data available for this compound, although its parent molecule digitoxin is cardiotoxic. D-Digitoxose has been studied in lean and obese mice to investigate its effects on insulin secretion, showing potential for diabetes research.
Enzyme Assay
There is no specific enzyme/receptor binding protocol for this compound. A typical protocol for studying its effect on insulin release involves incubating isolated pancreatic islets in Krebs-Ringer buffer containing glucose (e.g., 2.8 or 16.7 mM) and various concentrations of Digitoxose (e.g., 0.1-10 mM) at 37degC in a CO2 incubator, followed by measurement of insulin in the supernatant by ELISA.
Cell Assay
There is no specific cell-based protocol for this compound. If used in cellular studies, a general protocol would involve treating pancreatic beta-cell lines (e.g., INS-1 or MIN6 cells) with Digitoxose (1-20 mM) in low-glucose or high-glucose medium for 1-4 hours, followed by assessment of insulin secretion by ELISA.
Animal Protocol
There is no standard in vivo protocol for this compound. A general protocol for studying its effect on glucose homeostasis involves administering Digitoxose (e.g., 1-100 mg/kg) intraperitoneally to mice, followed by a glucose tolerance test to measure insulin release and blood glucose levels over time.
ADME/Pharmacokinetics
General PK properties for Digitoxose are not applicable for its use as a research reagent. Being a sugar, it is water-soluble and likely undergoes renal clearance, but detailed data for the free sugar are not available. Formulation is typically in PBS or saline.
Toxicity/Toxicokinetics
Toxicity data for Digitoxose are not well documented. As a deoxy sugar, it is expected to have low toxicity compared to the aglycone cardenolides. Standard safety precautions for handling laboratory chemicals should be observed.
References

[1]. The effect of digitoxose on insulin release, glucose oxidation and oxygen consumption by islets of lean and genetically obese diabetic (ob/ob) mice. Biochem Biophys Res Commun. 1985 Jun 14;129(2):358-67.

Additional Infomation
Digoxin is a dideoxyhexose.
See also: D-Digoxin (note moved to).
Digitoxose is a research tool for studying carbohydrate chemistry, glycosylation reactions, and insulin secretion pathways. As a building block for cardiac glycosides, it is used in medicinal chemistry to investigate structure-activity relationships. This product is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H12O4
Molecular Weight
148.16
Exact Mass
148.074
CAS #
527-52-6
PubChem CID
94168
Appearance
Typically exists as solid at room temperature
Density
1.366g/cm3
Boiling Point
320.1ºC at 760mmHg
Melting Point
98-100 °C
Flash Point
147.4ºC
Index of Refraction
1.542
LogP
-1.8
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
10
Complexity
104
Defined Atom Stereocenter Count
3
SMILES
CC(O)C(O)C(O)CC=O.CC(O)C1OC(O)CC1O.CC1OC(O)CC(O)C1O
InChi Key
JWFRNGYBHLBCMB-NGJCXOISSA-N
InChi Code
InChI=1S/C6H12O4/c1-4(8)6(10)5(9)2-3-7/h3-6,8-10H,2H2,1H3/t4-,5+,6-/m1/s1
Chemical Name
(3S,4R,5R)-3,4,5-trihydroxyhexanal
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.7495 mL 33.7473 mL 67.4946 mL
5 mM 1.3499 mL 6.7495 mL 13.4989 mL
10 mM 0.6749 mL 3.3747 mL 6.7495 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.

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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)
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  • 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:
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  • 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:
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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.
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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.)
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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.

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