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4'-Demethylepipodophyllotoxin

Cat No.:V9098 Purity: ≥98%
4'-Demethylepipodophyllotoxin (4'-DMEP) is an intermediate compound that can inhibit microtubule assembly.
4'-Demethylepipodophyllotoxin
4'-Demethylepipodophyllotoxin Chemical Structure CAS No.: 6559-91-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
4'-Demethylepipodophyllotoxin (4'-DMEP) is an intermediate compound that can inhibit microtubule assembly.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
4'-Demethylepipodophyllotoxin has antibacterial actions on Xanthomonas oryzae pv (EC50 = 38.7 μg/mL) and decreases XooFtsZ'GTPase activity [3]. The cytotoxic effect of 4'-Demethylepipodophyllotoxin (Xoo) against tumor cells is demonstrated by its EC50 values of 0.31, 0.32, 0.37, and 0.43 μM for HepG2, KB, HL-60, and K-562 cells [1].
ln Vivo
In a DMBA/TPA-induced skin carcinogenesis model, 4'-Demethylepipodophyllotoxin (1 µg/mL, 200 µL, topical, 24 weeks) decreases tumor incidence, tumor volume, and papilloma-to-squamous cell carcinoma transformation efficiency [1].
References

[1]. Tang YJ, Zhao W, Li HM. Novel tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4'-demethylepipodophyllotoxin. Appl Environ Microbiol. 2011 May;77(9):3023-34.

[2]. Dhawan D, Balasubramanian S, Amonkar AJ, Chemopreventive effect of 4'-demethyl epipodophyllotoxin on DMBA/TPA-induced mouse skin carcinogenesis. Carcinogenesis. 1999 Jun;20(6):997-1003.

[3]. The discovery of natural 4'-demethylepipodophyllotoxin from renewable Dysosma versipellis species as a novel bacterial cell division inhibitor for controlling intractable diseases in rice. Industrial Crops and Products. Volume 174, 15 December 2021, 114182.

Additional Infomation
4'-demethylepipodophyllotoxin is an organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin. It has a role as an antineoplastic agent. It is a furonaphthodioxole, an organic heterotetracyclic compound and a member of phenols.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H20O8
Molecular Weight
400.3787
Exact Mass
400.115
CAS #
6559-91-7
PubChem CID
122797
Appearance
Light yellow to yellow solid powder
Density
1.4±0.1 g/cm3
Boiling Point
626.5±55.0 °C at 760 mmHg
Melting Point
246-248ºC
Flash Point
224.4±25.0 °C
Vapour Pressure
0.0±1.9 mmHg at 25°C
Index of Refraction
1.638
LogP
0.71
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
3
Heavy Atom Count
29
Complexity
614
Defined Atom Stereocenter Count
4
SMILES
O1C([C@]2([H])[C@]([H])(C3C([H])=C(C(=C(C=3[H])OC([H])([H])[H])O[H])OC([H])([H])[H])C3=C([H])C4=C(C([H])=C3[C@]([H])([C@@]2([H])C1([H])[H])O[H])OC([H])([H])O4)=O
InChi Key
YVCVYCSAAZQOJI-JHQYFNNDSA-N
InChi Code
InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
Chemical Name
(5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
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 : ~3.33 mg/mL (~8.32 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.4976 mL 12.4881 mL 24.9763 mL
5 mM 0.4995 mL 2.4976 mL 4.9953 mL
10 mM 0.2498 mL 1.2488 mL 2.4976 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:

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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)
  • 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)
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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:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • 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.)
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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.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT00026208 COMPLETEDWITH RESULTS Drug: Vincristine
Drug: Cyclophosphamide
Drug: Doxorubicin
Hodgkin Disease
Lymphoma
Lymphoma, Hodgkin Disease
Lymphoma: Hodgkin
Stanford University 2001-06 Phase 2
Biological Data
  • Tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4′-demethylepipodophyllotoxin (4-TMP-DMEP), from podophyllotoxin (PTOX).[1].Tang YJ, Zhao W, Li HM. Novel tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4'-demethylepipodophyllotoxin. Appl Environ Microbiol. 2011 May;77(9):3023-34.
  • 13C NMR spectra of podophyllotoxin (PTOX) (A) and 4-(2,3,5,6-tetramethylpyrazine-1)-4′-demethylepipodophyllotoxin (4-TMP-DMEP) (B).[1].Tang YJ, Zhao W, Li HM. Novel tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4'-demethylepipodophyllotoxin. Appl Environ Microbiol. 2011 May;77(9):3023-34.
  • 1H NMR spectra of podophyllotoxin (PTOX) (A) and 4-(2,3,5,6-tetramethylpyrazine-1)-4′-demethylepipodophyllotoxin (4-TMP-DMEP) (B).[1].Tang YJ, Zhao W, Li HM. Novel tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4'-demethylepipodophyllotoxin. Appl Environ Microbiol. 2011 May;77(9):3023-34.
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