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Ethynylcytidine

Alias: SB596168 3Ethynylcytidine; ECydTAS106TAS 1063CEthynylcytidineAIDS241582AIDS241582
Cat No.:V20811 Purity: ≥98%
Ethynylcytidine (ECyD) is a nucleoside analog that is a potent inhibitor of RNA synthesis and can inhibit RNA polymerase I, II and II.
Ethynylcytidine
Ethynylcytidine Chemical Structure CAS No.: 180300-43-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
Official Supplier of:
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Product Description
Ethynylcytidine (ECyD) is a nucleoside analog that is a potent inhibitor of RNA synthesis and can inhibit RNA polymerase I, II and II. Ethynylcytidine has potent anti-tumor effects in multiple cancer models. Ethynylcytidine is a reagent for click chemistry. It has Alkyne groups and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing Azide groups.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
At 4, 24, and 72 hours of exposure, the cytidine ethinyl IC50 values in five human cancers were 0.114 to 1.032 μM, 0.015 to 0.067 μM, and 0.008 to 0.058 μM, respectively. These findings suggest that cytidine ethinyl's cytotoxicity tends to rise with longer exposure times. At the 24-hour exposure time, cytidine ethinyl seemed to demonstrate adequately strong cytotoxicity against all five human cancers, and the difference in IC50 values between the 24- and 72-hour exposure times was not significant. Cytidine ethinyl exhibits strong cytotoxicity even after four hours of treatment, as evidenced by IC50 values in four out of five human malignancies at submicromolar doses [1].
ln Vivo
Tumor growth inhibition ratio (IR) on day 15 of approximately OCUM-2MD3 and LX-1 xenografts showed tumor regression and a strong antitumor effect at the lowest toxic dose of cytidine ethinyl. 90% or higher. TAS-106 in each of the three management schemes. Specifically, once-weekly treatment with 6 mg/kg cytidine ethinyl resulted in a 98% internal rate of decay (IR) for LX-1 tumors. While once-weekly cytidine ethinyl treatment has an IR of less than 60% and a very weak anti-tumor effect, treatment with cytidine ethinyl three or five times a week has an effective anti-tumor effect with an IR of about 85%[1].
References

[1]. Antitumor activity and pharmacokinetics of TAS-106, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine. Jpn J Cancer Res. 2001 Mar;92(3):343-51.

[2]. TAS-106: preclinical, clinical and beyond. Oncology. 2013;85(6):356-363.

[3]. Phase I and pharmacokinetic study of 3'-C-ethynylcytidine (TAS-106), an inhibitor of RNA polymerase I, II and III,in patients with advanced solid malignancies. Invest New Drugs. 2012;30(1):316-326.

Additional Infomation
3'-C-Ethynylcytidine is a pyrimidine nucleoside.
TAS-106 is a new nucleoside antimetabolite. TAS-106 has demonstrated strong antitumor activity without serious toxicity in nude rat models bearing human tumours.
3'-C-ethynylcytidine is a synthetic cytidine nucleoside containing a covalently bound ethynyl group with potential antineoplastic and radiosensitizing activities. 3'-C-ethynylcytidine is metabolized in tumor cells to ethynylcytidine triphosphate (ECTP), which inhibits RNA synthesis by competitive inhibition of RNA polymerases I, II and III; subsequently, RNase L is activated, resulting in apoptosis. RNase L is a potent antiviral and antiproliferative endoribonuclease that cleaves singled stranded RNA, causes 28s rRNA fragmentation, and activates Janus Kinase (JAK), a mitochondrial-dependent apoptosis signaling molecule.
Drug Indication
Investigated for use/treatment in solid tumors and cancer/tumors (unspecified).
Mechanism of Action
3'-C-ethynylcytidine is metabolized in tumor cells to ethynylcytidine triphosphate (ECTP), which inhibits RNA synthesis by competitive inhibition of RNA polymerases I, II and III; subsequently, RNase L is activated, resulting in apoptosis. RNase L is a potent antiviral and antiproliferative endoribonuclease that cleaves singled stranded RNA, causes 28s rRNA fragmentation, and activates Janus Kinase (JAK), a mitochondrial-dependent apoptosis signaling molecule.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H13N3O5
Molecular Weight
267.23802
Exact Mass
267.086
CAS #
180300-43-0
PubChem CID
176885
Appearance
White to yellow solid powder
Density
1.61g/cm3
Boiling Point
536.4ºC at 760 mmHg
Flash Point
278.2ºC
Vapour Pressure
9.56E-14mmHg at 25°C
Index of Refraction
1.677
LogP
-2.7
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
3
Heavy Atom Count
19
Complexity
508
Defined Atom Stereocenter Count
4
SMILES
C#C[C@]1([C@H](O[C@H]([C@@H]1O)N2C=CC(=NC2=O)N)CO)O
InChi Key
JFIWEPHGRUDAJN-DYUFWOLASA-N
InChi Code
InChI=1S/C11H13N3O5/c1-2-11(18)6(5-15)19-9(8(11)16)14-4-3-7(12)13-10(14)17/h1,3-4,6,8-9,15-16,18H,5H2,(H2,12,13,17)/t6-,8+,9-,11-/m1/s1
Chemical Name
4-amino-1-[(2R,3R,4S,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Synonyms
SB596168 3Ethynylcytidine; ECydTAS106TAS 1063CEthynylcytidineAIDS241582AIDS241582
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 : ~250 mg/mL (~935.49 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.78 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 20.8 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: ≥ 2.08 mg/mL (7.78 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 20.8 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: ≥ 2.08 mg/mL (7.78 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 20.8 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 3.7420 mL 18.7098 mL 37.4195 mL
5 mM 0.7484 mL 3.7420 mL 7.4839 mL
10 mM 0.3742 mL 1.8710 mL 3.7420 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)
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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:
  • 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:
  • 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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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.

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