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5-Azacytidine (Synonyms: Antibiotic U 18496, 5AzaC, Ladakamycin, Mylosar, NSC 102816, NSC 103627, U 18496, WR 183027)

Catalog No.GC10946

A DNA methyltransferase inhibitor

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5-Azacytidine Chemical Structure

Cas No.: 320-67-2

Size Price Stock Qty
10mM (in 1mL DMSO)
$42.00
In stock
250mg
$42.00
In stock
1g
$129.00
In stock

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Sample solution is provided at 25 µL, 10mM.

Product has been cited by 1 publications

Product Documents

Quality Control & SDS

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Protocol

Cell experiment [1]:

Cell lines

Leukemia L1210 cells

Preparation method

The solubility of this compound in DMSO is > 12.2 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months.

Reacting condition

80 μM; 0 ~ 120 mins

Applications

In leukemia L1210 cells, 5-Azacytidine showed greater inhibition on DNA synthesis instead of RNA synthesis. After a 90-min preincubation, TdR-3H incorporation was inhibited by about 74%, whilst UR-3H incorporation was inhibited by only 32%.

Animal experiment [2]:

Animal models

BDF1 mice bearing lymphoid leukemia L1210 cells

Dosage form

3 mg/kg; i.p.; q.d.

Applications

In BDF1 mice bearing lymphoid leukemia L1210 cells, 5-Azacytidine increased the mean survival time. Moreover, 5-Azacytidine significantly suppressed all enzymes activity in the polyamine-biosynthetic pathway. In addition, 5-Azacytidine inhibited accumulation of polyamines in leukemic mice.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Li LH, Olin EJ, Buskirk HH, Reineke LM. Cytotoxicity and mode of action of 5-azacytidine on L1210 leukemia. Cancer Res. 1970 Nov;30(11):2760-9.

[2]. Heby O, Russell DH. Depression of polyamine synthesis in L1210 leukemic mice during treatment with a potent antileukemic agent, 5-azacytidine. Cancer Res. 1973 Jan;33(1):159-65.

Background

5-Azacytidine (also known as 5-AzaC), a compound belonging to a class of cytosine analogues, is a DNA methyl transferase (DNMT) inhibitor that exerts potent cytotoxicity against multiple myeloma (MM) cells, including MM.1S, MM.1R, RPMI-8266, RPMI-LR5, RPMI-Dox40 and Patient-derived MM, with the half maximal inhibition concentration IC50 values of 1.5 μmol/L, 0.7 μmol/L, 1.1 μmol/L, 2.5 μmol/L, 3.2 μmol/L and 1.5 μmol/L respectively [1].

5-Azacytidine incorporates into cellular DNA and/or RNA, subsequently sequesters DNMT and forms a covalent bond between C6 of 5-Azacytidine and cysteine thiolate of DNMTs resulting in depletion of DNMT activity in cells and demethylation of cellular DNA [1].

References:
[1] Kiziltepe T, Hideshima T, Catley L, Raje N, Yasui H, Shiraishi N, Okawa Y, Ikeda H, Vallet S, Pozzi S, Ishitsuka K, Ocio EM, Chauhan D, Anderson KC. 5-Azacytidine, a DNA methyltransferase inhibitor, induces ATR-mediated DNA double-strand break responses, apoptosis, and synergistic cytotoxicity with doxorubicin and bortezomib against multiple myeloma cells. Mol Cancer Ther. 2007 Jun;6(6):1718-27.

Chemical Properties

Cas No. 320-67-2 SDF
Synonyms Antibiotic U 18496, 5AzaC, Ladakamycin, Mylosar, NSC 102816, NSC 103627, U 18496, WR 183027
Chemical Name 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
Canonical SMILES C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
Formula C8H12N4O5 M.Wt 244.2
Solubility ≥ 12.21mg/mL in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 4.095 mL 20.475 mL 40.95 mL
5 mM 0.819 mL 4.095 mL 8.19 mL
10 mM 0.4095 mL 2.0475 mL 4.095 mL
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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.

Related Video

    5-Azacytidine -GlpBio

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