A1287

Sigma-Aldrich

5-Azacytidine

Hybri-Max, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma

Synonym(s):
4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin
Empirical Formula (Hill Notation):
C8H12N4O5
CAS Number:
Molecular Weight:
244.20
Beilstein/REAXYS Number:
620461
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.75

Quality Level

biological source

synthetic (organic)

grade

Hybri-Max

sterility

γ-irradiated

product line

BioXtra

form

lyophilized powder

application(s)

cell culture | hybridoma: suitable

impurities

endotoxin, tested

mp

226-232 °C (dec.) (lit.)

solubility

acetic acid: water (1:1): 5 mg/mL, clear, colorless

Mode of action

DNA synthesis | interferes

antibiotic activity spectrum

viruses

storage temp.

−20°C

SMILES string

NC1=NC(=O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O

InChI

1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1

InChI key

NMUSYJAQQFHJEW-KVTDHHQDSA-N

Gene Information

human ... DNMT1(1786), DNMT3A(1788)

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General description

Chemical structure: nucleoside

Application

5-Azacytidine may be used to induce in vitro cardiomyogenic differentiation of adult human bone marrow mesenchymal stem cells. It may also be used to study the effects of 5-Azacytidine on the immune regulatory myeloid-derived suppressor cells (MDSCs) and regulatory T cells (Tregs).
Used to study the effects of the DNA incorporated molecule on DNA methylation processes.

Biochem/physiol Actions

5-Azacytidine is a deoxycytidine analog and a demethylating agent. It acts as a potential antineoplastic agent for acute myelogenous leukemia. 5-Azacytidine activates repressed genes by inhibiting DNA methylation. 5-Azacytidine also affects protein synthesis by altering the RNA function and stability.
A potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase, an important regulatory mechanism of gene expression, gene activation and silencing.

Reconstitution

Reconstitute contents of vial with 10 mL sterile cell culture medium. Stock solution is sufficient to prepare 500ml medium. Final working concentration: 10 μM 5-azacytidine.

Legal Information

Hybri-Max is a trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the concentration of Product A1287, 5-Azacytidine - Hybri-Max?

    The working concentration is 10 μM, so the 50X stock is 500 μM.

  4. How much is contained in the 1 vial of Product A1287, 5-Azacytidine - Hybri-Max?

    1 vial contains 1.2 mg.

  5. How is Product A1287, 5-Azacytidine - Hybri-Max, to be dissolved? And once dissolved, is the solution stable?

    Dissolve each 1.2 mg vial in 10 mL of culture medium. This compound is very unstable in aqueous solutions; we have found a 10% loss after just 2-3 hours at room temperature in phosphate buffer pH 7.4, even faster loss at 50°C. We generally recommend keeping solutions on ice during the course of a day. If stock solution must be kept, store them in the freezer at -20°C in single use aliquots.  

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

5-azacytidine treatment reorganizes genomic histone modification patterns
Komashko VM and Farnham PJ
Epigenetics, 5(3), 229-240 (2010)
DNA methyltransferase inhibitors for cancer therapy
Epigenetics, 5(3), 265-290 (2015)
Manuel Luís Orta et al.
Nucleic acids research, 41(11), 5827-5836 (2013-04-24)
5-Aza-2'-deoxycytidine (5-azadC) is a DNA methyltransferase (DNMT) inhibitor increasingly used in treatments of hematological diseases and works by being incorporated into DNA and trapping DNMT. It is unclear what DNA lesions are caused by 5-azadC and if such are substrates...
Rena Buckstein et al.
Cancer treatment reviews, 37(2), 160-167 (2010-07-02)
Myelodysplastic syndrome (MDS) is a clonal disorder of hematopoiesis that results in peripheral blood cytopenias and a marked propensity to progress to acute myelogenous leukemia. With 40,000-76,000 new cases per year in the USA, MDS is the commonest of the...
5-Azacytidine treatment sensitizes tumor cells to T-cell mediated cytotoxicity and modulates NK cells in patients with myeloid malignancies
Gang AO, et al.
Blood Cancer Journal, 4(3), e197-e197 (2014)

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