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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

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About This Item

Empirical Formula (Hill Notation):
C8H12N4O5
CAS Number:
Molecular Weight:
244.20
Beilstein:
620461
EC Number:
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.75

biological source

synthetic (organic)

Quality Level

grade

Hybri-Max

sterility

γ-irradiated

product line

BioXtra

form

lyophilized powder

technique(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

antibiotic activity spectrum

viruses

Mode of action

DNA synthesis | interferes

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

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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

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 1 - Carc. 1A - Muta. 2 - Repr. 1B - STOT RE 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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DNA methyltransferase inhibitors for cancer therapy
Epigenetics, 5(3), 265-290 (2015)
5-azacytidine treatment reorganizes genomic histone modification patterns
Komashko VM and Farnham PJ
Epigenetics, 5(3), 229-240 (2010)
Agata Magdalena Wasik et al.
Scientific reports, 3, 1400-1400 (2013-03-08)
The related transcription factors SOX11, SOX4 and SOX12 (classified as the SOXC family) compete for the same target genes. SOX11 is expressed in most mantle cell lymphomas (MCL) but a small subset is, like normal lymphocytes, SOX11 negative. Here we
Martin F Kaiser et al.
Blood, 122(2), 219-226 (2013-05-24)
Outcome in multiple myeloma is highly variable and a better understanding of the factors that influence disease biology is essential to understand and predict behavior in individual patients. In the present study, we analyzed combined genomewide DNA methylation and gene
S Massah et al.
BMC genetics, 21(1), 3-3 (2020-01-17)
DNA methylation is an epigenetic modification that mainly repress expression of genes essential during embryogenesis and development. There are key ATPase-dependent enzymes that read or write DNA methylation to remodel chromatin and regulate gene expression. Structural maintenance of chromosome hinge

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