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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/REAXYS Number:
620461
EC Number:
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.75

$29.80


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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.[1] 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).[2]
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.[3] It acts as a potential antineoplastic agent for acute myelogenous leukemia.[4] 5-Azacytidine activates repressed genes by inhibiting DNA methylation.[5] 5-Azacytidine also affects protein synthesis by altering the RNA function and stability.[4]
A potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase, an important regulatory mechanism of gene expression, gene activation and silencing.
Potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase.

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Certificates of Analysis (COA)

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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)
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
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)
In vitro cardiomyogenic differentiation of adult human bone marrow mesenchymal stem cells. The role of 5-azacytidine
Antonitsis P, et al.
Interactive Cardiovascular and Thoracic Surgery, 6(5), 593-597 (2007)

Questions

1–3 of 3 Questions  
  1. What is the vial content of A1287, what is the solubility, and what are to storage conditions for the prepared stock solution?

    1 answer
    1. Each vial contains a minimum of 1 mg of 5-Azacytidine. The exact quantity may vary from lot to lot and is reported in the Certificate of Analysis. This product is tested for solubility at 5 mg/mL in a 1:1 mixture of acetic acid and water. For use in cell culture, the material may be prepared at 1.2 mg in 10 mL of sterile medium without supplements. The stock solution should be stored in aliquots at -20°C. Avoid repeated freeze/thaw cycles. Please see the link below to review a sample or lot specific Certificate:

      https://www.sigmaaldrich.com/product/sigma/a1287#product-documentation

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

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

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

    1 answer
    1. 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.

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