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A2385

Sigma-Aldrich

5-Azacytidine

≥98% (HPLC), powder, DNA methyltransferase inhibitor

Synonym(s):

5-Azacitidine, 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:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

5-Azacytidine, ≥98% (HPLC)

Quality Level

Assay

≥98% (HPLC)

form

powder

mp

226-232 °C (dec.) (lit.)

antibiotic activity spectrum

viruses

Mode of action

DNA synthesis | interferes

originator

Celgene

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

5-Azacytidine is a chemical analog of cytidine. It functions as a hypomethylating agent. 5-Azacytidine is used to treat myelodysplastic syndrome (MDS).
Chemical structure: nucleoside

Application

5-Azacytidine has been used:
  • for cell induction
  • to study its effects on bovine fetal mesenchymal stem cells (bfMSC)
  • to study its effects on human bone marrow stromal cells (hBMSCs)
  • to study its effects on and DNA methyltransferase 1 (DNMT1) and Ras protein activator like 1 (RASAL1) expression
  • to interfere with DNA methylation and histone acetylation
  • to determine its effects on the conversion of control fibroblasts
  • for optical coherence tomography (OCT) and fluorescein angiography (FA)
  • for the reactivation of Sal-like protein (SALL)3 expression

Biochem/physiol Actions

5-Azacytidine (Aza-CR) acts as a potential chemotherapeutic regimen for acute myelogenous leukemia. This drug has an ability to selectively increase γ-globin synthesis. Therefore, 5-azacytidine is used in treating severe β-thalassemia. Aza-CR acts as a potential bacteriostatic, antitumor and mutagenic agent. In addition, it also exhibits various biological activity such as, immunosuppressive, antimitotic, radioprotective and virostatic effects.
A potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase, an important regulatory mechanism of gene expression, gene activation and silencing.
Causes DNA demethylation or hemi-demethylation, creating openings that allow transcription factors to bind to DNA and reactivate tumor suppressor genes.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Signal Word

Danger

Hazard Classifications

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

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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  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. 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.

  4. 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. 

  5. What is the solution stability of Product No. A2385? That is, how should I store solutions of 5-Azacytidine?

    We generally don't recommend storing solutions, since it has such poor solution stability. In Cancer Res., 61, 6331-6334 (2001), A. Chetcuti et al. describe preparing a 5 micromolar working concentration from a 5 Molar freshly prepared stock solution in DMSO.

  6. What is Product No. A2385 (5-Azacytidine) used for?

    This nucleoside analog has been used variously as an antitumor agent and as a mutagenic agent.

  7. I need to perform an identity test on Product No. A2385 (5-Azacytidine). What would you recommend?

    This means that each lot is tested according to the list of tests (left hand column), and must meet or exceed the specifications (right hand column). HPLC. The elemental analyses for carbon and nitrogen content are identity tests (albeit not absolutely conclusive identity tests). I would say that the HPLC, using a previous lot of A2385 as a control sample, provides the best evidence for identity and purity.

  8. I just need to perform a purity assay on Product No. A2385 (5-Azacytidine). What would you recommend?

    We assay the purity of this product by HPLC. If you would like to obtain a copy of our HPLC parameters/method, please contact your local Sigma-Aldrich Technical Service group.

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

    Ask a Scientist here.

Epigenetic modifications in hyperhomocysteinemia: potential role in diabetic retinopathy and age-related macular degeneration
Elmasry K, et al.
Testing, 9(16), 12562-12562 (2018)
5-Azacytidine selectively increases gamma-globin synthesis in a patient with beta thalassemia
Ley TJ and DeSimone, et al.
The New England Journal of Medicine, 307(24), 1469-1475 (1982)
Functional striated muscle cells from non-myoblast precursors following 5-azacytidine treatment
Constantinides PG, et al.
Nature, 267(5609), 364-364 (1977)
Dexamethasone regulates EphA5, a potential inhibitory factor with osteogenic capability of human bone marrow stromal cells
Yamada T, et al.
Stem Cells International, 2016 (2016)
Myogenic differentiation potential of mesenchymal stem cells derived from fetal bovine bone marrow
Okamura LH, et al.
Animal Biotechnology, 29(1), 1-11 (2018)

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