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Merck

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:
320-67-2
Molecular Weight:
244.20
Beilstein:
620461
EC Number:
206-280-2
MDL number:
MFCD00006539
UNSPSC Code:
12352200
PubChem Substance ID:
24278211
NACRES:
NA.77

Key Documents

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Product Name

5-Azacytidine, ≥98% (HPLC)

Quality Level

200

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

human ... DNMT1(1786), DNMT3A(1788), DNMT3B(1789)

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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.
Potent growth inhibitor and cytotoxic agent; inhibits DNA methyltransferase.

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
SLCF3041
BCCF1285
WXBD5537V
BCCC8387
BCCC6523

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Circular RNA expression profiles during the differentiation of human umbilical cord-derived mesenchymal stem cells into cardiomyocyte-like cells
Ruan ZB, et al.
Journal of Cellular Physiology (2019)
Hypoxia-induced changes in DNA methylation alter RASAL1 and TGFbeta1 expression in human trabecular meshwork cells
McDonnell F, et al.
PLoS ONE, 11(4), e0153354-e0153354 (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)
5-Azacytidine in the Treatment of Intermediate-2 and High-risk Myelodysplastic Syndromes and Acute Myeloid Leukemia. A Five-year Experience with 44 Consecutive Patients.
Diamantopoulos P, et al.
Anticancer Research, 35(9), 5141-5147 (2015)
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)
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당사는 유전자 조절 연구 분야에서 표적 식별 및 검증을 위해 전사 인자 조절인자, 염색질 변형 효소 억제제, 작용제/길항제와 같은 여러 저분자 연구 툴을 제공합니다. 이러한 연구 툴 제품군은 아래에 나와 있습니다.

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