A2385

5-Azacytidine

Name: 5-Azacytidine
Brand: SIGMA

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

동의어(들):

5-Azacitidine, 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin

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크기 선택

제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):

C₈H₁₂N₄O₅

CAS 번호:

320-67-2

Molecular Weight:

244.20

NACRES:

NA.77

PubChem Substance ID:

24278211

UNSPSC Code:

12352200

EC Number:

206-280-2

MDL number:

MFCD00006539

Beilstein/REAXYS Number:

620461

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제품 이름

5-Azacytidine, ≥98% (HPLC)

InChI key

NMUSYJAQQFHJEW-KVTDHHQDSA-N

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

SMILES string

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

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

Quality Level

200

Gene Information

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

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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.

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

pictograms

GHS08,GHS07,GHS09

signalword

Danger

hcodes

H302,H341,H350,H360FD,H372,H410

pcodes

P202 - P260 - P264 - P273 - P301 + P312 - P308 + P313

Hazard Classifications

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

저장 등급

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

wgk

WGK 3

ppe

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

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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

Epigenetic modifications in hyperhomocysteinemia: potential role in diabetic retinopathy and age-related macular degeneration

Elmasry K, et al.

Testing, 9(16), 12562-12562 (2018)

Epigenetic silencing of SALL3 is an independent predictor of poor survival in head and neck cancer

Misawa K, et al.

Clinical epigenetics, 9(1), 64-64 (2017)

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)

Functional striated muscle cells from non-myoblast precursors following 5-azacytidine treatment

Constantinides PG, et al.

Nature, 267(5609), 364-364 (1977)

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문서

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

5-Azacytidine

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

크기 선택

제품정보 (DICE 배송 시 비용 별도)

주요 문서

속성

제품 이름

InChI key

InChI

SMILES string

assay

form

mp

antibiotic activity spectrum

mode of action

originator

storage temp.

Quality Level

Gene Information

관련 카테고리

설명

Application

Biochem/physiol Actions

Features and Benefits

General description

안전성 정보

pictograms

signalword

hcodes

pcodes

Hazard Classifications

저장 등급

wgk

ppe

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