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Merck

A3656

5-Aza-2′-deoxycytidine

≥97% (HPLC), powder, DNA methyltransferase inhibitor

동의어(들):

2′-Deoxy-5-azacytidine, 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Decitabine

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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):
C8H12N4O4
CAS 번호:
Molecular Weight:
228.21
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
219-089-4
MDL number:
Beilstein/REAXYS Number:
617982
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제품 이름

5-Aza-2′-deoxycytidine, ≥97%

InChI

1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1

InChI key

XAUDJQYHKZQPEU-KVQBGUIXSA-N

SMILES string

NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2

assay

≥97%

form

powder

solubility

acetic acid: water (1:1): 50 mg/mL

originator

Eisai

Quality Level

Gene Information

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관련 카테고리

Application

5-Aza-2′-deoxycytidine has been used as a demethylating agent in breast cancer cell line, chromatin, DNA and promoter region of p16 gene.

Biochem/physiol Actions

5′-Azadeoxycytidine causes DNA demethylation or hemi-demethylation. DNA demethylation can regulate gene expression by "opening" the chromatin structure detectable as increased nuclease sensitivity. This remodeling of chromatin structure allows transcription factors to bind to the promoter regions, assembly of the transcription complex, and gene expression. Decitabine is an epigenetic modifier that inhibits DNA methyltransferase activity which results in DNA demethylation (hypomethylation) and gene activation by remodeling "opening" chromatin. Genes are synergistically reactivated when demethylation is combined with histone hyperacetylation.

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 Eisai. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

General description

5-Aza-2′-deoxycytidine is a DNA-hypomethylating agent, which stimulates differentiation and apoptosis of leukemic cells. It is a 2′-deoxycytidine analogue. 5-Aza-2′-deoxycytidine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome and acute myeloid leukemia.
5-Aza-2′-deoxycytidine, also known as Decitabine, is a DNA-hypomethylating agent that promotes differentiation and apoptosis in leukemic cells. It is a 2′-deoxycytidine analog that causes DNA demethylation or hemi-demethylation, which can regulate gene expression by "opening" the chromatin structure, making it more sensitive to nucleases. This chromatin remodeling allows transcription factors to bind to promoter regions, facilitating the assembly of the transcription complex and subsequent gene expression. As an epigenetic modifier, Decitabine inhibits DNA methyltransferase activity, leading to DNA hypomethylation and gene activation. The reactivation of genes is further enhanced when demethylation is combined with histone hyperacetylation. Decitabine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome, and acute myeloid leukemia.

Preparation Note

When prepared properly, there may be a small amount of undissolved substance.

pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

저장 등급

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

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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이 제품을 이미 가지고 계십니까?

문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

Zhen Liang et al.
Molecular cancer, 16(1), 96-96 (2017-05-28)
Current evidence indicates that miR-608 is widely down-regulated in various malignant tumors including liver cancer, colon cancer, lung cancer and glioma, and acts as a tumor suppressor by inhibiting cell proliferation, invasion and migration or by promoting apoptosis. The specific
Hypermethylation in the p16 promoter region in the carcinogenesis of endometrial cancer in Japanese patients
Yanokura M, et al.
Anticancer Research, 26(2A), 851-856 (2006)
Enhancement of chemotherapeutic efficacy in hypermethylator breast cancer cells through targeted and pharmacologic inhibition of DNMT3b
Sandhu R, et al.
Breast Cancer Research and Treatment, 131(2), 385-399 (2012)
Decitabine
Gore SD, et al.
Nature Reviews Drug Discovery (2006)
Vinay Koshy Varghese et al.
Life sciences, 232, 116668-116668 (2019-07-22)
Gene regulatory mechanisms determine the multistep carcinogenesis process. Two aspects of epigenetics are microRNA (miRNAs) and DNA methylation that regulate distinct biological mechanisms such as metastasis, apoptosis cell proliferation and induction of senescence. Although critical, the interplay between these two

문서

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