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A3656

Sigma-Aldrich

5-氮杂-2′-脱氧胞苷

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

别名:

2′-脱氧-5-氮杂胞苷, 4-氨基-1-（2-脱氧-β-D-呋喃核糖基）-1,3,5-三嗪-2（1H）- 酮, 地西他滨

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About This Item

经验公式（希尔记法）:
C8H12N4O4
CAS号:
2353-33-5
分子量:
228.21
Beilstein:
617982
EC 号:
219-089-4
MDL编号:
MFCD00043011
UNSPSC代码:
12352200
PubChem化学物质编号:
24890797
NACRES:
NA.77

产品名称

5-氮杂-2′-脱氧胞苷, ≥97%

质量水平

200

方案

≥97%

表单

powder

溶解性

acetic acid: water (1:1): 50 mg/mL

创始人

Eisai

SMILES字符串

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

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

基因信息

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

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一般描述

5-氮杂-2′-脱氧胞苷是一种DNA次甲基化剂，可刺激白血病细胞分化和凋亡。它是一种2′-脱氧胞苷类似物。5-氮杂-2′-脱氧胞苷用于治疗慢性粒细胞单核细胞白血病、难治性贫血、骨髓增生异常综合症和急性髓细胞性白血病。
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.

应用

5-氮杂-2′-脱氧胞苷已被用作乳腺癌细胞系、染色质、DNA和p16基因启动子区域的脱甲基剂。

生化/生理作用

5′-脱氧杂氮胞苷可引起DNA去甲基化或半去甲基化。DNA去甲基化可通过随着提高的核酸酶活性而“打开”染色质的结构来调控基因的表达。这种染色质结构的重塑可实现转录因子与启动子区域的结合、转录复合物的组装及基因表达。地西他滨是一种表观遗传修饰因子，可抑制DNA甲基转移酶活性而重塑“开放的”染色质，导致DNA去甲基化（低甲基化）和基因活化。当去甲基化与组蛋白超乙酰化组合时，基因会被协同重新激活。

特点和优势

该化合物是基因调控研究的特色产品。点击此处以了解更多的基因调控特色产品。可访问sigma.com/discover-bsm了解更多关于用于其他研究领域生物活性小分子。
该化合物由Eisai开发。如需浏览其他药物开发的化合物和批准的药物/候选药物清单，请单击此处。

制备说明

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

象形图

Health hazardExclamation mark
GHS08,GHS07

警示用语：

Danger

危险分类

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

靶器官

Respiratory system

储存分类代码

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

WGK

WGK 3

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

从最新的版本中选择一种：

分析证书(COA)

Lot/Batch Number
BCCF7170
BCCD6249
SLCD8823
SLCD3551
WXBC9633V

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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 should Product A3656, 5-Aza-2´-deoxycytidine, be dissolved?

    This product is typically dissolved at 50 mg/ml in 50% acetic acid to yield a clear colorless solution. This product is also soluble at 50 mg/ml in DMSO or 0.25 mg/ml in water.

  4. What is the solution stability of Product A3656, 5-Aza-2´-deoxycytidine? 

    Aqueous solutions of this product appear to be very unstable, probably by analogy to A2385, aza-cytidine. We suggest preparing solution fresh for each use and storing solutions on ice until use within a few hours.  

  5. What is the difference between 5-Aza-2´-deoxycytidine Products A3656 and A1287?

    Both of these products inhibit DNA methyltransferase.  However, they are different chemicals.  Product No. A3656 is 5-Aza-2´-deoxycytidine and A1287 is 5-Azacytidine. Product No. A1287 is γ-irradiated, hybridoma- and endotoxin-tested, and Product No. A3656 is not.

  6. 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.

  7. 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. 

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

    Ask a Scientist here.

Molecular, cellular and animal pharmacology of 5-aza-2'-deoxycytidine.
R L Momparler
Pharmacology & therapeutics, 30(3), 287-299 (1985-01-01)
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
Amanda Cabrera-Mulero et al.
Journal of clinical medicine, 8(7) (2019-07-20)
The relationship between body weight and different cancers is now well-recognized and among such cancers, colorectal cancer (CRC) is reported most frequently. Our group recently published findings, through an epigenome-wide association study, suggesting that body mass index (BMI) could act
Decitabine in the treatment of acute myeloid leukemia in elderly patients
Malik P and Cashen AF
Cancer Management and Research, 6, 53-53 (2014)
Jia-Yu Zhong et al.
Aging, 11(14), 5232-5245 (2019-07-29)
Cortisol-producing adenoma (CPA) is the main cause of Adrenal Cushing syndrome. However, its molecular mechanism is not fully understood. Previous study revealed Synaptophysin (SYP) is ubiquitously expressed in adrenocortical tumors, but its function in CPA still need to be discovered.
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