Yes it is soluble in DMSO. In the publication "Cancer Res., 61, 6331-6334 (2001)" by A. Chetcuti et al., there are further details on the preparation of a 5 micromolar working concentration from a 5 Molar freshly prepared stock solution in DMSO.
A2385
5-Azacytidine
≥98% (HPLC), powder, DNA methyltransferase inhibitor
Sinônimo(s):
5-Azacitidine, 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin
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About This Item
Fórmula empírica (Notação de Hill):
C8H12N4O5
Número CAS:
Peso molecular:
244.20
Beilstein:
620461
Número CE:
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77
Preço e disponibilidade não estão disponíveis no momento.
Produtos recomendados
Nome do produto
5-Azacytidine, ≥98% (HPLC)
Ensaio
≥98% (HPLC)
Formulário
powder
pf
226-232 °C (dec.) (lit.)
espectro de atividade do antibiótico
viruses
Modo de ação
DNA synthesis | interferes
originador
Celgene
temperatura de armazenamento
−20°C
cadeia de caracteres SMILES
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
chave InChI
NMUSYJAQQFHJEW-KVTDHHQDSA-N
Informações sobre genes
human ... DNMT1(1786) , DNMT3A(1788) , DNMT3B(1789)
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Descrição geral
5-Azacytidine is a chemical analog of cytidine. It functions as a hypomethylating agent. 5-Azacytidine is used to treat myelodysplastic syndrome (MDS).[1]
Chemical structure: nucleoside
Aplicação
5-Azacytidine has been used:
- for cell induction[2]
- to study its effects on bovine fetal mesenchymal stem cells (bfMSC)[3]
- to study its effects on human bone marrow stromal cells (hBMSCs)[4]
- to study its effects on and DNA methyltransferase 1 (DNMT1) and Ras protein activator like 1 (RASAL1) expression[5]
- to interfere with DNA methylation and histone acetylation[6]
- to determine its effects on the conversion of control fibroblasts[7]
- for optical coherence tomography (OCT) and fluorescein angiography (FA)[8]
- for the reactivation of Sal-like protein (SALL)3 expression[9]
Ações bioquímicas/fisiológicas
5-Azacytidine (Aza-CR) acts as a potential chemotherapeutic regimen for acute myelogenous leukemia.[10] This drug has an ability to selectively increase γ-globin synthesis. Therefore, 5-azacytidine is used in treating severe β-thalassemia.[11] 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.[12]
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.
Características e benefícios
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.
Palavra indicadora
Danger
Frases de perigo
Declarações de precaução
Classificações de perigo
Acute Tox. 4 Oral - Aquatic Chronic 1 - Carc. 1A - Muta. 2 - Repr. 1B - STOT RE 1
Código de classe de armazenamento
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
Classe de risco de água (WGK)
WGK 3
Equipamento de proteção individual
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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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 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)
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)
Enhanced conversion of induced neuronal cells (iN cells) from human fibroblasts: utility in uncovering cellular deficits in mental illness-associated chromosomal abnormalities
Passeri E, et al.
Neuroscience Research, 101, 57-61 (2015)
Functional striated muscle cells from non-myoblast precursors following 5-azacytidine treatment
Constantinides PG, et al.
Nature, 267(5609), 364-364 (1977)
Artigos
Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.
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.
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Is Product A2385 soluble in DMSO?
1 answer-
Helpful?
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I just need to perform a purity assay on Product No. A2385 (5-Azacytidine). What would you recommend?
1 answer-
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.
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What is Product No. A2385 (5-Azacytidine) used for?
1 answer-
This nucleoside analog has been used variously as an antitumor agent and as a mutagenic agent.
Helpful?
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What is the solution stability of Product No. A2385? That is, how should I store solutions of 5-Azacytidine?
1 answer-
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.
Helpful?
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What is the Department of Transportation shipping information for this product?
1 answer-
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.
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I need to perform an identity test on Product No. A2385 (5-Azacytidine). What would you recommend?
1 answer-
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.
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