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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
Synonyme(s) :
5-Azacitidine, 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin
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100 MG
126.00 CHF
250 MG
239.00 CHF
1 G
402.00 CHF
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Changer de vue
100 MG
126.00 CHF
250 MG
239.00 CHF
1 G
402.00 CHF
About This Item
Formule empirique (notation de Hill) :
C8H12N4O5
Numéro CAS:
Poids moléculaire :
244.20
Beilstein:
620461
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77
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Nom du produit
5-Azacytidine, ≥98% (HPLC)
Essai
≥98% (HPLC)
Forme
powder
Pf
226-232 °C (dec.) (lit.)
Spectre d'activité de l'antibiotique
viruses
Mode d’action
DNA synthesis | interferes
Auteur
Celgene
Température de stockage
−20°C
Chaîne 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
Clé InChI
NMUSYJAQQFHJEW-KVTDHHQDSA-N
Informations sur le gène
human ... DNMT1(1786) , DNMT3A(1788) , DNMT3B(1789)
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Description générale
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
Application
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]
Actions biochimiques/physiologiques
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.
Caractéristiques et avantages
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.
Mention d'avertissement
Danger
Mentions de danger
Conseils de prudence
Classification des risques
Acute Tox. 4 Oral - Aquatic Chronic 1 - Carc. 1A - Muta. 2 - Repr. 1B - STOT RE 1
Code de la classe de stockage
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
Classe de danger pour l'eau (WGK)
WGK 3
Équipement de protection individuelle
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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Les clients ont également consulté
Myogenic differentiation potential of mesenchymal stem cells derived from fetal bovine bone marrow
Okamura LH, et al.
Animal Biotechnology, 29(1), 1-11 (2018)
Functional striated muscle cells from non-myoblast precursors following 5-azacytidine treatment
Constantinides PG, et al.
Nature, 267(5609), 364-364 (1977)
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)
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)
Articles
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-
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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.
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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.
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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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