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Sigma
5-Azacytidine
A2385 -
≥98% (HPLC)
DOWNLOAD MSDS (PDF)Synonym: 4-Amino-1-(β-
CAS Number: 320-67-2
Empirical Formula (Hill Notation): C8H12N4O5
Molecular Weight: 244.20
Beilstein Registry Number: 620461
EC Number: 206-280-2
MDL number: MFCD00006539
PubChem Substance ID: 24278211
Properties
| Related Categories | A - K, AN-AZ, Antibacterial, Antibiotics, Antibiotics A to Z, |
| assay | ≥98% (HPLC) |
| mp | 226-232 °C (dec.)(lit.) |
| storage temp. | −20°C |
| Gene Information | Research your gene in Your Favorite Gene powered by Ingenuity human ... DNMT1(1786), DNMT3A(1788), DNMT3B(1789) |
Description
Frequently Asked Questions
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Packaging
1 g in poly btl
100, 250 mg in poly btl
Biochem/physiol Actions
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.
Price and Availability
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Documents
Certificate of Analysis
Certificate of Origin
| A2385 - Product Information Sheet (37 KB) |
| FT-IR Raman |  |
| FT-NMR |  |
| Gene Information |
| Structure Search |  |
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Safety Information
| Symbol |   GHS07, GHS08 |
| Signal word | Danger |
| Hazard statements | H302-H350 |
| Precautionary statements | P201-P308 + P313 |
| Personal Protective Equipment | Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges |
| Hazard Codes | T |
| Risk Statements | 45-46-22 |
| Safety Statements | 53-22-36/37/39-45 |
| WGK Germany | 3 |
| RTECS | XZ3017500 |
Technical information & documentation associated with this product is available in the Safety & Documentation tab.
Articles
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. The expansion of the carcinogenesi...
Vicki Caligur
BioFiles 2008, 3.5, 18.
Keywords: Acetylations, Adhesion, Alkylations, Apoptosis, Cancer, Carcinogens, Cell division, Cell proliferation, Cell signaling, DNA microarrays, Drug discovery, Environmental, Epigenetics, Gene expression, Genetic, Hormones, Metabolism, Methylations, Microarray Analysis, Mutagens, PAGE, Recombination, Reductions, Transcription, transformation
References
Makino, H., et al., Mesenchymal To Embryonic Incomplete Transition Of Human Cells By Chimeric OCT4/3 (POU5F1) With Physiological Co-activator EWS. Exp. Cell Res. 315, 2727-40, (2009) Abstract
Long, J., et al., Multiple Distinct Molecular Mechanisms Influence Sensitivity And Resistance To MDM2 Inhibitors In Adult Acute Myelogenous Leukemia. Blood 116, 71-80, (2010) Abstract
Kuo, C.C., et al., Selective Activation Of SHP2 Activity By Cisplatin Revealed By A Novel Chemical Probe-based Assay. Biochem. Biophys. Res. Commun. 391, 230-4, (2010) Abstract
Chang, J., et al., Nicotinamide Adenine Dinucleotide (NAD)-regulated DNA Methylation Alters CCCTC-binding Factor (CTCF)/cohesin Binding And Transcription At The BDNF Locus. Proc. Natl. Acad. Sci. U. S. A. 107, 21836-41, (2010) Abstract
Kusaba H., et al., Association of 5′-CpG demethylation and altered chromatin structure in the promoter region with transcriptional activation of the multidrug resistance 1 gene in human cancer cells. Eur. J. Biochem. 262, 924-932, (1999)
Broday L., et al., 5-Azacytidine induces transgene silencing by DNA methylation in Chinese hamster cells. Mol. Cell. Biol. 19, 3198-3204, (1999)
Qian X., et al., DNA methylation regulates p27kip1 expression in rodent pituitary cell lines. Am. J. Pathol. 153, 1475-1482, (1998)
Canova C., et al., Epigenetic control of programmed cell death: inhibition by 5-azacytidine of 1,25-dihydroxyvitamin D3-induced programmed cell death in C6.9 glioma cells. Mech. Ageing Dev. 101, 153-166, (1998)
Merck 14,890
Aldrich MSDS 1, 139:B / Corp MSDS 1 (1), 321:D / FT-IR 2 (3), 3896:C / FT-IR 1 (2), 831:D / FT-NMR 1 (3), 418:B / IR-Spectra (2), 1191:F / IR-Spectra (3), 1367:E / RegBook 1 (2), 2603:A / Sax 6, 332 / Sigma FT-IR 1 (1), 758:C / Structure Index 1, 411:B:5
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