5-Azacytidine

SKU: A0271

Category: Antibiotics

Synonyms: 5-Azacitidine , Antibiotic U18496 , 5-AzaC , Ladakamycin , Mylosar , NSC102816 , NSC103-627 , U18496 , WR183027 , 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; 320-67-2
CAS-Number: C₈H₁₂N₄O₅
Molecular Formula: 244.20
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Identity: 1H-NMR
Appearance: White to off-white powder

Properties

Melting Point: 226-232 °C (dec.)(lit.)
Solvents: ethanol, DMSO, DMF (30mg/ml), water, PBS (10mg/ml)

Long Term Storage: -20°C
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.
Handling Advice: Protect from light and moisture.
Short Term Storage: +4°C
Shipping: AMBIENT

Transportation: Not dangerous goods
Signal word: Danger
GHS Symbol: GHS07+GHS08
Precautionary statements: P201-P308 + P313
Hazard statements: H302-H350

Description: 5-Azacytidine, a chemical analogue of the DNA and RNA nucleoside cytidine, is an cell permeable inhibitor of DNA methyltransferases, potentially serving to reverse epigenetic changes. It reduces hypermethylation associated with certain diseases, including myelodysplastic syndromes (IC50s = 2.4 and 2.6?M for in vitro anti-myeloma activity) and cancer (IC50s ~ 0.4?M for inhibiting proliferation of various cancer cell lines). It has a reported half-life of 17 hours and is considerably cytotoxic, it must be incorporated into DNA to covalently trap DNA methyltransferases. Induces demethylation and reactivation of silenced genes. Improves the efficiency of reprogramming of stem cells, induces differentiation of mesenchymal stem cells into cardiomyocytes.
References: (1) H. Kusaba, et al., Eur. J. Biochem. 262, 924 (1999) , (2) B. Brueckner, et al., Cancer Res. 65, 6305 (2005) , (3) F. Lyko & R. Brown, J. Natl. Cancer Inst. 97, 1498 (2005) , (4) C. Stresemann, et al., Cancer Res. 66, 2794 (2006) , (5) M. Esteller, N. Engl. J. Med. 358, 1148 (2008) , (6) T.S. Mikkelsen, et al., Nature 454, 49 (2008) , (7) A.M. Giraldo, et al., Methods Mol. Biol. 791, 145 (2011) , (8) J.J. Chong, et al., Cell Res. 22, 1932 (2013) , (9) M. Bhuvanagiri, et al., EMBO Mol. Med. 6, 1593 (2014)
InChi Key: NMUSYJAQQFHJEW-KVTDHHQDSA-N
Smiles: OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC(N)=NC2=O)O1

5-Azacytidine, a chemical analogue of the DNA and RNA nucleoside cytidine, is an cell permeable inhibitor of DNA methyltransferases, potentially serving to reverse epigenetic changes. It reduces hypermethylation associated with certain diseases, including myelodysplastic syndromes (IC50s = 2.4 and 2.6?M for in vitro anti-myeloma activity) and cancer (IC50s ~ 0.4?M for inhibiting proliferation of various cancer cell lines). It has a reported half-life of 17 hours and is considerably cytotoxic, it must be incorporated into DNA to covalently trap DNA methyltransferases. Induces demethylation and reactivation of silenced genes. Improves the efficiency of reprogramming of stem cells, induces differentiation of mesenchymal stem cells into cardiomyocytes.

SKU: A0271 Category: Antibiotics

Additional information

Additional information

Synonyms	5-Azacitidine, Antibiotic U18496, 5-AzaC, Ladakamycin, Mylosar, NSC102816, NSC103-627, U18496, WR183027, 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
Purity	≥98% (HPLC)
Appearance	White to off-white powder
CAS-Number	320-67-2
Molecular Formula	C8H12N4O5
Molecular Weight	244.20
Identity	1H-NMR
Solvents	ethanol, DMSO, DMF (30mg/ml), water, PBS (10mg/ml)
Melting Point	226-232 °C (dec.)(lit.)
Smiles	OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC(N)=NC2=O)O1
InChi Key	NMUSYJAQQFHJEW-KVTDHHQDSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H302-H350
Precautionary statements	P201-P308 + P313
GHS Symbol	GHS07+GHS08
Signal word	Danger
Transportation	Not dangerous goods
References	(1) H. Kusaba, et al., Eur. J. Biochem. 262, 924 (1999), (2) B. Brueckner, et al., Cancer Res. 65, 6305 (2005), (3) F. Lyko & R. Brown, J. Natl. Cancer Inst. 97, 1498 (2005), (4) C. Stresemann, et al., Cancer Res. 66, 2794 (2006), (5) M. Esteller, N. Engl. J. Med. 358, 1148 (2008), (6) T.S. Mikkelsen, et al., Nature 454, 49 (2008), (7) A.M. Giraldo, et al., Methods Mol. Biol. 791, 145 (2011), (8) J.J. Chong, et al., Cell Res. 22, 1932 (2013), (9) M. Bhuvanagiri, et al., EMBO Mol. Med. 6, 1593 (2014)
Quantity	250 mg, 1 g, Bulk