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    5-Azacytidine

    Available from stock

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      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

      For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

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

      Properties

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

      Documentation

      Safety Data Sheet (SDS)
      CDX A0271 MSDS.pdf
      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
      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.
      Smiles
      OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC(N)=NC2=O)O1
      InChi Key
      NMUSYJAQQFHJEW-KVTDHHQDSA-N
      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)

      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

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