Inhibition of DNA Methyl Transferases

Cytosine-5-methyltransferases are found in everything from archaebacteria to mammals and when the regulation of cytosine-5-methyltransferases goes awry, cancer can result. The mechanism of action for this family of enzymes involves attack of a cysteine thiol group on the C6 position of cytosine, leading to a transient dihydrocytosine intermediate, which then facilitates the nucleophilic attack by C5 on the activated methyl group of the S-adenosyl-L-methionine cofactor. As with many enzymes, the intermediate can be trapped using a suicide substrate and 5-fluoro-cytosine has been used extensively in this role. An alternate strategy is to use a transition-state mimic that binds to the active site with high affinity. An excellent candidate was found in 5-aza-5,6-dihydrocytosine. Despite not being covalently bound to the enzyme, it was found to be a more potent inhibitor of cytosine-5-methyltransferases than 5-fluoro-cytosine.

4 Product Results
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  • Pyrrolidine-CE Phosphoramidite
    Pyrrolidine-CE Phosphoramidite (10-1915)
    Catalog #: 10-1915  |  CAS #: 1221186-22-6
    Formal Name: (2R, 3S)-2-Dimethoxytrityloxymethyl-N-(fluorenylmethyl)-pyrrolidin-3-yl-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite
  • 5-F-dU-CE Phosphoramidite
    5-F-dU-CE Phosphoramidite (10-1092)
    Catalog #: 10-1092  |  CAS #: 142246-63-7
    Formal Name: 5'-Dimethoxytrityl-5-fluoro-2'-deoxyUridine,3'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite
  • 5-Me-2'-deoxyZebularine-CE Phosphoramidite
    5-Me-2'-deoxyZebularine-CE Phosphoramidite (10-1061)
    Catalog #: 10-1061  |  CAS #: 125258-62-0
    Formal Name: 5'-Dimethoxytrityl-5-methyl-pyrimidin-2-one-2'-deoxyriboside, 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite
  • TMP-F-dU-CE Phosphoramidite
    TMP-F-dU-CE Phosphoramidite (10-1016)
    Catalog #: 10-1016  |  CAS #: 198080-36-3
    Formal Name: O4-(2,4,6-Trimethylphenyl)-5'-Dimethoxytrityl-5-fluoro-2'-deoxyUridine,3'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite
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