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Literature summary for 2.1.1.37 extracted from

  • Saavedra, O.M.; Isakovic, L.; Llewellyn, D.B.; Zhan, L.; Bernstein, N.; Claridge, S.; Raeppel, F.; Vaisburg, A.; Elowe, N.; Petschner, A.J.; Rahil, J.; Beaulieu, N.; MacLeod, A.R.; Delorme, D.; Besterman, J.M.; Wahhab, A.
    SAR around (L)-S-adenosyl-L-homocysteine, an inhibitor of human DNA methyltransferase (DNMT) enzymes (2009), Bioorg. Med. Chem. Lett., 19, 2747-2751.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
expressed in High Five insect cells Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
Homo sapiens
2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
Homo sapiens
2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
Homo sapiens
2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
Homo sapiens
2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methyl-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
Homo sapiens
2-amino-4-[([(2S,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydrofuran-2-yl]methyl)sulfanyl]butanoic acid
-
Homo sapiens
additional information not inhibited by 0.045 mM 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid Homo sapiens
S-(1-deazaadenosyl)-L-homocysteine
-
Homo sapiens
S-(3-deazaadenosyl)-L-homocysteine
-
Homo sapiens
S-(8-azaadenosyl)-L-homocysteine
-
Homo sapiens
S-(N-(2-biphenyl-4-ylethyl)-2-chloroadenosyl)-L-homocysteine
-
Homo sapiens
S-(N-(2-biphenyl-4-ylethyl)adenosyl)-L-homocysteine
-
Homo sapiens
S-(N-(3,5-dimethoxybenzyl)adenosyl)-L-homocysteine
-
Homo sapiens
S-(N-(pyridin-4-ylmethyl)adenosyl)-L-homocysteine
-
Homo sapiens
S-(N-benzyladenosyl)-L-homocysteine
-
Homo sapiens
S-(N-phenyladenosyl)-L-homocysteine
-
Homo sapiens
S-(N-phenylethyladenosyl)-L-homocysteine
-
Homo sapiens
S-(N-phenylpropyladenosyl)-L-homocysteine
-
Homo sapiens
S-adenosyl-L-homocysteine
-
Homo sapiens
S-inosinylhomocysteine
-
Homo sapiens
S-nebularinehomocysteine
-
Homo sapiens
S-Tubercidinylhomocysteine
-
Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
S-adenosyl-L-methionine + DNA Homo sapiens the enzyme catalyzes the transfer of a methyl group from S-adenosyl-L-methionine onto the 5'-position of the cytosine ring of the DNA S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine
-
?
S-adenosyl-L-methionine + DNA Homo sapiens the enzyme catalyzes the transfer of a methyl group from S-adenosyl-L-methionine onto the 5‘ position of the cytosine ring of the DNA S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens P26358
-
-
Homo sapiens Q9UBC3
-
-

Purification (Commentary)

Purification (Comment) Organism
Hitrap SP-Sepharose column chromatography Homo sapiens
Q-Sepharose column chromatography and Hitrap heparin column chromatography Homo sapiens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
S-adenosyl-L-methionine + DNA the enzyme catalyzes the transfer of a methyl group from S-adenosyl-L-methionine onto the 5'-position of the cytosine ring of the DNA Homo sapiens S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine
-
?
S-adenosyl-L-methionine + DNA the enzyme catalyzes the transfer of a methyl group from S-adenosyl-L-methionine onto the 5‘ position of the cytosine ring of the DNA Homo sapiens S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine
-
?

Synonyms

Synonyms Comment Organism
DNA methyltransferase
-
Homo sapiens
DNMT
-
Homo sapiens
Dnmt1 isoform Homo sapiens
DNMT3b2 isoform Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0003
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-adenosyl-L-homocysteine
0.0003
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-Tubercidinylhomocysteine
0.0006
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenylpropyladenosyl)-L-homocysteine
0.0006
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(2-biphenyl-4-ylethyl)adenosyl)-L-homocysteine
0.0009
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(3,5-dimethoxybenzyl)adenosyl)-L-homocysteine
0.001
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methyl-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.001
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-benzyladenosyl)-L-homocysteine
0.0015
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-Tubercidinylhomocysteine
0.002
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-adenosyl-L-homocysteine
0.002
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenyladenosyl)-L-homocysteine
0.002
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenylethyladenosyl)-L-homocysteine
0.0025
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.0029
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.003
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(8-azaadenosyl)-L-homocysteine
0.0036
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(pyridin-4-ylmethyl)adenosyl)-L-homocysteine
0.0054
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(2-biphenyl-4-ylethyl)adenosyl)-L-homocysteine
0.006
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methyl-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.0067
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(2-biphenyl-4-ylethyl)-2-chloroadenosyl)-L-homocysteine
0.0068
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(3-deazaadenosyl)-L-homocysteine
0.0068
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.0074
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenylpropyladenosyl)-L-homocysteine
0.008
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 8-aza-S-adenosyl-L-homocysteine
0.018
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(3,5-dimethoxybenzyl)adenosyl)-L-homocysteine
0.021
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.022
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(pyridin-4-ylmethyl)adenosyl)-L-homocysteine
0.027
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenylethyladenosyl)-L-homocysteine
0.028
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-nebularinehomocysteine
0.029
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(2-biphenyl-4-ylethyl)-2-chloroadenosyl)-L-homocysteine
0.045
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 3-deaza-S-adenosyl-L-homocysteine
0.045
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 1-deaza-S-adenosyl-L-homocysteine
0.045
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(1-deazaadenosyl)-L-homocysteine
0.0572
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.061
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-benzyladenosyl)-L-homocysteine
0.075
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.154
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenyladenosyl)-L-homocysteine
0.216
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-[([(2S,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydrofuran-2-yl]methyl)sulfanyl]butanoic acid
0.256
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
0.3
-
isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-nebularinehomocysteine
0.5
-
isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-[([(2S,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydrofuran-2-yl]methyl)sulfanyl]butanoic acid
1
-
IC50 above 1 mM, isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-inosinylhomocysteine
1
-
IC50 above 1 mM, isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-inosinylhomocysteine