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Literature summary for 1.14.99.66 extracted from

  • Sharma, S.K.; Wu, Y.; Steinbergs, N.; Crowley, M.L.; Hanson, A.S.; Casero, R.A.; Woster, P.M.
    (Bis)urea and (bis)thiourea inhibitors of lysine-specific demethylase 1 as epigenetic modulators (2010), J. Med. Chem., 53, 5197-5212.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.14.99.66

Cloned(Commentary)

Cloned (Comment) Organism
expression of His6-tagged LSD1 in Escherichia coli strain BL21(DE3) Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
1,11-bis-[3-[1-(1,1-diphenylmethyl)thioureado]]-4,8-diazaundecane 48.9% inhibition at 0.01 mM Homo sapiens
1,11-bis-[3-[1-(2,2-diphenylethyl)thioureado]]-4,8-diazaundecane 75.2% inhibition at 0.01 mM Homo sapiens
1,11-bis-[3-[1-(3,3-diphenylpropyl)thioureado]]-4,8-diazaundecane 7.8% inhibition at 0.01 mM Homo sapiens
1,11-bis-[3-[1-(3,3-diphenylpropyl)ureado]]-4,8-diazaundecane 7.1% inhibition at 0.01 mM Homo sapiens
1,11-bis-[3-[1-(benzyl)thioureado]]-4,8-diazaundecane 47.9% inhibition at 0.01 mM Homo sapiens
1,11-bis-[3-[1-(benzyl)ureado]]-4,8-diazaundecane 39.5% inhibition at 0.01 mM Homo sapiens
1,11-bis-[3-[1-(ethyl)thioureado]]-4,8-diazaundecane 63.8% inhibition at 0.01 mM Homo sapiens
1,11-bis-[3-[1-(ethyl)ureado]]-4,8-diazaundecane 34.5% inhibition at 0.01 mM Homo sapiens
1,11-bis-[3-[1-(n-propyl)ureado]]-4,8-diazaundecane 48.7% inhibition at 0.01 mM Homo sapiens
1,11-bis-[5-[1-(N,N-diphenyl)carbamyl]ureado]-4,8-diazaundecane 8.5% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(1,1-diphenylmethyl)thioureado]]-4,9-diazadodecane 65.6% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(2,2-diphenylethyl)thioureado]]-4,9-diazadodecane 82.9% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(3,3-diphenylpropyl)thioureado]]-4,9-diazadodecane 21.4% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(3,3-diphenylpropyl)ureado]]-4,9-diazadodecane 25.4% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(benzyl)ureado]]-4,9-diazadodecane 50.5% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(ethyl)thioureado]]-4,9-diazadodecane 60% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(ethyl)ureado]]-4,9-diazadodecane 50.8% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(n-propyl)thioureado]]-4,9-diazadodecane 10.4% inhibition at 0.01 mM Homo sapiens
1,12-bis-[3-[1-(n-propyl)ureado]]-4,9-diazadodecane 21% inhibition at 0.01 mM Homo sapiens
1,12-bis-[5-[1-(N,N-diphenyl)carbamyl]ureado]-4,9-diazadodecane 73.9% inhibition at 0.01 mM Homo sapiens
1,15-bis-[3-[1-(1,1-diphenylmethyl)thioureado]]-4,12-diazapentadecane 71.1% inhibition at 0.01 mM Homo sapiens
1,15-bis-[3-[1-(2,2-diphenylethyl)thioureado]]-4,12-diazapentadecane 80.5% inhibition at 0.01 mM Homo sapiens
1,15-bis-[3-[1-(3,3-diphenylpropyl)thioureado]]-4,12-diazapentadecane 22.7% inhibition at 0.01 mM Homo sapiens
1,15-bis-[3-[1-(3,3-diphenylpropyl)ureado]]-4,12-diazapentadecane 48.5% inhibition at 0.01 mM Homo sapiens
1,15-bis-[3-[1-(benzyl)thioureado]]-4,12-diazapentadecane 64.1% inhibition at 0.01 mM Homo sapiens
1,15-bis-[3-[1-(benzyl)ureado]]-4,12-diazapentadecane
-
 Homo sapiens
1,15-bis-[3-[1-(ethyl)ureado]]-4,12-diazapentadecane
-
 Homo sapiens
1,15-bis-[3-[1-(n-propyl)ureado]]-4,12-diazapentadecane 8.5% inhibition at 0.01 mM Homo sapiens
1,15-bis-[5-[1-(N,N-diphenyl)carbamyl]ureado]-4,12-diazapentadecane 30.0% inhibition at 0.01 mM Homo sapiens
bis-[3-[1-(benzyl)thioureado]]-4,9-diazadodecane 25.2% inhibition at 0.01 mM Homo sapiens
additional information (bis)urea and (bis)thiourea inhibitors of lysine-specific demethylase 1 as epigenetic modulators with the potential for use as antitumor agents, overview. No inhibition by 7 and 17, poor inhibition by 11 Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
histone H3 N6,N6-dimethyl-L-lysine4 + 2-oxoglutarate + O2 Homo sapiens
-
 histone H3 N6-methyl-L-lysine4 + succinate + formaldehyde + CO2
-
 ?
histone H3 N6-methyl-L-lysine4 + 2-oxoglutarate + O2 Homo sapiens
-
 histone H3 L-lysine4 + succinate + formaldehyde + CO2
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
Calu-6 cell
-
 Homo sapiens
-
lung carcinoma cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
histone H3 N6,N6-dimethyl-L-lysine4 + 2-oxoglutarate + O2
-
 Homo sapiens histone H3 N6-methyl-L-lysine4 + succinate + formaldehyde + CO2
-
 ?
histone H3 N6-methyl-L-lysine4 + 2-oxoglutarate + O2
-
 Homo sapiens histone H3 L-lysine4 + succinate + formaldehyde + CO2
-
 ?

Synonyms

Synonyms Comment Organism
LSD1
-
 Homo sapiens
lysine-specific demethylase 1
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8.5
-
 assay at Homo sapiens

General Information

General Information Comment Organism
metabolism histone methylation is a dynamic process regulated by the addition of methyl groups by histone methyltransferases and removal of methyl groups from mono- and dimethyllysines by lysine specific demethylase 1, LSD1, and from mono-, di, and trimethyllysines by specific JumonjiC, JmjC, domain-containing demethylases Homo sapiens
physiological function LSD1 plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 overexpression is thought to contribute to the development of cancer Homo sapiens