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Literature summary extracted from

  • Ferla, S.; Gomaa, M.S.; Brancale, A.; Zhu, J.; Ochalek, J.T.; DeLuca, H.F.; Simons, C.
    Novel styryl-indoles as small molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): Synthesis and biological evaluation (2014), Eur. J. Med. Chem., 87, 39-51.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.15.16 gene CYP24A1, overexpression of N-terminally maltose-binding-protein fused enzyme in Escherichia coli Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.15.16 (E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate
-
 Homo sapiens
1.14.15.16 1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole
-
 Homo sapiens
1.14.15.16 1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole
-
 Homo sapiens
1.14.15.16 1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole
-
 Homo sapiens
1.14.15.16 1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole
-
 Homo sapiens
1.14.15.16 1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole
-
 Homo sapiens
1.14.15.16 1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole
-
 Homo sapiens
1.14.15.16 4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide
-
 Homo sapiens
1.14.15.16 4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide
-
 Homo sapiens
1.14.15.16 ketoconazole
-
 Homo sapiens
1.14.15.16 additional information synthesis of a series of imidazole styrylindoles and sulfonyl styrylindoles derivatives and evaluation of binding affinity and inhibitory activity against recombinant MBP-tagged CYP24A1, the imidazole styrylindoles act as potent inhibitors with activity greater or comparable with the standard ketoconazole. Docking studies of the inhibitors in the CYP24A1 enzyme active site, molecular modelling, overview. Complete occupation of the vitamin D access tunnel is essential to inhibitory activity, allowing exposure to multiple hydrophobic binding interactions and optimal conformation for the interaction of the imidazole nitrogen lone pair and the active site heme Homo sapiens
1.14.15.16 N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide
-
 Homo sapiens
1.14.15.16 N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide
-
 Homo sapiens
1.14.15.16 N-[2-(1H-imidazol-1-yl)-2-phenylethyl]-4-[(E)-2-phenylethenyl]benzamide
-
 Homo sapiens
1.14.15.16 toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester
-
 Homo sapiens
1.14.15.16 toluene-4-sulfonic acid 3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1-yl)-propyl ester
-
 Homo sapiens
1.14.15.16 vitamin D sulfonate
-
 Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
1.14.15.16 Homo sapiens Q07973 gene CYP24A1
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.15.16 recombinant N-terminally maltose-binding-protein fused enzyme from Escherichia coli by affinity chromatography to homogeneity Homo sapiens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.15.16 calcitriol + 2 reduced adrenodoxin + 2 H+ + O2
-
 Homo sapiens calcitetrol + 2 oxidized adrenodoxin + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.15.16 25-hydroxyvitamin D-24-hydroxylase
-
 Homo sapiens
1.14.15.16 CYP24A1
-
 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.15.16 37
-
 assay at Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.15.16 7.5
-
 assay at Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.15.16 NADPH
-
 Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.14.15.16 0.000014
-
 1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole pH 7.5, 37°C Homo sapiens
1.14.15.16 0.000014
-
 1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole pH 7.5, 37°C Homo sapiens
1.14.15.16 0.000026
-
 1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole pH 7.5, 37°C Homo sapiens
1.14.15.16 0.000031
-
 1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole pH 7.5, 37°C Homo sapiens
1.14.15.16 0.000035
-
 ketoconazole pH 7.5, 37°C Homo sapiens
1.14.15.16 0.000037
-
 1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole pH 7.5, 37°C Homo sapiens
1.14.15.16 0.000037
-
 1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole pH 7.5, 37°C Homo sapiens
1.14.15.16 0.000039
-
 vitamin D sulfonate pH 7.5, 37°C Homo sapiens
1.14.15.16 0.00023
-
 4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide pH 7.5, 37°C Homo sapiens
1.14.15.16 0.00034
-
 4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide pH 7.5, 37°C Homo sapiens
1.14.15.16 0.00054
-
 (E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate pH 7.5, 37°C Homo sapiens
1.14.15.16 0.00064
-
 toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester pH 7.5, 37°C Homo sapiens
1.14.15.16 0.00073
-
 N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide pH 7.5, 37°C Homo sapiens
1.14.15.16 0.00074
-
 N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide pH 7.5, 37°C Homo sapiens
1.14.15.16 0.00119
-
 toluene-4-sulfonic acid 3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1-yl)-propyl ester pH 7.5, 37°C Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.15.16 0.00019
-
 pH 7.5, 37°C Homo sapiens 1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole
1.14.15.16 0.0002
-
 pH 7.5, 37°C Homo sapiens 1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole
1.14.15.16 0.0003
-
 pH 7.5, 37°C Homo sapiens N-[2-(1H-imidazol-1-yl)-2-phenylethyl]-4-[(E)-2-phenylethenyl]benzamide
1.14.15.16 0.00036
-
 pH 7.5, 37°C Homo sapiens 1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole
1.14.15.16 0.00044
-
 pH 7.5, 37°C Homo sapiens 1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole
1.14.15.16 0.00047
-
 pH 7.5, 37°C Homo sapiens ketoconazole
1.14.15.16 0.00052
-
 pH 7.5, 37°C Homo sapiens 1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole
1.14.15.16 0.00052
-
 pH 7.5, 37°C Homo sapiens 1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole
1.14.15.16 0.0033
-
 pH 7.5, 37°C Homo sapiens 4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide
1.14.15.16 0.0048
-
 pH 7.5, 37°C Homo sapiens 4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide
1.14.15.16 0.0076
-
 pH 7.5, 37°C Homo sapiens (E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate
1.14.15.16 0.009
-
 pH 7.5, 37°C Homo sapiens toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester
1.14.15.16 0.0104
-
 pH 7.5, 37°C Homo sapiens N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide
1.14.15.16 0.0105
-
 pH 7.5, 37°C Homo sapiens N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide
1.14.15.16 0.0169
-
 pH 7.5, 37°C Homo sapiens toluene-4-sulfonic acid 3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1-yl)-propyl ester