BRENDA - Enzyme Database show
show all sequences of 1.14.15.16

Novel styryl-indoles as small molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): Synthesis and biological evaluation

Ferla, S.; Gomaa, M.S.; Brancale, A.; Zhu, J.; Ochalek, J.T.; DeLuca, H.F.; Simons, C.; Eur. J. Med. Chem. 87, 39-51 (2014)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
gene CYP24A1, overexpression of N-terminally maltose-binding-protein fused enzyme in Escherichia coli
Homo sapiens
Inhibitors
Inhibitors
Commentary
Organism
Structure
(E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate
-
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole
-
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole
-
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole
-
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole
-
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole
-
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole
-
Homo sapiens
4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide
-
Homo sapiens
4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide
-
Homo sapiens
ketoconazole
-
Homo sapiens
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
N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide
-
Homo sapiens
N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide
-
Homo sapiens
N-[2-(1H-imidazol-1-yl)-2-phenylethyl]-4-[(E)-2-phenylethenyl]benzamide
-
Homo sapiens
toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester
-
Homo sapiens
toluene-4-sulfonic acid 3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1-yl)-propyl ester
-
Homo sapiens
vitamin D sulfonate
-
Homo sapiens
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Homo sapiens
Q07973
gene CYP24A1
-
Purification (Commentary)
Commentary
Organism
recombinant N-terminally maltose-binding-protein fused enzyme from Escherichia coli by affinity chromatography to homogeneity
Homo sapiens
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
calcitriol + 2 reduced adrenodoxin + 2 H+ + O2
-
736056
Homo sapiens
calcitetrol + 2 oxidized adrenodoxin + H2O
-
-
-
?
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
37
-
assay at
Homo sapiens
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Homo sapiens
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
-
Homo sapiens
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.000014
-
1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000014
-
1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000026
-
1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000031
-
1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000035
-
ketoconazole
pH 7.5, 37°C
Homo sapiens
0.000037
-
1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000037
-
1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000039
-
vitamin D sulfonate
pH 7.5, 37°C
Homo sapiens
0.00023
-
4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide
pH 7.5, 37°C
Homo sapiens
0.00034
-
4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide
pH 7.5, 37°C
Homo sapiens
0.00054
-
(E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate
pH 7.5, 37°C
Homo sapiens
0.00064
-
toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester
pH 7.5, 37°C
Homo sapiens
0.00073
-
N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide
pH 7.5, 37°C
Homo sapiens
0.00074
-
N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide
pH 7.5, 37°C
Homo sapiens
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
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.00019
-
pH 7.5, 37°C
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole
0.0002
-
pH 7.5, 37°C
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole
0.0003
-
pH 7.5, 37°C
Homo sapiens
N-[2-(1H-imidazol-1-yl)-2-phenylethyl]-4-[(E)-2-phenylethenyl]benzamide
0.00036
-
pH 7.5, 37°C
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole
0.00044
-
pH 7.5, 37°C
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole
0.00047
-
pH 7.5, 37°C
Homo sapiens
ketoconazole
0.00052
-
pH 7.5, 37°C
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole
0.00052
-
pH 7.5, 37°C
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole
0.0033
-
pH 7.5, 37°C
Homo sapiens
4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide
0.0048
-
pH 7.5, 37°C
Homo sapiens
4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide
0.0076
-
pH 7.5, 37°C
Homo sapiens
(E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate
0.009
-
pH 7.5, 37°C
Homo sapiens
toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester
0.0104
-
pH 7.5, 37°C
Homo sapiens
N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide
0.0105
-
pH 7.5, 37°C
Homo sapiens
N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide
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
Cloned(Commentary) (protein specific)
Commentary
Organism
gene CYP24A1, overexpression of N-terminally maltose-binding-protein fused enzyme in Escherichia coli
Homo sapiens
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
-
Homo sapiens
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.00019
-
pH 7.5, 37°C
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole
0.0002
-
pH 7.5, 37°C
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole
0.0003
-
pH 7.5, 37°C
Homo sapiens
N-[2-(1H-imidazol-1-yl)-2-phenylethyl]-4-[(E)-2-phenylethenyl]benzamide
0.00036
-
pH 7.5, 37°C
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole
0.00044
-
pH 7.5, 37°C
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole
0.00047
-
pH 7.5, 37°C
Homo sapiens
ketoconazole
0.00052
-
pH 7.5, 37°C
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole
0.00052
-
pH 7.5, 37°C
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole
0.0033
-
pH 7.5, 37°C
Homo sapiens
4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide
0.0048
-
pH 7.5, 37°C
Homo sapiens
4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide
0.0076
-
pH 7.5, 37°C
Homo sapiens
(E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate
0.009
-
pH 7.5, 37°C
Homo sapiens
toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester
0.0104
-
pH 7.5, 37°C
Homo sapiens
N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide
0.0105
-
pH 7.5, 37°C
Homo sapiens
N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide
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
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate
-
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole
-
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole
-
Homo sapiens
1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole
-
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole
-
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole
-
Homo sapiens
1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole
-
Homo sapiens
4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide
-
Homo sapiens
4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide
-
Homo sapiens
ketoconazole
-
Homo sapiens
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
N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide
-
Homo sapiens
N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide
-
Homo sapiens
N-[2-(1H-imidazol-1-yl)-2-phenylethyl]-4-[(E)-2-phenylethenyl]benzamide
-
Homo sapiens
toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester
-
Homo sapiens
toluene-4-sulfonic acid 3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1-yl)-propyl ester
-
Homo sapiens
vitamin D sulfonate
-
Homo sapiens
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.000014
-
1-[4-(1H-imidazol-1-yl)butyl]-4-(3,5-dimethoxystyryl)-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000014
-
1-[4-(1H-imidazol-1-yl)butyl]-4-styryl-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000026
-
1-[3-(1H-imidazol-1-yl)propyl]-4-styryl-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000031
-
1-[3-(1H-imidazol-1-yl)propyl]-4-(3,5-dimethoxystyryl)-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000035
-
ketoconazole
pH 7.5, 37°C
Homo sapiens
0.000037
-
1-[3-(1H-imidazol-1-yl)propyl]-5-styryl-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000037
-
1-[4-(1H-imidazol-1-yl)butyl]-5-styryl-1H-indole
pH 7.5, 37°C
Homo sapiens
0.000039
-
vitamin D sulfonate
pH 7.5, 37°C
Homo sapiens
0.00023
-
4-methyl-N-[4-(4-styryl-indol-1-yl)butyl]benzenesulfonamide
pH 7.5, 37°C
Homo sapiens
0.00034
-
4-methyl-N-[3-(4-styryl-indol-1-yl)propyl]benzenesulfonamide
pH 7.5, 37°C
Homo sapiens
0.00054
-
(E)-3-(4-styryl-1H-indol-1-yl)propyl benzenesulfinate
pH 7.5, 37°C
Homo sapiens
0.00064
-
toluene-4-sulfonic acid 3-(4-styryl-indol-1-yl)-propyl ester
pH 7.5, 37°C
Homo sapiens
0.00073
-
N-(3-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-propyl)-4-methyl-benzenesulfonamide
pH 7.5, 37°C
Homo sapiens
0.00074
-
N-(4-(4-[2-(3,5-dimethoxy-phenyl)-vinyl]-indol-1yl)-butyl)-4-methyl-benzenesulfonamide
pH 7.5, 37°C
Homo sapiens
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
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant N-terminally maltose-binding-protein fused enzyme from Escherichia coli by affinity chromatography to homogeneity
Homo sapiens
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
calcitriol + 2 reduced adrenodoxin + 2 H+ + O2
-
736056
Homo sapiens
calcitetrol + 2 oxidized adrenodoxin + H2O
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
37
-
assay at
Homo sapiens
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Homo sapiens
Other publictions for EC 1.14.15.16
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
736557
Mugg
Quantitation of CYP24A1 enzyma ...
Homo sapiens
J. Clin. Endocrinol. Metab.
100
684-688
2015
-
-
1
-
11
-
-
2
1
-
-
4
-
2
-
-
-
-
-
3
-
-
5
-
-
-
-
-
-
-
-
3
-
-
-
-
-
1
3
-
11
-
-
-
-
2
1
-
-
4
-
-
-
-
-
3
-
-
5
-
-
-
-
-
-
-
-
-
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1
1
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-
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736056
Ferla
Novel styryl-indoles as small ...
Homo sapiens
Eur. J. Med. Chem.
87
39-51
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-
-
1
-
-
-
17
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
1
-
1
-
-
-
1
-
-
1
15
-
15
-
-
1
1
-
-
-
15
17
15
-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
736086
Tieu
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Homo sapiens, Rattus norvegicus
FEBS J.
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1
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1
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1
3
-
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-
2
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-
-
-
-
-
16
1
1
-
-
-
1
-
-
6
-
-
-
-
-
1
6
-
1
-
-
-
-
1
3
-
1
15
-
-
-
1
-
-
-
-
16
1
1
-
-
-
1
-
-
-
-
2
2
-
-
-
736616
Ferla
Small-molecule inhibitors of 2 ...
Homo sapiens
J. Med. Chem.
57
7702-7715
2014
-
-
-
-
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
724907
Urbschat
Vitamin D hydroxylases CYP2R1, ...
Homo sapiens
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43
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-
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
2
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
2
-
-
1
-
-
-
-
-
-
-
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1
1
1
1
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728214
Luo
24-Hydroxylase in cancer: impa ...
Homo sapiens
J. Steroid Biochem. Mol. Biol.
136
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2013
-
1
-
-
-
-
6
-
1
-
-
2
-
1
-
-
-
-
-
1
-
-
2
-
-
-
-
-
-
-
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Evidence for the activation of ...
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Structure-function analysis of ...
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C-25 hydroxylation of 1alpha,2 ...
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2004
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Kusudo
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Homo sapiens, Rattus norvegicus
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2004
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Sawada
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Homo sapiens
Biochemistry
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2004
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716973
Prosser
Enzymes involved in the activa ...
Homo sapiens, Mus musculus
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2004
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714836
Akeno
Mouse vitamin D-24-hydroxylase ...
Mus musculus
Endocrinology
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1997
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14
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714138
Beckman
Human 25-hydroxyvitamin D3-24- ...
Homo sapiens
Biochemistry
35
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1996
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Patel
Effect of vitamin D metabolite ...
Rattus norvegicus
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45
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1994
1
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Tenenhouse
Effect of the X-linked Hyp mut ...
Mus musculus
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120
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Danan
Presence of 25-hydroxyvitamin ...
Rattus norvegicus
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257
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1982
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