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Literature summary extracted from

  • Huang, Q.; Zheng, M.; Yang, S.; Kuang, C.; Yu, C.; Yang, Q.
    Structure-activity relationship and enzyme kinetic studies on 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase (IDO) inhibitors (2011), Eur. J. Med. Chem., 46, 5680-5687.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.13.11.52 drug development the enzyme is a promising therapeutic target of cancer Homo sapiens

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.13.11.52 expression in Escherichia coli Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.52 1-methyl-tryptophan competitive Homo sapiens
1.13.11.52 1H-benzotriazole
-
 Homo sapiens
1.13.11.52 3-(1H-1,2,3-triazol-5-yl)pyridine
-
 Homo sapiens
1.13.11.52 4-bromo-5-(4-methylphenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 4-iodo-5-phenyl-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 4-nitro-5-(4-nitrophenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 5-(2-bromophenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 5-(2-chlorophenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 5-(2-methoxyphenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 5-(4-bromophenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 5-(4-chlorophenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 5-(4-fluorophenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 5-(4-methoxyphenyl)-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 5-phenyl-1H-1,2,3-triazole
-
 Homo sapiens
1.13.11.52 ethyl 1-(4-chlorophenyl)-1H-1,2,3-triazole-4-carboxylate
-
 Homo sapiens
1.13.11.52 additional information structure-activity relationship and enzyme kinetics of 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase inhibitors, molecular docking studies, overview. An electron-withdrawing group with low steric hindrance near the NH group of triazoles is necessary for the IDO inhibition. No inhibition by 5-(4-methylphenyl)-1H-1,2,3-triazole, methyl 4-(1H-1,2,3-triazol-5-yl)benzoate, 4-bromo-5-phenyl-1H-1,2,3-triazole, 4-chloro-5-phenyl-1H-1,2,3-triazole, 1H-benzotriazol-1-ol, and 5-(4-bromophenyl)-1H-tetrazole Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.13.11.52 D-tryptophan + O2 Homo sapiens
-
 N-formyl-D-kynurenine
-
 ?
1.13.11.52 L-tryptophan + O2 Homo sapiens
-
 N-formyl-L-kynurenine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.52 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.13.11.52 HEK-293 cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.52 D-tryptophan + O2
-
 Homo sapiens N-formyl-D-kynurenine
-
 ?
1.13.11.52 L-tryptophan + O2
-
 Homo sapiens N-formyl-L-kynurenine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.13.11.52 IDO
-
 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.13.11.52 37
-
 assay at Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.13.11.52 6.5
-
 assay at Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.13.11.52 0.0145
-
 5-(2-chlorophenyl)-1H-1,2,3-triazole pH 6.5, 37°C, recombinant enzyme Homo sapiens
1.13.11.52 0.018
-
 5-(2-bromophenyl)-1H-1,2,3-triazole pH 6.5, 37°C, recombinant enzyme Homo sapiens
1.13.11.52 0.0225
-
 5-phenyl-1H-1,2,3-triazole pH 6.5, 37°C, recombinant enzyme Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.11.52 0.086
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 5-(2-chlorophenyl)-1H-1,2,3-triazole
1.13.11.52 0.143
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 5-phenyl-1H-1,2,3-triazole
1.13.11.52 0.148
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 5-(2-bromophenyl)-1H-1,2,3-triazole
1.13.11.52 0.533
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 4-nitro-5-(4-nitrophenyl)-1H-1,2,3-triazole
1.13.11.52 0.58
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 5-(4-fluorophenyl)-1H-1,2,3-triazole
1.13.11.52 0.708
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 3-(1H-1,2,3-triazol-5-yl)pyridine
1.13.11.52 0.817
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 5-(4-chlorophenyl)-1H-1,2,3-triazole
1.13.11.52 1.028
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 5-(2-methoxyphenyl)-1H-1,2,3-triazole
1.13.11.52 1.028
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 4-bromo-5-(4-methylphenyl)-1H-1,2,3-triazole
1.13.11.52 1.256
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 5-(4-bromophenyl)-1H-1,2,3-triazole
1.13.11.52 1.371
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 4-iodo-5-phenyl-1H-1,2,3-triazole
1.13.11.52 2
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens ethyl 1-(4-chlorophenyl)-1H-1,2,3-triazole-4-carboxylate
1.13.11.52 2.57
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 1H-benzotriazole
1.13.11.52 6
-
 pH 6.5, 37°C, recombinant enzyme Homo sapiens 5-(4-methoxyphenyl)-1H-1,2,3-triazole