Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary extracted from

  • Peduto, A.; Bruno, F.; Dehm, F.; Krauth, V.; de Caprariis, P.; Weinigel, C.; Barz, D.; Massa, A.; De Rosa, M.; Werz, O.; Filosa, R.
    Further studies on ethyl 5-hydroxy-indole-3-carboxylate scaffold design, synthesis and evaluation of 2-phenylthiomethyl-indole derivatives as efficient inhibitors of human 5-lipoxygenase (2014), Eur. J. Med. Chem., 81, 492-498 .
    View publication on PubMed

Application

EC Number Application Comment Organism
1.13.11.34 medicine the enzyme is an attractive drug target for the pharmacotherapy of inflammatory and allergic diseases Homo sapiens

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.13.11.34 gene alox5, recombinant expression in Escherichia coli strain BL21 Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.34 ethyl 2-((2,4-difluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 2-((2,6-dichlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 2-((2,6-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 2-((3,5-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 2-((3-chlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 2-((4-fluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 5-hydroxy-1-methyl-2-((2-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethoxy)phenylthio)methyl)-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 5-hydroxy-1-methyl-2-(phenylthiomethyl)-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 5-hydroxy-2-((2-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 5-hydroxy-2-((4-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 ethyl 5-hydroxy-2-(mesitylthiomethyl)-1-methyl-1H-indole-3-carboxylate
-
 Homo sapiens
1.13.11.34 additional information design, synthesis, and evaluation of 2-phenylthiomethyl-indole derivatives from an ethyl 5-hydroxy-indole-3-carboxylate scaffold as efficient inhibitors of human 5-lipoxygenase, structure-activity relationships, overview. The potency of compounds is closely related to the positioning of the substituents at the phenylthiomethyl ring. The introduction of methyl or chlorine groups in ortho- and ortho/para-position of thiophenol represent the most favorable modifications. Among all tested compounds, ethyl 5-hydroxy-2-(mesitylthiomethyl)-1-methyl-1H-indole-3-carboxylate is the most potent derivative which blocks 5-LO activity in cell-free assays and suppresses 5-LO product synthesis in polymorphonuclear leukocytes. The compounds are not active against 12-LO and 15-LO, EC 1.13.11.31 and EC 1.13.11.33 Homo sapiens
1.13.11.34 zileuton
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.13.11.34 (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate Homo sapiens epoxidation (5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
 ?
1.13.11.34 arachidonate + O2 Homo sapiens hydroperoxidation (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
 ?
1.13.11.34 arachidonate + O2 Homo sapiens overall reaction (5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.34 Homo sapiens P09917
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.13.11.34 recombinant enzyme from Escherichia coli strain BL21 by ATP affinity chromatography Homo sapiens

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.13.11.34 leukocyte
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.34 (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate epoxidation Homo sapiens (5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
 ?
1.13.11.34 arachidonate + O2 hydroperoxidation Homo sapiens (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
 ?
1.13.11.34 arachidonate + O2 overall reaction Homo sapiens (5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.13.11.34 5-lipoxygenase
-
 Homo sapiens
1.13.11.34 5-LO
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.11.34 0.0003
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
1.13.11.34 0.0007
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 5-hydroxy-2-(mesitylthiomethyl)-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0008
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 5-hydroxy-1-methyl-2-((2-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate
1.13.11.34 0.0008
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 2-((2,6-dichlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0008
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 2-((2,6-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0009
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethoxy)phenylthio)methyl)-1H-indole-3-carboxylate
1.13.11.34 0.0018
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 2-((3,5-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0023
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 5-hydroxy-2-((4-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0029
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 5-hydroxy-2-((2-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0032
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 2-((2,4-difluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0038
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 2-((3-chlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0042
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate
1.13.11.34 0.005
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 2-((4-fluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
1.13.11.34 0.0057
-
 pH 7.4, 37°C, cell-free enzyme extract Homo sapiens ethyl 5-hydroxy-1-methyl-2-(phenylthiomethyl)-1H-indole-3-carboxylate

General Information

EC Number General Information Comment Organism
1.13.11.34 physiological function 5-lipoxygenase enzyme catalyzes the initial steps in the biosynthesis of pro-inflammatory leukotrienes Homo sapiens