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Literature summary extracted from

  • Becker, A.; Kohfeld, S.; Lader, A.; Preu, L.; Pies, T.; Wieking, K.; Ferandin, Y.; Knockaert, M.; Meijer, L.; Kunick, C.
    Development of 5-benzylpaullones and paullone-9-carboxylic acid alkyl esters as selective inhibitors of mitochondrial malate dehydrogenase (mMDH) (2010), Eur. J. Med. Chem., 45, 335-342.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.1.1.37 drug development mitochondrial malate dehydrogenase is a biological target for antiproliferative activity Sus scrofa

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.37 11-chloro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 65.3% inhibition at 0.010 mM Sus scrofa
1.1.1.37 2,3-dimethoxy-6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carbonitrile 89.2% inhibition at 0.010 mM Sus scrofa
1.1.1.37 2,3-dimethoxy-9-(trifluoromethyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 97.7% inhibition at 0.010 mM Sus scrofa
1.1.1.37 3-methoxy-9-trifluormethyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 83.9% inhibition at 0.010 mM Sus scrofa
1.1.1.37 4-methoxy-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 87.6% inhibition at 0.010 mM Sus scrofa
1.1.1.37 5-(3,4-dichlorobenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 5-(4-methylbenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 5-benzyl-9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 8.6% inhibition at 0.010 mM Sus scrofa
1.1.1.37 5-benzyl-9-chloro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 5-benzyl-9-methoxy-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 5-benzyl-9-methyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 5-benzyl-9-tert-butyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 5-benzyl-9-trifluoromethyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carbonitrile 91.3% inhibition at 0.010 mM Sus scrofa
1.1.1.37 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylic acid 98.7% inhibition at 0.010 mM Sus scrofa
1.1.1.37 7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 78.7% inhibition at 0.010 mM Sus scrofa
1.1.1.37 8,10-dichloro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 28.7% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-(methylsulfinyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 96.2% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-(methylthio)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 76.6% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-(trifluoromethyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 88.3% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-12-(prop-2-en-1-yl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 74.1% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-12-methyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 98.0% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-2,3-dimethoxy-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 56.3% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-2-methoxy-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 58.7% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-3-methoxy-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 15.0% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-4-hydroxy-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 25.9% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-4-methoxy-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 82.0% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-5-(3,4-dichlorobenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 9-bromo-5-(4-methoxybenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 9-bromo-5-(4-methylbenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 9-bromo-5-methyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 81.9% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 74.5% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-chloro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 73.4% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-fluoro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 46.2% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-methyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 87.8% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-nitro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 54.2% inhibition at 0.010 mM Sus scrofa
1.1.1.37 9-tert-butyl-5-(3,4-dichlorobenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
-
 Sus scrofa
1.1.1.37 butyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
-
 Sus scrofa
1.1.1.37 ethyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
-
 Sus scrofa
1.1.1.37 hexyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
-
 Sus scrofa
1.1.1.37 methyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate 60.9% inhibition at 0.010 mM Sus scrofa
1.1.1.37 additional information development of 5-benzylpaullones and paullone-9-carboxylic acid alkyl esters as selective inhibitors of mMDH, overview Sus scrofa
1.1.1.37 octyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
-
 Sus scrofa
1.1.1.37 pentyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
-
 Sus scrofa
1.1.1.37 propyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
-
 Sus scrofa

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.1.1.37 mitochondrion isozyme mMDH Sus scrofa 5739
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.37 (S)-malate + NAD+ Sus scrofa
-
 oxaloacetate + NADH + H+
-
 r

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.37 Sus scrofa
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.37 commercial preparation
-
 Sus scrofa
-
1.1.1.37 heart
-
 Sus scrofa
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.37 (S)-malate + NAD+
-
 Sus scrofa oxaloacetate + NADH + H+
-
 r

Synonyms

EC Number Synonyms Comment Organism
1.1.1.37 mitochondrial malate dehydrogenase
-
 Sus scrofa
1.1.1.37 mMDH
-
 Sus scrofa

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.37 25
-
 assay at Sus scrofa

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.37 8.5
-
 assay at Sus scrofa

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.37 NAD+
-
 Sus scrofa
1.1.1.37 NADH
-
 Sus scrofa

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.37 0.00077
-
 pH 8.5, 25°C Sus scrofa 9-tert-butyl-5-(3,4-dichlorobenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0011
-
 pH 8.5, 25°C Sus scrofa 9-bromo-5-(3,4-dichlorobenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0016
-
 pH 8.5, 25°C Sus scrofa 5-benzyl-9-tert-butyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0016
-
 pH 8.5, 25°C Sus scrofa 9-bromo-5-(4-methylbenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0018
-
 pH 8.5, 25°C Sus scrofa 9-bromo-5-(4-methoxybenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0024
-
 pH 8.5, 25°C Sus scrofa 5-benzyl-9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0027
-
 pH 8.5, 25°C Sus scrofa 5-benzyl-9-chloro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0027
-
 pH 8.5, 25°C Sus scrofa octyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
1.1.1.37 0.0042
-
 pH 8.5, 25°C Sus scrofa 5-benzyl-9-trifluoromethyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0043
-
 pH 8.5, 25°C Sus scrofa hexyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
1.1.1.37 0.0044
-
 pH 8.5, 25°C Sus scrofa pentyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
1.1.1.37 0.0062
-
 pH 8.5, 25°C Sus scrofa 5-benzyl-9-methyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0062
-
 pH 8.5, 25°C Sus scrofa propyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
1.1.1.37 0.0079
-
 pH 8.5, 25°C Sus scrofa 5-(3,4-dichlorobenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0099
-
 pH 8.5, 25°C Sus scrofa butyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
1.1.1.37 0.0105
-
 pH 8.5, 25°C Sus scrofa 5-(4-methylbenzyl)-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0119
-
 pH 8.5, 25°C Sus scrofa 5-benzyl-9-methoxy-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one
1.1.1.37 0.0135
-
 pH 8.5, 25°C Sus scrofa methyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate
1.1.1.37 0.02
-
 pH 8.5, 25°C Sus scrofa ethyl 6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine-9-carboxylate

General Information

EC Number General Information Comment Organism
1.1.1.37 additional information mMDH inhibition is of minor relevance for the growth inhibition caused by paullones Sus scrofa