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Literature summary extracted from

  • Stump, B.; Kaiser, M.; Brun, R.; Krauth-Siegel, R.L.; Diederich, F.
    Betraying the parasites redox system: diaryl sulfide-based inhibitors of trypanothione reductase: subversive substrates and antitrypanosomal properties (2007), ChemMedChem, 2, 1708-1712.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.8.1.12 medicine promising trypanothione reductase inhibitors Trypanosoma brucei rhodesiense

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.8.1.12 3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide cationic diaryl sulphide-based inhibitor, 99% growth inhibition Trypanosoma brucei rhodesiense
1.8.1.12 3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride cationic diaryl sulphide-based inhibitor Trypanosoma brucei rhodesiense
1.8.1.12 3-([5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide cationic diaryl sulphide-based inhibitor, 99% growth inhibition Trypanosoma brucei rhodesiense
1.8.1.12 3-([5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride cationic diaryl sulphide-based inhibitor Trypanosoma brucei rhodesiense
1.8.1.12 3-[(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide cationic diaryl sulphide-based inhibitor, 99% growth inhibition Trypanosoma brucei rhodesiense
1.8.1.12 3-[(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride cationic diaryl sulphide-based inhibitor, 38% growth inhibition Trypanosoma brucei rhodesiense
1.8.1.12 3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide cationic diaryl sulphide-based inhibitor, 99% growth inhibition Trypanosoma brucei rhodesiense
1.8.1.12 3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride cationic diaryl sulphide-based inhibitor, 0% growth inhibition Trypanosoma brucei rhodesiense
1.8.1.12 chinifur inhibits trypanothione reductase and acts as subversive substrate Trypanosoma brucei rhodesiense
1.8.1.12 nifurtimox weak inhibitor of trypanothione reductase Trypanosoma brucei rhodesiense

Organism

EC Number Organism UniProt Comment Textmining
1.8.1.12 Trypanosoma brucei rhodesiense
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.8.1.12 trypanothione + 5,5'-dithiobis-(2-nitrobenzoic acid)
-
 Trypanosoma brucei rhodesiense trypanothione disulfide + thionitrobenzoate
-
 ?
1.8.1.12 trypanothione + NADP+
-
 Trypanosoma brucei rhodesiense trypanothione disulfide + NADPH + H+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.8.1.12 trypanothione reductase TR Trypanosoma brucei rhodesiense

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.8.1.12 0.006
-
 3-[(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride
-
 Trypanosoma brucei rhodesiense
1.8.1.12 0.007
-
 3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
-
 Trypanosoma brucei rhodesiense
1.8.1.12 0.007
-
 3-([5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
-
 Trypanosoma brucei rhodesiense
1.8.1.12 0.008
-
 3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride
-
 Trypanosoma brucei rhodesiense
1.8.1.12 0.009
-
 3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
-
 Trypanosoma brucei rhodesiense
1.8.1.12 0.009
-
 3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride
-
 Trypanosoma brucei rhodesiense
1.8.1.12 0.01
-
 3-([5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride
-
 Trypanosoma brucei rhodesiense
1.8.1.12 0.02
-
 3-[(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
-
 Trypanosoma brucei rhodesiense

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.8.1.12 0.000059
-
-
 Trypanosoma brucei rhodesiense 3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
1.8.1.12 0.000068
-
-
 Trypanosoma brucei rhodesiense 3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
1.8.1.12 0.000077
-
-
 Trypanosoma brucei rhodesiense 3-([5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
1.8.1.12 0.000102
-
-
 Trypanosoma brucei rhodesiense 3-[(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide