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Literature summary for 1.8.1.12 extracted from

  • Stump, B.; Eberle, C.; Kaiser, M.; Brun, R.; Krauth-Siegel, R.L.; Diederich, F.
    Diaryl sulfide-based inhibitors of trypanothione reductase: inhibition potency, revised binding mode and antiprotozoal activities (2008), Org. Biomol. Chem., 6, 3935-3947.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
2-[(4-bromophenyl)sulfanyl]-5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]aniline 39% inhibition at 0.1 mM Plasmodium falciparum
2-[(4-bromophenyl)sulfanyl]-5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]aniline
-
Trypanosoma brucei rhodesiense
3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
-
Plasmodium falciparum
3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
-
Trypanosoma brucei rhodesiense
3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride
-
Plasmodium falciparum
3-([5-chloro-2-[(4'-methylbiphenyl-4-yl)thio]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-ammonium chloride
-
Plasmodium falciparum
3-([5-chloro-2-[(4'-methylbiphenyl-4-yl)thio]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-ammonium chloride
-
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
-
Plasmodium falciparum
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
3-([5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride
-
Plasmodium falciparum
3-([5-chloro-2-[1-naphthylthio]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethyl-propan-1-ammonium chloride
-
Plasmodium falciparum
3-([5-chloro-2-[1-naphthylthio]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethyl-propan-1-ammonium chloride
-
Trypanosoma brucei rhodesiense
3-([5-chloro-2-[2-naphthylthio]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethyl-propan-1-ammonium chloride
-
Plasmodium falciparum
3-([5-chloro-2-[2-naphthylthio]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethyl-propan-1-ammonium chloride
-
Trypanosoma brucei rhodesiense
3-[(5-chloro-2-[[2-(trifluoromethyl)phenyl]thio]phenyl)amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-ammonium chloride
-
Plasmodium falciparum
3-[(5-chloro-2-[[2-(trifluoromethyl)phenyl]thio]phenyl)amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-ammonium chloride
-
Trypanosoma brucei rhodesiense
3-[(5-chloro-2-[[3-(trifluoromethyl)phenyl]thio]phenyl)amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-ammonium chloride
-
Plasmodium falciparum
3-[(5-chloro-2-[[3-(trifluoromethyl)phenyl]thio]phenyl)amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-ammonium chloride
-
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
-
Plasmodium falciparum
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
3-[(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride
-
Plasmodium falciparum
3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
-
Plasmodium falciparum
3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
-
Trypanosoma brucei rhodesiense
3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-ammonium chloride about 60% inhibition at 0.04 mM Plasmodium falciparum
3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-ammonium chloride
-
Trypanosoma brucei rhodesiense
5-chloro-2-[(4-chlorophenyl)sulfanyl]-N-[3-(4-methylpiperazin-1-yl)propyl]aniline
-
Plasmodium falciparum
5-chloro-2-[(4-chlorophenyl)sulfanyl]-N-[3-(4-methylpiperazin-1-yl)propyl]aniline
-
Trypanosoma brucei rhodesiense
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-(phenylsulfanyl)aniline 33% inhibition at 0.1 mM Plasmodium falciparum
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-(phenylsulfanyl)aniline
-
Trypanosoma brucei rhodesiense
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[(2-naphthalen-1-ylphenyl)sulfanyl]aniline
-
Plasmodium falciparum
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[(2-naphthalen-1-ylphenyl)sulfanyl]aniline
-
Trypanosoma brucei rhodesiense
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[(2-naphthalen-2-ylphenyl)sulfanyl]aniline less than 5% inhibition at 0.04 mM Plasmodium falciparum
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[(2-naphthalen-2-ylphenyl)sulfanyl]aniline
-
Trypanosoma brucei rhodesiense
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[(2-pyridin-2-ylphenyl)sulfanyl]aniline
-
Plasmodium falciparum
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[2-(trifluoromethyl)phenyl]sulfanyl]aniline
-
Plasmodium falciparum
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[2-(trifluoromethyl)phenyl]sulfanyl]aniline
-
Trypanosoma brucei rhodesiense
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[3-(trifluoromethyl)phenyl]sulfanyl]aniline
-
Plasmodium falciparum
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[3-(trifluoromethyl)phenyl]sulfanyl]aniline
-
Trypanosoma brucei rhodesiense
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[4-(trifluoromethyl)phenyl]sulfanyl]aniline
-
Plasmodium falciparum
5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[4-(trifluoromethyl)phenyl]sulfanyl]aniline
-
Trypanosoma brucei rhodesiense
N'-(5-chloro-2-[[2-(trifluoromethyl)phenyl]sulfanyl]phenyl)-N,N-dimethylpropane-1,3-diamine
-
Plasmodium falciparum
N'-(5-chloro-2-[[2-(trifluoromethyl)phenyl]sulfanyl]phenyl)-N,N-dimethylpropane-1,3-diamine
-
Trypanosoma brucei rhodesiense
N'-(5-chloro-2-[[3-(trifluoromethyl)phenyl]sulfanyl]phenyl)-N,N-dimethylpropane-1,3-diamine
-
Plasmodium falciparum
N'-(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)-N,N-dimethylpropane-1,3-diamine
-
Plasmodium falciparum
N'-(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)-N,N-dimethylpropane-1,3-diamine
-
Trypanosoma brucei rhodesiense
N'-[2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]-N,N-dimethylpropane-1,3-diamine
-
Plasmodium falciparum
N'-[2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]-N,N-dimethylpropane-1,3-diamine
-
Trypanosoma brucei rhodesiense
N'-[5-chloro-2-(naphthalen-1-ylsulfanyl)phenyl]-N,N-dimethylpropane-1,3-diamine
-
Plasmodium falciparum
N'-[5-chloro-2-(naphthalen-1-ylsulfanyl)phenyl]-N,N-dimethylpropane-1,3-diamine
-
Trypanosoma brucei rhodesiense
N'-[5-chloro-2-(naphthalen-2-ylsulfanyl)phenyl]-N,N-dimethylpropane-1,3-diamine
-
Plasmodium falciparum
N'-[5-chloro-2-(naphthalen-2-ylsulfanyl)phenyl]-N,N-dimethylpropane-1,3-diamine
-
Trypanosoma brucei rhodesiense
N'-[5-chloro-2-(phenylsulfanyl)phenyl]-N,N-dimethylpropane-1,3-diamine
-
Plasmodium falciparum
N'-[5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]-N,N-dimethylpropane-1,3-diamine
-
Plasmodium falciparum
N'-[5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]-N,N-dimethylpropane-1,3-diamine
-
Trypanosoma brucei rhodesiense
N-[2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]-3-(4-methylpiperazin-1-yl)propanamide 5% inhibition at 0.1 mM Plasmodium falciparum
N-[5-chloro-2-(phenylsulfanyl)phenyl]-3-(4-methylpiperazin-1-yl)propanamide 0% inhibition at 0.04 mM Plasmodium falciparum
N-[5-chloro-2-(phenylthio)phenyl]-3-(4-methylpiperazine-1-yl)-propanamidine
-
Plasmodium falciparum
N-[5-chloro-2-(phenylthio)phenyl]-3-(4-methylpiperazine-1-yl)-propanamidine
-
Trypanosoma brucei rhodesiense

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
trypanothione disulfide + NADPH + H+ Plasmodium falciparum
-
trypanothione + NADP+
-
?
trypanothione disulfide + NADPH + H+ Trypanosoma brucei rhodesiense
-
trypanothione + NADP+
-
?
trypanothione disulfide + NADPH + H+ Trypanosoma brucei rhodesiense STIB900
-
trypanothione + NADP+
-
?

Organism

Organism UniProt Comment Textmining
Plasmodium falciparum
-
-
-
Trypanosoma brucei rhodesiense
-
-
-
Trypanosoma brucei rhodesiense STIB900
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
trypanothione disulfide + NADPH + H+
-
Plasmodium falciparum trypanothione + NADP+
-
?
trypanothione disulfide + NADPH + H+
-
Trypanosoma brucei rhodesiense trypanothione + NADP+
-
?
trypanothione disulfide + NADPH + H+
-
Trypanosoma brucei rhodesiense STIB900 trypanothione + NADP+
-
?

Synonyms

Synonyms Comment Organism
EC 1.6.4.8 formerly Plasmodium falciparum
EC 1.6.4.8 formerly Trypanosoma brucei rhodesiense
trypanothione reductase
-
Plasmodium falciparum
trypanothione reductase
-
Trypanosoma brucei rhodesiense

Cofactor

Cofactor Comment Organism Structure
FAD
-
Plasmodium falciparum
FAD
-
Trypanosoma brucei rhodesiense
NADPH
-
Plasmodium falciparum
NADPH
-
Trypanosoma brucei rhodesiense

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.006
-
3-[(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)amino]-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride competitive inhibition, at 25°C Plasmodium falciparum
0.008
-
3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride competitive inhibition, at 25°C Plasmodium falciparum
0.01
-
3-([5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]amino)-N-(3,4-dichlorobenzyl)-N,N-dimethylpropan-1-aminium chloride competitive inhibition, at 25°C Plasmodium falciparum

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00059
-
-
Trypanosoma brucei rhodesiense 3-[[5-chloro-2-(phenylsulfanyl)phenyl]amino]-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
0.00068
-
-
Trypanosoma brucei rhodesiense 3-([2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]amino)-N,N-dimethyl-N-[(5-nitrofuran-2-yl)methyl]propan-1-aminium bromide
0.0007
-
-
Trypanosoma brucei rhodesiense 5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[(2-naphthalen-1-ylphenyl)sulfanyl]aniline
0.0007
-
-
Trypanosoma brucei rhodesiense 5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[(2-naphthalen-2-ylphenyl)sulfanyl]aniline
0.00077
-
-
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
0.0009
-
-
Trypanosoma brucei rhodesiense 5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[2-(trifluoromethyl)phenyl]sulfanyl]aniline
0.00097
-
-
Trypanosoma brucei rhodesiense 5-chloro-2-[(4-chlorophenyl)sulfanyl]-N-[3-(4-methylpiperazin-1-yl)propyl]aniline
0.00102
-
-
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
0.00106
-
-
Trypanosoma brucei rhodesiense 5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[3-(trifluoromethyl)phenyl]sulfanyl]aniline
0.001144
-
-
Trypanosoma brucei rhodesiense N'-[5-chloro-2-[(4-chlorophenyl)sulfanyl]phenyl]-N,N-dimethylpropane-1,3-diamine
0.00116
-
-
Trypanosoma brucei rhodesiense N'-(5-chloro-2-[[4-(trifluoromethyl)phenyl]sulfanyl]phenyl)-N,N-dimethylpropane-1,3-diamine
0.00132
-
-
Trypanosoma brucei rhodesiense 2-[(4-bromophenyl)sulfanyl]-5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]aniline
0.00162
-
-
Trypanosoma brucei rhodesiense N'-[5-chloro-2-(naphthalen-2-ylsulfanyl)phenyl]-N,N-dimethylpropane-1,3-diamine
0.00189
-
-
Trypanosoma brucei rhodesiense N'-[5-chloro-2-(naphthalen-1-ylsulfanyl)phenyl]-N,N-dimethylpropane-1,3-diamine
0.00203
-
-
Trypanosoma brucei rhodesiense 5-chloro-N-[3-(4-methylpiperazin-1-yl)propyl]-2-[[4-(trifluoromethyl)phenyl]sulfanyl]aniline
0.00206
-
-
Trypanosoma brucei rhodesiense N'-(5-chloro-2-[[2-(trifluoromethyl)phenyl]sulfanyl]phenyl)-N,N-dimethylpropane-1,3-diamine
0.00233
-
-
Trypanosoma brucei rhodesiense N'-[2-[(4-bromophenyl)sulfanyl]-5-chlorophenyl]-N,N-dimethylpropane-1,3-diamine