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Literature summary for 1.8.1.7 extracted from

  • Grellier, P.; Maroziene, A.; Nivinskas, H.; Sarlauskas, J.; Aliverti, A.; Cenas, N.
    Antiplasmodial activity of quinones: roles of aziridinyl substituents and the inhibition of Plasmodium falciparum glutathione reductase (2010), Arch. Biochem. Biophys., 494, 32-39.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1,4-dihydroxy-9,10-anthraquinone
-
Homo sapiens
1,4-dihydroxy-9,10-anthraquinone complete inhibition at 0.05 mM Plasmodium falciparum
1,4-Naphthoquinone
-
Homo sapiens
1,4-Naphthoquinone complete inhibition at 0.05 mM Plasmodium falciparum
1,8-dihydroxy-9,10-anthraquinone
-
Homo sapiens
1,8-dihydroxy-9,10-anthraquinone complete inhibition at 0.05 mM Plasmodium falciparum
11-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)undecanoic acid
-
Homo sapiens
11-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)undecanoic acid
-
Plasmodium falciparum
2,5-bis(aziridin-1-yl)-3,6-bis[(2-hydroxyethyl)amino]cyclohexa-2,5-diene-1,4-dione
-
Plasmodium falciparum
2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione
-
Plasmodium falciparum
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione
-
Homo sapiens
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione
-
Plasmodium falciparum
2,5-bis(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione
-
Plasmodium falciparum
2,5-bis(ethylamino)-3,6-di(aziridinyl)-1,4-benzoquinone
-
Homo sapiens
2,5-bis(ethylamino)-3,6-di(aziridinyl)-1,4-benzoquinone complete inhibition at 0.05 mM Plasmodium falciparum
2,6-dimethyl-1,4-benzoquinone
-
Homo sapiens
2,6-dimethyl-1,4-benzoquinone 74% inhibition at 0.05 mM Plasmodium falciparum
2-Hydroxy-1,4-naphthoquinone
-
Homo sapiens
2-Hydroxy-1,4-naphthoquinone complete inhibition at 0.05 mM Plasmodium falciparum
2-hydroxy-3-methyl-1,4-naphthoquinone
-
Homo sapiens
2-hydroxy-3-methyl-1,4-naphthoquinone complete inhibition at 0.05 mM Plasmodium falciparum
2-methyl-1,4-naphthoquinone
-
Homo sapiens
2-methyl-1,4-naphthoquinone complete inhibition at 0.05 mM Plasmodium falciparum
3-[5-[8-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)octyl]-1H-tetrazol-1-yl]propanenitrile
-
Homo sapiens
3-[5-[8-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)octyl]-1H-tetrazol-1-yl]propanenitrile
-
Plasmodium falciparum
5,8-Dihydroxy-1,4-naphthoquinone
-
Homo sapiens
5,8-Dihydroxy-1,4-naphthoquinone 58% inhibition at 0.05 mM Plasmodium falciparum
5-hydroxy-1,4-naphthoquinone
-
Homo sapiens
5-hydroxy-1,4-naphthoquinone 65% inhibition at 0.05 mM Plasmodium falciparum
9,10-phenanthrene quinone
-
Homo sapiens
9,10-phenanthrene quinone complete inhibition at 0.05 mM Plasmodium falciparum
diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate
-
Plasmodium falciparum
N-(2-cyanoethyl)-9-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)nonanamide
-
Homo sapiens
N-(2-cyanoethyl)-9-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)nonanamide
-
Plasmodium falciparum
tetramethyl-1,4-benzoquinone
-
Homo sapiens
tetramethyl-1,4-benzoquinone complete inhibition at 0.05 mM Plasmodium falciparum
trimethyl-1,4-benzoquinone
-
Homo sapiens
trimethyl-1,4-benzoquinone 84% inhibition at 0.05 mM Plasmodium falciparum
trimethyl-aziridinyl-1,4-benzoquinone
-
Homo sapiens
trimethyl-aziridinyl-1,4-benzoquinone complete inhibition at 0.05 mM Plasmodium falciparum

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
glutathione disulfide + NADPH + H+ Homo sapiens
-
glutathione + NADP+
-
?
glutathione disulfide + NADPH + H+ Plasmodium falciparum
-
glutathione + NADP+
-
?
glutathione disulfide + NADPH + H+ Plasmodium falciparum FcB1
-
glutathione + NADP+
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Plasmodium falciparum
-
-
-
Plasmodium falciparum FcB1
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
erythrocyte
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1,4-dihydroxy-9,10-anthraquinone + NADPH
-
Plasmodium falciparum ?
-
?
1,4-dihydroxy-9,10-anthraquinone + NADPH
-
Plasmodium falciparum FcB1 ?
-
?
1,4-naphthoquinone + NADPH + H+
-
Plasmodium falciparum ?
-
?
1,4-naphthoquinone + NADPH + H+
-
Plasmodium falciparum FcB1 ?
-
?
1,8-dihydroxy-9,10-anthraquinone + NADPH
-
Plasmodium falciparum ?
-
?
2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione + NADPH
-
Plasmodium falciparum ?
-
?
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione + NADPH
-
Plasmodium falciparum ?
-
?
2,5-bis(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione + NADPH
-
Plasmodium falciparum ?
-
?
2,5-bis(ethylamino)-3,6-di(aziridinyl)-1,4-benzoquinone + NADPH
-
Plasmodium falciparum ?
-
?
2,6-dimethyl-1,4-benzoquinone + NADPH
-
Plasmodium falciparum ?
-
?
2-hydroxy-1,4-naphthoquinone + NADPH
-
Plasmodium falciparum ?
-
?
2-hydroxy-3-methyl-1,4-naphthoquinone + NADPH
-
Plasmodium falciparum ?
-
?
2-methyl-1,4-naphthoquinone + NADPH
-
Plasmodium falciparum ?
-
?
5,8-dihydroxy-1,4-naphthoquinone + NADPH
-
Plasmodium falciparum ?
-
?
5,8-dihydroxy-1,4-naphthoquinone + NADPH
-
Plasmodium falciparum FcB1 ?
-
?
5-hydroxy-1,4-naphthoquinone + NADPH
-
Plasmodium falciparum ?
-
?
5-hydroxy-1,4-naphthoquinone + NADPH
-
Plasmodium falciparum FcB1 ?
-
?
9,10-phenanthrene quinone + NADPH
-
Plasmodium falciparum ?
-
?
diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate + NADPH
-
Plasmodium falciparum ?
-
?
glutathione disulfide + NADPH + H+
-
Homo sapiens glutathione + NADP+
-
?
glutathione disulfide + NADPH + H+
-
Plasmodium falciparum glutathione + NADP+
-
?
glutathione disulfide + NADPH + H+
-
Plasmodium falciparum FcB1 glutathione + NADP+
-
?
tetramethyl-1,4-benzoquinone + NADPH
-
Plasmodium falciparum ?
-
?
trimethyl-1,4-benzoquinone + NADPH
-
Plasmodium falciparum ?
-
?
trimethyl-aziridinyl-1,4-benzoquinone + NADPH
-
Plasmodium falciparum ?
-
?

Synonyms

Synonyms Comment Organism
glutathione reductase
-
Homo sapiens
glutathione reductase
-
Plasmodium falciparum

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.1
-
diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate kcat_Km above 0.8 1/sec*mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°Ckcat above 0.1 1/sec, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.1
-
1,8-dihydroxy-9,10-anthraquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.11
-
1,4-dihydroxy-9,10-anthraquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.14
-
2-methyl-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.2
-
trimethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.22
-
9,10-phenanthrene quinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.3
-
tetramethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
1
-
1,4-Naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
1.1
-
2,6-dimethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
5
-
2,5-bis(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°CpH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
5.5
-
5-hydroxy-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
7
-
5,8-Dihydroxy-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum

Cofactor

Cofactor Comment Organism Structure
FAD
-
Homo sapiens
FAD
-
Plasmodium falciparum
NADPH
-
Homo sapiens
NADPH
-
Plasmodium falciparum

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00015
-
5-hydroxy-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0006
-
5,8-Dihydroxy-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0013
-
1,4-Naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.002
-
2,5-bis(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0025
-
1,4-Naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0025
-
9,10-phenanthrene quinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0025
-
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0028
-
2,6-dimethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0032
-
11-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)undecanoic acid pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.009
-
trimethyl-aziridinyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.01
-
trimethyl-aziridinyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0108
-
N-(2-cyanoethyl)-9-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)nonanamide pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.012
-
9,10-phenanthrene quinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.012
-
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.016
-
3-[5-[8-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)octyl]-1H-tetrazol-1-yl]propanenitrile pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.0162
-
trimethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.0227
-
N-(2-cyanoethyl)-9-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)nonanamide pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.028
-
2-methyl-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.03
-
2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.035
-
1,8-dihydroxy-9,10-anthraquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.039
-
2-methyl-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.057
-
11-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)undecanoic acid pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.09
-
1,8-dihydroxy-9,10-anthraquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.15
-
1,4-dihydroxy-9,10-anthraquinone Ki above 0.15 mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.15
-
1,4-dihydroxy-9,10-anthraquinone Ki above 0.15 mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.16
-
tetramethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.16
-
3-[5-[8-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)octyl]-1H-tetrazol-1-yl]propanenitrile pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.25
-
tetramethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.3
-
diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.5
-
2-Hydroxy-1,4-naphthoquinone Ki above 0.5 mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.5
-
2-Hydroxy-1,4-naphthoquinone Ki above 0.5 mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.5
-
2,5-bis(ethylamino)-3,6-di(aziridinyl)-1,4-benzoquinone Ki above 0.5 mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Homo sapiens
0.5
-
2,5-bis(ethylamino)-3,6-di(aziridinyl)-1,4-benzoquinone Ki above 0.5 mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.5
-
2-hydroxy-3-methyl-1,4-naphthoquinone Ki above 0.5 mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.5
-
2,5-bis(aziridin-1-yl)-3,6-bis[(2-hydroxyethyl)amino]cyclohexa-2,5-diene-1,4-dione pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00001
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum 2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione
0.00004
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum 2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione
0.00043
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum 2,5-bis(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione
0.0014
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum 3-[5-[8-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)octyl]-1H-tetrazol-1-yl]propanenitrile
0.0015
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum N-(2-cyanoethyl)-9-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)nonanamide
0.0018
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate
0.0024
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum 2,5-bis(aziridin-1-yl)-3,6-bis[(2-hydroxyethyl)amino]cyclohexa-2,5-diene-1,4-dione
0.0035
-
pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum 11-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)undecanoic acid

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.1
-
2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione kcat_Km above 0.1 1/sec*mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.25
-
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione kcat_Km above 0.25 1/sec*mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.4
-
1,8-dihydroxy-9,10-anthraquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.65
-
trimethyl-aziridinyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.7
-
trimethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
0.8
-
diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate kcat_Km above 0.8 1/sec*mM, pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
1
-
tetramethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
1.8
-
2-methyl-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
3.2
-
1,4-dihydroxy-9,10-anthraquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
4.2
-
9,10-phenanthrene quinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
5.2
-
1,4-Naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
6.5
-
2,6-dimethyl-1,4-benzoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
40
-
2,5-bis(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
360
-
5-hydroxy-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum
430
-
5,8-Dihydroxy-1,4-naphthoquinone pH 7.0, 0.1 M potassium phosphate, 1 mM EDTA, 25°C Plasmodium falciparum