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Literature summary for 1.8.1.7 extracted from

  • Bauer, H.; Fritz-Wolf, K.; Winzer, A.; Kuehner, S.; Little, S.; Yardley, V.; Vezin, H.; Palfey, B.; Schirmer, R.H.; Davioud-Charvet, E.
    A fluoro analogue of the menadione derivative 6-[2-(3-methyl)-1,4-naphthoquinolyl]hexanoic acid is a suicide substrate of glutathione reductase. Crystal structure of the alkylated human enzyme (2006), J. Am. Chem. Soc., 128, 10784-10794.
    View publication on PubMed
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Crystallization (Commentary)

Crystallization (Comment) Organism
hanging drop vapour diffusion method Homo sapiens
hanging drop vapour diffusion method Plasmodium falciparum

Inhibitors

Inhibitors Comment Organism Structure
6-[2-(3-fluoromethyl)-1,4-naphthoquinolyl]hexanoic acid IC50: 0.0041 mM, irreversible inhibition Homo sapiens
6-[2-(3-fluoromethyl)-1,4-naphthoquinolyl]hexanoic acid IC50: 0.0064 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG, irreversible inhibition Plasmodium falciparum
6-[2-(3-methyl)-1,4-naphthoquinolyl]hexanoic acid IC50: 0.0032 mM, uncompetitive inhibitor Homo sapiens
6-[2-(3-methyl)-1,4-naphthoquinolyl]hexanoic acid IC50: 0.0045 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG, uncompetitive inhibitor Plasmodium falciparum
menadione IC50: 0.0275 mM Homo sapiens
menadione IC50: 0.042 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG Plasmodium falciparum
[4-(3-methyl-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetic acid IC50: 0.0014 mM Homo sapiens
[4-(3-methyl-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetic acid IC50: 0.0077 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG Plasmodium falciparum
[4-[3-(fluoromethyl)-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl]phenyl]acetic acid IC50: 0.0035 mM Homo sapiens
[4-[3-(fluoromethyl)-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl]phenyl]acetic acid IC50: 0.002 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG Plasmodium falciparum

Organism

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

Substrates and Products (Substrate)

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

Subunits

Subunits Comment Organism
homodimer
-
 Homo sapiens
homodimer
-
 Plasmodium falciparum

Synonyms

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

Cofactor

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

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0014
-
 IC50: 0.0014 mM Homo sapiens [4-(3-methyl-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetic acid
0.002
-
 IC50: 0.002 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG Plasmodium falciparum [4-[3-(fluoromethyl)-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl]phenyl]acetic acid
0.0032
-
 IC50: 0.0032 mM, uncompetitive inhibitor Homo sapiens 6-[2-(3-methyl)-1,4-naphthoquinolyl]hexanoic acid
0.0035
-
 IC50: 0.0035 mM Homo sapiens [4-[3-(fluoromethyl)-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl]phenyl]acetic acid
0.0041
-
 IC50: 0.0041 mM, irreversible inhibition Homo sapiens 6-[2-(3-fluoromethyl)-1,4-naphthoquinolyl]hexanoic acid
0.0045
-
 IC50: 0.0045 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG, uncompetitive inhibitor Plasmodium falciparum 6-[2-(3-methyl)-1,4-naphthoquinolyl]hexanoic acid
0.0064
-
 IC50: 0.0064 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG, irreversible inhibition Plasmodium falciparum 6-[2-(3-fluoromethyl)-1,4-naphthoquinolyl]hexanoic acid
0.0077
-
 IC50: 0.0077 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG Plasmodium falciparum [4-(3-methyl-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetic acid
0.0275
-
 IC50: 0.0275 mM Homo sapiens menadione
0.042
-
 IC50: 0.042 mM, at pH 6.9 and 25°C in the presence of 1 mM GSSG Plasmodium falciparum menadione