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Literature summary for 1.1.1.21 extracted from

  • Stefek, M.; Soltesova Prnova, M.; Majekova, M.; Rechlin, C.; Heine, A.; Klebe, G.
    Identification of novel aldose reductase inhibitors based on carboxymethylated mercaptotriazinoindole scaffold (2015), J. Med. Chem., 58, 2649-2657.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene AKR1B1, recombinant expression of His6-tagged enzyme in Escherichia coli strain BL21 gold (DE3) Homo sapiens

Crystallization (Commentary)

Crystallization (Comment) Organism
purified recombinant enzyme ALR2 in complex with inhibitor 17744184, hanging drop vapour diffusion method, mixing of 15 mg/mL ALR2 protein solution with reservoir solution containing 5% w/v PEG 6000, 5.15 mg/mL DTT, 0.66 mg/mL NADP+, and 50 mM diammonium hydrogen citrate, pH 5.0, equilibration against 1 mL of well solution containing 20% w/v PEG 6000 in 120 mM diammonium hydrogen citrate, pH 5.0, 3 days at 4°C and 2-4 days at 18°C, X-ray diffraction structure determination and analysis at 1.26 A resolution Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(1H-indol-1-yl)acetic acid
-
Homo sapiens
(2,3-dihydrocyclopenta[b]indol-4(1H)-yl)acetic acid
-
Homo sapiens
(3-sulfanyl-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
-
Homo sapiens
(3-[[(2-fluorophenyl)methyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
-
Homo sapiens
(3-[[2-oxo-2-(2,4,6-trimethylanilino)ethyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
-
Homo sapiens
(4-oxo-3,4-dihydro-5H-pyridazino[4,5-b]indol-5-yl)acetic acid
-
Homo sapiens
(6H-indolo[2,3-b]quinoxalin-6-yl)acetic acid
-
Homo sapiens
(7H-indolo[2',3':5,6][1,2,4]triazino[2,3-a]benzimidazol-7-yl)acetic acid uncompetitive Homo sapiens
(8-methyl-3-[[2-oxo-2-(propylamino)ethyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
-
Homo sapiens
2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione
-
Homo sapiens
3-(1H-indol-1-yl)propanoic acid
-
Homo sapiens
3-[3-[(diethylamino)methyl]-1H-indol-1-yl]propanoic acid
-
Homo sapiens
epalrestat
-
Homo sapiens
indole-1-acetic acid
-
Homo sapiens
lidorestat binding mode, overview Homo sapiens
additional information identification of aldose reductase inhibitors based on carboxymethylated mercaptotriazinoindole scaffold, structure-activity relationships, overview Homo sapiens
zopolrestat
-
Homo sapiens
[(5H-[1,2,4]triazino[5,6-b]indol-3-yl)sulfanyl]acetic acid
-
Homo sapiens
[3-(2,2-dimethylpropanoyl)-1H-indol-1-yl]acetic acid
-
Homo sapiens
[3-[(diethylamino)methyl]-1H-indol-1-yl]acetic acid
-
Homo sapiens
[3-[(dimethylamino)methyl]-2-methyl-1H-indol-1-yl]acetic acid
-
Homo sapiens
[3-[(morpholin-4-yl)methyl]-1H-indol-1-yl]acetic acid
-
Homo sapiens
[3-[(propan-2-yl)sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl]acetic acid
-
Homo sapiens
[3-[(pyrrolidin-1-yl)methyl]-1H-indol-1-yl]acetic acid
-
Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens P15121
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His6-tagged enzyme from Escherichia coli strain BL21 gold (DE3) by nickel affinity chromatography, tag cleavage by thrombin, followed by anion exchange chromatography Homo sapiens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
DL-glyceraldehyde + NADPH + H+
-
Homo sapiens ?
-
?

Synonyms

Synonyms Comment Organism
AKR1B1
-
Homo sapiens
aldose reductase
-
Homo sapiens
ALR2
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
additional information inhibition kinetics Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.097
-
pH and temperature not specified in the publication Homo sapiens (3-sulfanyl-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
0.33
-
pH and temperature not specified in the publication Homo sapiens (8-methyl-3-[[2-oxo-2-(propylamino)ethyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
2.05
-
pH and temperature not specified in the publication Homo sapiens [3-[(propan-2-yl)sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl]acetic acid
2.24
-
pH and temperature not specified in the publication Homo sapiens (3-[[(2-fluorophenyl)methyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
2.75
-
pH and temperature not specified in the publication Homo sapiens (6H-indolo[2,3-b]quinoxalin-6-yl)acetic acid
2.87
-
pH and temperature not specified in the publication Homo sapiens (2,3-dihydrocyclopenta[b]indol-4(1H)-yl)acetic acid
3.46
-
pH and temperature not specified in the publication Homo sapiens [(5H-[1,2,4]triazino[5,6-b]indol-3-yl)sulfanyl]acetic acid
4.06
-
pH and temperature not specified in the publication Homo sapiens (3-[[2-oxo-2-(2,4,6-trimethylanilino)ethyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
4.41
-
pH and temperature not specified in the publication Homo sapiens 2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione
7.3
-
pH and temperature not specified in the publication Homo sapiens (1H-indol-1-yl)acetic acid
9.95
-
pH and temperature not specified in the publication Homo sapiens (7H-indolo[2',3':5,6][1,2,4]triazino[2,3-a]benzimidazol-7-yl)acetic acid
11.46
-
pH and temperature not specified in the publication Homo sapiens (4-oxo-3,4-dihydro-5H-pyridazino[4,5-b]indol-5-yl)acetic acid
13.76
-
pH and temperature not specified in the publication Homo sapiens [3-(2,2-dimethylpropanoyl)-1H-indol-1-yl]acetic acid
19.85
-
pH and temperature not specified in the publication Homo sapiens 3-[3-[(diethylamino)methyl]-1H-indol-1-yl]propanoic acid
30.14
-
pH and temperature not specified in the publication Homo sapiens [3-[(diethylamino)methyl]-1H-indol-1-yl]acetic acid
34.52
-
pH and temperature not specified in the publication Homo sapiens [3-[(morpholin-4-yl)methyl]-1H-indol-1-yl]acetic acid
42.16
-
pH and temperature not specified in the publication Homo sapiens [3-[(dimethylamino)methyl]-2-methyl-1H-indol-1-yl]acetic acid
46.48
-
pH and temperature not specified in the publication Homo sapiens [3-[(pyrrolidin-1-yl)methyl]-1H-indol-1-yl]acetic acid
53.54
-
pH and temperature not specified in the publication Homo sapiens 3-(1H-indol-1-yl)propanoic acid