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Literature summary extracted from

  • Maccari, R.; Ottana, R.; Curinga, C.; Vigorita, M.G.; Rakowitz, D.; Steindl, T.; Langer, T.
    Structure-activity relationships and molecular modelling of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors (2005), Bioorg. Med. Chem., 13, 2809-2823.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.21 (5-biphenyl-4-ylmethylene-2,4-dioxothiazolidin-3-yl)-acetic acid IC50: 0.00026 mM Bos taurus
1.1.1.21 (5-biphenyl-4-ylmethylene-2,4-dioxothiazolidin-3-yl)-acetic acid methyl ester 35% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 (5-naphthalen-1-ylmethylene-2,4-dioxothiazolidin-3-yl)acetic acid IC50: 0.00017 mM Bos taurus
1.1.1.21 (5-naphthalen-1-ylmethylene-2,4-dioxothiazolidin-3-yl)acetic acid methyl ester 12% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 4-(5-biphenyl-4-ylmethylene-2,4-dioxothiazolidin-3-yl)-2-butenoic acid 21% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 4-(5-biphenyl-4-ylmethylene-2,4-dioxothiazolidin-3-yl)-2-butenoic acid methyl ester 6% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 4-[2,4-dioxo-5-(3-phenoxybenzylidene)thiazolidin-3-yl]-2-butenoic acid 19% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 4-[2,4-dioxo-5-(3-phenoxybenzylidene)thiazolidin-3-yl]-2-butenoic acid methyl ester 25% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 4-[2,4-dioxo-5-(4-phenoxybenzylidene)thiazolidin-3-yl]-2-butenoic acid 57% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 4-[5-(4-benzyloxybenzylidene)-2,4-dioxothiazolidin-3-yl]-2-butenoic acid methyl ester 23% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 4-[5-(4-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]-2-butenoic acid IC50: 0.0042 mM Bos taurus
1.1.1.21 5-(3-aminobenzylidene)-2,4-thiazolidinedione IC50: 0.0202 mM Bos taurus
1.1.1.21 5-(3-hydroxybenzylidene)-2,4-thiazolidinedione IC50: 0.0107 mM Bos taurus
1.1.1.21 5-(3-nitrobenzylidene)-2,4-thiazolidinedione 21% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 5-(4-aminobenzylidene)-2,4-thiazolidinedione 44% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 5-(4-benzyloxybenzylidene)-2,4-thiazolidinedione 10% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione IC50: 0.009 mM Bos taurus
1.1.1.21 5-(4-nitrobenzylidene)-2,4-thiazolidinedione 37% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 5-biphenyl-4-ylmethylene-2,4-thiazolidinedione 20% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 5-naphthalen-1-ylmethylene-2,4-thiazolidinedione IC50: 0.0107 mM Bos taurus
1.1.1.21 epalrestat
-
 Bos taurus
1.1.1.21 additional information molecular modelling, enzyme docking at the active site of the enzyme, structure-activity relationships of 5-arylidene-2,4-thiazolidinediones, an additional aromatic ring or an H-bond donor group on the 5-benzylidene ring enhance ALR2 inhibitory potency, the presence of a carboxylic anionic chain on N-3 is important, and the length of the carboxylic chain is critical, overview, no inhibition by 5b 4-[2,4-dioxo-5-(4-phenoxybenzylidene)thiazolidin-3-yl]-2-butenoic acid methyl ester Bos taurus
1.1.1.21 ponalrestat IC50: 80 nM Bos taurus
1.1.1.21 sorbinil IC50: 0.0011 mM Bos taurus
1.1.1.21 zopolrestat
-
 Bos taurus
1.1.1.21 [2,4-dioxo-5-(4-phenoxybenzylidene)thiazolidin-3-yl]acetic acid IC50: 0.00082 mM Bos taurus
1.1.1.21 [2,4-dioxo-5-(4-phenoxybenzylidene)thiazolidin-3-yl]acetic acid methyl ester 33% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 [5-(3-aminobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid methyl ester IC50: 0.039 mM Bos taurus
1.1.1.21 [5-(3-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid IC50: 0.00066 mM Bos taurus
1.1.1.21 [5-(3-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid methyl ester 43% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 [5-(3-nitrobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid IC50: 0.00049 mM Bos taurus
1.1.1.21 [5-(3-nitrobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid methyl ester 22% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 [5-(4-aminobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid methyl ester 25% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 [5-(4-benzyloxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid IC50: 0.00028 mM Bos taurus
1.1.1.21 [5-(4-benzyloxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid methyl ester 12% inhibition of ALR2 at 0.05 mM Bos taurus
1.1.1.21 [5-(4-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid IC50: 0.00015 mM Bos taurus
1.1.1.21 [5-(4-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid methyl ester IC50: 0.0062 mM Bos taurus
1.1.1.21 [5-(4-nitrobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid IC50: 0.0012 mM Bos taurus
1.1.1.21 [5-(4-nitrobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid methyl ester 8% inhibition of ALR2 at 0.05 mM Bos taurus

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.21 Bos taurus
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.21 native enzyme from lens by anion exchange chromatography Bos taurus

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.21 lens
-
 Bos taurus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.21 glyceraldehyde + NADPH + H+
-
 Bos taurus glycerol + NADP+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.21 aldose reductase
-
 Bos taurus
1.1.1.21 ALR2
-
 Bos taurus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.21 37
-
 assay at Bos taurus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.21 6.8
-
 assay at Bos taurus

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.21 NADPH
-
 Bos taurus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.21 0.00008
-
 IC50: 80 nM Bos taurus ponalrestat
1.1.1.21 0.00015
-
 IC50: 0.00015 mM Bos taurus [5-(4-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid
1.1.1.21 0.00017
-
 IC50: 0.00017 mM Bos taurus (5-naphthalen-1-ylmethylene-2,4-dioxothiazolidin-3-yl)acetic acid
1.1.1.21 0.00026
-
 IC50: 0.00026 mM Bos taurus (5-biphenyl-4-ylmethylene-2,4-dioxothiazolidin-3-yl)-acetic acid
1.1.1.21 0.00028
-
 IC50: 0.00028 mM Bos taurus [5-(4-benzyloxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid
1.1.1.21 0.00049
-
 IC50: 0.00049 mM Bos taurus [5-(3-nitrobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid
1.1.1.21 0.00066
-
 IC50: 0.00066 mM Bos taurus [5-(3-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid
1.1.1.21 0.00082
-
 IC50: 0.00082 mM Bos taurus [2,4-dioxo-5-(4-phenoxybenzylidene)thiazolidin-3-yl]acetic acid
1.1.1.21 0.0011
-
 IC50: 0.0011 mM Bos taurus sorbinil
1.1.1.21 0.0012
-
 IC50: 0.0012 mM Bos taurus [5-(4-nitrobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid
1.1.1.21 0.0042
-
 IC50: 0.0042 mM Bos taurus 4-[5-(4-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]-2-butenoic acid
1.1.1.21 0.0062
-
 IC50: 0.0062 mM Bos taurus [5-(4-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid methyl ester
1.1.1.21 0.009
-
 IC50: 0.009 mM Bos taurus 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione
1.1.1.21 0.0107
-
 IC50: 0.0107 mM Bos taurus 5-naphthalen-1-ylmethylene-2,4-thiazolidinedione
1.1.1.21 0.0107
-
 IC50: 0.0107 mM Bos taurus 5-(3-hydroxybenzylidene)-2,4-thiazolidinedione
1.1.1.21 0.0202
-
 IC50: 0.0202 mM Bos taurus 5-(3-aminobenzylidene)-2,4-thiazolidinedione
1.1.1.21 0.039
-
 IC50: 0.039 mM Bos taurus [5-(3-aminobenzylidene)-2,4-dioxothiazolidin-3-yl]-acetic acid methyl ester