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Literature summary extracted from

  • Da Settimo, F.; Primofiore, G.; La Motta, C.; Sartini, S.; Taliani, S.; Simorini, F.; Marini, A.M.; Lavecchia, A.; Novellino, E.; Boldrini, E.
    Naphtho[1,2-d]isothiazole acetic acid derivatives as a novel class of selective aldose reductase inhibitors (2005), J. Med. Chem., 48, 6897-6907.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.21 (1,1-dihydroxy-3-oxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetic acid i.e. BiT, 1,1-dioxide-benzo[d]isothiazol-3-one alkanoic acid derivatives Rattus norvegicus
1.1.1.21 (1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.010 mM Rattus norvegicus
1.1.1.21 (1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
 Rattus norvegicus
1.1.1.21 (1,3,3-trioxo-2,3-dihydronaphtho[2,3-d]isothiazol-2-yl)acetic acid ethyl ester
-
 Rattus norvegicus
1.1.1.21 (3,3-dihydroxy-1-oxo-1,3-dihydro-2H-3lambda4-naphtho[1,2-d]isothiazol-2-yl)acetic acid i.e. NiT Rattus norvegicus
1.1.1.21 (6-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.10 mM Rattus norvegicus
1.1.1.21 (6-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
 Rattus norvegicus
1.1.1.21 (6-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.180 mM Rattus norvegicus
1.1.1.21 (6-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
 Rattus norvegicus
1.1.1.21 (9-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.10 mM Rattus norvegicus
1.1.1.21 (9-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
 Rattus norvegicus
1.1.1.21 (9-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.190 mM Rattus norvegicus
1.1.1.21 (9-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
 Rattus norvegicus
1.1.1.21 1,1-dioxidenaphtho[2,3-d]isothiazole-3(2H)-one
-
 Rattus norvegicus
1.1.1.21 1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
-
 Rattus norvegicus
1.1.1.21 2-benzyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid IC50: 0.068 mM; IC50: 0.10 mM Rattus norvegicus
1.1.1.21 2-benzyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid methyl ester
-
 Rattus norvegicus
1.1.1.21 2-carboxymethyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid IC50: 140 nM, binding structure analysis Rattus norvegicus
1.1.1.21 2-carboxymethyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid carboxymethyl ester IC50: 550 nM, binding structure analysis Rattus norvegicus
1.1.1.21 2-ethoxycarbonyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid ethoxycarbonylmethyl ester
-
 Rattus norvegicus
1.1.1.21 2-isopropoxycarbonylmethyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid isopropyl ester
-
 Rattus norvegicus
1.1.1.21 2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid IC50: 0.088 mM Rattus norvegicus
1.1.1.21 2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid ethoxycarbonyl methylester
-
 Rattus norvegicus
1.1.1.21 2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid methyl ester
-
 Rattus norvegicus
1.1.1.21 2-tert-butylsulfonylnaphthalene-1,3-dicarboxylic acid
-
 Rattus norvegicus
1.1.1.21 2-tert-butylsulfonylnaphthalene-1-carboxylic acid
-
 Rattus norvegicus
1.1.1.21 3,3-dioxidenaphtho[1,2-d]isothiazole-1(2H)-one
-
 Rattus norvegicus
1.1.1.21 3-tert-butylsulfonylnaphthalene-2-carboxylic acid
-
 Rattus norvegicus
1.1.1.21 epalrestat
-
 Rattus norvegicus
1.1.1.21 additional information inhibitor synthesis, overview, enzyme docking study, modeling, no inhibition by (1,3,3-trioxo-2,3-dihydronaphtho[2,3-d]isothiazol-2-yl)acetic acid and 2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid Rattus norvegicus
1.1.1.21 naphtho[1,2-d]isothiazole acetic acid derivatives
-
 Rattus norvegicus
1.1.1.21 sorbinil
-
 Rattus norvegicus
1.1.1.21 Tolrestat
-
 Rattus norvegicus
1.1.1.21 zopolrestat
-
 Rattus norvegicus

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.21 Rattus norvegicus P07943 Sprague-Dawley rats
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.21 native enzyme partially from lens by ammonium sulfate fractionation and dialysis Rattus norvegicus

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.21 lens
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

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

Synonyms

EC Number Synonyms Comment Organism
1.1.1.21 aldose reductase
-
 Rattus norvegicus
1.1.1.21 ALR2
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.21 30
-
 assay at Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.21 6.2
-
 assay at Rattus norvegicus

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.21 NADPH
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.21 0.00014
-
 IC50: 140 nM, binding structure analysis Rattus norvegicus 2-carboxymethyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
1.1.1.21 0.00055
-
 IC50: 550 nM, binding structure analysis Rattus norvegicus 2-carboxymethyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid carboxymethyl ester
1.1.1.21 0.01
-
 IC50: 0.010 mM Rattus norvegicus (1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid
1.1.1.21 0.068
-
 IC50: 0.068 mM Rattus norvegicus 2-benzyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
1.1.1.21 0.088
-
 IC50: 0.088 mM Rattus norvegicus 2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
1.1.1.21 0.1
-
 IC50: 0.10 mM Rattus norvegicus 2-benzyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
1.1.1.21 0.1
-
 IC50: 0.10 mM Rattus norvegicus (9-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid
1.1.1.21 0.1
-
 IC50: 0.10 mM Rattus norvegicus (6-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid
1.1.1.21 0.18
-
 IC50: 0.180 mM Rattus norvegicus (6-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid
1.1.1.21 0.19
-
 IC50: 0.190 mM Rattus norvegicus (9-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid