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Literature summary for 1.1.1.21 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

Inhibitors Comment Organism Structure
(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
(1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.010 mM Rattus norvegicus
(1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
Rattus norvegicus
(1,3,3-trioxo-2,3-dihydronaphtho[2,3-d]isothiazol-2-yl)acetic acid ethyl ester
-
Rattus norvegicus
(3,3-dihydroxy-1-oxo-1,3-dihydro-2H-3lambda4-naphtho[1,2-d]isothiazol-2-yl)acetic acid i.e. NiT Rattus norvegicus
(6-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.10 mM Rattus norvegicus
(6-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
Rattus norvegicus
(6-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.180 mM Rattus norvegicus
(6-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
Rattus norvegicus
(9-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.10 mM Rattus norvegicus
(9-amino-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
Rattus norvegicus
(9-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid IC50: 0.190 mM Rattus norvegicus
(9-nitro-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid ethyl ester
-
Rattus norvegicus
1,1-dioxidenaphtho[2,3-d]isothiazole-3(2H)-one
-
Rattus norvegicus
1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
-
Rattus norvegicus
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
2-benzyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid methyl ester
-
Rattus norvegicus
2-carboxymethyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid IC50: 140 nM, binding structure analysis Rattus norvegicus
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
2-ethoxycarbonyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid ethoxycarbonylmethyl ester
-
Rattus norvegicus
2-isopropoxycarbonylmethyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid isopropyl ester
-
Rattus norvegicus
2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid IC50: 0.088 mM Rattus norvegicus
2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid ethoxycarbonyl methylester
-
Rattus norvegicus
2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid methyl ester
-
Rattus norvegicus
2-tert-butylsulfonylnaphthalene-1,3-dicarboxylic acid
-
Rattus norvegicus
2-tert-butylsulfonylnaphthalene-1-carboxylic acid
-
Rattus norvegicus
3,3-dioxidenaphtho[1,2-d]isothiazole-1(2H)-one
-
Rattus norvegicus
3-tert-butylsulfonylnaphthalene-2-carboxylic acid
-
Rattus norvegicus
epalrestat
-
Rattus norvegicus
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
naphtho[1,2-d]isothiazole acetic acid derivatives
-
Rattus norvegicus
sorbinil
-
Rattus norvegicus
Tolrestat
-
Rattus norvegicus
zopolrestat
-
Rattus norvegicus

Organism

Organism UniProt Comment Textmining
Rattus norvegicus P07943 Sprague-Dawley rats
-

Purification (Commentary)

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

Source Tissue

Source Tissue Comment Organism Textmining
lens
-
Rattus norvegicus
-

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
aldose reductase
-
Rattus norvegicus
ALR2
-
Rattus norvegicus

Temperature Optimum [°C]

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

pH Optimum

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

Cofactor

Cofactor Comment Organism Structure
NADPH
-
Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
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
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
0.01
-
IC50: 0.010 mM Rattus norvegicus (1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazol-2-yl)acetic acid
0.068
-
IC50: 0.068 mM Rattus norvegicus 2-benzyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
0.088
-
IC50: 0.088 mM Rattus norvegicus 2-methyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
0.1
-
IC50: 0.10 mM Rattus norvegicus 2-benzyl-1,3,3-trioxo-1,2-dihydronaphtho[1,2-d]isothiazole-4-carboxylic acid
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
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
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
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