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Literature summary for 1.1.1.239 extracted from

  • Brozic, P.; Turk, S.; Adeniji, A.O.; Konc, J.; Janezic, D.; Penning, T.M.; Lanisnik Rizner, T.; Gobec, S.
    Selective inhibitors of aldo-keto reductases AKR1C1 and AKR1C3 discovered by virtual screening of a fragment library (2012), J. Med. Chem., 55, 7417-7424.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
10 ns molecular dynamics simulations of inhibitor bound to isofrom AKR1C3. Binding could induce conformational changes to both inhibitor and enzyme. The compound presumably assumes a stable, energetically favored, planar conformation, with an estimated free energy of binding of ?5 kcal/mol Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide inhibitor is about 1000times more selective for isoform AKR1C3 over AKR1C2, and selectivity is even higher when compared with AKR1C1 and AKR1C4 Homo sapiens
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one inhibitor shows 17fold and 30fold selectivity against isoforms AKR1C2 and AKR1C1, respectively, and much higher selectivity against AKR1C4 Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens P42330
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(S)-alpha-tetralol + NADP+
-
Homo sapiens alpha-tetralone + NADPH + H+
-
?

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000107
-
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide pH 7.0, temperature not specified in the publication Homo sapiens
0.00273
-
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one pH 7.0, temperature not specified in the publication Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000213
-
pH 7.0, temperature not specified in the publication Homo sapiens 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
0.00546
-
pH 7.0, temperature not specified in the publication Homo sapiens 3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one