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Literature summary for 1.2.1.36 extracted from

  • Jimenez, R.; Pequerul, R.; Amor, A.; Lorenzo, J.; Metwally, K.; Aviles, F.X.; Pares, X.; Farres, J.
    Inhibitors of aldehyde dehydrogenases of the 1A subfamily as putative anticancer agents kinetic characterization and effect on human cancer cells (2019), Chem. Biol. Interact., 306, 123-130 .
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene ALDH1A1, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)pLys Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
additional information [(5E)-2,4-dioxo-5-([4-[(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)methoxy]phenyl]methylidene)-1,3-thiazolidin-3-yl]acetic acid, a 2,4-thiazolidinedione-3-acetic acid derivative, is inactive as inhibitor; no inhibition of ALDH1A1 by [3-benzyl-5-(4-chlorophenyl)-1-oxopyrimido[4,5-c]quinolin-2(1H)-yl]acetic acid Homo sapiens
N,N'-(octane-1,8-diyl)bis(2,2-dichloroacetamide) WIN 18,446; WIN 18,446, strong irreversible inhibition; WIN 18,446, weak inhibition Homo sapiens
N,N-diethylaminobenzaldehyde DEAB; DEAB; DEAB Homo sapiens
[(5E)-2,4-dioxo-5-([4-[(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)methoxy]phenyl]methylidene)-1,3-thiazolidin-3-yl]acetic acid a 2,4-thiazolidinedione-3-acetic acid derivative Homo sapiens
[3-benzyl-5-(4-chlorophenyl)-1-oxopyrimido[4,5-c]quinolin-2(1H)-yl]acetic acid a 1-oxopyrimido[4,5-c]quinoline-2-acetic acid derivative; a 1-oxopyrimido[4,5-c]quinoline-2-acetic acid derivative and a non-competitive inhibitor of ALDH1A3 Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information Michaelis-Menten kinetics Homo sapiens
0.008
-
hexanal pH 8.0, 25°C, recombinant enzyme Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
cytosol
-
Homo sapiens 5829
-

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
all-trans-retinal + H2O + NAD+ Homo sapiens
-
all-trans-retinoate + NADH + 2 H+
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens O94788
-
-
Homo sapiens P00352
-
-
Homo sapiens P47895
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3)pLys by nickel affinity chromatography Homo sapiens

Source Tissue

Source Tissue Comment Organism Textmining
A-549 cell
-
Homo sapiens
-
additional information no activity in HL-60 cells Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
all-trans-retinal + H2O + NAD+
-
Homo sapiens all-trans-retinoate + NADH + 2 H+
-
?
hexanal + H2O + NAD+
-
Homo sapiens hexanoate + NADH + 2 H+
-
?

Synonyms

Synonyms Comment Organism
ALDH1A1
-
Homo sapiens
Aldh1a2
-
Homo sapiens
Aldh1a3
-
Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
assay at Homo sapiens

Cofactor

Cofactor Comment Organism Structure
NAD+
-
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
0.00007
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens N,N'-(octane-1,8-diyl)bis(2,2-dichloroacetamide)
0.00018
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens N,N-diethylaminobenzaldehyde
0.0012
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens [3-benzyl-5-(4-chlorophenyl)-1-oxopyrimido[4,5-c]quinolin-2(1H)-yl]acetic acid
0.0035
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens [3-benzyl-5-(4-chlorophenyl)-1-oxopyrimido[4,5-c]quinolin-2(1H)-yl]acetic acid
0.0054
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens [(5E)-2,4-dioxo-5-([4-[(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)methoxy]phenyl]methylidene)-1,3-thiazolidin-3-yl]acetic acid
0.0095
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens N,N-diethylaminobenzaldehyde
0.023
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens [(5E)-2,4-dioxo-5-([4-[(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)methoxy]phenyl]methylidene)-1,3-thiazolidin-3-yl]acetic acid
0.031
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens N,N'-(octane-1,8-diyl)bis(2,2-dichloroacetamide)
0.047
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens N,N-diethylaminobenzaldehyde
0.056
-
pH 8.0, 25°C, recombinant enzyme Homo sapiens N,N'-(octane-1,8-diyl)bis(2,2-dichloroacetamide)

General Information

General Information Comment Organism
physiological function the cytosolic isozymes ALDH1A1, ALDH1A2, and ALDH1A3 play important roles in cell signaling via oxidation of retinaldehyde to retinoic acid. In the cell, retinoic acid produced in the cytoplasm binds to cellular retinoic acid binding protein type II, and is transferred to the nucleus where it binds to heterodimers of retinoic acid receptor (RAR) and retinoid X receptor (RXR). Once activated, these receptor complexes bind to retinoic acid response elements (RAREs), which are regulatory sequences that induce gene transcription and modulate a wide range of biological processes, including cell proliferation, differentiation, cell cycle arrest and apoptosis Homo sapiens