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Literature summary for 1.10.5.1 extracted from

  • John, S.E.St.; Jensen, K.C.; Kang, S.; Chen, Y.; Calamini, B.; Mesecar, A.D.; Lipton, M.A.
    Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2 (2013), Bioorg. Med. Chem., 21, 6022-6037.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli strain BL21(DE3) Homo sapiens

Crystallization (Commentary)

Crystallization (Comment) Organism
purified recombinant enzyme, hanging-drop, vapor-diffusion method, mixing of 0.001 ml of 4 mg/ml protein solution with 0.001 ml of reservoir solution containing 1.3-1.7 M ammonium sulfate, 0.1 M Bis-Tris buffer, pH 6.0-7.0, 0.1 M NaCl, 5 mM DTT, 0.012 mM FAD, and resveratrol, complexed with different inhibitors, X-ray diffraction structure determination and analysis at resolutions of 1.40-1.63 A Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(E)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylaldehyde
-
Homo sapiens
(E)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-ol
-
Homo sapiens
(Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-acrylamide
-
Homo sapiens
(Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylonitrile
-
Homo sapiens
(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylaldehyde
-
Homo sapiens
(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile
-
Homo sapiens
(Z)-5-(3-hydroxy-2-(4-hydroxyphenyl)prop-1-en-1-yl)benzene-1,3-diol
-
Homo sapiens
1,1'-(1E)-but-1-ene-1,2-diylbis(3,5-dimethoxybenzene)
-
Homo sapiens
1,2-dimethoxy-4-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene
-
Homo sapiens
1,2-dimethoxy-4-[(E)-2-(3-methoxyphenyl)ethenyl]benzene
-
Homo sapiens
1,2-dimethoxy-4-{(1Z)-3,3,3-trifluoro-2-[3-(trifluoromethyl)phenyl]prop-1-en-1-yl}benzene
-
Homo sapiens
1,3-dimethoxy-5-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene
-
Homo sapiens
1,3-dimethoxy-5-[(1Z)-3,3,3-trifluoro-1-(4-methoxyphenyl)prop-1-en-2-yl]benzene
-
Homo sapiens
1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
Homo sapiens
1-[(E)-2-(4-fluorophenyl)ethenyl]-3,5-dimethoxybenzene
-
Homo sapiens
2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]naphthalene
-
Homo sapiens
2-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]naphthalene
-
Homo sapiens
4-[(1E)-1-(3,5-dimethoxyphenyl)prop-1-en-2-yl]-1,2-dimethoxybenzene
-
Homo sapiens
4-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-N,N-dimethylaniline
-
Homo sapiens
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-1,2-dimethoxybenzene
-
Homo sapiens
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
-
Homo sapiens
4-[(E)-2-(3-fluorophenyl)ethenyl]benzene-1,2-diol
-
Homo sapiens
4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,2-diol
-
Homo sapiens
4-[(E)-2-(4-methoxyphenyl)ethenyl]benzene-1,2-diol
-
Homo sapiens
4-{(1E)-1-[4-(trifluoromethyl)phenyl]prop-1-en-2-yl}phenol
-
Homo sapiens
4-{(E)-2-[3-(trifluoromethyl)phenyl]ethenyl}benzene-1,2-diol
-
Homo sapiens
5-[(1E)-1-(4-hydroxyphenyl)prop-1-en-2-yl]benzene-1,3-diol
-
Homo sapiens
5-[(1E)-2-(3,4-dimethoxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
Homo sapiens
5-[(1E)-2-(4-hydroxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
Homo sapiens
5-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
Homo sapiens
5-{(1E)-1-[4-(dimethylamino)phenyl]but-1-en-2-yl}benzene-1,3-diol
-
Homo sapiens
additional information enzyme inhibitor design, synthesiis, and evaluation, inhibitory potencies of resveratrol analogues, overview. Inhibitor binding structure, modelling, overview Homo sapiens
N-(3,5-dihydroxyphenyl)-4-hydroxybenzamide
-
Homo sapiens
resveratrol i.e. 3,5,4'-trihydroxylstilbene, resveratrol binds tightly to the oxidized, FAD-form of the enzyme, and it acts as a competitive inhibitor against N-methyldihydronicotinamide. The amount of resveratrol consumed from dietary sources may be sufficient for effective inhibition of QR2 Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information steady-state kinetic, overview Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme from Escherichia coli strain BL21(DE3) Homo sapiens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
N-methyldihydronicotinamide + 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide
-
Homo sapiens N-methylnicotinamide + ?
-
?
N-methyldihydronicotinamide + menadione
-
Homo sapiens N-methylnicotinamide + menadiol
-
?

Synonyms

Synonyms Comment Organism
QR2
-
Homo sapiens
quinone reductase 2
-
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
7.5
-
assay at Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000088
-
resveratrol versus N-methyldihydronicotinamide, pH and temperature not specified in the publication Homo sapiens

General Information

General Information Comment Organism
physiological function the enzyme functions in metabolic reduction and detoxification processes. Evidence exists linking QR2 to the metabolic activation of quinones, which can lead to cell toxicity. Inhibition of the enzymme by resveratrol may protect cells against reactive intermediates and eventually cancer Homo sapiens