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(A)-2-Azido-NAD+
-
photodependent inhibition
(A)-8-azido-NAD+
-
photodependent inhibition
1,4-diaminoanthraquinone-2-sulfonic acid
-
-
1,4-Naphthohydroquinone
-
competitive vs. 1,4-naphthohydroquinone, noncompetitive vs. NADPH
1-amino-4-[(3-carboxyphenyl)amino]-anthraquinone-2-sulfonic acid
-
-
1-amino-4-[(4-amino-3-sulfophenyl)amino]-anthraquinone-2-sulfonic acid
-
-
1-aminoanthraquinone-2-carboxylic acid
-
-
1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
1-hydroxy-2-dodecyl-4(1H)-quinolone
-
-
1-hydroxy-2-dodecyl-4(1H)quinolone
-
-
1-hydroxy-2-octyl-4(1H)quinolone
-
-
1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium
-
competitive
1-[3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-1-oxohydrazinium
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-8-carboxamide 12-oxide
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
-
-
2,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
2,2'-dimethoxy-trans-stilbene
2,4'-dimethoxy-cis-stilbene
2,4'-dimethoxy-trans-stilbene
2,4,4'-trimethoxy-cis-stilbene
2,4,4'-trimethoxy-trans-stilbene
2,4,6-trinitrotoluene
-
competitive
2,4-dinitro-5-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-dinitro-5-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-dinitro-5-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-Dinitroaniline
-
0.1 mM, 33% inhibition
2,4-Dinitronaphthol
-
0.1 mM, 90% inhibition
2,6,4'-trimethoxy-trans-stilbene
2-(2,4,6-trinitrophenyl)-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-5-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-7-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-(4'-chlorophenyl)-indan-1,3-dione
-
0.0002 mM, 50% inhibition
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
-
2-Heptyl-4-hydroxyquinoline-N-oxide
-
-
2-hydroxy-4'-methoxy-trans-stilbene
2-Pivaloyl-1,3-indanedione
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalene
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-7-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate
-
competitive
3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
3,3'-methylene-bis(4-hydroxycoumarin)
3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
-
3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,4'-dimethoxy-cis-stilbene
3,4'-dimethoxy-trans-stilbene
-
-
3,4,4'-trimethoxy-cis-stilbene
3,4,4'-trimethoxy-trans-stilbene
3,4,5,4'-tetramethoxy-cis-stilbene
3,4,5,4'-tetramethoxy-trans-stilbene
3,5,4'-trimethoxy-cis-stilbene
3,5,4'-trimethoxy-trans-stilbene
3,5-dihydroxy-4'-methoxy-cis-stilbene
3,5-dihydroxy-4'-methoxy-trans-stilbene
3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3,5-dinitro-2-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3,5-dinitro-2-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3-(2,4-difluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione
-
-
3-(2-fluoro-4-nitrophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
-
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
3-(4-aminophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(4-cyanophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 22, dose dependent inhibition of NQO1 activity in MiaPaCa-2
3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
indolequinone derivative 24, dose dependent inhibition of NQO1 activity in MiaPaCa-2
3-(alpha-phenylpropyl)-4-hydroxycoumarin
-
0.01 mM, 50% inhibition
3-([[4-Iodophenyl]thio]methyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
compound based on the selective binding of indolequinone analogs to the active site of NQO1 by the stacking effect. [125]I-marked compound can be used as an internal radiation agent for the treatment of cancer
-
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
-
3-benzyl-4-hydroxy-2H-chromen-2-one
-
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
3-hydroxy-4'-methoxy-cis-stilbene
3-hydroxy-4'-methoxy-trans-stilbene
3-hydroxy-4,4'-dimethoxy-cis-stilbene
3-hydroxy-4,4'-dimethoxy-trans-stilbene
3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
-
3-[alpha-(4'-nitrophenyl)-beta-acetylethyl]-4-hydroxycoumarin
-
0.02 mM, 50% inhibition
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
-
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
4',5,7-trihydroxyflavone
-
0.01 mM, 61% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
-
-
4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
4,4'-dichlorodicoumarol
-
0.001 mM, 50% inhibition
4,4'-dimethoxy-cis-stilbene
4,4'-dimethoxy-trans-stilbene
4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one
-
competitive
4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one
-
competitive
4-amino-2H-chromen-2-one
-
4-chloromercuribenzoate
-
74% residual activity at 0.15 mM
4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
-
4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
-
4-hydroxy-3-(naphthalen-1-yl)cyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-3-(naphthalen-2-yl)cyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-3-phenylcyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2H-1-benzopyran-2-one
10 microM, 89.2% inhibition. At 0.0084 microM, 50% toxicity in A549 cells in the presence of 20 mM beta-lapachone. Inhibitor is used to built a functional affinity-based small-molecule fluoresent probe composed of the NQO1 inhibitor as the recognition group, a linker and the fluorophores group FITC
-
4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
-
4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
-
4-hydroxy-6,7-dimethyl-3-(naphthalen-1-yl)-2H-chromen-2-one
-
-
4-hydroxy-6,7-dimethyl-3-(naphthalen-2-yl)-2H-chromen-2-one
-
-
4-hydroxy-6,7-dimethyl-3-phenyl-2H-chromen-2-one
-
-
4-hydroxymercuribenzoate
-
0.067 mM, 50% inhibition
4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
-
5,5'-dithiobis(2-nitrobenzoic acid)
5,6-dimethylxanthenone-4-acetic acid
-
tumour blood flow inhibitor, competitive vs. NADH
5-hydroxy-7-bromoacetylflavone
-
0.00018 mM, 50% inhibition, irreversible, useful as affinity label
5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 10, mechanism based 80% inhibition
5-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
5-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCaa-2 cells; indolequinone derivative 6, dose dependent inhibition of NQO1 activity in MiaPaCa-2
5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
indolequinone derivative 12, dose dependent inhibition of NQO1 activity in MiaPaCa-2
5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 11, mechanism based 90% inhibition
5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-indole-4,7-dione
-
ES936, potent mechanism-based inhibitor of NQO1, complete inhibition at 0.001 mM
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
5-methoxy-1,2-dimethyl-3-[(4-pyridinyloxy)methyl]indole-4,7-dione
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-[(4-nitrophenoxy)methyl]indole-4,7-dione
6-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 26, mechanism based 90% inhibition
6-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCaa-2 cells
6-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
6-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 15, mechanism based 85% inhibition
6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
-
-
6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 27, mechanism based 90% inhibition
6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 29, mechanism based 95% inhibition
6-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[(4-pyridinyloxy)methyl]indole-4,7-dione
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[(acetoxy)methyl]indole-4,7-dione
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[2-nitrophenoxymethyl]indole-4,7-dione
-
indolequinone derivative 19, mechanism based 95% inhibition, dose dependent inhibition of NQO1 activity in MiaPaCa-2
6-methoxy-1,2-dimethyl-3-[4-(trifluoromethyl)phenoxymethyl]-indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 23, dose dependent inhibition of NQO1 activity in MiaPaCa-2
7,8-dibromoacetylflavone
-
0.00003 mM, 50% inhibition
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
-
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
-
7-bromoacetylflavone
-
time-dependent inactivation within 30 s, 0.00074 mM, 50% inhibition
7-hydroxylflavone
-
competitive inhibition, 0.00074 mM, 50% inhibition
7-N-acetyldemethyllavendamycin n-butyl amide
lavendamycin analogue 12, selective toxic toward NQO1-rich cells
8-hydroxyquinoline
-
1 mM, 50% inhibition
ADP
-
86% residual activity at 0.2 mM
Alizarin Red S
-
0.04 mM, 38% inhibition
alpha,alpha'-dipyridyl
-
IC50: 1 mM
alpha-naphthoflavone
-
0.01 mM, 75% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
Amytal
-
6.6 mM, 55% inhibition
anthraquinone-2-carboxylic acid
-
-
anthraquinone-2-sulfonic acid
-
-
ATP
-
91% residual activity at 0.2 mM
benzoquinol
-
shows noncompetitive inhibition in all conditions, it can bind to multiple enzyme forms or sites, even when either of the substrates (NADH or benzoquinone) is present at high concentrations
beta-naphthoflavone
-
0.01 mM, 76% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
capsaicin
-
activity is decreased after the treatment with capsaicin or dicoumarol. Quinone metabolites or other reactive forms of capsaicin may bind covalently to NQO1 and thereby inhibit its activity, leading to production of reactive oxygen species; suppresses NQO1 expression and activity. Quinone metabolites or other reactive forms of capsaicin may bind covalently to NQO1 and thereby inhibit its activity, leading to production of reactive oxygen species
Cibacron Blue F3G-A
-
0.04 mM, 75% inhibition
Cr6+
-
decrease of enzyme mRNA level together with heme oxygenase-1 and glutathione S-transferase Ya
Cu2+
-
decrease of enzyme mRNA expression, via a transcriptional mechanism
curcumin
-
inhibition of enzyme activity in vivo and in vitro. Inducues dissociation of complexes of enzyme with tumor suppressor protein p53 leading to degradation of p53, but not of p53 cancer hot-spot mutant R273H
Dicoumarol dimethylether
-
0.0005, 50% inhibition
diphenylene iodonium chloride
-
-
EGTA
-
95% residual activity at 5 mM
ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate
-
competitive
ethyl bis(2-hydroxy-4-oxo-4H-chromen-3-yl)acetate
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
-
flavone-8-acetic acid
-
tumour blood flow inhibitor, competitive vs. NADH
galangin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
HgCl2
-
0.2 mM, 94% inhibition
hydroxy(oxo)(3,6,8-trinitro-9H-carbazol-1-yl)ammonium
-
competitive
lavendamycin beta-hydroxyethyl ester
lavendamycin analogue 12, selective toxic toward NQO1-rich cells
Mersalyl
-
68% residual activity at 0.15 mM
methylene-5,5'-bis(4,6-dioxo-2-methyldihydropyran)
-
0.003 mM, 50% inhibition
morin
-
0.01 mM, 95% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
N-ethyl maleimide
-
0.33 mM, complete inhibition
N-methyl-N,2,4,6-tetranitroaniline
-
competitive
N-methyl-N,2,4-trinitroaniline
-
competitive
p-chloromercuribenzoate
-
-
Phenindione
-
0.1 mM, 92% inhibition
phenylmercuric acetate
-
-
Procion blue MX-R
-
0.04 mM, 75% inhibition
quinacrine dihydrochloride
-
0.05 mM, 65-95% inhibition depending on substrate
reserpine
-
competitive inhibitor of DT-diaphorase
salicylate
-
1 mM, 62% inhibition
siRNA
-
siRNA for NQO1 inhibits clonogenic cell death caused by beta-lap
-
SOD
-
inhibits the NADPH:chromate reductase reaction of NQO1
-
Thenoyltrifluoroacetone
-
-
warfarin
-
1 mM, 70% inhibition
1,10-phenanthroline
-
-
1,10-phenanthroline
-
1 mM, 50% inhibition
2,2'-dimethoxy-trans-stilbene
-
-
2,2'-dimethoxy-trans-stilbene
-
-
2,4'-dimethoxy-cis-stilbene
-
-
2,4'-dimethoxy-cis-stilbene
-
-
2,4'-dimethoxy-trans-stilbene
-
-
2,4'-dimethoxy-trans-stilbene
-
-
2,4,4'-trimethoxy-cis-stilbene
-
-
2,4,4'-trimethoxy-cis-stilbene
-
-
2,4,4'-trimethoxy-trans-stilbene
-
-
2,4,4'-trimethoxy-trans-stilbene
-
-
2,4-dinitrophenol
-
0.067 mM, 56% inhibition
2,4-dinitrophenol
-
0.1 mM, 39% inhibition
2,6,4'-trimethoxy-trans-stilbene
-
-
2,6,4'-trimethoxy-trans-stilbene
-
-
2-hydroxy-4'-methoxy-trans-stilbene
-
-
2-hydroxy-4'-methoxy-trans-stilbene
-
-
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
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3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
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3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
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3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
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-
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
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3,3'-methylene-bis(4-hydroxycoumarin)
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0.000033 mM, 56% inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
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-
3,3'-methylene-bis(4-hydroxycoumarin)
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0.1 mM, 97% inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.04 mM, complete inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
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0.01 mM, 25% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
only in the presence of glutathione
3,3'-methylene-bis(4-hydroxycoumarin)
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trivial name dicoumarol, slight inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH, uncompetitive vs. vitamin K1
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH
3,4'-dimethoxy-cis-stilbene
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-
3,4'-dimethoxy-cis-stilbene
-
-
3,4,4'-trimethoxy-cis-stilbene
-
-
3,4,4'-trimethoxy-cis-stilbene
-
-
3,4,4'-trimethoxy-trans-stilbene
-
-
3,4,4'-trimethoxy-trans-stilbene
-
-
3,4,5,4'-tetramethoxy-cis-stilbene
-
-
3,4,5,4'-tetramethoxy-cis-stilbene
-
-
3,4,5,4'-tetramethoxy-trans-stilbene
-
-
3,4,5,4'-tetramethoxy-trans-stilbene
-
-
3,5,4'-trimethoxy-cis-stilbene
-
-
3,5,4'-trimethoxy-cis-stilbene
-
-
3,5,4'-trimethoxy-trans-stilbene
-
-
3,5,4'-trimethoxy-trans-stilbene
-
-
3,5-dihydroxy-4'-methoxy-cis-stilbene
-
-
3,5-dihydroxy-4'-methoxy-cis-stilbene
-
-
3,5-dihydroxy-4'-methoxy-trans-stilbene
-
-
3,5-dihydroxy-4'-methoxy-trans-stilbene
-
-
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
-
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
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3-hydroxy-4'-methoxy-cis-stilbene
-
-
3-hydroxy-4'-methoxy-cis-stilbene
-
-
3-hydroxy-4'-methoxy-trans-stilbene
-
-
3-hydroxy-4'-methoxy-trans-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-trans-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-trans-stilbene
-
-
4,4'-dimethoxy-cis-stilbene
-
-
4,4'-dimethoxy-cis-stilbene
-
-
4,4'-dimethoxy-trans-stilbene
-
-
4,4'-dimethoxy-trans-stilbene
-
-
5,5'-dithiobis(2-nitrobenzoic acid)
-
1 mM, 67% inhibition, 10 mM, complete inhibition
5,5'-dithiobis(2-nitrobenzoic acid)
-
-
5,7-dihydroxyflavone
-
0.009 mM, approx. 90% inhibition
5,7-dihydroxyflavone
-
0.009 mM, approx. 20% inhibition
5,7-dihydroxyflavone
-
0.009 mM, approx. 80% inhibition
5,7-dihydroxyflavone
-
0.00018 mM, 50% inhibition
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
mechanism-based inhibitor, time- and concentration dependent inhibition that requires the presence of NAD(P)H, 0.0015 mM, complete inhibition after 4 min
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
ES936, potent inhibitor of NQO1 activity and cell proliferation. Approximately 90% inhibition of enzyme activity after 4 h. Inactivation is dependent upon NADH
5-methoxy-1,2-dimethyl-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
-
chrysin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
Cibacron blue
-
and related anthraquinone dyes
dicoumarol
binding of dicoumarol induces conformational changes involving Y128 and F232 on the surface of enzyme catalytic pocket
dicoumarol
-
inhibitor of NQO1, inhibits clonogenic cell death caused by beta-lap
dicoumarol
i.e. 3,3'-methylenebis(4-hydroxycoumarin), potent competitive inhibitor of NQO1
dicoumarol
-
lack of effect of inhibition of DT-diaphorase by dicoumarol, when the cells are incubated with dopamine and reserpine. Significant cell death only when RCSN-3 cells are incubated with reserpine and dopamine together with the DT-diaphorase inhibitor dicoumarol
dicoumarol
-
in the presence of 0.050 mM of dicoumarol, the protective effect of bromocriptine against H2O2 is completely abolished
dicumarol
-
most potent inhibitor, 12% residual activity at 0.15 mM
dicumarol
most potent competitive inhibitor of QO1. Disadvantages with dicumarol in that it is not selective and can inhibit other enzymes in addition to NQO1 and it can also be extensively protein bound complicating its use in cellular assays
dicumarol
-
inhibits the reduction of chromate by the digiton-permeabilized FLK cells in the presence of NADPH regeneration system. Protects against cytotoxicity by inhibiting NQO1
ES936
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i.e. 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, suicide inhibitor
ES936
effective mechanism-based inhibitor. Inhibits NQO1 in a time- and concentration-dependent manner. In agreement with its role as mechanism-based (suicide substrate) inhibitor, requires the presence of cofactor NADH, and therefore a catalytic turnover, for effective enzyme inhibition. At 100 nanomol concentration, ES936 inhibits more than 95% of NQO1 activity in cells within 30 min, and since it is specific, appears to be a more useful biochemical tool than dicumarol for use in routine NQO1 assays
ES936
-
is an irreversible mechanism-based inhibitor of QR1
ES936
-
pancreatic tumour xenografts in mice grow significantly slower following treatment with ES936
ethyl bis(2-hydroxy-4-oxo-4H-chromen-3-yl)acetate
-
-
ethyl bis(2-hydroxy-4-oxo-4H-chromen-3-yl)acetate
-
trivial tromexan, 0.1 mM, 79% inhibition
mitomycin C
-
mechanism-based inhibitor, in a pH-dependent manner
mitomycin C
-
mechanism-based inhibitor, in a pH-dependent manner
mitomycin C
-
mechanism-based inhibitor, in a pH-dependent manner
NAD+
-
96% residual activity at 0.2 mM
NAD+
-
noncompetitive inhibition with either substrate when the other substrate is at low concentrations. At high NADH concentrations, NAD and benzoquinone are competitive, indicating they bind to a common site or sites
NADP+
-
95% residual activity at 0.2 mM
NADP+
-
noncompetitive vs. NADPH
quercetin
-
-
quercetin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
resveratrol
-
-
additional information
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insensitive to rotenone, Ca2+, platanetin and flavone have no effect on the NADH:2,3-dimethoxy-5-methyl-1,4-benzoquinone reductase activity of the purified enzyme
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additional information
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not inhibited by iodoacetate, 4-chloromercuribenzoate, Cu2+, FeSO4, FeCl3, CdSO4, ZnSO4, CuSO4, EDTA, alpha,alpha'-dipyridiyl, o-phenanthroline, dimethylglyoxime, dithizon, NaCN, amytal, veronal, antimycin, 2,4-dinitrophenol and thyroxin
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additional information
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not inhibited by o-phenanthroline, KCN, quinacrine, EDTA and 2,3-dimercapto-1-propanol
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additional information
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compounds 5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(2,4-dinitrophenoxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(2,4-dinitrophenoxymethyl)indole-4,7-dione, 3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione, 3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione, 3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione, and 5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione are relatively ineffective at inducing growth inhibition. Inhibition of recombinant NQO1 is related to the pKa of the leaving group: compounds with poorer phenolic leaving groups are poor inhibitors whereas those with more acidic leaving groups are more efficient inhibitors
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additional information
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fruit and vegetable consumption may repress rather than induce rectal NQO1 phenotype. Consumption of Compositae is associated with lower rectal NQO1 mRNA level. Consumption of Apiaceae is associated with lower rectal NQO1 activity
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additional information
fruit and vegetable consumption may repress rather than induce rectal NQO1 phenotype. Consumption of Compositae is associated with lower rectal NQO1 mRNA level. Consumption of Apiaceae is associated with lower rectal NQO1 activity
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additional information
indolequinones with 4-nitrophenoxy, 4-pyridinyloxy, and acetoxy substituents at the (indol-3-yl)methyl position are NADH-dependent inhibitors of recombinant human NQO1, indicative of mechanism-based inhibition. However, those with hydroxy and phenoxy substituents are poor inhibitors of NQO1 enzyme activity, due to attenuated elimination of the leaving group. 4-pyridinyloxy and acetoxy compounds are potent inhibitors of NQO1 activity but relatively poor inhibitors of cell proliferation. Phenoxy compounds, which are not inhibitors of NQO1 enzymatic activity, demonstrate potent growth inhibition
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additional information
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indolequinones with 4-nitrophenoxy, 4-pyridinyloxy, and acetoxy substituents at the (indol-3-yl)methyl position are NADH-dependent inhibitors of recombinant human NQO1, indicative of mechanism-based inhibition. However, those with hydroxy and phenoxy substituents are poor inhibitors of NQO1 enzyme activity, due to attenuated elimination of the leaving group. 4-pyridinyloxy and acetoxy compounds are potent inhibitors of NQO1 activity but relatively poor inhibitors of cell proliferation. Phenoxy compounds, which are not inhibitors of NQO1 enzymatic activity, demonstrate potent growth inhibition
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additional information
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growth inhibitory effects of series of methoxystilbenes (E and Z isomers) related to resveratrol on human cancer cell lines, overview
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additional information
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synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1, NQO1, overview
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additional information
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almond skin polyphenol extracted with agastrointestinal juice mimic decreases quinone reductase activity. Combining almond skin polyphenol extracted with agastrointestinal juice mimic plus vitamin C has an antagonistic effect
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additional information
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enzyme induction effects of series of methoxystilbenes (E and Z isomers) related to resveratrol on murine hepatoma cells, overview
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additional information
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-
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additional information
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microsomal enzyme: not inhibited by dicoumarol, lapachol and p-chloromercuribenzoate
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additional information
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the product inhibition pattern expected if WrbA follows a ping pong mechanism is that the pairs NAD/BQ and NADH/BQH2 display competitive inhibition, whereas the pairs NAD/NADH and BQ/BQH2 display non-competitive inhibition
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