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(2E)-1-(2,4-dihydroxyphenyl)-3-(2',4',6-trihydroxy-5'-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]biphenyl-3-yl)prop-2-en-1-one
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14,16-dihydroxy-3,8-dimethyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
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zearalenone analogue
18beta-glycyrrhetinic acid
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inhibits the reduction of bupropion in liver microsomes
2,3,4-trinitrobenzenesulfonate sodium
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acts on a catalytic lysine located at the cofactor binding site, rapid inactivation of the liver enzyme, kinetics, NADP+, 2'-AMP, 2',5'-ADP, and 2'-phospho-5'-ADP-ribose partly protect, but 4-acetylpyridine, 5'-AMP, 5'-ADP, NMN and NAD+ do not
2,3-Butanedione
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irreversible inactivation
2,4-Dinitrophenylhydrazine
-
1mM, 0.9% residual activity
2-nitrobenzoate
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1mM, 8.6% residual activity
21-Hydroxy-5alpha-pregnane-3,20-dione
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-
3',4',7-tris[O-(2-hydroxyethyl)]rutin
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3,3-Tetramethyleneglutaric acid
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enzyme form CR2 inhibited, CR1 slightly
3-(2-(2,4-dihydroxyphenyl)-1-[hydroxy(4-hydroxyphenyl)methyl]-2-oxoethyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
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3-[2,3-dihydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one
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3-[2-(2,4-dihydroxyphenyl)-1-(4-hydroxybenzyl)-2-oxoethyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
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4-amino-1-tert-butyl-3-(2-hydroxyphenyl)pyrazolo[3,4-d]pyrimidine
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4-hexanoylpyridine
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competitive
4-hydroxymercuribenzoate
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0.025 mM, complete inhibition
4-Methylpyrazole
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2 mM, 17% inhibition
4-Oxo-4H-benzopyran-2-carboxylic acid
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-
4-oxonon-2-enal
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the substrate is also a mechanism-based inhibitor of the enzyme resulting in 50% inactivation of the enzyme-NADPH complex, presence of cofactor is required for inhibition
5,5 dithiobis(2-nitrobenzoate)
-
-
5beta-androstane-3alpha,17beta-diol
-
-
5beta-pregnane-3,20-dione
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-
7-monohydroxyethylrutoside
inhibits the activity of CBR1 V88 and CBR1 I88 in a concentration-dependent manner. It acts as a competitive CBR1 inhibitor when using daunorubicin as a substrate and acts as an uncompetitive CBR1 inhibitor for the small quinone substrate menadione. It inhibits the binding of NADPH in an uncompetitive manner for both substrates
7-O-beta-D-glucopyranos2-ulosyl-quercetin
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9,10-phenanthroline
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strong inhibition
acetonitrile
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37.7% residual activity at 5% (v/v)
Acetylsalicylate
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IC50 for the 3 isozymes CHCR1-3, overview
Ammonium molybdate
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enzyme form CR1 inhibited, CR2 not
androsterone
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CR2 inhibited, CR1 not
ascorbic acid
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1mM, 14% residual activity
Ba2+
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92.24% residual activity at 1 mM
butyrophenone
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inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
Ca2+
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80.2% residual activity in the presence of Ca2+
cibacron
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IC50 for the 3 isozymes CHCR1-3, overview
citrate
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1mM, 48.3% residual activity
CuCl2
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only enzyme forms CR2, CR3
daidzein
71% residual activity at 0.05 mM
daidzin
74% residual activity at 0.05 mM
Dehydrolithocholic acid
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-
diethyldicarbonate
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1mM, 32.8% residual activity
dimethyl sulfoxide
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32.6% residual activity at 5% (v/v)
Diphenylhydantoin
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68% inhibition at 0.5 mM
ethanol
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73.6% residual activity at 5% (v/v)
Furosemide
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inhibition of V1, V2 and T3
glycyrrhetinic acid
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inhibits both 11beta-hydroxysteroid dehydrogenase and carbonyl reductase activities of the enzyme potently
heptanophenone
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inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
hexanophenone
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competitive. Inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
hydroxylamine
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1mM, 29.5% residual activity
Hydroxyquinoline
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1mM, 45% residual activity
iodoacetamide
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46% inhibition at 1 mM
Isopropanol
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41.1% residual activity at 5% (v/v)
L-cysteine
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1mM, 18.5% residual activity
megestrol acetate
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IC50 for the 3 isozymes CHCR1-3, overview
Methyl vinyl ketone
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74% inhibition at 10 mM
methyltestosterone
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IC50 for the 3 isozymes CHCR1-3, overview
NADPH
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competitive to NADH
NEM
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30% inhibition at 1 mM
Norethindrone
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IC50 for the 3 isozymes CHCR1-3, overview
o-phenanthroline
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about 11% inhibition at 1 mM
oxalate
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1mM, 42.8% residual activity
Pb2+
Candida macedoniensis
-
-
PMSF
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about 10% inhibition at 1 mM
propiophenone
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inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
Pyridine
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19.8% residual activity at 5% (v/v)
pyruvate
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inactivation of isozyme CHCR2, not of isozymes CHCR1 and 3
Sn2+
Candida macedoniensis
-
-
sodium dodecylsulfate
0.1% w/v, complete loss of activity
Sodium phenobarbitone
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enzyme form CR2 inhibited, CR1 slightly
tetrahydrofuran
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24.1% residual activity at 5% (v/v)
Tetramethyleneglutaric acid
-
-
Triton X-100
1% v/v, 88% residual activity
valerophenone
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inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
warfarin
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IC50 for the 3 isozymes CHCR1-3, overview
1,10-phenanthroline
-
-
1,10-phenanthroline
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5 mM, 17% inhibition
2,4-dinitrophenol
Candida macedoniensis
-
-
2,4-dinitrophenol
Cylindrocarpon sclerotigenum
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19% inhibition at 0.1 mM
2,4-dinitrophenol
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complete inhibition at 1 mM
2-mercaptoethanol
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-
2-mercaptoethanol
1 mM, 20.3% residual activity
2-mercaptoethanol
17% reduced activity; 87% residual activity
Ag+
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1mM, 18% residual activity
Ag+
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complete inhibition at 1 mM
AgNO3
-
-
AgNO3
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enzyme form CR1 inhibited, CR2 not
Barbital
-
-
Barbital
18% inhibition at 1 mM
Barbital
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18% inhibition at 1 mM
Benzamide
-
-
Biochanin A
-
-
Cd2+
Candida macedoniensis
-
-
Cd2+
Cylindrocarpon sclerotigenum
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16% inhibition at 1 mM
chlorpromazine
-
-
Cibacron blue
-
-
Co2+
-
70.7% residual activity in the presence of Co2+
Co2+
Candida macedoniensis
-
-
Cu2+
Candida macedoniensis
-
-
Cu2+
the enzyme activity is affected by Cu2+
Cu2+
Cylindrocarpon sclerotigenum
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46% inhibition at 1 mM
Cu2+
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complete inhibition at 1 mM
Cu2+
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1mM, 32% residual activity
Cu2+
-
7.2 % residual activity at 5 mM
dicoumarol
Candida macedoniensis
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-
dicoumarol
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enzyme form CR2 inhibited, CR1 not
dicoumarol
Cylindrocarpon sclerotigenum
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42% inhibition at 0.3 mM
Disulfiram
43.5% inhibition at 0.1 mM
dithiothreitol
-
-
DTNB
Cylindrocarpon sclerotigenum
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56% inhibition at 0.05 mM
DTNB
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complete inhibition at 1 mM
EDTA
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96.8% residual activity in the presence of EDTA
EDTA
addition of EDTA to the enzyme solution in a 1:3 enzyme: EDTA mole ratio, results in a drop of the specific activity of the enzyme immediately by 30%
EDTA
Cylindrocarpon sclerotigenum
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30% inhibition at 1 mM
EDTA
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89.8% residual activity at 5 mM
Ethacrynic acid
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IC50 for the 3 isozymes CHCR1-3, overview
Ethacrynic acid
34.4% inhibition at 0.1 mM
Ethacrynic acid
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inhibition of enzyme forms V1, V2 and T3
Fe3+
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1mM, 29% residual activity
Fe3+
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2.2 % residual activity at 5 mM
FeSO4
-
-
flavonoids
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-
genistein
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-
genistein
63% residual activity at 0.05 mM
genistein
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50% inhibition at 0.028 mM
Hg2+
Candida macedoniensis
-
-
Hg2+
Cylindrocarpon sclerotigenum
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complete inhibition at 1 mM
Hg2+
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complete inhibition at 0.01 mM
Hg2+
-
complete inhibition at 1 mM
indomethacin
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-
indomethacin
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IC50 for the 3 isozymes CHCR1-3, overview
iodoacetate
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-
iodoacetate
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2 mM, complete inhibition
iodoacetate
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19% inhibition at 1 mM
kaempferol
-
-
kaempferol
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50% inhibition at 0.015 mM
menadione
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inhibits the reduction of bupropion in liver cytosol
menadione
32.6% inhibition at 0.01 mM, 95.7% inhibition at 0.1 mM
Mg2+
-
73.9% residual activity in the presence of Mg2+
Mg2+
-
94.22% residual activity at 1 mM
Mg2+
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40.5% residual activity at 5 mM
Mn2+
-
97.6% residual activity in the presence of Mn2+
myristic acid
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-
myristic acid
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50% inhibition at 0.025 mM
N-ethylmaleimide
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-
N-ethylmaleimide
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80% inhibition at 1 mM
N-ethylmaleimide
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1mM, 5.3% residual activity
NADP+
-
-
NADP+
NADPH-linked reductase activities of CHCRs are partly inhibited by 2 mM NADP+; NADPH-linked reductase activities of CHCRs are partly inhibited by 2 mM NADP+; NADPH-linked reductase activities of CHCRs are partly inhibited by 2 mM NADP+
p-chloromercuribenzoate
Candida macedoniensis
-
-
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
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complete inhibition at 0.05 mM
p-chloromercuribenzoate
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76% inhibition at 1 mM
p-hydroxymercuribenzoate
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-
p-hydroxymercuribenzoate
-
-
p-hydroxymercuribenzoate
-
-
p-hydroxymercuribenzoate
-
-
Phenylglyoxal
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irreversible inactivation
Phenylglyoxal
-
acts on a catalytic arginine located at the cofactor binding site, rapid inactivation of the liver enzyme, kinetics, NADP+, 2'-AMP, 2',5'-ADP, and 2'-phospho-5'-ADP-ribose partly protect, but 4-acetylpyridine, 5'-AMP, 5'-ADP, NMN and NAD+ do not
pyrazole
-
-
pyrazole
-
IC50 for the 3 isozymes CHCR1-3, overview
quercetin
Candida macedoniensis
-
-
quercetin
Cylindrocarpon sclerotigenum
-
16% inhibition at 0.1 mM
quercetin
56.4% inhibition at 0.01 mM, 81.6% inhibition at 0.1 mM
quercetin
-
31.5% inhibition at 0.1 mM
quercetin
-
complete inhibition at 0.1 mM
quercetin
-
50% inhibition at 0.016 mM
quercitrin
-
-
quercitrin
-
IC50 for the 3 isozymes CHCR1-3, overview
rutin
J9P7P2
competitive
S-nitrosoglutathione
substrate inhibition above 5 * Km, enzyme is covalantly modified. Treatment with dithiothreitol, but not with ascorbic acid, rescues the activity
S-nitrosoglutathione
treatment leads concentration-dependent S-glutathionylation of cysteines at positions 122, 150, 226, 227. Residues C226/C227 form a disulfide bond. Treatment results in a 25fold decrease in kcat with menadione, 4-benzoylpyridine, 2,3-hexanedione, daunorubicinand 1,4-naphthoquinone, with concomitant increase in kcat for substrates containing a 1,2-diketo group in a ring structure. Except for 9,10-phenanthrenequinone, all changes in kcat are at least in part compensated for by a similar change in Km, overall yielding no drastic changes in catalytic efficiency
Zn2+
-
-
Zn2+
-
88% inhibition at 1 mM
Zn2+
-
43% inhibition at 1 mM
Zn2+
1 mM, 97% inhibition; 97% inhibition at 1 mM
additional information
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not inhibited by EDTA
-
additional information
Cylindrocarpon sclerotigenum
-
no inhibition by diphenylhydantoin, N-ethylmaleimide, p-chloromercuribenzoate, PMSF, Mg2+, and Zn2+
-
additional information
not inhibitory: up to 1.0 mM Zn2+, Mg2+, Mn2+, Fe2+, or EDTA
-
additional information
not inhibitory: up to 1.0 mM Zn2+, Mg2+, Mn2+, Fe2+, or EDTA
-
additional information
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no inhibition by NADP+
-
additional information
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no inhibition by EDTA and crotonic acid
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additional information
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no inhibition by 5 mM 2,2'-dipyridyl, EDTA does not inhibit up to 5 mM
-
additional information
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protective effects of cofactor derivatives against inactivation by phenylglyoxal and 2,3,4-trinitrobenzenesulfonate sodium, overview
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additional information
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not affected by EDTA and 1,10-phenanthroline at 1 mM
-
additional information
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adrenochrome is a poor inhibitor
-
additional information
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the inhibitory potencies of alkyl 4-pyridyl ketones increases with an increase in the number up to five carbon atoms in the alkyl group, and 4-hexanoylpyridine is the most potent inhibitor of the enzyme activity. The inhibitory potencies of 4-heptanoylpyridine and 4-octanoylpyridine are lower than that of 4-hexanoylpyridine
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additional information
the nonionic surfactants Tween 80 and Triton X-100 have only weak impacts on the enzyme activity
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additional information
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the nonionic surfactants Tween 80 and Triton X-100 have only weak impacts on the enzyme activity
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