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1.17.1.4: xanthine dehydrogenase

This is an abbreviated version!
For detailed information about xanthine dehydrogenase, go to the full flat file.

Word Map on EC 1.17.1.4

Reaction

xanthine
+
NAD+
 +
H2O
=
Urate
 +
NADH
 +
H+

Synonyms

AtXDH1, EC 1.1.1.204, EC 1.2.1.37, IAO1, More, NAD-xanthine dehydrogenase, PaoABC, Retinol dehydrogenase, Rosy locus protein, VvXDH, xanthine dehydrogenase, xanthine dehydrogenase-1, xanthine dehydrogenase-2, xanthine dehydrogenase/oxidase, xanthine oxidoreductase, xanthine-NAD oxidoreductase, xanthine/NAD+ oxidoreductase, xanthine:NAD+ oxidoreductase, XDH, XDH/XO, XDH1, XDH2, XdhC, XOR, YagR, YagS, YagT

ECTree

     1 Oxidoreductases
         1.17 Acting on CH or CH2 groups
             1.17.1 With NAD+ or NADP+ as acceptor
                1.17.1.4 xanthine dehydrogenase

Inhibitors

Inhibitors on EC 1.17.1.4 - xanthine dehydrogenase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-methylhypoxanthine
-
17% inhibition of xanthine dehydrogenase at 0.25 mM
17beta-estradiol
-
inhibition of enzyme activity in malignant and non-malignant mammary epithelial cells
2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acid
i.e. TEI-6720, mixed type inhibitor, binds very tightly to active and inactive desulfo-form of enzyme
2-amino-4-hydroxypteridine-6-carboxyaldehyde
2-amino-4-hydroxypterin
-
substrate inhibition above 0.01 mM
2-Iodosobenzoic acid
4-(5-pyridin-4-yl-1H-1,2,4-triazol-3-yl)pyridine-2-carbonitrile
i.e. FYX-051, strong, in absence of xanthine slow hydroxylation of inhibitor
4-(5-pyridin-4-yl-1H-[1,2,4]triazol-3-yl) pyridine-2-carbonitrile
-
i.e. FYX-051, inhibition of xanthine oxidoreductase. In vivo, the inhibitor is modified by N1- and N2-glucuronidation, mainly catalyzed by UDP-glucuronosyltransferase UGT1A9
4-Amino-2,6-dihydroxypyrimidine
-
competitive inhibition of xanthine oxidation, Ki: 0.106 mM
4-chloromercuribenzoate
4-chloromercuriphenyl sulfonic acid
-
98% inhibition at 0.001 mM
4-hydroxymercuribenzoate
4-hydroxypyrazolo(3,4-d)pyrimidine
5,5-dithiobis-(2-nitrobenzoate)
6-chloro-2-[3-(4-hydroxyphenyl)-1-phenyl-1-H-pyrazol-4-yl]-chromen-4-one
6-chloro-7-methyl-2-[3-(4-chlorophenyl)-1-phenyl-1-H-pyrazol-4-yl]-chromen-4-one
6-Mercaptopurine
-
90% inhibition of hypoxanthine-NADP+-activity at 1 mM
8-Azaadenine
8-Azaguanine
8-Azaxanthine
-
50% inhibition of ferricyanide reduction in xanthine oxidation assay at 5 mM
8-azohypoxanthine
-
40% inhibition of xanthine dehydrogenase at 0.25 mM
acetaldehyde
-
inactivation
adenine
Ag2+
-
complete inhibition of hypoxanthine oxidation at 0.01 mM
allopurinol
alloxanthine
-
a mechanism-based inhibitor, binding structure, overview. Inhibition mechanism involves binding to molybdenum, overview
amflutizole
-
blocks xanthine dehydrogenase activity, without influencing xanthine oxidase activity
ammeline
ammonium acetate
-
inhibits the enzyme in vivo after injection into the brain, blocked by MK-801, which alone does not affect the enzyme activity itself
arsenite
cassia oil
-
oral adminstration of cassia oil significantly reduces serum and hepatic urate levels in hyperuricemic mice. At 600 mg/kg, cassia oil is as potent as allopurinol. This hypouricemic effect is explained by inhibiting activities of liver xanthine oxidase and xanthine oxidoreductase
Cu2+
-
14% inhibition of hypoxanthine oxidation at 0.1 mM
CuSO4
-
conversion of the dehydrogenase type D to oxidase type O, prolonged incubation leads to complete inactivation, conversion can be reversed and prevented by dithioerythritol
diethyl dicarbonate
-
90% loss of NAD+ dependent activity at 1 mM, retains more than 90% of oxygen-dependent and 3-acetylpyridine adenine dinucleotide+-dependent NADH oxidation activity
diethyldithiocarbamate
-
72% inhibition of xanthine-NAD+-activity at 10 mM
diphenylen iodinium
diphenylene iodonium
-
powerful inhibition of NADH oxidation
EDTA
-
19.8% inhibition of hypoxanthine oxidation at 10 mM
febuxostat
-
structure-based inhibitor, forms numerous hydrogen bonds, slat bridges, and hydrophobic interactions with amino acids in the active site and nearly completely fills the narrow channel leading to the molydbenum center of the enzyme
FYX-051
GSH
-
45% of the oxidase activity converted to dehydrogenase activity at 10 mM
GSSG
-
75% of the dehydrogenase activity converted to oxidase activity at 0.5 mM
Guanidine-HCl
guanine
hesperetin
-
i.e. 3',5,7-trihydroxy-4'-methoxyflavanone, major flavanone component of orange juice, inhibits hepatic XDH activity and decreases serum uric acid levels, exhibits antioxidative and antihyperuricemic properties
Hg2+
-
complete inhibition of hypoxanthine oxidation at 0.1 mM
hypoxanthine
-
inactivation of xanthine oxidase activity, not in the presence of NAD+
iodoacetic acid
-
21% inhibition at 1 mM
Leucopterin
-
competitive inhibition of xanthopterin oxidation, Ki: 0.0109 mM
methanol
N-ethylmaleimide
-
conversion of dehydrogenase type D to oxidase type O, prevented by dithioerythritol but no reversible conversion
N6-furfuryladenine
-
0.1 mM, 59% residual activity
NaCN
-
69% inhibition of xanthine-NAD+-activity at 3.3 mM
NAD+
-
competitive inhibition of NADH oxidation, Ki: 0.0143 mM
NADPH
-
inactivation closely related to diaphorase activity
NaN3
-
slight inhibition of dehydrogenase activity
NO
-
dose-dependent inhibition of xanthine dehydrogenase and oxidase activity, reaction with an essential sulfur in the molybdenum center, that damages the molybdopterin
o-phenanthroline
Oxipurinol
-
crystal structure of reduced enzyme in complex with oxipurinol at 2.0 A resolution. Electron density is observed between the N2 nitrogen atom of oxipurinol and the molybdenum atom of the molybdopterin cofactor. Oxipurinol forms hydrogen bonds with residues E802, R880, and E1261
oxypurinol
p-hydroxymercuribenzoate
strong
potassium cyanide
strong
pterin-6-aldehyde
competitive inhibition pattern, mechanism of inhibitor binding at the active site, overview
purine
-
some inhibition
pyridoxal
-
Ki for 2-amino-4-hydroxypterine oxidation: 0.08 mM at 30 and 50°C, competitive; Ki for xanthine oxidation: 0.05 mM at 30°C, 0.11 mM at 50°C, competitive
Quinacrine
-
29.7% inhibition of hypoxanthine oxidation at 1 mM
Salicylhydroxamic acid
Sodium dithionite
Superoxide dismutase
-
complete inhibition of the xanthine-cytochrome c activity for oxidase type O, lesser inhibition for dehydrogenase type D
-
tetraethyldithiodicarbonic diamide
-
i.e. disulfiram; transformation of the NAD+- to the O2-dependent activity up to 0.025 mM, up to 80% loss of NAD+-dependent activity, modification of one thiol group in the active centre, NAD+ protects against modification due to a single thiol group involved in NAD+-binding within the active centre
Tetraethylthiuram disulfide
-
conversion of dehydrogenase type D to oxidase type O, can be prevented and reversed by dithioerythritol
Thiourea
-
65% inhibition of xanthine dehydrogenase activity at 20 mM
Tiron
-
36.8% inhibition of hypoxanthine oxidation at 10 mM
Urate
xanthine
additional information
-