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3.5.1.2: glutaminase

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

Word Map on EC 3.5.1.2

Reaction

L-glutamine
+
H2O
=
L-glutamate
+
NH3

Synonyms

AnsB, AoGls, GA, GAB, GAC, GahB, GLA, GLNase, GLS, GLS1, GLS2, GlsA, glutaminase, glutaminase 1, glutaminase 2, glutaminase A, glutaminase B, glutaminase C, glutaminase I, glutaminase K, glutaminase L, glutaminase-1, glutaminase-2, glutaminase-B, glutamine amidohydrolase, glutamine aminohydrolase, glutamine deamidating enzyme, K-glutaminase, KAG, KGA, kidney-type glutaminase, kidney-type-glutaminase, L-glutaminase, L-glutamine amidohydrolase, LAG, LGA, liver-type glitaminase, liver-type glutaminase, Mglu, Micrococcus glutaminase Mglu, Micrococcus luteus K-3-type glutaminase, mitochondrial glutaminase, N-PAG, neuroblastoma glutaminase, neuroblastoma PAG, Nit 2, nitrilase 2, omega-amidase, PAG, PDX2, phosphate activated glutaminase, phosphate-activated glutaminase, phosphate-activated L-glutamine amidohydrolase, salt-tolerant glutaminase, YaaE

ECTree

     3 Hydrolases
         3.5 Acting on carbon-nitrogen bonds, other than peptide bonds
             3.5.1 In linear amides
                3.5.1.2 glutaminase

Inhibitors

Inhibitors on EC 3.5.1.2 - glutaminase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2R)-1-(2-formyl-3,6-dihydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
-
-
(2R)-1-(2-hydroxy-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)pentadecan-2-yl acetate
-
-
(2R)-1-(2-hydroxy-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
-
-
(2R)-1-(3,6-dihydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
-
-
(2R)-1-(5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)pentadecan-2-yl acetate
-
-
(2R)-1-(5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
-
-
(2R)-1-[3-(acetyloxy)-6-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl]pentadecan-2-yl acetate
-
-
(2R)-1-[3-(acetyloxy)-6-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl]tridecan-2-yl acetate
-
-
(2S)-1-(5-methoxycyclohexa-1,4-dien-1-yl)heptan-2-ol
-
-
(2S)-2-amino-6-imino-5-oxohexanoic acid
-
1,2-naphthoquinone 4-sulfonate
-
-
1,4-Naphthoquinone
-
-
1-amino-8-naphthol-2,4-disulfonic acid
-
weak
2,2-dimethyl-5-[4-(methylsulfanyl)phenyl]-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
97% inhibition at 0.05 mM
2,2-dimethyl-5-[4-(naphthalen-1-yl)phenyl]-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
97% inhibition at 0.05 mM
2,2-dimethyl-5-[4-(propan-2-yl)phenyl]-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
91% inhibition at 0.05 mM
2,4-dinitro-1-naphthol-7-sulfonic acid
-
i.e. flavianic acid
2-bromo-4-(2,2-dimethyl-4-oxo-1,2,3,4,5,6-hexahydrobenzo[a]phenanthridin-5-yl)-6-methoxyphenyl acetate
-
84% inhibition at 0.05 mM
2-hydroxy-5-methoxy-3-tridecylcyclohexa-2,5-diene-1,4-dione
-
-
2-methoxy-6-pentadecylcyclohexa-2,5-diene-1,4-dione
-
-
2-methoxy-6-tridecylcyclohexa-2,5-diene-1,4-dione
-
-
2-methyl-5-[(7Z)-pentadec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
-
-
2-methyl-5-[(7Z)-tridec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
-
-
2-oxoglutarate
2-phenyl isoindolin-1-one
-
-
2-phenylbenzo[d] isoxazol-3(2H)-one
-
-
2-phenylbenzo[d]isothiazol-3(2H)-one
-
-
3-[(2S)-2-hydroxypentadecyl]-5-methoxycyclohexa-2,5-dien-1-ol
-
-
4-hydroxy-2-methoxy-6-(2-oxopentadecyl)cyclohexa-2,5-dien-1-yl acetate
-
-
5,5'-(sulfanediyldiethane-2,1-diyl)bis(1,3,4-thiadiazol-2-amine)
-
5-(3-bromo-4,5-dimethoxyphenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
complete inhibition at 0.05 mM
5-(3-bromo-4-(dimethylamino)phenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
-
5-(3-chloro-4,5-dimethoxyphenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
88% inhibition at 0.05 mM
5-(4-tert-butylphenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
99% inhibition at 0.05 mM
5-[(6Z)-13-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]-2-methylbenzene-1,3-diol
-
-
5-[(6Z)-13-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]benzene-1,3-diol
-
-
5-[(6Z)-13-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]benzene-1,3-diol
-
-
5-[(7Z)-13-(3-hydroxy-5-methoxyphenyl)tridec-7-en-1-yl]-2-methylcyclohexa-1,4-diene-1,3-diol
-
-
5-[(7Z)-15-(3-hydroxy-5-methoxyphenyl)pentadec-7-en-1-yl]-2-methylcyclohexa-1,4-diene-1,3-diol
-
-
5-[(7Z)-pentadec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
-
-
5-[(7Z)-tridec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
-
-
5-[(8Z)-15-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]-2-methylbenzene-1,3-diol
-
-
5-[(8Z)-15-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]benzene-1,3-diol
-
-
5-[(8Z)-15-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]benzene-1,3-diol
-
-
5-[14-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tetradecyl]benzene-1,3-diol
-
-
5-[3-bromo-4-(dimethylamino)phenyl]-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
5-[4-(diethylamino)phenyl]-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
96% inhibition at 0.05 mM
5-[4-(dimethylamino)phenyl]-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
59% inhibition at 0.05 mM
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(4-phenylpiperidin-1-yl)ethyl]pentanamide
-
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(piperidin-1-yl)ethyl]pentanamide
-
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(pyrrolidin-1-yl)ethyl]pentanamide
-
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[4-(trifluoromethyl)benzyl]pentanamide
-
6-diazo-5-oxo-L-norleucine
6-diazo-5-oxo-Lnorleucine
-
time-dependent inhibition
8-[3-bromo-4-(diethylamino)phenyl]-11,11-dimethyl-8,10,11,12-tetrahydrobenzo[a][4,7]phenanthrolin-9(7H)-one
-
96% inhibition at 0.05 mM
8-[3-bromo-4-(dimethylamino)phenyl]-11,11-dimethyl-8,10,11,12-tetrahydrobenzo[a][4,7]phenanthrolin-9(7H)-one
-
91% inhibition at 0.05 mM
Al3+
-
46% residual activity at 1 mM
anthraquinone-1,8-disulfonate
-
-
apomorphine
-
competitive inhibition, i.e. 5,6,6a,7-tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol
arsenate
-
0.5 M, 74% inhibition
azaserine
about 19% inhibition at about 1 mM
BaCl2
-
inhibition to a variable extent
Berberine
-
-
bicarbonate
-
0.5 M, complete inhibition
bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl) ethyl sulfide
-
i.e. BPTES, binds to an allosteric pocket at the dimer interface of kidney-type glutaminase, triggering a dramatic conformational change of the key loop (Glu312-Pro329) near the catalytic site and rendering it inactive, allosteric inhibition. Binding of BPTES stabilizes the inactive tetramers of the catalytic domain of kidney-type glutaminase. The binding mode of BPTES on the hydrophobic pocket determines its specificity to the kidney-type glutaminase isoform KGA
bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide
bis-2-(5-phenylacetimido-1,2,4,thiadiazol-2-yl)ethyl sulfide
inhibits specifically GLS1 and its splice variant GAC, two inhibitor molecules bind at an interface region of the GAC tetramer in a manner that appears to lock the GAC tetramer into a nonproductive conformation, binding structure and mechanism of glutaminase inhibition, overview; inhibits specifically GLS1 splice variant GAC, two inhibitor molecules bind at an interface region of the GAC tetramer in a manner that appears to lock the GAC tetramer into a nonproductive conformation, binding structure and mechanism of glutaminase inhibition, overview
bis-2-(5-phenylacetimido-1,2,4-thiadiazol-2-yl) ethyl sulfide
-
glutaminase-1-selective inhibitor
bis-2-(5-phenylacetimido-1,2,4-thiadiazol-2-yl)ethyl sulfide
-
uncompetitive inhibition
Bromocresol green
-
-
bromocresol purple
-
-
CaCl2
-
inhibition to a variable extent
CB-839
i.e. N-[5-[4-[6-[[2-[3-(trifluoromethoxy)phenyl]acetyl]amino]-3-pyridazinyl]butyl]-1,3,4-thiadiazol-2-yl]-2-pyridineacetamide, is the best inhibitor as designated by the binding free energy changes
Cd2+
-
complete inhibition at 50 mM
chelerythrine
-
competitive inhibition, i.e. 1,2-dimethoxy-N-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
citrate
-
enzyme from mesenteric lymph nodes
Cl-
-
0.5 M, complete inhibition
CN-
-
0.5 M, complete inhibition
CoCl2
-
14% inhibition at 1 mM
compound 968
-
i.e. 5-(3-bromo-4-(dimethylamino)phenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one, combined with erlotinib down-regulates the glutamine and glycolysis metabolism in erlotinib-resistant non-small cell lung cancer cells
CuCl2
-
20% inhibition at 1 mM, 17% at 0.1 mM
CuSO4
-
inhibition to a variable extent
D-glucose
-
negative influence in media with glucose as carbon source
diazo-5-oxo-L-norleucine
diethyl dicarbonate
-
-
dimethyl 2-[1-(4-tert-butylbenzoyl)-2,2,7-trimethyl-3-methylidene-2,3-dihydroquinolin-4(1H)-ylidene]-1,3-dithiole-4,5-dicarboxylate
-
97% inhibition at 0.05 mM
diphenylarsinic acid
-
the protein level of GAC significantly decrease in an concentration manner. The PAG activities are also decreased in parallel with the decrease in GAC
diphosphate
-
0.1 M, 98% inhibition
dithiothreitol
ebselen
-
mixed non-competitive inhibition, i.e. 2-phenyl-1,2-benzisoselenazol-3[2H]-one
FeCl3
-
glutaminase II
glufosinate ammonium
about 23% inhibition at about 1 mM
glutamate
HgCl2
iodoacetamide
iodoacetate
L-glutamate
L-Glutamic acid
Triticale sp.
-
5 mM, about a 40% inhibition
L-glutamine
L-methionine sulfoximine
about 21% inhibition at about 1 mM
Mersalyl
metformin
-
68% inhibition at 100 mM
methylene blue
-
0.005%, irreversible inactivation
MgCl2
-
20% inhibition at 1 mM, 12% at 0.1 mM
MnCl2
-
22% inhibition at 1 mM, 13% at 0.1 mM
N'-[(E)-[3-bromo-4-(dimethylamino)phenyl]methylidene]-2-(9-oxoacridin-10(9H)-yl)acetohydrazide
-
93% inhibition at 0.05 mM
N,N'-[sulfanediylbis(ethane-2,1-diyl-1,3,4-thiadiazole-5,2-diyl)]bis(2-phenylacetamide)
-
N-(2-aminoethyl)-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
N-(5-[2-[2-(5-amino-[1,3,4]thiadiazol-2-yl)-ethylsulfanyl]-ethyl]-[1,3,4]thiadiazol-2-yl)-2-phenyl-acetamide
-
N-benzyl-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
N-bromosuccinimide
-
5 mM, 19% of initial activity
N-ethylmaleimide
N-methyl-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(pyrrolidin-1-yl)ethyl]pentanamide
-
N-tert-butyl-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
N-tert-butyl-N-methyl-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
N-[2-(1-methylpyrrolidin-2-yl)ethyl]-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
N-[2-(4-hydroxypiperidin-1-yl)ethyl]-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
N-[2-(diethylamino)ethyl]-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
N-[4-(dimethylamino)benzyl]-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
N-[4-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3-thiazol-2-yl]-2-phenylacetamide
-
N-[5-(2-[[2-(5-amino-1,3,4-thiadiazol-2-yl)ethyl]sulfinyl]ethyl)-1,3,4-thiadiazol-2-yl]-2-phenylacetamide
-
N-[5-[2-(5-amino-1,3,4-thiadiazol-2-yl)ethyl]-1,3,4-thiadiazol-2-yl]-2-phenylacetamide
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-(4-fluorophenyl)acetamide
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-(4-methylphenyl)acetamide
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-cyclohexylacetamide
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-phenylacetamide
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-phenylpropanamide
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-3-phenylpropanamide
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]benzamide
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3-thiazol-2-yl]-2-phenylacetamide
-
Na2SO4
-
glutaminase I and II
NaCIO4
-
0.3 M, 25% inhibition
NaF
-
inhibition to a variable extent
NaH2PO4
-
0.3 M, complete inhibition
NaI
-
above 0.3 M
NaN3
-
complete inhibition at 1 mM
NaNO3
-
0.3 M, 15% inhibition
Ngamma,Ngamma-diethyl-L-glutamine
-
-
Ngamma,Ngamma-dimethyl-L-glutamine
-
-
Ngamma-ethyl-L-glutamine
-
-
Ngamma-methyl-L-glutamine
-
-
nitidine
-
-
nitrite
-
0.5 M, complete inhibition
norsanguinarine
-
-
O-(diazoacetyl)-L-serine
-
-
p-benzoquinone
-
-
p-chloromercuribenzoate
-
p-chloromercuribenzoic acid
-
complete inhibition at 10 mM
p-mercuribenzoate
Pb2+
-
69.27% residual activity at 100 mM
phenylarsonic acid
-
causes a decrease in GAC levels
phenylmethylarsinic acid
-
causes a decrease in GAC levels
protein BNIP-H
i.e. Caytaxin or brain-specific BNIP-2-homology protein, encoded by gene ATCAY, important in neuromal function, inhibits the enzyme and alters its steady-state kinetics, relocalises glutaminase to neurite terminals and reduces glutamate levels in vivo, effects on glutamate levels in overexpressing cell lines, e.g. murine Neuro2A cells or rat PC-12 cells, or in female rat brain, detailed overview
-
pyruvate
R(-)-apocodeine
-
-
R(-)-propylnorapomorphine
-
-
Rose bengal
-
0.01%, irreversible inactivation
sanguinarine
-
-
succinate
-
enzyme from mesenteric lymph nodes
TLCK
-
5 mM, 12% of initial activity
Tris
-
0.5 M, complete inhibition
Triton X-100
-
-
ZnCl2
-
7% inhibition at 1 mM
additional information
-