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(10E,12Z)-octadeca-10,12-dienoic acid
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non-competitive inhibition mechanism
1-butane boronic acid
-
-
1-ethyl-3,3'-dimethylaminopropylcarbodiimide
-
-
1-methylethyl dodecylphosphonofluoridoate
2-(octyloxy)-4H-1,3,2-benzodioxaphosphinine 2-oxide
2-(pentylsulfanyl)-4H-1,3,2-benzodioxaphosphinine 2-oxide
2-heptyl-4H-1,3,2-benzodioxaphosphinine 2-oxide
4-(2-aminoethyl) benzenesulfonyl fluoride
-
-
5,5'-dithiobis-(2-nitrobenzoate)
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partial
Ac-Ala
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competitive inhibitor
Ac-Gly-prolineboronic acid
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-
Ac-Leu-CH2-Cl
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irreversible inhibitor
Ac-Met
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competitive inhibitor
Ac-Phe-OH
product-like inhibitor
acephate
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IC50: 0.0062 mM
acetyl-Gly-prolineboronic acid
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selectivity for APH 25fold higher than for fibroblast activation protein
activated-thiol-Sepharose
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-
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benzyloxycarbonyl-Gly-Gly-Phe-chloromethyl ketone
CMK, chloromethyl ketone inhibitor, enzyme binding structure analysis, molecular dynamics studies, overview
bis(1-methylethyl) 4-nitrophenyl phosphate
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IC50: 0.016 mM
bis(sulfosuccinimidyl)suberate
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-
CaCl2
100 mM, 52% inhibition
carbodiimide/aminoalkyl-agarose
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-
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carbodiimide/dicarboxylic acid
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-
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chlorfenvinphos
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IC50 at pH 7.4, 37°C: 1386 nM
chlorpyrifos isopropyl
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IC50: 0.0033 mM
chlorpyrifos n-butyl
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IC50: 0.00006 mM
chlorpyrifos n-propyl
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IC50: 0.00007 mM
chlorpyrifos-methyl oxon
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IC50 at pH 7.4, 37°C: 18.3 nM
chlorpyrifosmethyl oxon
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Cl-
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activity towards N-acetyl-Ala-Ala and N-acetyl-Ala-Ala-Ala
CoCl2
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1 mM, 21% inhibition
di(2-pyridyl)disulfide
-
-
dicyclohexyl 2,2-dichloroethenyl phosphate
diethyl 4-methyl-3-nitrophenyl phosphate
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IC50: 0.002 mM
diisopropyl fluorophosphate
diisopropylfluorophosphate
diphenylphosphinic fluoride
EDTA
1 mM, 10% inhibition
ethyl octylphosphonofluoridoate
FeCl2
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1 mM, 21% inhibition
Guanidine-HCl
1 M, complete loss of activity, after removal of guanidine-HCl the enzyme recovers 25% of its activity
guanidine/HCl
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1 M, complete inactivation
heptyl ethylphosphonofluoridoate
malaoxon
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IC50 at pH 7.4, 37°C: 1400000 nM
malathion
significantly inhibits the activity of enzyme APH both in vitro and in vivo
Mipafox
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IC50 at pH 7.4, 37°C: 3013 nM
N,N-Dimethylformamide
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-
N-acetyl-Ala chloromethyl ketone
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inactivation follows first order kinetics, acetyl-Ala protects
N-acetyl-Leu chloromethyl ketone
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-
N-ethyl-5-phenylisoxazolium 3'-sulfonate
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i.e. Woodward's reagent
N-hydroxysuccinimide agarose
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-
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NaCl
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1 mM, 78% loss of activity
nonyl ethylphosphonofluoridoate
octane-1-sulfonyl fluoride
octyl methylphosphonofluoridoate
p-hydroxymercuribenzoate
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-
p-nitrophenyl-N-propyl carbamate
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potent active site-directed, pseudo-first-order kinetics
pentyl ethylphosphonofluoridoate
peptide SsCEI 2
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specific and efficient inhibition. No inhibition in presence of peptide SsCEI 3 and peptide SsCEI 4
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phenylmethylsulfonyl fluoride
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-
phosphatidylethanolamine-binding protein inhibitor SsCEI
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phoxim
significantly inhibits the activity of enzyme APH both in vitro and in vivo
profenofos
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IC50: 0.002 mM
SCN-
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activity towards N-acetyl-Ala-Ala and N-acetyl-Ala-Ala-Ala
Sulfolobus solfataricus chymotrypsin-elastase inhibitor
specific inhibition
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Trichlorfon
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IC50: 0.018 mM
tridecyl methylphosphonofluoridoate
Triton X-100
1 mg/ml, 4% inhibition
Tween 20
1 mg/ml, 10% inhibition
Tween 80
1 mg/ml, 18% inhibition
1-methylethyl dodecylphosphonofluoridoate
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IC50: 0.00026 mM
1-methylethyl dodecylphosphonofluoridoate
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IC50: 0.0015 mM
2-(octyloxy)-4H-1,3,2-benzodioxaphosphinine 2-oxide
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IC50: 0.00018 mM
2-(octyloxy)-4H-1,3,2-benzodioxaphosphinine 2-oxide
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IC50: 0.00023 mM
2-(pentylsulfanyl)-4H-1,3,2-benzodioxaphosphinine 2-oxide
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IC50: 0.0015 mM
2-(pentylsulfanyl)-4H-1,3,2-benzodioxaphosphinine 2-oxide
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IC50: 0.0011 mM
2-heptyl-4H-1,3,2-benzodioxaphosphinine 2-oxide
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IC50: 0.0014 mM
2-heptyl-4H-1,3,2-benzodioxaphosphinine 2-oxide
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IC50: 0.0016 mM
Acetyl-Phe
forms hydrogen bonds with both NH groups of the oxyanion binding site of AAP. In the mutant enzyme the NH bond of Gly369 points in a different direction
chlorpyrifos
binding structure, docking study, and molecular dynamics simulations using structure PDB ID 1VE7 as search model, and umbrella sampling calculations, molecular mechanical/GBSA calculations, enzyme-inhibitor complex structure, overview
chlorpyrifos
significantly inhibits the activity of enzyme APH both in vitro and in vivo
chlorpyrifos
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IC50: 0.000021 mM
chlorpyrifos
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IC50: 0.000071 mM
chlorpyrifos cyclohexyl
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IC50: 0.00086 mM
chlorpyrifos cyclohexyl
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IC50: 0.00035 mM
chlorpyrifos methyl
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IC50: 0.000080 mM
chlorpyrifos methyl
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IC50: 0.00031 mM
Cu2+
1 mM, complete inhibition of recombinant enzyme
Cu2+
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1 mM, complete inhibition of recombinant enzyme
DFP
-
-
DFP
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IC50 at pH 7.4, 37°C: 22.5 nM
DFP
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the reactive residue is Ser587
diazoxon
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IC50: 0.00093 mM
diazoxon
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IC50: 0.00089 mM
diazoxon
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IC50 at pH 7.4, 37°C: 1386 nM
dichlorvos
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dichlorvos
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IC50: 0.00023 mM
dichlorvos
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shows selectivity for acylpeptide hydrolase inhibition in vivo
dichlorvos
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IC50: 0.00056 mM
dichlorvos
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acylpeptide hydrolase activity shows a significant inhibition
dichlorvos
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IC50 at pH 7.4, 37°C: 118.6 nM
dichlorvos
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exhibits high affinity for acylpeptide hydrolase, possibly blocks its activity toward N-acylpeptide
dicyclohexyl 2,2-dichloroethenyl phosphate
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IC50: 0.00010 mM
dicyclohexyl 2,2-dichloroethenyl phosphate
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IC50: 0.00025 mM
diethyl dicarbonate
-
-
diisopropyl fluorophosphate
1 mM, complete inactivation
diisopropyl fluorophosphate
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1 mM, complete inactivation
diisopropyl fluorophosphate
-
-
diisopropyl fluorophosphate
-
-
diisopropylfluorophosphate
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IC50: 0.000011 mM
diisopropylfluorophosphate
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IC50: 0.000017 mM
dipentyl fluorophosphate
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IC50: 0.000011 mM
dipentyl fluorophosphate
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IC50: 0.0000099 mM
diphenylphosphinic fluoride
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IC50: 0.00041 mM
diphenylphosphinic fluoride
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IC50: 0.00024 mM
ethyl octylphosphonofluoridoate
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IC50: 0.00011 mM
ethyl octylphosphonofluoridoate
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IC50: 0.00021 mM
heptyl ethylphosphonofluoridoate
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IC50: 0.000027 mM
heptyl ethylphosphonofluoridoate
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IC50: 0.00023 mM
Hg2+
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-
iodoacetamide
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-
iodoacetic acid
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partial
N-acetyl-Ala
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-
N-acetyl-Ala
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competitive
N-acetyl-Ala
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N-acetyl-D-Ala; N-acetyl-L-Ala
N-acetyl-Met
-
-
naled
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IC50: 0.00037 mM
NEM
1 mM
nonyl ethylphosphonofluoridoate
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IC50: 0.000052 mM
nonyl ethylphosphonofluoridoate
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IC50: 0.00028 mM
octane-1-sulfonyl fluoride
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IC50: 0.073 mM
octane-1-sulfonyl fluoride
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IC50: 0.067 mM
octyl methylphosphonofluoridoate
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IC50: 0.000043 mM
octyl methylphosphonofluoridoate
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IC50: 0.00016 mM
paraoxon
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IC50: 0.0047 mM
paraoxon
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IC50 at pH 7.4, 37°C: 3805 nM
PCMB
0.1 mM
pentyl ethylphosphonofluoridoate
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IC50: 0.00013 mM
pentyl ethylphosphonofluoridoate
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IC50: 0.00027 mM
phosphatidylethanolamine-binding protein inhibitor SsCEI
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-
phosphatidylethanolamine-binding protein inhibitor SsCEI
-
-
PMSF
1 mM, 50% inhibition
PMSF
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1 mM, 50% inhibition
SDS
-
-
SDS
above 0.3 mM, complete inhibition
SDS
1 mg/ml, complete inhibition
tridecyl methylphosphonofluoridoate
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IC50: 0.00032 mM
tridecyl methylphosphonofluoridoate
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IC50: 0.0048 mM
Urea
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-
Urea
6 M, about 70% loss of activity, regains activity at almost all urea concentrations upon removal of the denaturinf agent
Zn2+
1 mM, complete inhibition of recombinant enzyme
Zn2+
-
1 mM, complete inhibition of recombinant enzyme
Zn2+
-
most potent inhibitor
additional information
different organophosphorous compounds bind to the enzyme inducing conformational changes in two domains, namely, alpha/beta hydrolase and beta-propeller, computational study of APH bound to chlorpyrifosmethyl oxon and dichlorvos, and molecular dynamics simulations of enzyme bound to the inhibitors, the starting model of APH is derived from 2.7 A resolution crystal structure of acylpeptide hydrolase/esterase from Aeropyrum pernix K1 (PDB ID 1VE7), overview. The docking study reveals that Val471 and Gly368 are important residues for chlorpyrifosmethyl oxon and dichlorvos binding
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additional information
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alphabeta peptide (1-40) can inhibit APH activity from the cell lysates of APH transfected cells after IP at 0.01 and 0.001 mM concentration, while reversed alphabeta peptide (40-1) at the same concentrations does not show any inhibitory effect
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additional information
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acylpeptide hydrolase is a direct target for some organophosphate compounds
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