Literature summary for 3.1.1.7 extracted from

Horn, G.; de Koning, M.C.; van Grol, M.; Thiermann, H.; Worek, F.
Interactions between acetylcholinesterase, toxic organophosphorus compounds and a short series of structurally related non-oxime reactivators analysis of reactivation and inhibition kinetics in vitro (2018), Toxicol. Lett., 299, 218-225 .

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Activating Compound

Activating Compound	Comment	Organism	Structure
additional information	poisoning by organophosphorus compounds (OP) is characterized by inhibition of the key enzyme acetylcholinesterase (AChE) and potentially fatal outcomes in humans. Insufficient efficacy of the standard therapy with atropine and AChE reactivators (oximes) against certain OP initiates synthesis of non-oxime reactivators, 4-amino-2-[(dimethylamino)methyl]phenol, 4-amino-2-((dimethylamino)methyl)phenol, and 4-amino-2-[[ethyl(methyl)amino]methyl]phenol, basing on the common structure 4-amino-2-((diethylamino)methyl)phenol (ADOC). 10 to 34Fold reactivation potency of compound 4-amino-2-[[ethyl(methyl)amino]methyl]phenol compared to 4-amino-2-((diethylamino)methyl)phenol mainly due to improved affinity, analysis of reactivation and inhibition kinetics in vitro, method. A combination of 4-amino-2-[[ethyl(methyl)amino]methyl]phenol and the bispyridinium oxime HI-6 is tested to reactivate OP-inhibited AChE, the superior reactivator of the respective OP-AChE combination dominates the reactivation process and a synergistic effect cannot be observed. Michaelis reactivation kinetics, Kr, and pseudo-first-order rate constant kobs, overview	Homo sapiens

Application

Application	Comment	Organism
pharmacology	poisoning by organophosphorus compounds (OP) is characterized by inhibition of the key enzyme acetylcholinesterase (AChE) and potentially fatal outcomes in humans. Insufficient efficacy of the standard therapy with atropine and AChE reactivators (oximes) against certain OP initiates synthesis of non-oxime reactivators basing on the common structure 4-amino-2-((diethylamino)methyl)phenol (ADOC). 10 to 34Fold reactivation potency of compound 4-amino-2-[[ethyl(methyl)amino]methyl]phenol compared to 4-amino-2-((diethylamino)methyl)phenol mainly due to improved affinity	Homo sapiens

Inhibitors

Inhibitors	Comment	Organism	Structure
cyclosarin	cyclohexylmethylphosphonofluoridate, GF	Homo sapiens
additional information	interactions between acetylcholinesterase, toxic organophosphorus compounds and a short series of structurally related non-oxime reactivators, analysis of reactivation and inhibition kinetics in vitro, overview. A combination of 4-amino-2-[[ethyl(methyl)amino]methyl]phenol and the bispyridinium oxime HI-6 is tested to reactivate OP-inhibited AChE, the superior reactivator of the respective OP-AChE combination dominates the reactivation process and a synergistic effect cannot be observed	Homo sapiens
O-ethyl-S-[2-(diisopropylamino)-ethyl]-methylphosphonothioate	VX	Homo sapiens
paraoxonethyl	diethyl-O-4-nitrophenylphosphate, paraoxon, PXE	Homo sapiens
sarin	isopropylmethylphosphonofluoridate, GB	Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
acetylcholine + H2O	Homo sapiens	-	choline + acetate	-	?

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	P22303	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
acetylcholine + H2O	-	Homo sapiens	choline + acetate	-	?
acetylthiocholine + H2O	-	Homo sapiens	thiocholine + acetate	-	?
additional information	interactions between acetylcholinesterase, toxic organophosphorus compounds and a short series of structurally related non-oxime reactivators, analysis of reactivation and inhibition kinetics in vitro, overview	Homo sapiens	?	-	?

Synonyms

Synonyms	Comment	Organism
AChE	-	Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C]	Temperature Optimum Maximum [°C]	Comment	Organism
37	-	assay at	Homo sapiens

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
7.4	-	assay at	Homo sapiens

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism	Structure
additional information	-	additional information	inhibition kinetics, KD, and Michaelis reactivation kinetics, Kr, and pseudo-first-order rate constant kobs	Homo sapiens

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Release 2023.1 (January 2023)