Inhibitory effects of organophosphate esters on carboxylesterase activity of rat liver microsomes

We investigated the inhibitory effects of 13 organophosphate esters (OPEs) and hydrolytic metabolites on the carboxylesterase activity of rat liver microsomes in vitro in order to examine whether there might be a potential impact on human health, and to elucidate the structure activity relationship....

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Published inChemico-biological interactions Vol. 327; p. 109148
Main Authors Tsugoshi, Yukie, Watanabe, Yoko, Tanikawa, Yuka, Inoue, Chika, Sugihara, Kazumi, Kojima, Hiroyuki, Kitamura, Shigeyuki
Format Journal Article
LanguageEnglish
Published Elsevier B.V 25.08.2020
Subjects
Carboxylesterase
Inhibition
Organophosphate esters
Rat liver microsomes
Organophosphate esters
Inhibition
Carboxylesterase
Rat liver microsomes
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Abstract We investigated the inhibitory effects of 13 organophosphate esters (OPEs) and hydrolytic metabolites on the carboxylesterase activity of rat liver microsomes in vitro in order to examine whether there might be a potential impact on human health, and to elucidate the structure activity relationship. Among the test compounds, 2-ethylhexyl diphenyl phosphate (EDPhP) was the most potent inhibitor of carboxylesterase activity, as measured in terms of 4-nitrophenol acetate hydrolase activity, followed by tri-m-cresyl phosphate (TmCP), cresyl diphenyl phosphate (CDPhP) and triphenyl phosphate (TPhP). The IC50 values were as follows: EDPhP (IC50: 0.03 μM) > TmCP (0.4 μM) > CDPhP (0.8 μM) > TPhP (14 μM) > tris(1,3-dichloro-2-propyl) phosphate (17 μM) > tris(2-ethylhexyl) phosphate (77 μM) > tri-n-propyl phosphate (84 μM) > tris(2-chloroethyl) phosphate (104 μM) > tris(2-butoxyethyl) phosphate (124 μM) > tri-n-butyl phosphate (230 μM). The IC50 value of EDPhP was three orders of magnitude lower than that of bis(4-nitrophenyl) phosphate, which is widely used as an inhibitor of carboxylesterase. Trimethyl phosphate, triethyl phosphate and tris(2-chloroisopropyl) phosphate slightly inhibited the carboxylesterase activity; their IC50 values were above 300 μM. Lineweaver-Burk plots indicated that the inhibition by several OPEs was non-competitive. Diphenyl and monophenyl phosphates, which are metabolites of TPhP, showed weaker inhibitory effects than that of TPhP. •We examined carboxylesterase inhibition by organophosphate esters (OPEs).•2-Ethylhexyl diphenyl phosphate was the most potent inhibitor among tested OPEs.•Aryl OPEs were strong rat liver microsomal carboxylesterase inhibitors.•Di- or mono-substituted derivatives of OPEs showed markedly decreased inhibition.•OPEs bearing a bulky substituent showed greater carboxylesterase-inhibitory effects.
AbstractList We investigated the inhibitory effects of 13 organophosphate esters (OPEs) and hydrolytic metabolites on the carboxylesterase activity of rat liver microsomes in vitro in order to examine whether there might be a potential impact on human health, and to elucidate the structure activity relationship. Among the test compounds, 2-ethylhexyl diphenyl phosphate (EDPhP) was the most potent inhibitor of carboxylesterase activity, as measured in terms of 4-nitrophenol acetate hydrolase activity, followed by tri-m-cresyl phosphate (TmCP), cresyl diphenyl phosphate (CDPhP) and triphenyl phosphate (TPhP). The IC50 values were as follows: EDPhP (IC50: 0.03 μM) > TmCP (0.4 μM) > CDPhP (0.8 μM) > TPhP (14 μM) > tris(1,3-dichloro-2-propyl) phosphate (17 μM) > tris(2-ethylhexyl) phosphate (77 μM) > tri-n-propyl phosphate (84 μM) > tris(2-chloroethyl) phosphate (104 μM) > tris(2-butoxyethyl) phosphate (124 μM) > tri-n-butyl phosphate (230 μM). The IC50 value of EDPhP was three orders of magnitude lower than that of bis(4-nitrophenyl) phosphate, which is widely used as an inhibitor of carboxylesterase. Trimethyl phosphate, triethyl phosphate and tris(2-chloroisopropyl) phosphate slightly inhibited the carboxylesterase activity; their IC50 values were above 300 μM. Lineweaver-Burk plots indicated that the inhibition by several OPEs was non-competitive. Diphenyl and monophenyl phosphates, which are metabolites of TPhP, showed weaker inhibitory effects than that of TPhP. •We examined carboxylesterase inhibition by organophosphate esters (OPEs).•2-Ethylhexyl diphenyl phosphate was the most potent inhibitor among tested OPEs.•Aryl OPEs were strong rat liver microsomal carboxylesterase inhibitors.•Di- or mono-substituted derivatives of OPEs showed markedly decreased inhibition.•OPEs bearing a bulky substituent showed greater carboxylesterase-inhibitory effects.
ArticleNumber 109148
Author Sugihara, Kazumi
Kitamura, Shigeyuki
Tsugoshi, Yukie
Tanikawa, Yuka
Watanabe, Yoko
Kojima, Hiroyuki
Inoue, Chika
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  organization: Nihon Pharmaceutical University, Komuro 10281, Inamachi, Kitaadachi-gun, Saitama, 362-0806, Japan
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Keywords Organophosphate esters
Inhibition
Carboxylesterase
Rat liver microsomes
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SSID ssj0000240
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Snippet We investigated the inhibitory effects of 13 organophosphate esters (OPEs) and hydrolytic metabolites on the carboxylesterase activity of rat liver microsomes...
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crossref
elsevier
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StartPage 109148
SubjectTerms Carboxylesterase
Inhibition
Organophosphate esters
Rat liver microsomes
Title Inhibitory effects of organophosphate esters on carboxylesterase activity of rat liver microsomes
URI https://dx.doi.org/10.1016/j.cbi.2020.109148
https://search.proquest.com/docview/2411103232
Volume 327
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