Effect of insecticidal cyclic phosphorothionates on adenylate cyclase and phosphodiesterase

Akinori Hirashima, Kazuhiko Oyama, Morifusa Eto

研究成果: ジャーナルへの寄稿記事

16 引用 (Scopus)

抄録

Octopamine (0.1 and 1 mM) stimulated the adenylate cyclase prepared from Periplaneta americana ventral nerve cords (615 and 1112% relative to the control). d-(-)-2-Amino-1-phenylethanol (APE) was more potent than 2-amino-1-(4-fluorophenyl)ethanol (an octopamine agonist) and l-(+)-APE in stimulating the adenylate cyclase. 2-Methoxy-5-phenyl-1,3,2,-oxazaphospholidine 2-sulfide (5-PMOS) derived from dl-(±)-APE did not activate adenylate cyclase at 0.75 and 7.5 mM (91 and 95% relative to the control) but suppressed the octopamine (0.1 mM) potency to 268% at 1 mM relative to the control. Salithion (2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-sulfide) at 0.1 mM, fenitrothion (dimethyl 3-methyl-4-nitrophenyl phosphorothionate), 2-amino-1-(2,3-dimethoxy)phenylethanol, 5-PMOS, and other oxazaphospholidines at 1 mM showed similar phenomena. 1-Naphthyl-, 2-naphthyl-, 4-ethylphenyl-, and 4-isopropylphenyloxazaphospholidine derivatives at 0.1 mM reduced the octopamine potency at 0.1 mM more severely than the octopamine-receptor antagonists (chlordimeform and cyproheptadine) at 1 mM. 5-(2,3-Dimethoxyphenyl)-2-methoxy-1,3,2-oxazaphospholidine 2-sulfide (Ki = 107.9 μM), fenitrothion (Ki = 37.3 μM), and 3-isobutyl-1-methylxanthine (Ki = 1.5 μM) reduced the phosphodiesterase activity of beef heart in a competitive manner with respect to cyclic adenosine 3′,5′-monophosphate (cAMP). At 50 μM, salithion, salioxon (2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-oxide), and other oxazaphospholidines reduced phosphodiesterase activity. Hence, d-(-)-APE could be an agonist, and 5-PMOS and salithion analogs and fenitrothion could be partial antagonists to the octopamine receptor. The increased level of whole-body cAMP of Musca domestica and Tribolium castaneum larvae treated with these phosphorothionates is due to reduction of phosphodiesterase activity.

元の言語英語
ページ(範囲)186-195
ページ数10
ジャーナルPesticide Biochemistry and Physiology
38
発行部数2
DOI
出版物ステータス出版済み - 1 1 1990

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Octopamine
octopamine
adenylate cyclase
Phosphoric Diester Hydrolases
Fenitrothion
Adenylyl Cyclases
Sulfides
fenitrothion
sulfides
Adenosine
Chlorphenamidine
cyclic AMP
Tribolium
Phenylethyl Alcohol
Periplaneta
Cyproheptadine
Houseflies
1-Methyl-3-isobutylxanthine
agonists
antagonists

All Science Journal Classification (ASJC) codes

  • Agronomy and Crop Science
  • Health, Toxicology and Mutagenesis

これを引用

Effect of insecticidal cyclic phosphorothionates on adenylate cyclase and phosphodiesterase. / Hirashima, Akinori; Oyama, Kazuhiko; Eto, Morifusa.

:: Pesticide Biochemistry and Physiology, 巻 38, 番号 2, 01.01.1990, p. 186-195.

研究成果: ジャーナルへの寄稿記事

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title = "Effect of insecticidal cyclic phosphorothionates on adenylate cyclase and phosphodiesterase",
abstract = "Octopamine (0.1 and 1 mM) stimulated the adenylate cyclase prepared from Periplaneta americana ventral nerve cords (615 and 1112{\%} relative to the control). d-(-)-2-Amino-1-phenylethanol (APE) was more potent than 2-amino-1-(4-fluorophenyl)ethanol (an octopamine agonist) and l-(+)-APE in stimulating the adenylate cyclase. 2-Methoxy-5-phenyl-1,3,2,-oxazaphospholidine 2-sulfide (5-PMOS) derived from dl-(±)-APE did not activate adenylate cyclase at 0.75 and 7.5 mM (91 and 95{\%} relative to the control) but suppressed the octopamine (0.1 mM) potency to 268{\%} at 1 mM relative to the control. Salithion (2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-sulfide) at 0.1 mM, fenitrothion (dimethyl 3-methyl-4-nitrophenyl phosphorothionate), 2-amino-1-(2,3-dimethoxy)phenylethanol, 5-PMOS, and other oxazaphospholidines at 1 mM showed similar phenomena. 1-Naphthyl-, 2-naphthyl-, 4-ethylphenyl-, and 4-isopropylphenyloxazaphospholidine derivatives at 0.1 mM reduced the octopamine potency at 0.1 mM more severely than the octopamine-receptor antagonists (chlordimeform and cyproheptadine) at 1 mM. 5-(2,3-Dimethoxyphenyl)-2-methoxy-1,3,2-oxazaphospholidine 2-sulfide (Ki = 107.9 μM), fenitrothion (Ki = 37.3 μM), and 3-isobutyl-1-methylxanthine (Ki = 1.5 μM) reduced the phosphodiesterase activity of beef heart in a competitive manner with respect to cyclic adenosine 3′,5′-monophosphate (cAMP). At 50 μM, salithion, salioxon (2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-oxide), and other oxazaphospholidines reduced phosphodiesterase activity. Hence, d-(-)-APE could be an agonist, and 5-PMOS and salithion analogs and fenitrothion could be partial antagonists to the octopamine receptor. The increased level of whole-body cAMP of Musca domestica and Tribolium castaneum larvae treated with these phosphorothionates is due to reduction of phosphodiesterase activity.",
author = "Akinori Hirashima and Kazuhiko Oyama and Morifusa Eto",
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T1 - Effect of insecticidal cyclic phosphorothionates on adenylate cyclase and phosphodiesterase

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N2 - Octopamine (0.1 and 1 mM) stimulated the adenylate cyclase prepared from Periplaneta americana ventral nerve cords (615 and 1112% relative to the control). d-(-)-2-Amino-1-phenylethanol (APE) was more potent than 2-amino-1-(4-fluorophenyl)ethanol (an octopamine agonist) and l-(+)-APE in stimulating the adenylate cyclase. 2-Methoxy-5-phenyl-1,3,2,-oxazaphospholidine 2-sulfide (5-PMOS) derived from dl-(±)-APE did not activate adenylate cyclase at 0.75 and 7.5 mM (91 and 95% relative to the control) but suppressed the octopamine (0.1 mM) potency to 268% at 1 mM relative to the control. Salithion (2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-sulfide) at 0.1 mM, fenitrothion (dimethyl 3-methyl-4-nitrophenyl phosphorothionate), 2-amino-1-(2,3-dimethoxy)phenylethanol, 5-PMOS, and other oxazaphospholidines at 1 mM showed similar phenomena. 1-Naphthyl-, 2-naphthyl-, 4-ethylphenyl-, and 4-isopropylphenyloxazaphospholidine derivatives at 0.1 mM reduced the octopamine potency at 0.1 mM more severely than the octopamine-receptor antagonists (chlordimeform and cyproheptadine) at 1 mM. 5-(2,3-Dimethoxyphenyl)-2-methoxy-1,3,2-oxazaphospholidine 2-sulfide (Ki = 107.9 μM), fenitrothion (Ki = 37.3 μM), and 3-isobutyl-1-methylxanthine (Ki = 1.5 μM) reduced the phosphodiesterase activity of beef heart in a competitive manner with respect to cyclic adenosine 3′,5′-monophosphate (cAMP). At 50 μM, salithion, salioxon (2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-oxide), and other oxazaphospholidines reduced phosphodiesterase activity. Hence, d-(-)-APE could be an agonist, and 5-PMOS and salithion analogs and fenitrothion could be partial antagonists to the octopamine receptor. The increased level of whole-body cAMP of Musca domestica and Tribolium castaneum larvae treated with these phosphorothionates is due to reduction of phosphodiesterase activity.

AB - Octopamine (0.1 and 1 mM) stimulated the adenylate cyclase prepared from Periplaneta americana ventral nerve cords (615 and 1112% relative to the control). d-(-)-2-Amino-1-phenylethanol (APE) was more potent than 2-amino-1-(4-fluorophenyl)ethanol (an octopamine agonist) and l-(+)-APE in stimulating the adenylate cyclase. 2-Methoxy-5-phenyl-1,3,2,-oxazaphospholidine 2-sulfide (5-PMOS) derived from dl-(±)-APE did not activate adenylate cyclase at 0.75 and 7.5 mM (91 and 95% relative to the control) but suppressed the octopamine (0.1 mM) potency to 268% at 1 mM relative to the control. Salithion (2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-sulfide) at 0.1 mM, fenitrothion (dimethyl 3-methyl-4-nitrophenyl phosphorothionate), 2-amino-1-(2,3-dimethoxy)phenylethanol, 5-PMOS, and other oxazaphospholidines at 1 mM showed similar phenomena. 1-Naphthyl-, 2-naphthyl-, 4-ethylphenyl-, and 4-isopropylphenyloxazaphospholidine derivatives at 0.1 mM reduced the octopamine potency at 0.1 mM more severely than the octopamine-receptor antagonists (chlordimeform and cyproheptadine) at 1 mM. 5-(2,3-Dimethoxyphenyl)-2-methoxy-1,3,2-oxazaphospholidine 2-sulfide (Ki = 107.9 μM), fenitrothion (Ki = 37.3 μM), and 3-isobutyl-1-methylxanthine (Ki = 1.5 μM) reduced the phosphodiesterase activity of beef heart in a competitive manner with respect to cyclic adenosine 3′,5′-monophosphate (cAMP). At 50 μM, salithion, salioxon (2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-oxide), and other oxazaphospholidines reduced phosphodiesterase activity. Hence, d-(-)-APE could be an agonist, and 5-PMOS and salithion analogs and fenitrothion could be partial antagonists to the octopamine receptor. The increased level of whole-body cAMP of Musca domestica and Tribolium castaneum larvae treated with these phosphorothionates is due to reduction of phosphodiesterase activity.

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