Phenyl-saligenin-phosphate~PSP

neurotoxic compound for chicken, close to CBDP. Poor inhibitor of A1CHE bu potent inhibitor of NTE Neurotoxic esterase

General

Type : Organophosphate, Cyclic OP, NTE inhibitor, Not A\/B H target

Chemical_Nomenclature : 9-phenoxy-8,10-dioxa-9Nk5-phosphabicyclo[4.4.0]deca-1,3,5-triene 9-oxide

Canonical SMILES : C1C2=CC=CC=C2OP(=O)(O1)OC3=CC=CC=C3

InChI : InChI=1S\/C13H11O4P\/c14-18(16-12-7-2-1-3-8-12)15-10-11-6-4-5-9-13(11)17-18\/h1-9H,10H2

InChIKey : BXVSAYBZSGIURM-UHFFFAOYSA-N

Other name(s) : phenylsaligenin cyclic phosphate, Salioxon-phenyl, K 2 (Pesticide), PBDP, Phenylsaligenin phosphate, Phenylsaligenyl phosphate, Phenyl saligenin phosphate, CCRIS 6422, Cyclic saligenin phenyl phosphate, Phenyl saligenin cyclic phosphate, Saligenin cyclic phenyl phosphate, Phenylsalioxon


MW : 262.20

Formula : C13H11O4P

CAS_number : 4081-23-6

PubChem : 104885

UniChem : BXVSAYBZSGIURM-UHFFFAOYSA-N

Target

Families : Phenyl-saligenin-phosphate~PSP ligand of proteins in family
BCHE

References (28)

Title : Phenyl Saligenin Phosphate Disrupts Cell Morphology and the Actin Cytoskeleton in Differentiating H9c2 Cardiomyoblasts and Human-Induced Pluripotent Stem-Cell-Derived Cardiomyocyte Progenitor Cells - Felemban_2020_Chem.Res.Toxicol_33_2310
Author(s) : Felemban SG , Vyas FS , Durose L , Hargreaves AJ , Dickenson JM
Ref : Chemical Research in Toxicology , 33 :2310 , 2020
PubMedID: 32786544

Title : Phenyl Saligenin Phosphate Induced Caspase-3 and c-Jun N-Terminal Kinase Activation in Cardiomyocyte-Like Cells - Felemban_2015_Chem.Res.Toxicol_28_2179
Author(s) : Felemban SG , Garner AC , Smida FA , Boocock DJ , Hargreaves AJ , Dickenson JM
Ref : Chemical Research in Toxicology , 28 :2179 , 2015
PubMedID: 26465378

Title : Organophosphorus compound effects on neurotrophin receptors and intracellular signaling - Pomeroy-Black_2012_Toxicol.In.Vitro_26_759
Author(s) : Pomeroy-Black M , Ehrich M
Ref : Toxicol In Vitro , 26 :759 , 2012
PubMedID: 22449548

Title : Effects of phenyl saligenin phosphate on cell viability and transglutaminase activity in N2a neuroblastoma and HepG2 hepatoma cell lines - Harris_2009_Toxicol.In.Vitro_23_1559
Author(s) : Harris W , Munoz D , Bonner PL , Hargreaves AJ
Ref : Toxicol In Vitro , 23 :1559 , 2009
PubMedID: 19735718

Title : Effects of organophosphate phenyl saligenin phosphate and polyether carboxylic ionophore lasalocid on motor nerve conduction velocity, neuropathy target esterase enzyme activity, and clinical ataxia in chickens - Kart_2009_Toxicol.Mech.Methods_19_351
Author(s) : Kart A , Bilgili A
Ref : Toxicol Mech Methods , 19 :351 , 2009
PubMedID: 19778211

Title : Early effects of neuropathy-inducing organophosphates on in vivo concentrations of three neurotrophins - Pomeroy-Black_2007_Neurotox.Res_11_85
Author(s) : Pomeroy-Black MJ , Jortner BS , Ehrich MF
Ref : Neurotox Res , 11 :85 , 2007
PubMedID: 17449451

Title : Inhibition of neurite outgrowth in differentiating mouse N2a neuroblastoma cells by phenyl saligenin phosphate: effects on MAP kinase (ERK 1\/2) activation, neurofilament heavy chain phosphorylation and neuropathy target esterase activity - Hargreaves_2006_Biochem.Pharmacol_71_1240
Author(s) : Hargreaves AJ , Fowler MJ , Sachana M , Flaskos J , Bountouri M , Coutts IC , Glynn P , Harris W , Graham McLean W
Ref : Biochemical Pharmacology , 71 :1240 , 2006
PubMedID: 16499876

Title : Effects of organophosphorus compounds on ATP production and mitochondrial integrity in cultured cells - Massicotte_2005_Neurotox.Res_7_203
Author(s) : Massicotte C , Knight K , Van der Schyf CJ , Jortner BS , Ehrich M
Ref : Neurotox Res , 7 :203 , 2005
PubMedID: 15897155

Title : Altered expression of transcripts for alpha-tubulin and an unidentified gene in the spinal cord of phenyl saligenin phosphate treated hens (Gallus gallus) - Fox_2003_J.Biochem.Mol.Toxicol_17_263
Author(s) : Fox JH , Jortner BS , Barber D , Ehrich MF
Ref : J Biochem Mol Toxicol , 17 :263 , 2003
PubMedID: 14595848

Title : The catalytic domain of human neuropathy target esterase mediates an organophosphate-sensitive ionic conductance across liposome membranes - Forshaw_2001_J.Neurochem_79_400
Author(s) : Forshaw PJ , Atkins J , Ray DE , Glynn P
Ref : Journal of Neurochemistry , 79 :400 , 2001
PubMedID: 11677268

Title : Nerve conduction and ATP concentrations in sciatic-tibial and medial plantar nerves of hens given phenyl saligenin phosphate - Massicotte_2001_Neurotoxicol_22_91
Author(s) : Massicotte C , Barber DS , Jortner BS , Ehrich M
Ref : Neurotoxicology , 22 :91 , 2001
PubMedID: 11307855

Title : Organophosphorus pesticide-induced butyrylcholinesterase inhibition and potentiation of succinylcholine toxicity in mice - Sparks_1999_J.Biochem.Mol.Toxicol_13_113
Author(s) : Sparks SE , Quistad GB , Casida JE
Ref : J Biochem Mol Toxicol , 13 :113 , 1999
PubMedID: 9890196

Title : Immunohistochemical study of phosphorylated neurofilaments during the evolution of organophosphorus ester-induced delayed neuropathy (OPIDN) - Jortner_1999_Neurotoxicol_20_971
Author(s) : Jortner BS , Perkins SK , Ehrich M
Ref : Neurotoxicology , 20 :971 , 1999
PubMedID: 10693978

Title : Inhibition of carboxylesterases in SH-SY5Y human and NB41A3 mouse neuroblastoma cells by organophosphorus esters - Ehrich_1998_J.Toxicol.Environ.Health_53_385
Author(s) : Ehrich M , Correll L
Ref : J Toxicol Environ Health , 53 :385 , 1998
PubMedID: 9515941

Title : Potentiation of organophosphorus-induced delayed neurotoxicity following phenyl saligenin phosphate exposures in 2-, 5-, and 8-week- old chickens - Harp_1997_Fundam.Appl.Toxicol_37_64
Author(s) : Harp P , Tanaka D, Jr. , Pope CN
Ref : Fundamental & Applied Toxicology , 37 :64 , 1997
PubMedID: 9193923

Title : Acetylcholinesterase and neuropathy target esterase inhibitions in neuroblastoma cells to distinguish organophosphorus compounds causing acute and delayed neurotoxicity - Ehrich_1997_Fundam.Appl.Toxicol_38_55
Author(s) : Ehrich M , Correll L , Veronesi B
Ref : Fundamental & Applied Toxicology , 38 :55 , 1997
PubMedID: 9268605

Title : Comparison of the relative inhibition of acetylcholinesterase and neuropathy target esterase in rats and hens given cholinesterase inhibitors - Ehrich_1995_Fundam.Appl.Toxicol_24_94
Author(s) : Ehrich M , Jortner BS , Padilla S
Ref : Fundamental & Applied Toxicology , 24 :94 , 1995
PubMedID: 7713347

Title : Effect of cyclic phenyl saligenin phosphate and paraoxon treatment on vascular response to adrenergic and cholinergic agents in hens - McCain_1995_J.Toxicol.Environ.Health_44_167
Author(s) : McCain WC , Wilcke J , Lee JC , Ehrich M
Ref : J Toxicol Environ Health , 44 :167 , 1995
PubMedID: 7853421

Title : Interaction of organophosphorus compounds with muscarinic receptors in SH-SY5Y human neuroblastoma cells - Ehrich_1994_J.Toxicol.Environ.Health_43_51
Author(s) : Ehrich M , Intropido L , Costa LG
Ref : J Toxicol Environ Health , 43 :51 , 1994
PubMedID: 8078092

Title : Calpain activity in organophosphorus-induced delayed neuropathy (OPIDN): effects of a phenylalkylamine calcium channel blocker - el-Fawal_1993_Ann.N.Y.Acad.Sci_679_325
Author(s) : el-Fawal HA , Ehrich MF
Ref : Annals of the New York Academy of Sciences , 679 :325 , 1993
PubMedID: 8512194

Title : Local application of neuropathic organophosphorus compounds to hen sciatic nerve: inhibition of neuropathy target esterase and peripheral neurological impairments - Carrera_1992_Toxicol.Appl.Pharmacol_117_218
Author(s) : Carrera V , Barril J , Mauricio M , Pellin M , Vilanova E
Ref : Toxicol Appl Pharmacol , 117 :218 , 1992
PubMedID: 1471154

Title : Nerve conduction studies in chickens given phenyl saligenin phosphate and corticosterone - Lidsky_1990_J.Toxicol.Environ.Health_29_65
Author(s) : Lidsky TI , Manetto C , Ehrich M
Ref : J Toxicol Environ Health , 29 :65 , 1990
PubMedID: 2299688

Title : Modification of phenyl saligenin phosphate-induced delayed effects by calcium channel blockers: in vivo and in vitro electrophysiological assessment - el-Fawal_1990_Neurotoxicol_11_573
Author(s) : el-Fawal HA , Jortner BS , Ehrich M
Ref : Neurotoxicology , 11 :573 , 1990
PubMedID: 2087284

Title : Use of the biventer cervicis nerve-muscle preparation to detect early changes following exposure to organophosphates inducing delayed neuropathy - el-Fawal_1990_Fundam.Appl.Toxicol_15_108
Author(s) : el-Fawal HA , Jortner BS , Ehrich M
Ref : Fundamental & Applied Toxicology , 15 :108 , 1990
PubMedID: 2373292

Title : The biventer cervicis nerve-muscle preparation of adult hens: effects of phenyl saligenin phosphate administration - el-Fawal_1988_Neurotoxicol_9_625
Author(s) : el-Fawal HA , Jortner BS , Eyre P , Ehrich M
Ref : Neurotoxicology , 9 :625 , 1988
PubMedID: 3244445

Title : Effects of paraoxon, p-nitrophenol, phenyl saligenin cyclic phosphate, and phenol on the rat interleukin 2 system - Pruett_1988_Toxicol.Lett_40_11
Author(s) : Pruett SB , Chambers JE
Ref : Toxicol Lett , 40 :11 , 1988
PubMedID: 3257593

Title : Neuropathological effects of phenyl saligenin phosphate in chickens [corrected and republished article originally printed in Neurotoxicology 1987 Spring\;8(1):98-108] - Jortner_1987_Neurotoxicol_8_303
Author(s) : Jortner BS , Ehrich M
Ref : Neurotoxicology , 8 :303 , 1987
PubMedID: 3601242

Title : The toxic and teratogenic effects of selected organophosphorus compounds on the embryos of three species of amphibians - Fulton_1985_Toxicol.Lett_26_175
Author(s) : Fulton MH , Chambers JE
Ref : Toxicol Lett , 26 :175 , 1985
PubMedID: 4035710