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 AlphaBeta Hydrolase 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 |
| Abstract : |
| PubMedSearch : Felemban_2020_Chem.Res.Toxicol_33_2310 |
| 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 |
| Abstract : |
| PubMedSearch : Felemban_2015_Chem.Res.Toxicol_28_2179 |
| 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 |
| Abstract : |
| PubMedSearch : Pomeroy-Black_2012_Toxicol.In.Vitro_26_759 |
| 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 |
| Abstract : |
| PubMedSearch : Harris_2009_Toxicol.In.Vitro_23_1559 |
| 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 |
| Abstract : |
| PubMedSearch : Kart_2009_Toxicol.Mech.Methods_19_351 |
| 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 |
| Abstract : |
| PubMedSearch : Pomeroy-Black_2007_Neurotox.Res_11_85 |
| 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 |
| Abstract : |
| PubMedSearch : Hargreaves_2006_Biochem.Pharmacol_71_1240 |
| 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 |
| Abstract : |
| PubMedSearch : Massicotte_2005_Neurotox.Res_7_203 |
| 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 |
| Abstract : |
| PubMedSearch : Fox_2003_J.Biochem.Mol.Toxicol_17_263 |
| PubMedID: 14595848 |
| 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 |
| Abstract : |
| PubMedSearch : Massicotte_2001_Neurotoxicol_22_91 |
| PubMedID: 11307855 |
| 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 |
| Abstract : |
| PubMedSearch : Forshaw_2001_J.Neurochem_79_400 |
| PubMedID: 11677268 |
| 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 |
| Abstract : |
| PubMedSearch : Jortner_1999_Neurotoxicol_20_971 |
| PubMedID: 10693978 |
| 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 |
| Abstract : |
| PubMedSearch : Sparks_1999_J.Biochem.Mol.Toxicol_13_113 |
| PubMedID: 9890196 |
| 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 |
| Abstract : |
| PubMedSearch : Ehrich_1998_J.Toxicol.Environ.Health_53_385 |
| PubMedID: 9515941 |
| 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 |
| Abstract : |
| PubMedSearch : Ehrich_1997_Fundam.Appl.Toxicol_38_55 |
| PubMedID: 9268605 |
| 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 |
| Abstract : |
| PubMedSearch : Harp_1997_Fundam.Appl.Toxicol_37_64 |
| PubMedID: 9193923 |
| 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 |
| Abstract : |
| PubMedSearch : Ehrich_1995_Fundam.Appl.Toxicol_24_94 |
| 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 |
| Abstract : |
| PubMedSearch : McCain_1995_J.Toxicol.Environ.Health_44_167 |
| 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 |
| Abstract : |
| PubMedSearch : Ehrich_1994_J.Toxicol.Environ.Health_43_51 |
| 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 |
| Abstract : |
| PubMedSearch : el-Fawal_1993_Ann.N.Y.Acad.Sci_679_325 |
| 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 |
| Abstract : |
| PubMedSearch : Carrera_1992_Toxicol.Appl.Pharmacol_117_218 |
| 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 |
| Abstract : |
| PubMedSearch : Lidsky_1990_J.Toxicol.Environ.Health_29_65 |
| 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 |
| Abstract : |
| PubMedSearch : el-Fawal_1990_Neurotoxicol_11_573 |
| 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 |
| Abstract : |
| PubMedSearch : el-Fawal_1990_Fundam.Appl.Toxicol_15_108 |
| PubMedID: 2373292 |
| 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 |
| Abstract : |
| PubMedSearch : Pruett_1988_Toxicol.Lett_40_11 |
| PubMedID: 3257593 |
| 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 |
| Abstract : |
| PubMedSearch : el-Fawal_1988_Neurotoxicol_9_625 |
| PubMedID: 3244445 |
| 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 |
| Abstract : |
| PubMedSearch : Jortner_1987_Neurotoxicol_8_303 |
| 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 |
| Abstract : |
| PubMedSearch : Fulton_1985_Toxicol.Lett_26_175 |
| PubMedID: 4035710 |