Structure-toxicity relationships of thiono and seleno phosphoramidate compounds: New type of acetylcholinesterase inhibitors

Molecular Diversity

Volumn 11, Issue 1, 2007, Pages 47-57

  Dehghanpour, Saeed ^a   Rasmi, Yousef ^b   Bagheri, Minoo ^a  

^a ALZAHRA UNIVERSITY   (Iran)

^b URMIA UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Human acetylcholinesterase; Hydrophobicity; IC 50; Inhibitor; Phosphoramidate; Synthesis

Indexed keywords

CHOLINESTERASE INHIBITOR; PHOSPHORAMIDIC ACID DERIVATIVE; SELENIUM DERIVATIVE;

ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVITY; ERYTHROCYTE; HUMAN; HUMAN CELL; HYDROPHOBICITY; IC 50; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; AMIDES; CHOLINESTERASE INHIBITORS; ERYTHROCYTES; HUMANS; HYDROPHOBICITY; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS; PHOSPHORIC ACIDS; SELENIUM; SPECTROPHOTOMETRY, INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR COMPOUNDS;

EID: 34247355562     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-007-9056-6     Document Type: Article

References (36)

1. Cohen SD, Williams RA, Killinger JM, Freudenthal RI (1985) Comparative sensitivity of bovine and rodent acetylcholinesterase to in vitro inhibition by organophosphate insecticides. Toxicol Appl Pharmacol 83:452-459
2. Pardio VT, Ibarra N, Rodriguez MA (2001) Use of cholinesterase activity in monitoring organophosphate pesticide exposure of cattle produced in tropical areas. J Agric Food Chem 9:6057-6052
3. Quistad GB, Zhang N, Sparks SE, Casida JE (2000) Phosphoacetylcholinesterase: toxicity of phosphorus oxychloride to mammals and insects that can be attributed to selective phosphorylation of acetylcholinesterase by phosphorodichloridic acid. Chem Res Toxicol 13:652-657
4. Mallender WD, Szegletes T, Rosenberry TL (2000) Acetylthiocholine binds to Asp74 at the peripheral site of human acetylcholinesterase at the first step in the catalytic pathway. Biochem 39:7753-7763
5. Massoulie J, Pezzementi L, Bon S, Krejci E, Vallette FM (1993) Molecular and cellular biology of cholinesterases, prog. Neurobiol 41:31-91
6. Casale GP, bavari S, Connolly J (1989) Inhibition of human serum complements activity by diisopropylfluorophosphates and selected anticholinestrase insecticides. Fundam Appl Toxicol 12:460-468
7. Jokanovic M, Maksimovic M, Kilibarda V, Jovanovic D, Savic D (1996) Qxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates. Toxicol Lett 85:35-39
8. Vilanova E, Johnson MK, Vicedo JL (1987) Interaction of some unsubstituted phosphoramidate analogs of methamidophos (O, S-dimethyl phosphorothioamidate) with acetylcholinesterase and neuropathy target esterase of hen brain. Pestic Biochem Physiol 28:224-238
9. Maxwell DM, Brecht KM (1992) Quantitative structure-activity analysis of acetylcholinesterase inhibition by oxono and thiono analogs of organophosphorus compounds. Chem Res Toxicol 5:66-71
10. Thompson CM, Frick JA, Natke BC, Hansen LK (1989) Preparetion, analysis and anticholinesterase properties of O, O-dimethyl phosphorothioate isomerides. Chem Res Toxicol 2:386-391
11. Yang H-Z, Zhang Y-J, Wang L-X, Tan H-F, Cheng MR, Xing X-D, Chen R-Y, Fujita T (1986) Quantitative structure-activity study of herbicidal O-aryl O-ethyl Nisopropylphosphoramidothioates Pesticide. Biochem Physiol 26:275-283
12. 3, and their diethyl esters) are anticholinesterase agents directly or on activation. Chem Res Toxicol 16:350-356
13. Ryu S, Lin J, Thompson CM (1991) Comparative anticholinesterase potency of chiral isoparathion methyl. Chem Res Toxicol 4:517-520
14. Metcalf RL, Francis BM, Metcalf RA, Farage-Elawar M, Hansen LG (1988) Structure- activity relationships in the acute and delayed neurotoxicity of methyl- and etylphosphonothionates. Pestic Biochem Physiol 30:46-56
15. Levi PE, Hollingworth RM, Hodgson E (1998) Differences in oxidative dearylation and desulfurration of fenitrothion by cytochrome p-450 isozymes and in the subsequent inhibition of monooxygenase activity. Pestic Biochem Physiol 32:224-231
16. Lee H, Kim YA, Cho YA, Lee YT (2002) Oxidation of organophosphorus pesticides for the sensitive detection by a cholinesterase-based biosensor. Chemosphere 46:571-576
17. Casida JE (1964) Esterase inhibitors as pesticides. Science 146:1011-1017
18. Chevykalova MN, Manzhukova LF, Artemova NV, Luzikov YN, Nifant'ev IE, Nifant'ev EE (2003) Electron-donating ability of triarylphosphines and related compounds studied by P-31 NMR spectroscopy. Russ Chem Bull 52:78-84
19. 4. Inorg Chim Acta 277:163-170
20. 4NH-1,2). J Organomet Chem 623:116-119
21. 2NPr, Polyhedron 23:1923-1929
22. 2 (E = S or Se). J Organomet Chem 690:4001-4017
23. Bayandina EV, Nuretdinov IA, Nurmukhamedova LV (1978) Synthesis of arylselenophosphinic acid derivatives and their properties. J Gen Chem USSR 48:2673-2677
24. 2 (E, E′ = Se, E = Se, E′ = S, E = S, E′ = O, E,E′ = O. Inorg Chim Acta 290:1-7
25. Schultz TW, Cronin MTD, Walker JD, Aptula AO (2003) Quantitative structure-activity relationships (QSARs) in toxicology: a historical perspective. J Mol Struct (Theochem), 622: 1-22
26. Karelson M, Lobanov VS, Katritzky AR (1996) Quantum-chemical descriptors in QSAR/QSPR studies. Chem Rev 96:1027-1044
27. Lewis DF V (2004) Quantitative structure-activity relationships (QSARs) for substrates of human cytochromes P450 CYP2 family enzymes. Toxicol In Vitro 18:89-97
28. Hansch C, Steinmetz WE, Leo AJ, Mekapati SB, Kurup A, Hoekman D (2003) On the role of polarizability in chemical-biological interactions. J Chem Inf Comput Sci 43:120-125
29. Hansch C, Dunn W (1972) Linear relationships between lipophilic chatacter and biological activity of drugs. J Pharm Sci-Us 61:1-19
30. Henchman RH, Tai K, Shen T, MaCammon JA (2002) Properties of water molecules in the active site gorge of acetylcholinesterase from computer simulation. Biophys J 82:2671-2682
31. Doorn JA, Gage DA, Schall M, Talley TT, Thompson CM, Richardson RJ (2000) Inhibition of acetylcholinesterase by (1S,3S)-isomalathion proceeds with loss of thiomethyl: kinetic and mass spectral evidence for an unexpected primary leaving group. Chem Res Toxicol 13:1313-1320
32. Barak D, Ordentlich A, Kaplan D, Barak R, Mizrahi D, Kronman C, Segall Y, Velan B, Shafferman A (2000) Evidence for P-N bond scission in phosphoroamidate nerve agent adducts of human acetylcholinesterase. Biochem 39:1156-1161
33. Tompson CM, Suarez AI, Rodriguez OP (1996) Synthesis and 31P chemical shift identification of tripeptide active site models that represent human serum acetylcholinesterase covalently modified at serine by certain organophosphates. Chem Res Toxicol 9:1325-1332
34. Corbridge DEC (1995) Phosphorus, an outline of its chemistry, biochemistry and technology. 5th edn. Elsevier, The Netherlands
35. Ellman GL, Courinfy KD, Andress V, Featherstone RM (1961) A new and rapid colorimetric determination of acethylcholinesterase activity. Biochem Pharmacol 7:88-95
36. Lee BH, Stelly TC, Colucci WJ, Garcia GJ, Gandour RD, Quinn DM (1992) Inhibition of acetylcholinesterase by hemicholiniums, conformationally constrained choline analogs. Evaluation of aryl and alkyl substituents. Comparisons with choline and (3-hydroxyphenyl) trimethylammonium. Chem Res Toxicol 5:411-418