Amidine-Oximes: Reactivators for organophosphate exposure

Journal of Medicinal Chemistry

Volumn 54, Issue 9, 2011, Pages 3319-3330

  Kalisiak, Jarosław ^a   Ralph, Erik C ^a   Zhang, Jun ^a   Cashman, John R ^a  

^a HUMAN BIOMOLECULAR RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (BENZYLOXYIMINO) N' ETHYL N,N DIMETHYLACETIMIDAMIDE; 2 (BENZYLOXYIMINO) N,N DIMETHYL N' PROPYLACETIMIDAMIDE; 2 (BENZYLOXYIMINO) N,N DIMETHYLACETIMIDAMIDE; 2 (BENZYLOXYIMINO) N,N,N' TRIMETHYLACETIMIDAMIDE; 2 (HYDROXYIMINO) N,N DIMETHYL N' PROPYLACETIMIDAMIDE; 2 (HYDROXYIMINO) N,N DIMETHYLACETIMIDAMIDE; 2 (HYDROXYIMINO) N,N,N' TRIMETHYLACETIMIDAMIDE; ACETYLCHOLINESTERASE; AMIDINE; CHOLINESTERASE; CHOLINESTERASE REACTIVATOR; ISONITROSOACETONE; N' BUTYL 2 (HYDROXYIMINO) N,N DIMETHYLACETIMIDAMIDE; N' ETHYL 2 (HYDROXYIMINO) N,N DIMETHYLACETIMIDAMIDE; ORGANOPHOSPHATE; OXIME; PRALIDOXIME; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME REACTIVATION; FEMALE; LIPOPHILICITY; MOUSE; NONHUMAN; PKA; PROTON TRANSPORT;

ACETYLCHOLINESTERASE; AMIDINES; ANIMALS; BLOOD-BRAIN BARRIER; BUTYRYLCHOLINESTERASE; CHEMICAL WARFARE AGENTS; CHOLINESTERASE INHIBITORS; CHOLINESTERASES; ENZYME REACTIVATORS; FEMALE; HUMANS; MICE; ORGANOPHOSPHORUS COMPOUNDS; OXIMES; PERMEABILITY; PHOSPHORIC ACID ESTERS; RECOMBINANT PROTEINS; SARIN; SOMAN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79955876627     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200054r     Document Type: Article

References (36)

1. Rosenstock, L.; Keifer, M.; Daniell, W. E.; McConnell, R.; Claypoole, K. Chronic central nervous system effects of acute organophosphate pesticide intoxication. The pesticide health effects study group Lancet 1991, 338, 223-227
2. Marrs, T. C. Organophosphate poisoning Pharmacol. Ther. 1993, 58, 51-66 (Pubitemid 23227698)
3. Taylor, P. Anticholinesterase agents. In Goodman & Gilmans the Pharmacological Basis of Therapeutics, 10th ed.; Hardman, J. G.; Limbird, L. E.; Gilman, A. G., Eds.; McGraw-Hill: New York, 2001; pp 175 - 191.
4. Bajgar, J. Organophosphates/nerve agent poisoning: Mechanism of action, diagnosis, prophylaxis, and treatment Adv. Clin. Chem. 2004, 38, 151-216
5. Wilson, I. B.; Ginsburg, B. A powerful reactivator of alkylphosphate-inhibited acetylcholinesterase Biochim. Biophys. Acta 1955, 18, 168-170
6. Kuca, K.; Juna, D.; Musilek, K. Structural requirements of acetylcholinesterase reactivators Mini Rev. Med. Chem. 2006, 6, 269-277
7. Bharate, S. B.; Guo, L.; Reeves, T. E.; Cerasoli, D. M.; Thompson, C. M. Bisquaternary pyridinium oximes: Comparison of in vitro reactivation potency of compounds bearing aliphatic linkers and heteroaromatic linkers for paraoxon-inhibited electric eel and recombinant human acetylcholinesterase Bioorg. Med. Chem. 2010, 18, 787-794
8. Kuca, K.; Bartosova, L.; Jun, D.; Patocka, J.; Cabal, J.; Kassa, J.; Kunesova, G. New quaternary pyridine aldoximes as casual antidotes against nerve agents intoxications Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub 2005, 149, 75-82
9. Okumura, T.; Hisaoka, T.; Yamada, A.; Naito, T.; Isonuma, H.; Okumura, S.; Miura, K.; Sakurada, M.; Maekawa, H.; Ishimatsu, S.; Takasu, N.; Suzuki, K. The Tokyo subway sarin attack - Lessons learned Toxicol. Appl. Pharmacol. 2005, 207, 471-476
10. Bedford, C. D.; Howd, R. A.; Dailey, O. D.; Miller, A.; Nolen, H. W., 3rd; Kenley, R. A.; Kern, J. R.; Winterle, J. S. Nonquaternary cholinesterase reactivators. 3. 3(5)-Substituted 1,2,4-oxadiazol-5(3)-aldoximes and 1,2,4-oxadiazole-5(3)-thiocarbohydroximates as reactivators of organophosphonate-inhibited eel and human acetylcholinesterase in vitro J. Med. Chem. 1986, 29, 2174-2183 (Pubitemid 17182290)
11. Okuno, S.; Sakurada, K.; Ohta, H.; Ikegaya, H.; Kazui, Y.; Akutsu, T.; Takatori, T.; Iwadate, K. Blood-brain barrier penetration of novel pyridinealdoxime methiodide (PAM)-type oximes examined by brain microdialysis with LC-MS/MS Toxicol. Appl. Pharmacol. 2008, 227, 8-15 (Pubitemid 351187945)
12. Garcia, G. E.; Campbell, A. J.; Olson, J.; Moorad-Doctor, D.; Morthole, V. I. Novel oximes as blood-brain barrier penetrating cholinesterase reactivators. Chem. Biol. Interact. 2010, 187, 199-206.
13. Shih, T.-M.; Skovira, J. W.; ODonnell, J. C.; McDonough, J. H. Central acetylcholinesterase reactivation by oximes improves survival and terminates seizures following nerve agent intoxication Adv. Stud. Biol. 2009, 1, 155-196
14. Skovira, J. W.; ODonnell, J. C.; Koplovitz, I.; Kan, R. K.; McDonough, J. H.; Shih, T. M. Reactivation of brain acetylcholinesterase by monoisonitrosoacetone increases the therapeutic efficacy against nerve agents in guinea pigs Chem. Biol. Interact. 2010, 187, 318-324
15. Shek, E.; Higuchi, T.; Bodor, N. Improved delivery through biological membranes. 3. Delivery of N-methylpyridinium-2-carbaldoxime chloride through the blood-brain barrier in its dihydropyridine pro-drug form J. Med. Chem. 1976, 19, 113-117
16. Shek, E.; Higuchi, T.; Bodor, N. Improved delivery through biological membranes. 2. Distribution, excretion, and metabolism of N -methyl-1,6- dihydropyridine-2-carbaldoxime hydrochloride, a pro-drug of N -methylpyridinium-2-carbaldoxime chloride J. Med. Chem. 1976, 19, 108-112
17. Demar, J. C.; Clarkson, E. D.; Ratcliffe, R. H.; Campbell, A. J.; Thangavelu, S. G.; Herdman, C. A.; Leader, H.; Schulz, S. M.; Marek, E.; Medynets, M. A.; Ku, T. C.; Evans, S. A.; Khan, F. A.; Owens, R. R.; Nambiar, M. P.; Gordon, R. K. Pro-2-PAM therapy for central and peripheral cholinesterases Chem. Biol. Interact. 2010, 187, 191-198
18. Bodor, N.; Shek, E.; Higuchi, T. Improved delivery through biological membranes. 1. Synthesis and properties of 1-methyl-1,6-dihydropyridine-2- carbaldoxime, a pro-drug of N -methylpyridinium-2-carbaldoxime chloride J. Med. Chem. 1976, 19, 102-107
19. Jaen, J. C.; Gregor, V. E.; Lee, C.; Davis, R.; Emmerling, M. Acetylcholinesterase inhibition by fused dihydroquinazoline compounds Bioorg. Med. Chem. Lett. 1996, 6, 737-742 (Pubitemid 26107909)
20. Sauvaitre, T.; Barlier, M.; Herlem, D.; Gresh, N.; Chiaroni, A.; Guenard, D.; Guillou, C. New potent acetylcholinesterase inhibitors in the tetracyclic triterpene series J. Med. Chem. 2007, 50, 5311-5323 (Pubitemid 350057843)
21. Cereda, E.; Ezhaya, A.; Gil Quintero, M.; Bellora, E.; Dubini, E.; Micheletti, R.; Schiavone, A.; Brambilla, A.; Schiavi, G. B.; Donetti, A. Synthesis and biological evaluation of new antimuscarinic compounds with amidine basic centers. A useful bioisosteric replacement of classical cationic heads J. Med. Chem. 1990, 33, 2108-2113 (Pubitemid 20236652)
22. Jencks, W. P.; Carriuolo, J. Reactivity of nucleophilic reagents toward esters J. Am. Chem. Soc. 1960, 82, 1778-1786
23. Dijkink, J.; Eriksen, K.; Goubitz, K.; van Zanden, M. N. A.; Hiemstra, H. Synthesis and X-ray crystal structure of (S)-9-hydroxymethyl-1,5- diazabicyclo[4.3.0]non-5-ene, an enantiopure DBN-analogue Tetrahedron: Asymmetry 1996, 7, 515-524 (Pubitemid 26064703)
24. Ostendorf, M.; van der Neut, S.; Rutjes, F. P. J. T.; Hiemstra, H. Enantioselective synthesis of hydroxy-substituted DBN-type amidines as potential chiral catalysts Eur. J. Org. Chem. 2000, 2000, 105-113
25. Wolfe, S.; Akuche, C.; Ro, S.; Wilson, M.-C.; Kim, C.-K.; Shi, Z. 5-hydroxy[1,2]oxazinan-3-ones as potential carbapenem and d -Ala- d -Ala surrogates Can. J. Chem. 2003, 81, 915-936 (Pubitemid 37289757)
26. Hagedorn, I.; Stark, I.; Lorenz, H. P. Reactivation of phosphorylated acetylcholinesterase - Dependence upon activator acidity Angew. Chem., Int. Ed. Engl. 1972, 11, 307-309
27. Gray, A. P. Design and structure-activity relationships of antidotes to organophosphorus anticholinesterase agents Drug Metab. Rev. 1984, 15, 557-589 (Pubitemid 14011860)
28. Barakat, N. H.; Zheng, X.; Gilley, C. B.; MacDonald, M.; Okolotowicz, K.; Cashman, J. R.; Vyas, S.; Beck, J. M.; Hadad, C. M.; Zhang, J. Chemical synthesis of two series of nerve agent model compounds and their stereoselective interaction with human acetylcholinesterase and human butyrylcholinesterase Chem. Res. Toxicol. 2009, 22, 1669-1679
29. Gilley, C.; MacDonald, M.; Nachon, F.; Schopfer, L. M.; Zhang, J.; Cashman, J. R.; Lockridge, O. Nerve agent analogues that produce authentic soman, sarin, tabun, and cyclohexyl methylphosphonate-modified human butyrylcholinesterase Chem. Res. Toxicol. 2009, 22, 1680-1688
30. Fleisher, J. H.; Harris, L. W.; Murtha, E. F. Reactivation by pyridinium aldoxime methochloride (PAM) of inhibited cholinesterase activity in dogs after poisoning with pinacolyl methylphosphonofluoridate (soman) J. Pharmacol. Exp. Ther. 1967, 156, 345-351
31. Shih, T. M. Comparison of several oximes on reactivation of soman-inhibited blood, brain and tissue cholinesterase activity in rats Arch. Toxicol. 1993, 67, 637-646
32. Fleisher, J. H.; Harris, L. W. Dealkylation as a mechanism for aging of cholinesterase after poisoning with pinacolyl methylphosphonofluoridate Biochem. Pharmacol. 1965, 14, 641-650
33. Clement, J.; Erhardt, N. In vitro oxime-induced reactivation of various molecular forms of soman-inhibited acetylcholinesterase in striated muscle from rat, monkey and human Arch. Toxicol. 1994, 68, 648-655 (Pubitemid 24316706)
34. Kalász, H.; Hasan, M.; Sheen, R.; Kuca, K.; Petroianu, G.; Ludányi, K.; Gergely, A.; Tekes, K. HPLC analysis of K-48 concentration in plasma Anal. Bioanal. Chem. 2006, 385, 1062-1067 (Pubitemid 43992162)
35. Brimijoin, S.; Hammond, P. Butyrylcholinesterase in human brain and acetylcholinesterase in human plasma: Trace enzymes measured by two-site immunoassay J. Neurochem. 1988, 51, 1227-1231
36. Ellman, G. L.; Courtney, K. D.; Andres, V., Jr.; Feather-Stone, R. M. A new and rapid colorimetric determination of acetylcholinesterase activity Biochem. Pharmacol. 1961, 7, 88-95