메뉴 건너뛰기




Volumn 22, Issue 4, 2007, Pages 425-432

Synthesis of a novel series of non-symmetrical bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity against tabun and paraoxon-inhibited acetylcholinesterase

Author keywords

Acetylcholinesterase; Nerve agent; Oxime; Paraoxon; Pesticide; Reactivation; Tabun

Indexed keywords

1 (2 BROMOETHYLBENZYL) 3 HYDROXYIMINOMETHYLPYRIDINIUM BROMIDE; 1 (2 BROMOETHYLBENZYL) 4 HYDROXYIMINOMETHYLPYRIDINIUM BROMIDE; 1 (3 BROMOETHYLBENZYL) 3 HYDROXYIMINOMETHYLPYRIDINIUM BROMIDE; 1 (3 BROMOETHYLBENZYL) 4 HYDROXYIMINOMETHYLPYRIDINIUM BROMIDE; 1 (4 BROMOETHYLBENZYL) 3 HYDROXYIMINOMETHYLPYRIDINIUM BROMIDE; 1 (4 BROMOETHYLBENZYL) 4 HYDROXYIMINOMETHYLPYRIDINIUM BROMIDE; 2,3' BIS(HYDROXYIMINOMETHYL) 1,1' (1,2 PHENYLENEDIMETHYL) BISPYRIDINIUM DIBROMIDE; 2,3' BIS(HYDROXYIMINOMETHYL) 1,1' (1,3 PHENYLENEDIMETHYL) BISPYRIDINIUM DIBROMIDE; 2,4' BIS(HYDROXYIMINOMETHYL) 1,1' (1,2 PHENYLENEDIMETHYL) BISPYRIDINIUM DIBROMIDE; 2,4' BIS(HYDROXYIMINOMETHYL) 1,1' (1,4 PHENYLENEDIMETHYL) BISPYRIDINIUM DIBROMIDE; 3,4' BIS(HYDROXYIMINOMETHYL) 1,1' (1,2 PHENYLENEDIMETHYL) BISPYRIDINIUM DIBROMIDE; 3,4' BIS(HYDROXYIMINOMETHYL) 1,1' (1,3 PHENYLENEDIMETHYL) BISPYRIDINIUM DIBROMIDE; ACETYLCHOLINESTERASE; BIS(PYRIDINIUM OXIME) DERIVATIVE; CHOLINESTERASE REACTIVATOR; OBIDOXIME; PARAOXON; PRALIDOXIME; TABUN; UNCLASSIFIED DRUG;

EID: 34547820435     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360601164960     Document Type: Article
Times cited : (52)

References (35)
  • 1
    • 0027281533 scopus 로고
    • Organophosphate poisoning
    • Marrs, TC (1993) Organophosphate poisoning. Pharmacol Therapeut, 58, pp. 51-66.
    • (1993) Pharmacol Therapeut , vol.58 , pp. 51-66
    • Marrs, T.C.1
  • 2
    • 10044275708 scopus 로고    scopus 로고
    • Organophosphates/nerve agent poisoning: Mechanism of action, diagnosis, prophylaxis, and treatment
    • Bajgar, J. (2004) Organophosphates/nerve agent poisoning: Mechanism of action, diagnosis, prophylaxis, and treatment. Adv Clin Chem, 38, pp. 151-216.
    • (2004) Adv Clin Chem , vol.38 , pp. 151-216
    • Bajgar, J.1
  • 3
    • 23844544475 scopus 로고    scopus 로고
    • Organophosphorus flame retardants and plasticizers in air from various indoor environments
    • Marklund, A., Andersson, B. and Haglund, P. (2005) Organophosphorus flame retardants and plasticizers in air from various indoor environments. J Environ Monit, 7, pp. 814-819.
    • (2005) J Environ Monit , vol.7 , pp. 814-819
    • Marklund, A.1    Andersson, B.2    Haglund, P.3
  • 4
    • 0032940239 scopus 로고    scopus 로고
    • Metrifonate (Trichlorfon): A review of the pharmacology, pharmacokinetics and clinical experience with a new acetylcholinesterase inhibitor for Alzheimer's disease
    • Ringman, JM and Cummings, JL (1999) Metrifonate (Trichlorfon): A review of the pharmacology, pharmacokinetics and clinical experience with a new acetylcholinesterase inhibitor for Alzheimer's disease. Opin Invest Drugs, 8, pp. 463-471.
    • (1999) Opin Invest Drugs , vol.8 , pp. 463-471
    • Ringman, J.M.1    Cummings, J.L.2
  • 5
    • 0034007911 scopus 로고    scopus 로고
    • Organophosphates and their impact on the global environment
    • Satoh, T. and Hosokawa, M. (2000) Organophosphates and their impact on the global environment. Neurotoxicol, 21, pp. 223-227.
    • (2000) Neurotoxicol , vol.21 , pp. 223-227
    • Satoh, T.1    Hosokawa, M.2
  • 7
    • 0036359395 scopus 로고    scopus 로고
    • The influence of anticholinergic drug and oxime selection on the effectiveness of antidotal treatment against tabun-induced poisoning in mice
    • Kassa, J. (2002) The influence of anticholinergic drug and oxime selection on the effectiveness of antidotal treatment against tabun-induced poisoning in mice. Acta Medica, 45, pp. 75-78.
    • (2002) Acta Medica , vol.45 , pp. 75-78
    • Kassa, J.1
  • 8
    • 29944445608 scopus 로고    scopus 로고
    • Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): In vitro effect of tiapride
    • Petroianu, GA, Hasan, MY, Arafat, K., Nurulain, SM and Schmitt, A. (2005) Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): In vitro effect of tiapride. J Appl Toxicol, 25, pp. 562-567.
    • (2005) J Appl Toxicol , vol.25 , pp. 562-567
    • Petroianu, G.A.1    Hasan, M.Y.2    Arafat, K.3    Nurulain, S.M.4    Schmitt, A.5
  • 9
    • 0024786306 scopus 로고
    • Pharmacology of HI-6, an H-series oxime
    • Rousseaux, CG and Dua, AK (1989) Pharmacology of HI-6, an H-series oxime. Can J Physiol Pharmacol, 67, pp. 1183-1189.
    • (1989) Can J Physiol Pharmacol , vol.67 , pp. 1183-1189
    • Rousseaux, C.G.1    Dua, A.K.2
  • 10
    • 0002654601 scopus 로고    scopus 로고
    • The choice: HI-6,. pralidoxime or obidoxime against nerve agents?
    • Kassa, J., Cabal, J., Bajgar, J. and Szinicz, L. (1997) The choice: HI-6,. pralidoxime or obidoxime against nerve agents?. ASA Newslett, 97, pp. 16-18.
    • (1997) ASA Newslett , vol.97 , pp. 16-18
    • Kassa, J.1    Cabal, J.2    Bajgar, J.3    Szinicz, L.4
  • 11
    • 10044256187 scopus 로고    scopus 로고
    • Antidotal treatment of GF-agent intoxication in mice with bispyridinium oximes
    • Sevelova, L., Kuca, K. and Krejcova-Kunesova, G. (2005) Antidotal treatment of GF-agent intoxication in mice with bispyridinium oximes. Toxicol, 207, pp. 1-6.
    • (2005) Toxicol , vol.207 , pp. 1-6
    • Sevelova, L.1    Kuca, K.2    Krejcova-Kunesova, G.3
  • 12
    • 17744420458 scopus 로고    scopus 로고
    • A comparison of the ability of new bispyridinium oxime 1-(4-hydroxyiminomethylpyridinium)-4-(4-carbamoylpyridinium)butane dibromide and currently used oximes to reactivate nerve agent-inhibited rat brain acetylcholinesterase by in vivo methods
    • Kuca, K. and Kassa, J. (2003) A comparison of the ability of new bispyridinium oxime 1-(4-hydroxyiminomethylpyridinium)-4-(4-carbamoylpyridinium)butane dibromide and currently used oximes to reactivate nerve agent-inhibited rat brain acetylcholinesterase by in vivo methods. J Enz Inhib Med Chem, 18, pp. 529-535.
    • (2003) J Enz Inhib Med Chem , vol.18 , pp. 529-535
    • Kuca, K.1    Kassa, J.2
  • 13
    • 10744232850 scopus 로고    scopus 로고
    • Reactivation of cyclosarin-inhibited rat brain acetylcholinesterase by pyridinium-oximes
    • Kuca, K. and Patocka, J. (2004) Reactivation of cyclosarin-inhibited rat brain acetylcholinesterase by pyridinium-oximes. J Enz Inhib Med Chem, 19, pp. 39-43.
    • (2004) J Enz Inhib Med Chem , vol.19 , pp. 39-43
    • Kuca, K.1    Patocka, J.2
  • 15
    • 29644446302 scopus 로고    scopus 로고
    • Synthesis of the novel series of bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase
    • Musilek, K., Kuca, K., Jun, D., Dohnal, V. and Dolezal, M. (2006) Synthesis of the novel series of bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase. Bioorg Med Chem Lett, 16, pp. 622-627.
    • (2006) Bioorg Med Chem Lett , vol.16 , pp. 622-627
    • Musilek, K.1    Kuca, K.2    Jun, D.3    Dohnal, V.4    Dolezal, M.5
  • 16
    • 28244442740 scopus 로고    scopus 로고
    • Synthesis of a novel series of bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase
    • Musilek, K., Kuca, K., Jun, D., Dohnal, V. and Dolezal, M. (2005) Synthesis of a novel series of bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase. J Enz Inhib Med Chem, 20, pp. 409-415.
    • (2005) J Enz Inhib Med Chem , vol.20 , pp. 409-415
    • Musilek, K.1    Kuca, K.2    Jun, D.3    Dohnal, V.4    Dolezal, M.5
  • 19
    • 27444442890 scopus 로고    scopus 로고
    • Oxime reactivation of acetylcholinesterase inhibited by toxic phosporus ester: In vitro kinetics and thermodynamics
    • Patocka, J., Cabal, J., Kuca, K. and Jun, D. (2005) Oxime reactivation of acetylcholinesterase inhibited by toxic phosporus ester: In vitro kinetics and thermodynamics. J Appl Biomed, 3, pp. 91-99.
    • (2005) J Appl Biomed , vol.3 , pp. 91-99
    • Patocka, J.1    Cabal, J.2    Kuca, K.3    Jun, D.4
  • 20
    • 17444416083 scopus 로고    scopus 로고
    • A comparison of the potency of newly developed oximes (K005, K027, K033, K048) and currently used oximes (pralidoxime, obidoxime, HI-6) to reactivate sarin-inhibited rat brain acetylcholinesterase by in vitro methods
    • Kuca, K., Cabal, J. and Kassa, J. (2005) A comparison of the potency of newly developed oximes (K005, K027, K033, K048) and currently used oximes (pralidoxime, obidoxime, HI-6) to reactivate sarin-inhibited rat brain acetylcholinesterase by in vitro methods. J Toxicol Env Health A, 68, pp. 677-686.
    • (2005) J Toxicol Env Health A , vol.68 , pp. 677-686
    • Kuca, K.1    Cabal, J.2    Kassa, J.3
  • 21
    • 22844435631 scopus 로고    scopus 로고
    • In vitro reactivation potency of some acetylcholinesterase reactivators against sarin- and cyclosarin-induced inhibitions
    • Kuca, K., Cabal, J., Jun, D., Kassa, J., Bartosova, L. and Kunesova, G. (2005) In vitro reactivation potency of some acetylcholinesterase reactivators against sarin- and cyclosarin-induced inhibitions. J Appl Toxicol, 25, pp. 296-300.
    • (2005) J Appl Toxicol , vol.25 , pp. 296-300
    • Kuca, K.1    Cabal, J.2    Jun, D.3    Kassa, J.4    Bartosova, L.5    Kunesova, G.6
  • 22
    • 23444441949 scopus 로고    scopus 로고
    • Evaluation of newly synthesized reactivators of the brain cholinesterase inhibited by sarin nerve agent
    • Kuca, K. and Cabal, J. (2005) Evaluation of newly synthesized reactivators of the brain cholinesterase inhibited by sarin nerve agent. Toxicol Mech Method, 15, pp. 247-252.
    • (2005) Toxicol Mech Method , vol.15 , pp. 247-252
    • Kuca, K.1    Cabal, J.2
  • 23
    • 0017614170 scopus 로고
    • In vitro inhibition of soluble brain acetylcholinesterase by organophosphates of the O-ethyl-S-(dialkylaminoethyl)-methylphosphonothiolate type
    • Bajgar, J. and Patocka, J. (1977) In vitro inhibition of soluble brain acetylcholinesterase by organophosphates of the O-ethyl-S-(dialkylaminoethyl)-methylphosphonothiolate type. Coll Czech Chem Commun, 42, pp. 770-776.
    • (1977) Coll Czech Chem Commun , vol.42 , pp. 770-776
    • Bajgar, J.1    Patocka, J.2
  • 24
    • 4744354029 scopus 로고    scopus 로고
    • Specification of the structure of oximes able to reactivate tabun-inhibited acetylcholinesterase
    • Cabal, J., Kuca, K. and Kassa, J. (2004) Specification of the structure of oximes able to reactivate tabun-inhibited acetylcholinesterase. Basic Clin Pharmacol Toxicol, 95, pp. 81-86.
    • (2004) Basic Clin Pharmacol Toxicol , vol.95 , pp. 81-86
    • Cabal, J.1    Kuca, K.2    Kassa, J.3
  • 26
    • 0027481819 scopus 로고
    • Ion channel blockade by oximes and recovery of diaphragm muscle from soman poisoning in vitro
    • Tattersall, JE (1993) Ion channel blockade by oximes and recovery of diaphragm muscle from soman poisoning in vitro. Br J Pharmacol, 108, pp. 1006-1015.
    • (1993) Br J Pharmacol , vol.108 , pp. 1006-1015
    • Tattersall, J.E.1
  • 27
    • 19544367621 scopus 로고    scopus 로고
    • Design and synthesis of new bis-pyridinium oxime reactivators for acetylcholinesterase inhibited by organophosphorous nerve agents
    • Kim, TH, Kuca, K., Jun, D. and Jung, YS (2005) Design and synthesis of new bis-pyridinium oxime reactivators for acetylcholinesterase inhibited by organophosphorous nerve agents. Bioorg Med Chem Lett, 15, pp. 2914-2917.
    • (2005) Bioorg Med Chem Lett , vol.15 , pp. 2914-2917
    • Kim, T.H.1    Kuca, K.2    Jun, D.3    Jung, Y.S.4
  • 29
    • 7444221716 scopus 로고    scopus 로고
    • Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes
    • Worek, F., Thiermann, H., Szinicz, L. and Eyer, P. (2004) Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes. Biochem Pharmacol, 68, pp. 2237-2248.
    • (2004) Biochem Pharmacol , vol.68 , pp. 2237-2248
    • Worek, F.1    Thiermann, H.2    Szinicz, L.3    Eyer, P.4
  • 30
    • 17444446525 scopus 로고    scopus 로고
    • Synthesis of a new reactivator of tabun-inhibited acetylcholinesterase
    • Kuca, K., Bielavsky, J., Cabal, J. and Kassa, J. (2003) Synthesis of a new reactivator of tabun-inhibited acetylcholinesterase. Bioorg Med Chem Lett, 13, pp. 3545-3547.
    • (2003) Bioorg Med Chem Lett , vol.13 , pp. 3545-3547
    • Kuca, K.1    Bielavsky, J.2    Cabal, J.3    Kassa, J.4
  • 31
    • 0037492336 scopus 로고    scopus 로고
    • Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators
    • Pang, YP, Kollmeyer, TM, Hong, F., Lee, JC, Hammond, PI, Haugabouk, SP and Brimijoin, S. (2003) Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators. Chem Biol, 10, pp. 491-502.
    • (2003) Chem Biol , vol.10 , pp. 491-502
    • Pang, Y.P.1    Kollmeyer, T.M.2    Hong, F.3    Lee, J.C.4    Hammond, P.I.5    Haugabouk, S.P.6    Brimijoin, S.7
  • 32
    • 19844367066 scopus 로고    scopus 로고
    • Quaternary salts of 4,3' and 4,4' bis-pyridinium monooximes: Synthesis and biological activity
    • Chennamaneni, SR, Vobalaboina, V. and Garlapati, A. (2005) Quaternary salts of 4,3' and 4,4' bis-pyridinium monooximes: Synthesis and biological activity. Bioorg Med Chem Lett, 15, pp. 3076-3080.
    • (2005) Bioorg Med Chem Lett , vol.15 , pp. 3076-3080
    • Chennamaneni, S.R.1    Vobalaboina, V.2    Garlapati, A.3
  • 33
    • 33644816547 scopus 로고    scopus 로고
    • Quaternary salts of 4,3' and 4,4' bis-pyridinium monooximes
    • Rao, C Srinivas, Venkateswarlu, V. and Achaiah, G. (2006) Quaternary salts of 4,3' and 4,4' bis-pyridinium monooximes. Part 2: Synthesis and biological activity. Bioorg Med Chem Lett, pp. 2134-2138.
    • (2006) Bioorg Med Chem Lett , pp. 2134-2138
    • Rao, C.S.1    Venkateswarlu, V.2    Achaiah, G.3
  • 34
    • 0019842460 scopus 로고
    • Nonquaternary cholinesterase reactivators
    • Kenley, RA, Howd, RA, Mosher, CW and Winterle, JS (1981) Nonquaternary cholinesterase reactivators. Dialkylaminoalkyl thioesters of alpha-ketothiohydroximic acids as reactivators of diisopropyl phosphorofluoridate inhibited acetylcholinesterase. J Med Chem, 24, pp. 1124-1133.
    • (1981) J Med Chem , vol.24 , pp. 1124-1133
    • Kenley, R.A.1    Howd, R.A.2    Mosher, C.W.3    Winterle, J.S.4
  • 35
    • 0022202576 scopus 로고
    • Reactivation of ethyl methylphosphonylated eel acetylcholinesterase in vitro by 2PAM, H16, and a series of nonquaternary alpha-ketothiohydroximates
    • Kenley, RA, Bedford, CD, Howd, RA and Jackson, SE (1985) Reactivation of ethyl methylphosphonylated eel acetylcholinesterase in vitro by 2PAM, H16, and a series of nonquaternary alpha-ketothiohydroximates. Biochem Pharmacol, 34, pp. 3606-3608.
    • (1985) Biochem Pharmacol , vol.34 , pp. 3606-3608
    • Kenley, R.A.1    Bedford, C.D.2    Howd, R.A.3    Jackson, S.E.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.