메뉴 건너뛰기




Volumn 78, Issue , 2014, Pages 455-467

Design, synthesis and biological evaluation of novel tetrahydroacridine pyridine- Aldoxime and -Amidoxime hybrids as efficient uncharged reactivators of nerve agent-Inhibited human acetylcholinesterase

Author keywords

Hybrids; Organophosphorus nerve agents; Oximes; Pyridinaldoximes; Reactivation of acetylcholinesterase; Tacrine

Indexed keywords

1,2,3,4 TETRAHYDRO 9 AMINOACRIDINE A HYDROXYPYRIDINE ALDOXIME; 1,2,3,4 TETRAHYDRO 9 AMINOACRIDINE ALPHA HYDROXYPYRIDINE AMIDOXIME; 1,2,3,4 TETRAHYDRO 9 THIOACRIDINE HYDROXYPYRIDINE ALDOXIME; 2 [(1E)(HYDROXYIMINO)METHYL] 6 [5 [(1,2,3,4 TETRAHYDROACRIDIN 9 YL)AMINO]PENTY]PYRIDIN 3 OL; 2 [1 (HYDROXYIMINO)METHYL] 6 [4 [(1,2,3,4 TETRAHYDROACRIDIN 9 YL)AMINO]BUTYL]PYRIDIN 3 OL; 3 HYDROXY 6 [4 [(1,2,3,4 TETRAHYDROACRIDIN 9 YL)AMINO]BUTYL]PYRIDINE 2 CARBALDEHYDE; 3 HYDROXY 6 [5 [(1,2,3,4 TETRAHYDROACRIDIN 9 YL)AMINO]PENTYL]PYRIDINE 2 CARBALDEHYDE; ACETYLCHOLINESTERASE; ALDOXIME; AMIDOXIME; HETERODIMER; METHYL 3 (BENZYLOXY) 6 [4 [(1,2,3,4 TETRAHYDROACRIDIN 9 YL)AMINO]BUT 1 YN 1 YL]PYRIDINE 2 CARBOXYLATE; METHYL 3 (BENZYLOXY) 6 [5 [(1,2,3,4 TETRAHYDROACRIDIN 9 YL)AMINO]PENT 1 YN 1 YL]PYRIDINE 2 CARBOXYLATE; METHYL 3 (BENZYLOXY) 6 [5 [(1,2,3,4 TETRAHYDROACRIDIN 9 YL)AMINO]PENTYL]PYRIDINE 2 CARBOXYLATE; METHYL 3 HYDROXY 6 [4 [(1,2,3,4 TETRAHYDROACRIDIN 9 YL)AMINO]BUTYL]PYRIDINE 2 CARBOXYLATE; METHYLPHOSPHONOTHIOIC ACID S (2 DIISOPROPYLAMINOETHYL) O ETHYL ESTER; PARAOXON; PYRIDINE DERIVATIVE; TABUN; TACRINE DERIVATIVE; UNCLASSIFIED DRUG; ACETALDOXIME; AMIDE; CHEMICAL WARFARE AGENT; CHOLINESTERASE INHIBITOR; OXIME; PYRIDINE; TACRINE;

EID: 84898755282     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.03.044     Document Type: Article
Times cited : (75)

References (51)
  • 3
    • 0027281533 scopus 로고
    • Organophosphate poisoning
    • T.C. Marrs Organophosphate poisoning Phamacology Therapy 58 1993 51 66
    • (1993) Phamacology Therapy , vol.58 , pp. 51-66
    • Marrs, T.C.1
  • 6
    • 38949115211 scopus 로고    scopus 로고
    • Management of acute organophosphorus pesticide poisoning
    • M. Eddleston, N.A. Buckley, P. Eyer, and A.H. Dawson Management of acute organophosphorus pesticide poisoning Lancet 371 2008 597 607
    • (2008) Lancet , vol.371 , pp. 597-607
    • Eddleston, M.1    Buckley, N.A.2    Eyer, P.3    Dawson, A.H.4
  • 11
    • 77149153494 scopus 로고    scopus 로고
    • Central acetylcholinesterase reactivation by oximes improves survival and terminates seizures following nerve agent intoxication
    • T.M. Shih, J.W. Skovira, J.C. O'Donnell, and J.H. McDonough Central acetylcholinesterase reactivation by oximes improves survival and terminates seizures following nerve agent intoxication Advanced Studies in Biology 1 2009 155 196
    • (2009) Advanced Studies in Biology , vol.1 , pp. 155-196
    • Shih, T.M.1    Skovira, J.W.2    O'Donnell, J.C.3    McDonough, J.H.4
  • 12
    • 80051814613 scopus 로고    scopus 로고
    • Peripheral site ligand conjugation to a non-quaternary oxime enhances reactivation of nerve agent-inhibited human acetylcholinesterase
    • M.C. de Koning, M. van Grol, and D. Noort Peripheral site ligand conjugation to a non-quaternary oxime enhances reactivation of nerve agent-inhibited human acetylcholinesterase Toxicology Letters 206 2011 54 59
    • (2011) Toxicology Letters , vol.206 , pp. 54-59
    • De Koning, M.C.1    Van Grol, M.2    Noort, D.3
  • 16
    • 84855849461 scopus 로고    scopus 로고
    • Nonquaternary reactivators for organophosphate-inhibited cholinesterases
    • J. Kalisiak, E.C. Ralph, and J.R. Cashman Nonquaternary reactivators for organophosphate-inhibited cholinesterases Journal of Medicinal Chemistry 55 2012 465 474
    • (2012) Journal of Medicinal Chemistry , vol.55 , pp. 465-474
    • Kalisiak, J.1    Ralph, E.C.2    Cashman, J.R.3
  • 18
    • 79960566938 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of new alpha-nucleophiles for the hydrolysis of organo-phosphorus nerve agents: Application to the reactivation of phosphorylated AChE
    • G. Saint-André, M. Kliachyna, S. Kodepelly, L. Louise-Leriche, E. Gillon, P.-Y. Renard, F. Nachon, R. Baati, and A. Wagner Design, synthesis, and evaluation of new alpha-nucleophiles for the hydrolysis of organo-phosphorus nerve agents: application to the reactivation of phosphorylated AChE Tetrahedron 67 2011 6352 6361
    • (2011) Tetrahedron , vol.67 , pp. 6352-6361
    • Saint-André, G.1    Kliachyna, M.2    Kodepelly, S.3    Louise-Leriche, L.4    Gillon, E.5    Renard, P.-Y.6    Nachon, F.7    Baati, R.8    Wagner, A.9
  • 23
    • 84896502407 scopus 로고    scopus 로고
    • Tryptoline-3-hydroxypyridinaldoxime conjugates as efficient reactivators of phosphylated human acetyl and butyrylcholinesterases
    • J. Renou, M. Loiodice, M. Arboléas, R. Baati, L. Jean, F. Nachon, and P.-Y. Renard Tryptoline-3-hydroxypyridinaldoxime conjugates as efficient reactivators of phosphylated human acetyl and butyrylcholinesterases Chemical Communications 50 2014 3947 3950
    • (2014) Chemical Communications , vol.50 , pp. 3947-3950
    • Renou, J.1    Loiodice, M.2    Arboléas, M.3    Baati, R.4    Jean, L.5    Nachon, F.6    Renard, P.-Y.7
  • 24
    • 0037756828 scopus 로고    scopus 로고
    • Inhibition of cholinesterases with cationic phosphonyl oximes highlights distinctive properties of the charged pyridine groups of quaternary oxime reactivators
    • Y. Ashani, A.K. Bhattacharjee, H. Leader, A. Saxena, and B.P. Doctor Inhibition of cholinesterases with cationic phosphonyl oximes highlights distinctive properties of the charged pyridine groups of quaternary oxime reactivators Biochemical Pharmacology 66 2003 191 202
    • (2003) Biochemical Pharmacology , vol.66 , pp. 191-202
    • Ashani, Y.1    Bhattacharjee, A.K.2    Leader, H.3    Saxena, A.4    Doctor, B.P.5
  • 25
    • 33646063571 scopus 로고    scopus 로고
    • Conformational flexibility in the peripheral site of Torpedo californica acetylcholinesterase revealed by the complex structure with a bifunctional inhibitor
    • J.P. Colletier, B. Sanson, F. Nachon, E. Gabellieri, C. Fattorusso, G. Campiani, and M. Weik Conformational flexibility in the peripheral site of Torpedo californica acetylcholinesterase revealed by the complex structure with a bifunctional inhibitor Journal of the American Chemical Society 128 2006 4526 4527
    • (2006) Journal of the American Chemical Society , vol.128 , pp. 4526-4527
    • Colletier, J.P.1    Sanson, B.2    Nachon, F.3    Gabellieri, E.4    Fattorusso, C.5    Campiani, G.6    Weik, M.7
  • 27
    • 0025778840 scopus 로고
    • Atomic structure of acetylcholinesterase from Torpedo californica: A prototypic acetylcholine-binding protein
    • J.L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, and I. Silman Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein Science 253 1991 872 879
    • (1991) Science , vol.253 , pp. 872-879
    • Sussman, J.L.1    Harel, M.2    Frolow, F.3    Oefner, C.4    Goldman, A.5    Toker, L.6    Silman, I.7
  • 29
    • 0037413712 scopus 로고    scopus 로고
    • Structural insights into ligand interactions at the acetylcholinesterase peripheral anionic site
    • Y. Bourne, P. Taylor, Z. Radic, and P. Marchot Structural insights into ligand interactions at the acetylcholinesterase peripheral anionic site Embo Journal 22 2003 1 12
    • (2003) Embo Journal , vol.22 , pp. 1-12
    • Bourne, Y.1    Taylor, P.2    Radic, Z.3    Marchot, P.4
  • 37
    • 80053608475 scopus 로고    scopus 로고
    • Straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals and agrochemicals
    • T. Verdelet, G. Mercey, N. Correa, L. Jean, and P.-Y. Renard Straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals and agrochemicals Tetrahedron 67 2011 8757 8762
    • (2011) Tetrahedron , vol.67 , pp. 8757-8762
    • Verdelet, T.1    Mercey, G.2    Correa, N.3    Jean, L.4    Renard, P.-Y.5
  • 40
    • 7444221716 scopus 로고    scopus 로고
    • Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes
    • F. Worek, H. Thiermann, L. Szinicz, and P. Eyer Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes Biochemical Pharmacology 68 2004 2237 2248
    • (2004) Biochemical Pharmacology , vol.68 , pp. 2237-2248
    • Worek, F.1    Thiermann, H.2    Szinicz, L.3    Eyer, P.4
  • 41
    • 84860139134 scopus 로고    scopus 로고
    • Reactivation kinetics of a series of related bispyridinium oximes with organophosphate-inhibited human acetylcholinesterase-Structure-activity relationships
    • F. Worek, T. Wille, M. Koller, and H. Thiermann Reactivation kinetics of a series of related bispyridinium oximes with organophosphate-inhibited human acetylcholinesterase-Structure-activity relationships Biochemical Pharmacology 83 2012 1700 1706
    • (2012) Biochemical Pharmacology , vol.83 , pp. 1700-1706
    • Worek, F.1    Wille, T.2    Koller, M.3    Thiermann, H.4
  • 42
    • 84875811964 scopus 로고    scopus 로고
    • A combination of [+] and [-]-Huperzine A improves protection against soman toxicity compared to [+]-Huperzine A in guinea pigs
    • Y. Wang, Y. Wei, S. Oguntayo, B.P. Doctor, and M.P. Nambiar A combination of [+] and [-]-Huperzine A improves protection against soman toxicity compared to [+]-Huperzine A in guinea pigs Chemico-Biological Interactions 203 2013 120 124
    • (2013) Chemico-Biological Interactions , vol.203 , pp. 120-124
    • Wang, Y.1    Wei, Y.2    Oguntayo, S.3    Doctor, B.P.4    Nambiar, M.P.5
  • 43
    • 0033533794 scopus 로고    scopus 로고
    • Heterodimeric tacrine-based acetylcholinesterase inhibitors: Investigating ligand-peripheral site interactions
    • P.R. Carlier, E.S.-H. Chow, Y. Han, J. Liu, J.E. Yazal, and Y.-P. Pang Heterodimeric tacrine-based acetylcholinesterase inhibitors: investigating ligand-peripheral site interactions Journal of Medicinal Chemistry 42 1999 4225 4231
    • (1999) Journal of Medicinal Chemistry , vol.42 , pp. 4225-4231
    • Carlier, P.R.1    Chow, E.S.-H.2    Han, Y.3    Liu, J.4    Yazal, J.E.5    Pang, Y.-P.6
  • 48
    • 33748518255 scopus 로고    scopus 로고
    • Comparison of multiple amber force fields and development of improved protein Backbone parameters
    • V. Hornak, R. Abel, A. Okur, B. Strockbine, A. Roitberg, and C. Simmerling Comparison of multiple amber force fields and development of improved protein Backbone parameters Proteins 65 2006 712 725
    • (2006) Proteins , vol.65 , pp. 712-725
    • Hornak, V.1    Abel, R.2    Okur, A.3    Strockbine, B.4    Roitberg, A.5    Simmerling, C.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.