Design, synthesis and evaluation of new α-nucleophiles for the hydrolysis of organophosphorus nerve agents: Application to the reactivation of phosphorylated acetylcholinesterase

Tetrahedron

Volumn 67, Issue 34, 2011, Pages 6352-6361

  Saint André, Géraldine ^a   Kliachyna, Maria ^a   Kodepelly, Sanjeevarao ^a   Louise Leriche, Ludivine ^b,c   Gillon, Emilie ^d   Renard, Pierre Yves ^b,c,e   Nachon, Florian ^d   Baati, Rachid ^a   Wagner, Alain ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b INSA   (France)

^c UNIVERSITÉ DE ROUEN   (France)

^d INSTITUT DE RECHERCHE BIOMÉDICALE DES ARMÉES   (France)

^e INSTITUT UNIVERSITAIRE DE FRANCE   (France)

Author keywords

Hydrolysis; Organo phosphono thioase activity; Organophosphorus nerve agents; ortho Hydroxyl effect; Reactivation of acetylcholine esterase; Nucleophiles

Indexed keywords

ACETYLCHOLINESTERASE; ALPHA NUCLEOPHILE; HYDROXYL GROUP; NUCLEOPHILE; ORGANOPHOSPHORUS COMPOUND; OXIME DERIVATIVE; PHOSPHORUS; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME MECHANISM; ENZYME PHOSPHORYLATION; ENZYME REACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; SURFACE CHARGE; SYNTHESIS;

EID: 79960566938     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.130     Document Type: Article

References (90)

1. P. Taylor J.G. Hardman, L.E. Limbird, A.G. Goodman, Goodman and Gilman's the Pharmacological Basis of Therapeutics 10th ed. 2001 McGraw-Hill New York, NY 175 192
2. R.E. Langford Introduction to Weapons of Mass Destruction, Radiological, Chemical and Biological 2004 Wiley New York, NY
3. T.C. Marrs Pharmacol. Ther. 58 1993 51 66
4. F.R. Sidell, and J. Borak Ann. Emerg. Med. 21 1992 865 871
5. Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction; the Technical Secretariat of the Organization for the Prohibition of Chemical Weapons 1993 Den Hague Netherlands
6. Y.C. Yang, L.L. Szafraniec, W.T. Beaudry, and C.A. Bunton J. Org. Chem. 58 1993 6964 6965
7. Y.C. Yang, F.J. Berg, L.L. Szafraniec, W.T. Beaudry, C.A. Bunton, and A. Kumar J. Chem. Soc., Perkin Trans. 2 1997 607 613
8. G.W. Wagner, and Y.-C. Yang Ind. Eng. Chem. Res. 41 2002 1925 1928
9. Wagner, G. W.; Procell, L. R.; Yang, Y.-C.; Bunton, C. A. U.S. Patent 6,723,891B1, 2004
10. G.W. Wagner, D.C. Sorrick, L.R. Procell, M.D. Brickhouse, I.F. Mcvey, and L.I. Schwartz Langmuir 23 2007 1178 1186
11. Y.C. Yang, J.A. Baker, and J.R. Ward Chem. Rev. 92 1992 1729 1743
12. F.R. Sidell, E.T. Takafuji, and D.R. Franz 'Decontamination': C. G. Hurst in Medical Aspects of Chemical and Biological Warfare 2008 The Borden Institute Washington, DC Chapter 15
13. Y.C. Yang, L.L. Szafraniec, W.T. Beaudry, and D.K. Rohrbaugh J. Am. Chem. Soc. 112 1990 6621 6627
14. T. Cassagne, H.-J. Cristau, G. Delmas, M. Desgranges, C. Lion, G. Magnaud, E. Torreilles, and D. Virieux Heteroat. Chem. 12 2001 485 490
15. P.S. Hammond, J.S. Forster, C.N. Lieske, and H.D. Durst J. Am. Chem. Soc. 111 1989 7860 7866
16. R.A. Moss, H. Morales-Rojas, H. Zhang, and B.-D. Park Langmuir 15 1999 2738 2744
17. F.J. Berg, R.A. Moss, Y.-C. Yang, and H. Zhang Langmuir 11 1995 411 413
18. H. Morales-Rojas, and R.A. Moss Chem. Rev. 102 2002 2497 2522
19. R. Ramaseshan, S. Sundarrajan, L. Yingjun, R.S. Barhate, N.L. Lada, and S. Ramakrishna Nanotechnology 17 2006 2947 2953
20. N. Masurier, F. Estour, M.-T. Froment, B. Lefevre, J.-C. Debouzy, B. Brasme, P. Masson, and O. Lafont Eur. J. Med. Chem. 40 2005 615 623
21. E. Gershonov, I. Columbus, and Y. Zafrani J. Org. Chem. 74 2009 329 338
22. G.W. Wagner, O.B. Koper, E. Lucas, S. Decker, and K.J. Klabunde J. Phys. Chem. B 104 2000 5118 5123
23. G.W. Wagner, P.W. Bartram, O.B. Koper, and K.J. Klabunde J. Phys. Chem. B 103 1999 3225 3228
24. G.W. Wagner, and P.W. Bartram Langmuir 15 1999 8113 8118
25. G.W. Wagner, L.R. Procell, R.J.O. Connor, S. Munavalli, C.L. Carnes, P.N. Kapoor, and K.J. Klabunde J. Am. Chem. Soc. 123 2001 1636 1644
26. G.W. Wagner, L.R. Procell, and S.J. Munavalli J. Phys. Chem. C 111 2007 17564 17569
27. G.W. Wagner, Q. Chen, and Y.J. Wu J. Phys. Chem. C 112 2008 11901 11906
28. I. Columbus, D. Waysbort, L. Shamueli, I. Nir, and D. Kaplan Environ. Sci. Technol. 40 2006 3952 3958
29. F.C.G. Hoskin, J.E. Walker, W.-D. Dettbarn, and J.R. Wild Biochem. Pharmacol. 49 1995 711 715
30. V.K. Rastogi, J.J. Defrank, T.-C. Cheng, and J.R. Wild Biochem. Biophys. Res. Commun. 241 1997 294 296
31. A.A. Wang, W. Chen, and A. Mulchandani Biotechnol. Bioeng. 91 2005 379 386
32. A. Singh, Y. Lee, and W. Dressick J. Adv. Mater. 16 2004 2112 2115
33. E. Ghanem, and F.M. Raushel Toxicol. Appl. Pharmacol. 207 2005 459 470
34. G. Amitai, R. Adani, G. Sod-Moriah, I. Rabinovitz, A. Vincze, H. Leader, B. Chefetz, L. Leibovitz-Persky, D. Friesem, and Y. Hadar FEBS Lett. 438 1998 195 200
35. G. Amitai, R. Adani, M. Hershkovitz, P. Bel, I. Rabinovitz, and H. Meshulam J. Appl. Toxicol. 23 2003 225 233
36. B.M. Smith Chem. Soc. Rev. 37 2008 470 478
37. L.M. Eubanks, T.J. Dickerson, and K.D. Janda Chem. Soc. Rev. 36 2007 458 470
38. P. Vayron, P.-Y. Renard, A. Valleix, and C. Mioskowski Chem. - Eur. J. 6 2000 1050 1063
39. F. Jovic, L. Louise, C. Mioskowski, and P.-Y. Renard Tetrahedron Lett. 46 2005 6809 6814
40. P. Vayron, P.-Y. Renard, F. Taran, C. Créminon, Y. Frobert, J. Grassi, and C. Mioskowski Proc. Natl. Acad. Sci. U.S.A. 97 2000 7058 7063
41. L. Bromberg, H. Schreuder-Gibson, W.R. Creasy, D.J. McGarvey, R.A. Fry, and T.A. Hatton Ind. Eng. Chem. Res. 48 2009 1650 1659
42. N.B. Munro, S.S. Talmage, G.D. Griffin, L.C. Waters, A.P. Watson, J.F. King, and V. Hauschild Environ. Health Perspect. 107 1999 933 974
43. Y.-C. Yang, L.L. Szafraniec, W.T. Beaudry, D.K. Rohrbaugh, L.R. Procell, and J.B. Samuel J. Org. Chem. 61 1996 8407 8413
44. G.W. Wagner, R.J. O'Connor, J.L. Edwards, and C.A.S. Brevett Langmuir 20 2004 7146 7150
45. P.-Y. Renard, H. Schwebel, P. Vayron, L. Josien, A. Valleix, and C. Mioskowski Chem. - Eur. J. 8 2002 2910 2916
46. C.o. Disarmament, The Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction, 1992, CD/1170.
47. G. Becker, A. Kawan, D. Gutzeit, F. Worek, and L. Szinicz Arch. Toxicol. 81 2007 415 420
48. V.P. Kumar, B. Ganguly, and S. Bhattacharya J. Org. Chem. 69 2004 8634 8642
49. J. Epstein, J.J. Kaminski, N. Bodor, R. Enever, J. Sowa, and T. Higuchi J. Org. Chem. 43 1978 2816 2821
50. R.E. Plapinger, and O.O. Owens J. Org. Chem. 21 1956 1186 1187
51. J.C. Lamb, G.M. Steinberg, S. Solomon, and B.E. Hackley Jr. Biochemistry 4 1965 2475 2484
52. I.B. Wilson J. Biol. Chem. 190 1951 111 117
53. K. Kuca, J. Cabal, J. Patocka, and J. Kassa Lett. Org. Chem. 1 2004 84 86
54. J. Wang, J. Gu, J. Leszczynski, M. Feliks, and A. Sokalski J. Phys. Chem. B 111 2007 2404 2408
55. A.S. Khan, M.K. Kesharwani, T. Bandyopadhyay, and B. Ganguly J. Mol. Graphics Modell. 28 2009 177 182
56. G.Y. Yang, K.-A. Oh, N.-J. Park, and Y.-S. Jung Bioorg. Med. Chem. 15 2007 7704 7710
57. K. Musilek, J. Kucera, D. Jun, V. Dohnal, V. Opletalova, and K. Kuca Bioorg. Med. Chem. 16 2008 8218 8223
58. T.-H. Kim, K. Kuca, D. Jun, and Y.-S. Jung Bioorg. Med. Chem. Lett. 15 2005 2914 2917
59. F. Terrier, P. Rodriguez-Dafonte, E. Le Guével, and G. Moutiers Org. Biomol. Chem. 4 2006 4352 4362
60. S. Eckert, P. Eyer, N. Herkert, R. Bumm, G. Weber, H. Thiermann, and F. Worek Biochem. Pharmacol. 75 2008 698 703
61. F. Worek, H. Thiermann, L. Szinicz, and P. Eyer Biochem. Pharmacol. 68 2004 2237 2248
62. M. Jokanović, and M.P. Stojiljković Eur. J. Pharmacol. 553 2006 10 17
63. C.M. Timperley, M. Bird, S.C. Heard, S. Notman, R.W. Read, J.E.H. Tattersall, and S.R. Turner J. Fluorine Chem. 126 2005 1160 1165
64. K. Musilek, K. Kuca, D. Jun, and M. Dolezal Curr. Org. Chem. 11 2007 229 238
65. J. Kassa, K. Kuca, L. Bartosova, and G. Kunesova Curr. Org. Chem. 11 2007 267 283
66. J. Bajgar, J. Fusek, K. Kuca, L. Bartosova, and D. Jun Mini-Rev. Med. Chem. 7 2007 461 466
67. K. Kuca, D. Jun, and K. Musilek Mini-Rev. Med. Chem. 6 2006 269 277
68. F. Worek, P. Eyer, N. Aurbek, L. Szinicz, and H. Thiermann Toxicol. Appl. Pharmacol. 219 2007 226 234
69. D.M. Maxwell, I. Koplovitz, F. Worek, and R.E. Sweeney Toxicol. Appl. Pharmacol. 231 2008 157 164
70. K. Kuca, J. Cabal, D. Jun, K. Musilek, O. Soukup, M. Pohanka, J. Pejchal, K.-A. Oh, G.-Y. Yang, and Y.-S. Jung Environ. Toxicol. Pharmacol. 30 2010 85 87
71. Mercey, G.; Verdelet, T.; Saint-André, G.; Gillon, E.; Wagner, A.; Baati, R.; Jean, L.; Nachon F.; Renard, P. Y. Chem. Commun. (Camb.) 2011, 5295-5297.
72. L. Louise-Leriche, E. Punescu, G. Saint-André, R. Baati, A. Romieu, A. Wagner, and P.-Y. Renard Chem. - Eur. J. 16 2010 3510 3523
73. J.E. Chambers, and S.F. Oppenheimer Toxicol. Sci. 77 2004 185 187
74. A.H. Blatt, and L.A. Russell J. Am. Chem. Soc. 58 1936 1903 1908
75. H.H. Freedmann J. Am. Chem. Soc. 83 1961 2900 2905
76. I. Hayashi, K. Ogihara, and K. Shimizu Bull. Chem. Soc. Jpn. 56 1983 2432 2437
77. I. Hayashi, and K. Shimizu Bull. Chem. Soc. Jpn. 56 1983 3197 3198
78. Y. Ashani, and S. Cohen J. Med. Chem. 14 1971 621 626
79. T.J. Dale, and J. Rebek Jr. Angew. Chem. 121 2009 7990 7992
80. Angew. Chem., Int. Ed. 48 2009 7850 7852
81. C. Luo, A. Saxena, Y. Ashani, H. Leader, Z. Radić, P. Taylor, and B.P. Doctor Chem.-Biol. Interact. 119-120 1999 129 135
82. Parsy, C.C.; Alexandre, F.-R.; Bonnaterre, F.; Surleraux, D. Patent WO 2010/090976A1, 2010.
83. D.J. Gale, and J.F.K. Wilshire Aust. J. Chem. 28 1975 2447 2458
84. Luo, Z.; Slee, D.; Tellew, J. E.; Williams, J.; Zhang, X. Patent WO 2005/063755 A1, 2005, p 86.
85. L. Panzella, M. De Lucia, C. Amalfitano, A. Pezzella, A. Evidente, A. Napolitano, and M. d'Ischia J. Org. Chem. 71 2006 4246 4254
86. Vourloumis, D.; Takahashi, M.; Winters, G.; Zhou, J.; Duchene, R. U.S. Patent 2004/015249, 2004, p 179.
87. N. Bajwa, and M.P. Jennings J. Org. Chem. 71 2006 3646 3649
88. R. Amaranatha Reddy, and B.K. Sadashiva Liq. Cryst. 30 2003 273 283
89. E. Carletti, H. Li, B. Li, F. Ekström, Y. Nicolet, M. Loiodice, E. Gillon, M.T. Froment, O. Lockridge, L.M. Schopfer, P. Masson, and F. Nachon J. Am. Chem. Soc. 130 2008 16011 16020
90. G.L. Ellman, K.D. Courtney, V. Andres, and R.M. Featherstone Biochem. Pharmacol. 7 1961 88 95