Design and synthesis of an a,a-difluorophosphinate hapten for antibody-catalyzed hydrolysis of organophosphorus nerve agents

Chemistry - A European Journal

Volumn 6, Issue 6, 2000, Pages 1050-1063

  Vayron, Philippe ^a,c   Renard, Pierre Yves ^a,c   Valleix, Alain ^a   Mioskowski, Charles ^a,b  

^a CEA SACLAY   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c CEB   (France)

Author keywords

Catalytic antibodies; Fluorine; Organophosphates; Phosphatases; Protein mimetics

Indexed keywords

ACETYLCHOLINESTERASE; CATALYTIC ANTIBODY; CHEMICAL WARFARE AGENT; HAPTEN; NEUROPROTECTIVE AGENT; NEUROTOXIN; ORGANOPHOSPHORUS COMPOUND; PHOSPHATASE; PHOSPHINIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMICAL WARFARE; CHEMISTRY; DRUG DESIGN; ENZYME ACTIVITY; HYDROLYSIS; IMMUNOLOGY; NEUROTOXICITY; SYNTHESIS;

ANTIBODIES, CATALYTIC; CHEMICAL WARFARE AGENTS; DRUG DESIGN; HAPTENS; MODELS, MOLECULAR; NEUROPROTECTIVE AGENTS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHINIC ACIDS;

EID: 0034677688     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000317)6:6<1050::AID-CHEM1050>3.0.CO;2-5     Document Type: Article

References (122)

1. a) Y.-C. Yang, J. A. Baker, J. R. Ward, Chem. Rev. 1992, 92, 1729-1743;
2. b) Y.-C. Yang, Acc. Chem. Res. 1999, 32, 109-115.
3. a) P. Taylor in The Pharmacological Basis of Therapeutics (Eds.: A. Goodman Gilman, T. W. Rall, A. S. Nied, P. Taylor), Pergamon, New York, 1990;
4. b) J. A. F. Compton, Military Chemical and Biological Agents, Chemical and Toxicological Properties, Telford, Caldwell (NJ), 1987.
5. a) C. Lion, M. Hedeyatullah, C. Charvy, C. Delmas, G. Magnaud, H. Sentenac-Roumanou, Bull. Soc. Chim. Belg. 1997, 106, 221-225;
6. b) Y. C. Yang, L. L. Szafraniec, W. T. Beaudry, D. K. Rohrbaugh, L. R. Procell, J. B. Samuel, J. Org. Chem. 1996, 61, 8407-8413;
7. c) F. M. Menger, M. J. Rourk, Langmuir, 1999, 15, 309-313.
8. G. Becker, A. Kawan, L. Szinicz, Arch. Toxicol. 1997, 71, 714-718.
9. a) F. W. Holmes, N. M. Placitas, USA NATO Sci. Ser. 1998, 22, 159-213;
10. b) Y. C. Yang, J. B. Samuel, W. T. Beaudry, L. L. Szafraniec, D. K. Rohrbaugh (US Dept. of the Army, USA), US 5678243 A, 1997;
11. c) L. Debordes, S. Bezeau, D. Charpagne, L. Coppet, H. Garrigue, P. Silvestre (DGA, Fr.), FR 2740347, 1997.
12. F. Worek, R. Widmann, O. Knopff, L. Szinicz, Arch. Toxicol. 1998, 72, 237-243.
13. C. B. Millard, O. Lockridge, C. A. Broomfield, Biochemistry 1998, 37, 237-247.
14. P. Masson, D. Josse, O. Lockridge, N. Viguie, C. Taupin, C. Buhler, J. Physiol. 1998, 92, 357-362.
15. G. Koler, C. Milstein, Nature 1975, 256, 495-497.
16. a) J. M. Grognet, T. Ardouin, M. Istin, A. Vandais, J. P. Noel, G. Rima, J. Satge, C. Pradel, H. Sentenac-Roumanou, C. Lion, Arch. Toxicol. 1993, 67, 66-71 (polyclonal rabbit antibodies);
17. b) W. G. Liao, K. T. Rong, Fundam. Appl. Toxicol. 1995, 27, 90-94 (polyclonal rabbit antibodies);
18. c) D. E. Lenz, A. A. Brimfield, K. W. Hunter, Jr., H. P. Benschop, L. P. de Jong, C. van Dijk, T. R. Clow, Fundam. Appl. Toxicol. 1984, 4, 156-164;
19. d) Y. X. Ci, Y. X. Zhou, Z. Q. Guo, K. T. Rong, W. B. Chang, Arch. Toxicol. 1995, 69, 565-567.
20. a) S. J. Pollack, J. W. Jacobs, P. G. Schultz, Science 1986, 234, 1570-1573;
21. b) A. Tramontano, K. D. Janda, R. A. Lerner, Science 1986, 234, 1566-1570;
22. c) for a recent review, see J. L. Reymond, Top. Curr. Chem. 1999, 200, 59-93.
23. B. Mets, G. Winger, C. Cabrera, S. Seo, S. Jamdar, G. Yang, K. Zhao, R. J. Briscoe, R. Almonte, J. H. Woods, D. W. Landry, Proc. Natl. Acad. Sci. USA, 1998, 95, 10176-10181.
24. P. Vayron, P. Y. Renard, F. Taran, C. Créminon, Y. Frobert, J. Grassi, C. Mioskowski, submitted for publication in Proc. Natl. Acad. Sci. USA.
25. a) A. A. Brimfeld, D. E. Lenz, D. M. Maxwell, C. A. Broomfield, Chem. Biol. Interactions 1993, 87, 95-102;
26. b) N. R. Thomas, Nat. Prod. Reports 1996, 479-511.
27. D. P. Weiner, T. Weinmann, M. M. Wolfe, P. Wentworth, K. D. Janda, J. Am. Chem. Soc. 1997, 119, 4088-4089.
28. P. G. Scanlan, J. R. Prudent, P. G. Schultz, J. Am. Chem. Soc. 1991, 113, 9397-9398.
29. a) J. S. Rosenblum, L-C. Lo, T. Li, K. D. Janda, R. A. Lerner, Angew.I1VU'. Chem. 1995, 107, 2448-2450; Angew. Chem. Int. Ed. Engl. 1995, 34, 2275-2277;
30. a) J. S. Rosenblum, L-C. Lo, T. Li, K. D. Janda, R. A. Lerner, Angew.I1VU'. Chem. 1995, 107, 2448-2450; Angew. Chem. Int. Ed. Engl. 1995, 34, 2275-2277;
31. b) B. J. Lavey, K. D. Janda, J. Org. Chem. 1996, 61, 7633-7636;
32. c) P. Wentworth, Y. O. Liu, A. D. Wentworth, P. Fan, M. J. Foley, K. D. Janda, Proc. Natl. Acad. Sci. USA 1998, 95, 5971-5975.
33. Y. C. Yang, L. L. Szafranice, W. T. Beaudry, D. K. Rohrbaugh, L. R. Procell, J. B. Samuel, J. Org. Chem. 1996, 61, 8407-8413.
34. Y. C. Yang, F. J. Berg, L. L. Szafranice, W. T. Beaudry, C. A. Bunton, A. Kumar, J. Chem. Soc. Perkin Trans. 2 1997, 607-613.
35. E. V. Patterson, C. J. Cramer, J. Phys. Org. Chem. 1998, 11, 232-240.
36. K. D. Janda, Biotechnol. Prog. 1990, 6, 178-181.
37. a) S. D. Taylor, C. C. Kotoris, A. N. Dinaut, M. J. Chen, Tetrahedron 1998, 54, 1691-1714;
38. b) D. B. Berkowitz, D. Bhuniya, G. Peris, Tetrahedron Lett. 1999, 40, 1869-1872, and references cited in these two articles.
39. a) T. R. Burke Jr., M. S. Smyth, M. Nomizu, A. Otaka, P. P. Roller,./. Org. Chem. 1993, 58, 1336-1340;
40. b) T. R. Burke, Jr., H. K. Kole, P. P. Roller, Biochem. Biophys. Res. Commun. 1994, 204, 129-134;
41. c) H. K. Kole, M. Akamatsu, B. Ye, X. Yan, D. Barford, P. P. Roller, T. R. Burke, Biochem. Biophys. Res. Commun. 1995, 209, 817-822;
42. d) L. Chen, L. Wu, A. Okata, M. S. Smyth, P. P. Roller, T. R. Burke, J. den Hertog, Z. Y. Zhang, Biochem. Biophys. Res. Commun. 1995, 216, 976-984.
43. a) R. Engel, Chem. Rev. 1977, 349-367;
44. b) D. F. Wiemer, Tetrahedron 1997, 53, 16609-16644.
45. a) G. M. Blackburn, Chem. Ind. (London) 1981, 134-138;
46. b) G. M. Blackburn, D. E. Kent, F. Kolkmann, J. Chem. Soc. Perkin Trans. I 1984, 1119-1125.
47. a) J. Nieschalk, D. O'Hagan, J. Chem. Soc. Chem. Commun. 1995, 719-720;
48. b) D. Solas, R. L. Hale, D. V. Patel, J. Org. Chem. 1996, 61, 1537-1539;
49. c) N. A. Caplan, C. I. Pogson, D. J. Hayes, G. M. Blackburn, Bioorg. Med. Chem. Lett. 1998, 8, 515-520.
50. a) J. P. Bégué, D. Bonnet-Delpon, Tetrahedron 1991, 47, 3207-3258;
51. b) T. Kitamuze, T. Tsukamoto, K. Yoshimura, J. Chem. Soc. Chem. Commun. 1994, 1355-1356.
52. a) R. Rabinowitz, J Org. Chem. 1963, 28, 2975-2978;
53. b) M. E. Jung, M. A. Lyster, J. Am. Chem. Soc. 1977, 99, 968-969;
54. c) C. E. McKenna, M. T. Higa, N. H. Cheung, M. C. McKenna, Tetrahedron Lett. 1977, 18, 155-158.
55. M. J. Tozer, T. F. Herpin, Tetrahedron 1996, 52, 8616-8683.
56. W. Froestl, S. J. Mickel, G. von Sprecher, P. J. Diel, R. G. Hall, L. Maier, D. Strub, V. Melillo, P. A. Baumann, R. Bernasconi, C. Gentsch, K. Hauser, J. Jaeckel, G. Karlson, K. Klebs, L. Maître, C. Marescaux, M. F. Pozza, M. Schmutz, M. W. Steinmann, H. van Riezen, A. Vassout, C. Mondadori, H. R. Olpe, P. C. Waldmeier, H. Bittiger, J. Med. Chem. 1995, 38, 3313-3331.
57. a) A. V. Garabadzhiu, A. A. Rodin, A. N. Lavrent'ev, E. G. Sochilin, J. Gen. Chem. USSR (Engl. Transl.) 1981, 51, 34-38;
58. b) A. V. Garabadzhiu, S. A. Ivanov, A. N. Lavrent'ev, V. I. Shibaev, J. Gen. Chem. USSR (Engl. Transl.) 1981, 51, 1905-1910.
59. R. Boetzel, G. Haegele, J. Fluorine Chem. 1994, 68, 11-14.
60. S. Z. Irvin, J. Appl. Chem. USSR (Engl. Transl.) 1969, 42, 444-445.
61. S. R. Piettre, Tetrahedron Lett. 1996, 37, 2233-2236.
62. S. Benefice-Malouet, H. Blanocu, A. Commeyras, J. Fluorine Chem. 1985, 30, 171-188.
63. C. E. McKenna, P.-T. T. Pham, M. E. Rassier, T. P. Dousa, J. Med. Chem. 1992, 35, 4885-4892.
64. K. Blades, S. T. Patel, J. M. Percy, R. D. Wolkes, Tetrahedron Lett. 1996, 37, 6403-6406.
65. D. J. Burton, Z. Y. Yang, Tetrahedron 1992, 48, 189-275.
66. a) T. Yokomatsu, T. Murano, K, Suemune, S. Shibuya, Tetrahedron 1997, 53, 815-822;
67. b) T. Yokomatsu, T. Minowa, T. Murano, S. Shibuya, Tethahedron 1998, 54, 9341-9156.
68. a) W. Qiu, D. J. Burton, Tetrahedron Letters 1996, 37, 2745-2748;
69. b) M. N. Qabar, J. Urban, M. Kahn, Tetrahedron 1997, 53, 11171-11178.
70. a,a-Difluoromethylenephosphonate lithium derivatives are described as poorly stahle : D. J. Burton, D. G. Nane, R. M. Flynn, B. E. Smart, D. R. Brittelli, J. Org. Chem. 1983, 48, 3616-3618.
71. + is stabilized, or when the solvent favors dissociation of the radical/radical anion pair. (I, Rico, D. Cantacuzene, C. Wakselman, J. Org. Chem. 1983, 48, 1979-1982.)
72. a) A. Michaelis, R. Kaehene, Chem. Ber. 1898, 31, 1408;
73. b) A. E. Arbuzov, J. Russ. Phys. Chem. Soc. 1906, 38, 687;
74. c) A. K. Bhattacharya, G. Thyagarajan, Chem. Rev. 1981, 81, 415-430.
75. a) I. L. Knunyants, E. Ya. Pervova, Bull. Acad. UUSR Div. Chem. Sci. (Engl. Transl.) 1962, 8, 1324-1326;
76. b) H. Machleidt, R. Wessendorf, Justus Liebigs Ann. Chem. 1964, 674, 1-10;
77. c) D. J. Burton, R. M. Flynn, J. Fluorine Chem. 1977, 10, 329-332;
78. d) M. I. Dawson, R. Chan, P. D. Hobbs, W. R. Chao, L. J. Schiff, J. Med. Chem. 1983, 26, 1282-1293;
79. e) V. I. Shibaev, A. V. Tarabadzhiu, A. A. Rodin, J. Gen. Chem. USSR (Engl. Transl.) 1983, 53, 1781-1784;
80. f) A. V. Garabadzhiu, A. A. Rodin, A. N. Lavrent'ev, E. G. Sochilin, J. Gen. Chem. USSR (Engl. Transl.) 1981, 51, 34-38;
81. g) A. V. Garabadzhiu, S.A. Ivanov, A. N. Lavrent'ev, V. I. Shibaev, J. Gen. Chem. USRR (Engl. Transl.) 1981, 51, 1905-1910;
82. h) R. Boetzel, G. Haegele, J. Fluorine Chem. 1994, 68, 11-14;
83. i) G. Etemad-Moghadam, J. Seyden-Penn, Bull Soc. Chim. Fr. 1985, 448-454.
84. a) R. N. Haszeldine, B. O. West, J. Chem. Soc. 1956, 3631-3637;
85. b) H. Teichman, Z. Chem. 1974, 14, 216-222.
86. c) P. J. Burton, J. Fluorine Chem. 1983, 23, 339-357;
87. d) H. K. Nair, D. J. Burton, J. Am. Chem. Soc. 1997, 119, 9137-9143.
88. M. Saady, L. Lebeau, C. Mioskowski, Tetrahedron Lett. 1995, 36, 5183-5186.
89. a) D. J. Burton, R. M. Flynn, Synthesis 1979, 615;
90. b) V. I. Shibaev, A. V. Garabadzhiu, A. A. Rodin, J. Gen. Chem. USSR (Engl. Transl.) 1983, 53, 1568-1570;
91. b) M. Kato, M. Yamabe, J. Chem. Soc. Chem. Commun. 1981, 1173-1174;
92. c) N. O. Bracce, J. Org. Chem. 1961, 26, 3197-3201;
93. d) S. Z. Ivin, V. K. Promonenkov, A. S. Baberkin, E. V. Volkova, N. F. Sarafanova, E. A. Forkin, J. Appl. Chem. USSR (Engl. Transl.) 1969, 42, 444-445.
94. a) L. Z. Soborovskii, N. N. F. Baina, J. Gen. Chem. USSR (Engl. Transl.) 1959, 29, 1110-1115;
95. b) A. V. Forkin, J. Org. Chem. USSR (Engl. Transl.) 1971, 7, 241-243;
96. c) G. M. Blackburn, M. J. Parratt, J. Chem. Soc. Perkin Trans. I 1986, 1425-1430;
97. d) M. L. Edwards, D. M. Stemerick, E. T. Jarvi, Tetrahedron Lett. 1990, 31, 5571-5574;
98. e) D. B. Berkowitz, D. G. Sloss, J. Org. Chem. 1995, 60, 7047-7050.
99. W. Cen, Y. Shen, J. Fluorine Chem. 1991, 52, 369.
100. a) S. A. Fuqua, Tetrahedron 1964, 20, 1625-1632;
101. b) A. Haas, M. Spitzerr, M. Lieb, Chem. Ber. 1988, 121, 1329-1340.
102. G. A. Olah, M. B. Comisarow, J. Am. Chem. Soc. 1969, 91, 2955-2961.
103. a) W. J. Middleton, J. Org. Chem. 1975, 40, 574-578;
104. b) M. Hudlicky, Org. React. (NY) 1988, 35, 513-637.
105. J. A. Wilkinson, Chem. Rev. 1992, 92, 505-519.
106. W. J. Middletown, E. M. Bingham, J. Org. Chem. 1980, 45, 2883-2887.
107. a) M. S. Smyth, H. Ford, Jr., T. R. Burke, Jr., Tetrahedron Lett. 1992, 33, 4137-4140;
108. b) F. Benayoud, G. B. Hammond, Chem. Commun. 1996, 1447-1448;
109. c) B. Ye, T. R. Burke, Jr., Tetrahedron 1996, 52, 9963-9970;
110. d) D. Solas, R. L. Hale, D. V. Patel, J. Org. Chem. 1996, 61, 1537-1539.
111. T. Yokomatsu, T. Murano, K. Suemune, S. Shibuya, Tetrahedron, 1997, 55, 815-822.
112. a) K. Boulton, B. E. Cross, J. Chem. Soc. Perkin Trans. I 1979, 1354-1357;
113. b) S. D. Taylor, A. N. Dinaut, A. T. Thadani, Z. Huang, Tetrahedron Lett. 1996, 37, 8089-8092.
114. R. A. Cherkasov, V. I. Galkin, A. B. Khabibullina, K. Al Kurdi, Phosphorus Sulfur Silicon Relat. Elem. 1990, 49-50, 61-64.
115. a) C. E. McKenna, P. D. Shen, J. Org. Chem. 1981, 46, 4573-4576;
116. b) G. M. Blackburn, D. A. England, F. Kolkmann, J. Chem. Soc. Chem. Commun. 1981, 930-932.
117. a) New Fluorinating Agents in Organic Synthesis (Eds.: L. German, S. Zemskov), Springer, Berlin, 1989;
118. b) T. Umemoto, G. Tomizawa, J. Org. Chem. 1995, 60, 6563-6570.
119. E. Differding, R. O. Duthaler, A. Krieger, G. M. Rüegg, C. Schmit, Synlett 1991, 395-396.
120. S. D. Taylor, C. C. Kotoris, A. N. Dibnaut, M.-J. Chen, Tetrahedron 1998, 54, 1691-1714.
121. P. Pradelles, C. Antoine, J. P. Lellouche, J. Maclouf, Methods Enzymol. 1990, 187, 82-89.
122. P. Pradelles, J. Grassi, J. Maclouf, Anal Chem. 1985, 57, 1170-1173.