Immunologically driven antibodies chemical engineering: Design and synthesis of a hapten aimed at nerve agent hydrolysis

Tetrahedron Letters

Volumn 46, Issue 40, 2005, Pages 6809-6814

  Jovic, Florence ^a   Louise, Ludivine ^b   Mioskowski, Charles ^c   Renard, Pierre Yves ^b  

^a CEA SACLAY   (France)

^b UNIVERSITÉ DE ROUEN   (France)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Bioorganic chemistry; Catalytic antibodies; Nerve agent; Organophosphorus chemistry

Indexed keywords

ALDEHYDE DERIVATIVE; HAPTEN; IMINE; METHYLPHOSPHONOTHIOIC ACID S (2 DIISOPROPYLAMINOETHYL) O ETHYL ESTER; MONOCLONAL ANTIBODY; ORGANOPHOSPHORUS COMPOUND; OXIME; PHOSPHINE OXIDE DERIVATIVE; PHOSPHOROTHIOIC ACID; SARIN; SOMAN; TABUN;

ARTICLE; BIOTECHNOLOGICAL PROCEDURES; CHEMICAL BOND; CHEMICAL ENGINEERING; DRUG DESIGN; DRUG HYDROLYSIS; DRUG SYNTHESIS; IMMUNOREACTIVITY;

EID: 27744464062     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.032     Document Type: Article

References (58)

1. Taylor, P. In Goodman and Gilman's the Pharmacological Basis of Therapeutics, 10th ed.; Hardman, J. G., Limbird, L. E., Goodman, A. G., Eds.; McGraw-Hill: New York, 2001; pp 175-192.
2. Langford, R. E. Introduction to Weapons of Mass Destruction, Radiological, Chemical and Biological; John Wiley and Sons: Chichester, 2004.
3. 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; Den Hague, Netherlands, 1993.
4. Yang, Y. C.; Baker, J. A.; Ward, J. R. Chem. Rev. 1992, 92, 1729-1743.
5. Yang, Y. C. Acc. Chem. Res. 1999, 32, 109-115.
6. Crabb, D.; DeFrank, J.; Penet, C. Chem. Ind. 2004, 14, 15.
7. Yang, Y. C.; Berg, F. J.; Szafraniec, L. L.; Beaudry, W. T.; Bunton, C. A.; Kumar, A. J. Chem. Soc., Perkin Trans. 2 1997, 607-613.
8. Yang, Y. C.; Szafraniec, L. L.; Beaudry, W. T.; Rohrbaugh, D. K.; Procell, L. R.; Samuel, J. B. J. Org. Chem. 1996, 61, 8407-8413.
9. Renard, P. Y.; Schwebel, H.; Vayron, P.; Josien, L.; Valleix, A.; Mioskowski, C. Chem. Eur. J. 2002, 8, 2910-2916.
10. Vayron, P.; Renard, P. Y.; Taran, F.; Créminon, C.; Frobert, Y.; Grassi, J.; Mioskowski, C. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 7058-7063.
11. Tramontano, A.; Janda, K. D.; Lerner, R. A. Science 1986, 234, 1566-1570.
12. Pollack, S. J.; Jacobs, J. W.; Schultz, P. G. Science 1986, 234, 1570-1573.
13. Schultz, P. G.; Yin, J.; Lerner, R. A. Angew. Chem., Int. Ed. 2002, 41, 4427-4437.
14. Hasserodt, J. Synlett 1999, 12, 2007-2022.
15. Reymond, J.-L. Top. Curr. Chem. 1999, 200, 59-93.
16. Vayron, P.; Renard, P. Y.; Valleix, A.; Mioskowski, C. Chem. Eur. J. 2000, 6, 1050-1063.
17. Dias, S.; Jovic, F.; Renard, P. Y.; Taran, F.; Créminon, C.; Mioskowski, C.; Grassi, J. J. Immun. Methods 2002, 269, 81-98.
18. Ersoy, O.; Fleck, R.; Blanco, M.-J.; Masamune, S. Bioorg. Med. Chem. 1999, 7, 279-286.
19. Ersoy, O.; Fleck, R.; Sinskey, A.; Masamune, S. J. Am. Chem. Soc. 1998, 120, 817-818.
20. Mahy, J. P.; Desfosses, B.; de Lauzon, S.; Quilez, R.; Desfosses, B.; Lion, L.; Mansuy, D. Appl. Biochem. Biotechnol. 1998, 75, 103-127.
21. Pollack, S. J.; Nakayama, G. R.; Schultz, P. G. Science 1988, 242, 1038-1040.
22. Pollack, S. J.; Schultz, P. G. J. Am. Chem. Soc. 1989, 111, 1929-1931.
23. Um, I. H.; Buncel, E. N. J. Org. Chem. 2000, 65, 577-582.
24. Um, I. K.; Hong, J.-Y.; Buncel, E. Chem. Commun. 2001, 27-28.
25. Hay, R. W.; Govan, N. Chem. Commun. 1990, 714-715.
26. Oh, S. J.; Yoon, C. W.; Park, J. W. J. Chem. Soc., Perkin Trans. 2 1996, 329-331.
27. Hay, R. W.; Govan, N. Polyhedron 1998, 17, 2079-2085.
28. Kazankov, G. M.; Seergeva, V. S.; Efremenko, E. N.; Alexandrova, L.; Varfolomeev, S. D.; Ryabov, A. D. Angew. Chem., Int. Ed. 2000, 39, 3117-3119.
29. Epstein, J.; Callahan, J. J.; Bauer, V. E. Phosphorus 1974, 4, 157-163.
30. Boulet, C. A.; Hansen, A. S. Phosphorus, Sulfur Silicon 1991, 57, 147-161.
31. Lundy, P. M.; Hansen, A. S.; Hand, B. T.; Boulet, C. A. Toxicology 1992, 72, 99-105.
32. Dawson, R. M. J. Appl. Toxicol. 1994, 14, 317-331.
33. Leikin, J. B.; Thomas, R. G.; Walter, F. G.; Klein, R.; Meislin, H. W. Crit. Care Med. 2002, 10, 2346-2354.
34. Cassagne, T.; Cristau, H. J.; Delmas, G.; Desgranges, M.; Lion, C.; Magnaud, G.; Torreilles, E.; Virieux, D. Heteroatom Chem. 2001, 12, 485-490.
35. Wagner, G. W.; Yang, Y. C. Ind. Eng. Chem. Res. 2002, 41, 1925-1928.
36. Morales-Rojas, H.; Moss, R. A. Chem. Rev. 2002, 102, 2497-2521.
37. Terrier, F.; MacCormack, P.; Kizilian, E.; Halle, J.-C.; Demersemen, P.; Guir, F.; Lion, C. J. Chem. Soc., Perkin Trans. 2 1991, 153-158, and references cited therein.
38. Koplovitz, I; Stewart, J. R. Toxicol Lett. 1994, 70, 269-279.
39. Cai, D.; Hughes, D. L.; Verhoeven, T. R. Tetrahedron Lett. 1996, 37, 2537-2540, and references cited therein.
40. Toyota, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110-7113.
41. Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538.
42. More, J. D.; Finney, N. S. Org. Lett. 2002, 4, 3001-3003.
43. Chini, M.; Crotti, L.; Favero, L.; Maccia, F. Tetrahedron Lett. 1994, 35, 761-764.
44. Pudovik, A. N. Dokl. Akad. Nauk SSSR 1952, 83, 865-868;
45. Chem. Abstr. 1953, 47, 4300.
46. Dhawan, B.; Redmore, D. Phosphorus, Sulfur Silicon Relat. Elem. 1987, 32, 119-144.
47. Kukhar, V. P.; Soloshonok, V. A.; Solodenko, V. A. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 92, 239-264.
48. Boduszek, B. Tetrahedron 1996, 52, 12483-12494.
49. Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332.
50. Qian, C. T.; Huang, T. S. J. Org. Chem. 1998, 63, 4125-4128.
51. Lee, S.; Park, J. H.; Kang, J.; Lee, J. K. Chem. Commun. 2001, 1698-1699.
52. Ranu, B. C.; Hajra, A.; Jana, U. Org. Lett. 1999, 1, 1141-1143.
53. Manabe, K.; Kobayashi, S. Chem. Commun. 2000, 669-670.
54. Xu, F.; Luo, Y.; Deng, M.; Shen, Q. Eur. J. Org. Chem. 2003, 4728-4730.
55. Hanaya, T.; Shigetoh, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2499-2505.
56. Thottathil, J. K. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992, p 55.
57. Hansen, H. I; Kehler, J. Synthesis 1999, 11, 1925-1930.
58. Matziari, M.; Georgiadis, D.; Dive, V.; Yiotakis, A. Org. Lett. 2001, 3, 659-662.