Design and synthesis of a Mn(III)-porphyrin steroid conjugate used as a new cleavable affinity label: On the road to semi-synthetic catalytic antibodies

Tetrahedron

Volumn 60, Issue 44, 2004, Pages 10049-10058

  Girgenti, Elodie ^a   Ricoux, Rémy ^a   Mahy, Jean Pierre ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

Artificial metalloprotein; Catalytic antibodies; Porphyrin steroid conjugate

Indexed keywords

CATALYTIC ANTIBODY; ESTRADIOL ANTIBODY; MANGANESE DERIVATIVE; PORPHYRIN DERIVATIVE; TESTOSTERONE; TESTOSTERONE DERIVATIVE;

ARTICLE; CATALYST; CROSS COUPLING REACTION; DISULFIDE BOND; DRUG BINDING SITE; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENZYME ACTIVITY; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 4644327908     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.057     Document Type: Article

References (45)

1. M.D. Distefano, H. Kuang, D. Qi, and M. Aram Curr. Opin. Struct. Biol. 8 1998 459 465
2. I. Hamachi, and S. Shinkai Eur. J. Org. Chem. 1999 539 549
3. M.G. Kennedy, and B.R. Gibney Curr. Opin. Struct. Biol. 11 2001 485 492
4. C.-M. Tann, D. Qi, and M.D. Distefano Curr. Opin. Chem. Biol. 5 2001 696 704
5. R.A. Lerner, S.J. Benkovic, and P.G. Schultz Science 252 1991 659 667
6. E. Keinan, and R.A. Lerner Isr. J. Chem. 36 1996 113 119
7. J.D. Stevenson, and N.R. Thomas Nat. Prod. Rep. 17 2000 535 577
8. J.-P. Mahy, B. Desfosses, S. de Lauzon, R. Quilez, B. Desfosses, L. Lion, and D. Mansuy Appl. Biochem. Biotechnol. 75 1998 103 127
9. S. Gramatikova, B. Mouratou, J. Stetefeld, P.K. Mehta, and P. Christen J. Immunol. Methods 260 2002 99 110
10. S. Dias, F. Jovic, P.-Y. Renard, F. Taran, C. Créminon, C. Mioskowski, and J. Grassi J. Immunol. Methods 260 2002 81 98
11. S. De Lauzon, B. Desfosses, D. Mansuy, and J.-P. Mahy FEBS Lett. 443 1999 229 234
12. S. Nimri, and E. Keinan J. Am. Chem. Soc. 121 1999 8978 8982
13. R. Ricoux, H. Sauriat-Dorizon, E. Girgenti, D. Blanchard, and J.-P. Mahy J. Immunol. Methods 269 2002 39 57
14. A.J. Chmura, M.S. Orton, and C.F. Meares Proc. Natl. Acad. Sci. U.S.A. 98 2001 8480 848415
15. S.J. Pollack, G.R. Nakayama, and P.G. Schultz Science 242 1988 1038 1040
16. S. De Lauzon, B. Desfosses, M.F. Moreau, N. Le Trang, K. Rajkowski, and N. Cittanova Hybridoma 9 1990 481 491
17. Marnett, L. J.; Kennedy, T. A. Comparison of the Peroxidase Activity of Hemoproteins and Cytochrome P450. In Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995; pp 49-80.
18. C.K. Chang, and M.S. Kuo J. Am. Chem. Soc. 101 1979 3413 3415
19. S. Shanmugathasan, C. Edwards, and R.W. Boyle Tetrahedron 56 2000 1025 1046
20. D. Mansuy, P. Battioni, and J.-P. Battioni Eur. J. Biochem. 184 1989 267 285
21. A.M.A. Rocha Gonsalves, and M.M. Pereira J. Mol. Catal. A: Chem. 113 1996 209 211
22. C.-Y. Won, and C.-C. Chu Carbohydr. Polym. 36 1998 327 334
23. S.J. Pollack, and P.G. Schultz J. Am. Chem. Soc. 111 1989 1929 1931
24. C.C. Goodno, H.E. Swaisgood, and G.L. Catignani Anal. Biochem. 115 1981 203 211
25. R.G. Little, J.A. Anton, P.A. Loach, and J.A. Ibers J. Heterocycl. Chem. 12 1975 343 349
26. J.P. Collman, R.R. Gagne, C.A. Reed, T.R. Halbert, G. Lang, and W.T. Robinson J. Am. Chem. Soc. 97 1975 1427 1439
27. C. Ruzié, L. Michaudet, and B. Boitrel Tetrahedron Lett. 43 2002 7420 7426
28. H.G. Forest, E. Mappus, and C.-Y. Cuilleron Steroids 28 1976 815 827
29. Buchler, J. W. Synthesis and Properties of Metalloporphyrins. In The Porphyrins: Structure and Synthesis, part A; Dolphin, D., Ed.; Academic: New York, 1978; pp 390-474.
30. E. Rose, A. Lecas, M. Quelquejeu, A. Kossanyi, and B. Boitrel Coord. Chem. Rev. 178-180 1998 1407 1431
31. L.K. Gottwald, and E.F. Ullman Tetrahedron Lett. 36 1969 3071 3074
32. S.S. Eaton, and G.R. Eaton J. Am. Chem. Soc. 97 1975 3660 3666
33. M.J. Nappa, and C.A. Tolman Inorg. Chem. 24 1985 4711 4719
34. R. Young, and C.K. Chang J. Am. Chem. Soc. 107 1985 898 909
35. C. Comte, C. Gros, S. Koeller, R. Guilard, D.J. Nurco, and K.M. Smith New J. Chem. 1998 621 626
36. B.F. Erlanger, F. Borek, S.M. Beiser, and S. Lieberman J. Biol. Chem. 228 1957 713 727
37. B.F. Erlanger, F. Borek, S.M. Beiser, and S. Lieberman J. Biol. Chem. 234 1959 1090 1094
38. A.H. Janoski, F.C. Shulman, and G. Wright Steroids 23 1974 49 64
39. A. Mares, J. DeBoever, G. Stans, E. Bosmans, and F. Kohen J. Immunol. Methods 183 1995 211 219
40. M. Adamczyk, Y.-Y. Chen, J.R. Fishpaug, and J.C. Gebler J. Chromatogr. A 657 1993 345 348
41. S.J. Pollack, G.R. Nakayama, and P.G. Schultz Methods Enzymol. 178 1989 551 568
42. B. Meunier Chem. Rev. 92 1992 1411 1456
43. J.T. Groves, W.J. Kruper Jr., and R.C. Haushalter J. Am. Chem. Soc. 102 1980 6375 6377
44. J.T. Groves, R.C. Haushalter, M. Nakamura, T.E. Nemo, and B.J. Evans J. Am. Chem. Soc. 103 1981 2884 2886
45. A.D. Adler, F.R. Longo, F. Kampas, and J.B. Kim J. Inorg. Nucl. Chem. 32 1970 2443 2445