Benzophenone-containing fatty acids and their related photosensitive fluorescent new probes: Design, physico-chemical properties and preliminary functional investigations

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 24, 2011, Pages 7464-7473

  Hilbold, Benoît ^a   Perrault, Marie ^b   Ehret, Christophe ^a   Niu, Song Lin ^a   Frisch, Benoît ^a   Pécheur, Eve Isabelle ^b   Bourel Bonnet, Line ^a  

^a Faculté de Pharmacie   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

Benzophenone; Fatty acid; Fluorescence; Membrane protein; Photolabeling

Indexed keywords

BACTERIORHODOPSIN; BENZOPHENONE DERIVATIVE; FATTY ACID DERIVATIVE; FLUORESCENT DYE;

ARTICLE; CONTROLLED STUDY; HYDROPHOBICITY; IN VITRO STUDY; PHOTOAFFINITY LABELING; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BACTERIORHODOPSINS; BENZOPHENONES; FATTY ACIDS; FLUORESCENT DYES; HALOBACTERIUM SALINARUM; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; RHODAMINES; SPECTROMETRY, FLUORESCENCE;

EID: 82255192212     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.10.043     Document Type: Article

References (43)

1. F. Kotzyba-Hibert, I. Kapfer, and M. Goeldner Angew. Chem., Int. Ed. Engl. 34 1995 1296
2. J. Brunner Annu. Rev. Biochem. 62 1993 483
3. G. Dorman, and G.D. Prestwich Biochemistry 33 1994 5661
4. G. Dorman, and G.D. Prestwich TIB Tech 18 2000 64
5. R. Kage, S.E. Leeman, J.E. Krause, C.E. Costello, and N.D. Boyd J. Biol. Chem. 271 1996 25797
6. E. Sachon, G. Bolbach, G. Chassaing, S. Lavielle, and S. Sagan J. Biol. Chem. 277 2002 50409
7. M. Ayoub, G. Chassaing, A. Loffet, and S. Lavielle Tetrahedron Lett. 23 1995 4069
8. P. Karoyan, S. Sagan, G. Clodic, S. Lavielle, and G. Chassaing Bioorg. Med. Chem. Lett. 8 1998 1369
9. S. Ponthieux, J. Cabot, B. Mouillac, R. Seyer, C. Barberis, and E. Carnazzi J. Med. Chem. 48 2005 3379
10. L. Li, W. Tang, and Z.K. Zhao Bioorg. Med. Chem. Lett. 19 2009 4824
11. C.R. Toh, T.A. Fraterman, D.A. Walker, and R.C. Bailey Langmuir 25 2009 8894
12. P. Yan, T. Wang, G.J. Newton, T.V. Knyushko, Y. Xiong, D.J. Bigelow, T.C. Squier, and M.U. Mayer Chem. Bio. Chem. 10 2009 1507
13. R.M. Epand Biopolymers 43 1997 15
14. P. Jolimaitre, A. Roux, A. Blanpain, C. Leduc, P. Bassereau, and L. Bourel-Bonnet Chem. Phys. Lipids 133 2005 215
15. L. Bourel-Bonnet, E.I. Pécheur, C. Grandjean, A. Blanpain, T. Baust, O. Melnyk, B. Hoflack, and H. Gras-Masse Bioconjugate Chem. 16 2005 450
16. P. Jolimaitre, C. Poirier, A. Richard, A. Blanpain, B. Delord, D. Roux, and L. Bourel-Bonnet Eur. J. Med. Chem. 42 2007 114
17. R. Breslow, S. Balwin, T. Flechtner, P. Kalicky, S. Liu, and W. Washburn J. Am. Chem. Soc. 95 1973 3251
18. M.F. Czarniecki, and R. Breslow J. Am. Chem. Soc. 101 1979 3675
19. D.Z. Markovic, T. Durand, and L.K. Patterson Photochem. Photobiol. 51 1990 389
20. D.Z. Markovic, and L.K. Patterson Photochem. Photobiol. 58 1993 329
21. A.K. Lala Chem. Phys. Lipids 116 2002 177
22. B. John, E.R. Kumar, and A.K. Lala Biophys. Chem. 87 2000 37
23. Y. Gan, P. Wang, and T.A. Spencer J. Org. Chem. 71 2006 9487
24. Y. Gan, D.H. Blank, J.E. Ney, and T.A. Spencer J. Org. Chem. 71 2006 5864
25. P. Wang, D.H. Blank, and T.A. Spencer J. Org. Chem. 69 2004 2693
26. R. Blumenthal, S.A. Gallo, M. Viard, Y. Raviv, and A. Puri Chem. Phys. Lipids 116 2002 39
27. A.K. Lala, and E.R. Kumar J. Am. Chem. Soc. 115 1993 3982
28. K. Nakatani, C. Dohno, T. Nakamura, and I. Saito Tetrahedron Lett. 39 1998 2779
29. K. Omura, and D. Swern Tetrahedron 34 1978 1651
30. K.F. Bernardy, M.B. Floyd, J.F. Poletto, and M.J. Weiss J. Org. Chem. 44 1979 1438
31. K.E. Harding, L.M. May, and K.F. Dick J. Org. Chem. 40 1975 1664
32. J.E. Whitaker, R.P. Haugland, D. Ryan, P.C. Hewitt, and F.G. Prendergast Anal. Biochem. 207 1992 267
33. M.R. Longmire, M. Ogawa, Y. Hama, N. Kosaka, C.A. Regino, P.L. Choyke, and H. Kobayashi Bioconjugate Chem. 19 2008 1735
34. M. Benchaib, R. Delorme, M. Pluvinage, P.A. Bryon, and C. Souchier Histochem. Cell Biol. 106 1996 253
35. D. Hoekstra, T. de Boer, K. Klappe, and J. Wilschut Biochemistry 23 1984 5675
36. R. Henderson J. Mol. Biol. 93 1975 123
37. E. Pebay-Peyroula, G. Rummel, J.P. Rosenbusch, and E.M. Landau Science 277 1997 1676
38. Pécheur, E. I., Hilbold, B., Bourel-Bonnet, L. French Patent Application 1152498, 2011.
39. B. John, E.R. Kumar, and A.K. Lala Biophys. Chem. 87 2000 37
40. Y.I. Matsushita, K. Sakamoto, T. Murakami, and T. Matsui Synth. Commun. 24 1994 3307
41. H. Brechbuehler, H. Buechi, E. Hatz, J. Schreiber, and A. Eschenmoser Helv. Chim. Acta 48 1965 1746
42. Bastian, J. A. et al. U.S. Patent 6025382, 2000.
43. D. Lavillette, B. Bartosch, D. Nourrisson, G. Verney, F.L. Cosset, F. Penin, and E.I. Pécheur J. Biol. Chem. 281 2006 3909