A structure-activity investigation of hemifluorinated bifunctional bolaamphiphiles designed for gene delivery

Comptes Rendus Chimie

Volumn 12, Issue 1-2, 2009, Pages 188-208

  Brunelle, Mélanie ^b   Polidori, Ange ^a   Denoyelle, Séverine ^a   Fabiano, Anne Sylvie ^a   Vuillaume, Pascal Y ^b   Laurent Lewandowski, Sylvette ^b   Pucci, Bernard ^a  

^a UNIVERSITY OF AVIGNON   (France)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Bolaamphiphile; Bolaplexes; Cationic polar head; Cell cytotoxicity; Gene transfer; Hemifluorinated surfactants

Indexed keywords

EID: 59249087564     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2008.05.018     Document Type: Article

References (75)

1. Kumar V.V., Singh R.S., and Chaudhuri A. Curr. Med. Chem. 10 (2003) 1297 and the references therein
2. Miller A.D. Angew. Chem., Int. Ed. 37 (1998) 1768 and the references therein
3. Felgner P.L., Gadek T.R., Holm M., Roman R., Chan W., Wenz M., Northorp J.P., Ringold G.M., and Danielsen M. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 7413
4. Bajaj A., Kondiah P., and Bhattacharya S. J. Med. Chem. 50 (2007) 2432
5. Antipina M.N., Schulze M., Dobner B., Langner A., and Brezesinski G. Langmuir 23 (2007) 3919
6. Leblond J., Mignet N., Largeau C., Spanedda M.-V., Seguin J., Scherman D., and Herscovici J. Bioconjugate Chem. 18 (2007) 484
7. Gopal V., Prasad T.K., Rao N.M., Takafuji M., Rahman M.M., and Ihara H. Bioconjugate Chem. 17 (2006) 1530
8. Ewert K.K., Evans H.M., Bouxsein N.F., and Safinya C.R. Bioconjugate Chem. 17 (2006) 877
9. Ilies M.A., Seitz W.A., Johnson B.H., Ezell E.L., Miller A.L., Thompson E.B., and Balaban A.T. J. Med. Chem. 49 (2006) 3872
10. Karmali P.P., Majeti B.K., Sreedhar B., and Chaudhuri A. Bioconjugate Chem. 17 (2006) 159
11. Picquet E., Le Ny K., Delépine P., Montier T., Yaouanc J.-J., Cartier D., des Abbayes H., Férec C., and Clément J.-C. Bioconjugate Chem. 16 (2005) 1051
12. Sen J., and Chaudhuri A. Bioconjugate Chem. 16 (2005) 903 and references therein
13. Chabaud P., Camplo M., Payet D., Serin G., Moreau L., Barthélémy P., and Grinstaff M.W. Bioconjugate Chem. 17 (2006) 466
14. Belting M., Sandgren S., and Wittrup A. Adv. Drug Deliv. Rev. 57 (2005) 505
15. Kostarelos K., and Miller A.D. Chem. Soc. Rev. 34 (2005) 970
16. Fuhrhop J.H., and Wang T. Chem. Rev. 104 (2004) 2901
17. Guilbot J., Benvegnu T., Legros N., Plusquellec D., Dedieu J.-C., and Gullik A. Langmuir 17 (2001) 613
18. Zelphati O., Uyechi L.S., Barron L.G., and Szoka F.C. Biochim. Biophys. Acta 1390 (1998) 119
19. Moret I., Peris J.E., Guillem V.M., Benet M., Revert F., Dasi F., Crespo A., and Alino S.F. J. Controlled Release 76 (2001) 169
20. Reimer D.L., Kong S., Monck M., Wyles J., Tam P., Wasan E.K., and Bally M.B. J. Pharmacol. Exp. Ther. 289 (1999) 807
21. Morgan D.M.L., Larvin V.L., and Pearson J.D. J. Cell Sci. 94 (1989) 553
22. Hill I.R.C., Garnett M.C., Bignotti F., and Davis S.S. Biochim. Biophys. Acta 1427 (1999) 161 (see references therein)
23. Toussignant J.D., Gates A.K., Ingram L.A., Johnson C.L., Nietupski J.B., Cheng S.H., Eastman S.J., and Scheule R.K. Hum. Gene Ther. 11 (2000) 2493
24. Loisel S., Le Gall C., Doucet L., Ferec C., and Floch V. Hum. Gene Ther. 12 (2001) 685
25. Eaton M.A.W., Baker T.S., Caterall C.F., Crook K., Macaulay G.S., Mason B., Norman T.J., Parker D., Perry J.J.B., Taylor R.J., Turner A., and Weir A.N. Angew. Chem. Int. Ed. 39 (2000) 4063
26. Weissig V., and Torchilin V.P. Adv. Drug Deliv. Rev. 49 (2001) 127
27. Yoshimura T., Hasegawa S., Hirashima N., Nakanishi M., and Ohwada T. Bioorg. Med. Chem. Lett. 11 (2001) 2897
28. Ren T., Zhang G., and Liu D. Tetrahedron Lett. 42 (2001) 1007
29. Ren T., Zhang G., and Liu D. Bioorg. Med. Chem. Lett. 9 (2001) 2969
30. Gaucheron J., Santaella C., and Vierling P. Bioconjugate Chem. 12 (2001) 569
31. Fabio K., Gaucheron J., Di Giorgio C., and Vierling P. Bioconjugate Chem. 14 (2003) 358
32. Miramon M.-L., Mignet N., and Herscovici J. J. Org. Chem. 69 (2004) 6949
33. Denoyelle S., Polidori A., Brunelle M., Vuillaume P.Y., Laurent S., El Azhary Y., and Pucci B. New J. Chem. 30 (2006) 629
34. Kissa E. Fluorinated Surfactants. Synthesis, Properties, Applications. Surfactants Sciences Series 50 (1994), Marcel Dekker, New York
35. Kadi M., Hanson P., and Almgren M. Langmuir 18 (2002) 9243
36. Barthelemy P., Tomao V., Selb J., Chaudier Y., and Pucci B. Langmuir 18 (2002) 2557
37. Liang K., and Hui Y. J. Am. Chem. Soc. 114 (1992) 6588
38. Vuillaume P.Y., Brunelle M., Van Calsteren M.R., Laurent-Lewandowski S., Bégin A., Lewandowski R., Talbot B.G., and El Azhary Y. Biomacromolecules 6 (2005) 1769
39. Izumrudov V.A., Zhiryakova M.V., and Goulko A.A. Langmuir 18 (2002) 10348
40. Gershon H., Ghirlando R., Guttman S.B., and Minsky A. Biochemistry 32 (1993) 7143
41. Boussif O., Lezoualch F., Zanta M.A., Mergny M.D., Scherman D., Demeneix B., and Behr J.P. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 7297
42. Faneca H., Simões S., and Pedroso de Lima M.C. Biochim. Biophys. Acta 1567 (2002) 23
43. Wolfert M.A., Dash P.R., Nazarova O., Oupicky D., Seymour L.W., Smart S., Strohalm J., and Ulbrich K. Bioconjugate Chem. 10 (1999) 993
44. Zuidam N.J., Hirsch-Lerner D., Margulies S., and Barenholz Y. Biochim. Biophys. Acta 1419 (1999) 207
45. Ito A., Miyazoe R., Mitoma J., Akao T., Osaki T., and Kunitake T. Biochem. Int. 22 (1990) 235
46. Akao T., and Ito A. J. Chem. Soc., Perkin Trans. 2 (1997) 213
47. Kogiso M., Ohnishi S., Yase K., Masuda M., and Shimizu T. Langmuir 14 (1998) 4978
48. Kogiso M., Hanada T., Yase K., and Shimizu T. Chem. Commun. (1998) 1791
49. Shimizu T., and Masuda M. J. Am. Chem. Soc. 119 (1997) 2812
50. Nakazawa I., Masuda M., Okada Y., Hanada T., Yase K., Asai M., and Shimizu T. Langmuir 15 (1999) 4757
51. Masuda M., and Shimizu T. Langmuir 20 (2004) 5969
52. Shimizu T., Iwaura R., Masuda M., Hanada T., and Yase K. J. Am. Chem. Soc. 123 (2001) 5947
53. Iwaura R., Yoshida K., Masuda M., Yase K., and Shimizu T. Chem. Mater. 14 (2002) 3047
54. Iwaura R., Yoshida K., Masuda M., Ohnishi-Kameyama M., Yoshida M., and Shimizu T. Angew. Chem., Int. Ed. 42 (2003) 1009
55. Zarif L., Gulik-Krzywicki T., Riess J.G., Pucci B., Guedj C., and Pavia A.A. Colloids Surf. A 84 (1996) 107
56. Giulieri F., Krafft M.-P., and Riess J.G. Angew. Chem., Int. Ed. Eng. 33 (1994) 1514
57. Giulieri F., Guillod F., Greiner J., Krafft M.-P., and Riess J.G. Chem.-Eur. J. 2 (1996) 1335
58. Giulieri F., and Krafft M.-P. J. Colloid Interface Sci. 258 (2003) 335
59. Dauty E., Remy J.-S., Zuber G., and Behr J.-P. Bioconjugate Chem. 13 (2002) 831
60. Miller A.D. Methods Mol. Med. 90 (2004) 107
61. Pouton C.W., and Seymour L.W. Adv. Drug Deliv. Rev. 34 (1998) 3
62. Zhang Y., and Anchordoquy T.J. Biochim. Biophys. Acta 1663 (2004) 143
63. Pitard B., Aguerre O., Airiau M., Lachagès A.-M., Boukhnikachvili T., Byk G., Dubertret C., Herviou C., Scherman D., Mayaux J.-F., and Crouzet J. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 14412
64. Cui L., and Zhu L. Langmuir 22 (2006) 5982
65. Smisterova J., Wagenaar A., Stuart M.C.A., Polushkin E., ten Brinke G., Hulst R., Engberts J.B., and Hoekstra D. J. Biol. Chem. 276 (2001) 47615
66. Majeti B.K., Karmali P.P., Madhavendra S.S., and Chaudhuri A. Bioconjugate Chem. 16 (2005) 676
67. Blessing T., Remy J.-S., and Behr J.-P. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 1427
68. Dauty E., Remy J.-S., Blessing T., and Behr J.-P. J. Am. Chem. Soc. 123 (2001) 9227
69. Gebhart C.L., and Kabanov A.V. J. Controlled Release 73 (2001) 401
70. Fyles T.M., and Zeng B. J. Org. Chem. 63 (1998) 8337
71. Salvati A., Ciani L., Ristori S., Martini G., Masi A., and Arcangeli A. Biophys. J. 121 (2006) 21
72. Mislick K.A., and Baldeschwieler J.D. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 12349
73. Zuhorn I.S., Oberle V., Visser W.H., Engberts J.B.F.N., Bakowsky U., Polushkin E., and Hoekstra D. Biophys. J. 83 (2002) 2096
74. Hirsch-Lerner D., Zhang M., Eliyahu H., Ferrari M.E., Wheeler C.J., and Barenholz Y. Biochim. Biophys. Acta 1714 (2005) 71
75. Honoré I., Grosse S., Frison N., Favatier F., Monsigny M., and Fajac I. J. Controlled Release 107 (2005) 537