Non-electrostatic complexes with DNA: Towards novel synthetic gene delivery systems

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 9, 2000, Pages 911-914

  Soto, Javier ^a   Bessodes, Michel ^a   Pitard, Bruno ^a   Mailhe, Philippe ^a   Scherman, Daniel ^a   Byk, Gerardo ^b  

^a SANOFI   (France)

^b BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL; DODECYL ISOCYANATE; OCTADECYL ISOCYANATE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DNA DRUG COMPLEX; DRUG STRUCTURE; DRUG SYNTHESIS; GENE TRANSFER; PHYSICAL CHEMISTRY; STRUCTURE ANALYSIS;

BISBENZIMIDE; CHEMISTRY, PHYSICAL; DNA; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ETHIDIUM; FLUORESCENT DYES; GENE TRANSFER TECHNIQUES; GENETIC VECTORS; HYDROGEN BONDING; LIPIDS; QUATERNARY AMMONIUM COMPOUNDS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0034192529     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00118-9     Document Type: Article

References (23)

1. (a) Lee, R. J.; Huang, L. Crit. Rev. Ther. Drug Carrier Sys. 1997, 14, 173.
2. (b) Scherman, D.; Bessodes, M.; Cameron, B.; Herscovici, J.; Hofland, H.; Pitard, B.; Soubrier, F.; Wils, P.; Crouzet, J. Curr. Opin. Biotechnol. 1998, 9, 480.
3. (a) Pitard, B.; Aguerre, O.; Airiau, M.; Lachagès, A.-M.; Boukhnikachvli, T.; Byk, G.; Dubertret, C.; Scherman, D.; Mayaux, J.-F.; Crouzet, J. Proc. Natl. Acad. Sci. USA 1997, 94, 14412.
4. (b) Pitard, B.; Oudrhiri, N.; Vigneron, J.-P.; Hauchecorne, M.; Aguerre, O.; Toury, R.; Airiau, M.; Ramasawmy, R.; Scherman, D.; Crouzet, J.; Lehn, J.-M.; Lehn, P. Proc. Natl. Acad. Sci. USA 1999, 96, 2621.
5. Perales J.P., Ferkol T., Beegen H., Ratnoff O.D., Hanson R.W. Proc. Natl. Acad. Sci. USA. 91:1994;4086.
6. Erbacher P., Remy J.-S., Behr J.-P. Gene Therapy. 6:1996;138.
7. Freimark B.D., Blezinger H.P., Florack V.J., Nordstrom J.L., Long S.D., Deshpande D.S., Nochumson S., Petrak K.L. J. Immunol. 160:1998;4580.
8. (a) Trauger, J. W.; Baird, E. E.; Dervan, P. B. Nature 1996, 382, 559.
9. (b) Kim, S. K.; Eriksson, S.; Kubista, M.; Nordén, B. J. Am. Chem. Soc. 1993, 115, 3441.
10. (c) Tanious, F. A.; Ding, D.; Patrick, D. A.; Tidwell, R. R.; Wilson, W. D. Biochemistry 1997, 36, 15315.
11. Suh D., Chaires J.B. Bioorg. Med. Chem. 3:1995;723.
12. (a) Loewe, H.; Urbanietz, J. Arzneim Forsch 1974, 24, 1927.
13. (b) French Patent No. 1.519.64.
14. Loontiens F.G., Regenfuss P., Zechel A., Dumortier L., Clegg R.M. Biochemistry. 29:1990;9029.
15. Wiederholt K., Rajur S.B., Giuliano J. Jr., O'Donnell M.J., McLaughlin L.W. J. Am. Chem. Soc. 118:1996;7055.
16. Muller W., Hattesohl I., Schuetz H.-J., Meyer G. Nucleics Acids Research. 9:1981;95.
17. Frau S., Bernadou J., Meunier B., Delaunay J.-C., Vercauteren J. New J. Chem. 19:1995;873.
18. Alisi M.A., Brufani M., Filocamo L., Gostoli G., Licandro E. Bioorg. Med. Chem. Lett. 5:1995;2077.
19. 2SO): δ 0.89 (t, J=7 Hz, 3H); 1.25-1.45 and 1.56 (2 mt, 20H); 2.93 (s, 3H); 3.15 (mt, 2H); 3.30-4.20 (mt, 8H:2H); 7.17 (dd, J=9 and 2 Hz, 1H); 7.22 (d, J=2 Hz, 1H); 7.34 (d, J=8.5 Hz, 2H); 7.45-7.60 (m, 1H); 7.63 (d, J=9 Hz, 1H); 7.81 (d, J=8 Hz, 1H); 8.06 (bd, J=9 Hz, 1H); 8.24 (d, J=8.5 Hz, 2H); 8.43 (bs, 1H). LSIMS m/z (MBA): 636 [M+H].
20. Fluorescence measurements were carried out on a Jobin-Yvon Spex fluoromax-2 spectrofluorometer (Longjumeau, France). Sample readings were conducted at an excitation wavelength of 350 nm and an emission wavelength of 450 nm. Complexes were prepared by mixing equal volumes of the product (2 or 3) solutions at different concentrations, strongly sonicated, and the plasmid DNA solution at the desired concentration. All solutions were in 1 mM Tris, pH 7.4, and 45 mM NaCl. Plasmid DNA used was pXL 3031; 1 μg of DNA corresponds to 0.4 pmol.
21. The vector (2 or 3)/DNA samples containing 1 μg of DNA were loaded on an agarose gel, and were run over 115 v during 40 min and direct detection of the complex grade under UV.
22. Byk G., Dubertret C., Escriou V., Frederic M., Jaslin G., Rangara R., Pitard B., Crouzet J., Wills P., Schwartz B., Scherman D. J. Med. Chem. 41:1998;224.
23. Byk G., Frederic M., Scherman D. Tetrahedron Lett. 38:1997;3219.