Novel Biodegradable Pyridinium Amphiphiles for Gene Delivery

European Journal of Organic Chemistry

Volumn , Issue 22, 2003, Pages 4406-4412

  Pijper, Dirk ^a   Bulten, Erna ^c   Šmisterová, Jarmila ^c   Wagenaar, Anno ^a   Hoekstra, Dick ^c   Engberts, Jan B F N ^a   Hulst, Ron ^a,b  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b Kiadis BV   (Netherlands)

^c UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Amphiphiles; Biodegradable; Gene technology; Vesicles

Indexed keywords

1 METHYL 3,5 BIS(HEXADEC 11 ENYLOXYCARBONYL)PYRIDINIUM CHLORIDE; 1 METHYL 3,5 BIS(HEXADECYLOXYCARBONYL)PYRIDINIUM CHLORIDE; 1 METHYL 3,5 BIS(METHYLOXYCARBONYL)PYRIDINIUM CHLORIDE; 1 METHYL 3,5 BIS(OCTADEC 11 ENYLOXYCARBONYL)PYRIDINIUM CHLORIDE; 1 METHYL 3,5 BIS(OCTADECYLOXYCARBONYL)PYRIDINIUM CHLORIDE; 1 METHYL 3,5 BIS(TETRADEC 11 ENYLOXYCARBONYL)PYRIDINIUM CHLORIDE; 1 METHYL 3,5 BIS(TETRADECYLOXYCARBONYL)PYRIDINIUM CHLORIDE; 3,5 PYRIDINEDICARBOXYLIC ACID; AMPHOPHILE; CATION; DICARBOXYLIC ACID DERIVATIVE; DNA; DRUG CARRIER; ESTER; PHENAZOPYRIDINE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ARTICLE; BIODEGRADATION; CELL CULTURE; CELL STRAIN COS7; CELL STRAIN HEPG2; CELL VACUOLE; CONTROLLED STUDY; CYTOTOXICITY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SYNTHESIS; EUKARYOTE; GENE TARGETING; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; HYDROLYSIS; HYDROPHOBICITY; MATERIALS; NONHUMAN; NONVIRAL GENE DELIVERY SYSTEM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0345276412     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300361     Document Type: Article

References (37)

1. R. C. Crystal, Science 1995, 270, 404-410.
2. W. F. Anderson, Nature 1998, 392 (Suppl.), 25-30.
3. K. K. Hunt, S. A. Vorburger, Science 2002, 297, 415-416.
4. I. MacLachlan, P. Cullis, R. W. Graham, Curr. Opin. Mol. Ther. 1999, 1, 252-259.
5. Y. Ilan, G. Droguett, N. R. Chowdhury, Y. Li, K. Sengupta, N. R. Thummala, A. Davidson, J. R. Chowdhury, MS Horwitz, Proc. Natl. Acad. Sci. USA 1997, 94, 2587-2592.
6. G. M. Rubanyi, Mol. Asp. Med. 2001, 22, 113-142.
7. D. Ferber, Science 2001, 294, 1638-1642.
8. A. D. Miller, Angew. Chem. Int. Ed. 1998, 37, 1768-1785.
9. J. P. Behr, Bioconj. Chem. 1994, 5, 382-389.
10. P. L. Felgner, T. R. Gadek, M. Holm, R. Roman, H. W. Chan, M. Wenz, J. P. Northrop, G. M. Ringold, M. Danielsen, Proc. Natl. Acad. Sci. USA 1987, 84, 7413-7417.
11. B. Abdallah, L. Sachs, B. A. Demeneix, Biol. Cell 1995, 85, 1-7.
12. G. Byk, C. Dubertret, V. Escriou, M. Frederic, G. Jaslin, R. Rangara, B. Pitard, J. Crouzet, P. Wils, B. Schwartz, D. Scherman, J. Med. Chem. 1998, 41, 229-235.
13. J. Marshall, J. B. Nietupski, E. R. Lee, C. S. Siegel, P. W. Rafter, S. A. Rudginsky, C. D. Chang, S. J. Eastman, D. J. Harris, R. K. Scheule, S. H. Cheng, J. Drug Target. 2000, 7, 453-469.
14. M. J. Bennett, A. M. Aberle, R. P. Balasubramaniam, J. G. Malone, R. W. Malone, M. H. Nantz, J. Med. Chem. 1997, 40, 4069-4078.
15. I. van der Woude, H. W. Visser, M. B. A. ter Beest, A. Wagenaar, M. H. J. Ruiters, J. B. F. N. Engberts, D. Hoekstra, Biochim. Biophys. Acta 1995, 1240, 34-40.
16. I. van der Woude, A. Wagenaar, A. A. P. Meekel, M. B. A. ter Beest, M. H. J. Ruiters, J. B. F. N. Engberts, D. Hoekstra, Proc. Natl. Acad. Sci. USA 1997, 94, 1160-1165.
17. A. A. P. Meekel, A. Wagenaar, J. Šmistrová, J. E. Kroeze, P. Haadsma, B. Bosgraaf, M. C. A. Stuart, A. Brisson, M. H. J. Ruiters, J. B. F. N. Engberts, D. Hoekstra, Eur J. Org. Chem. 2000, 4, 665-673.
18. A. Roosjen, J. Šmistrová, C. Driessen, J. T. Anders, A. Wagenaar, D. Hoekstra, R. Hulst, J. B. F. N. Engberts, Eur. J. Org. Chem. 2002, 7, 1271-1277.
19. J. A. Boomer, D. H. Thompson, S. M. Sullivan, Pharm. Res. 2002, 19, 1292-1301.
20. S. Obika, W. Yu, A. Shimoyama, T. Uneda, T. Minami, K. Miyashita, T. Doi, T. Imanishi, Biol. Pharm. Bull. 1999, 22, 187-190.
21. I. S. Zuhorn, R. Kalicharan, D. Hoekstra, J. Biol. Chem. 2002, 277, 18021-18028.
22. B. Tycko, F. R. Maxfield, Cell 1982, 28, 643-651.
23. I. Mellman, R. Fuchs, A. Helenius, Annu. Rev. Biochem. 1986, 55, 663-700.
24. H. Farhood, R. Bottega, R. M. Epand, L. Huang, Biochim. Biophys. Acta 1992, 1111, 239-346.
25. R. Leventis, J. R. Silvius, Biochim. Biophys. Acta 1990, 1023, 124-132.
26. A. M. Aberle, F. Tablin, J. Zhu, N. J. Walker, D. C. Gruenert, M. H. Nantz, Biochemistry 1998, 37, 6533-6540.
27. For an example of the morphological behaviour of SAINT materials see: J. Šmisterová, A. Wagenaar, M. C. A. Stuart, E. Polushkin, E. ten Brinke, R. Hulst, J. B. F. N. Engberts, D. Hoekstra, J. Biol. Chem. 2001, 276, 47615-47622.
28. S. Audouy, D. Hoekstra, Mol. Membr. Biol. 2001, 18, 129-143.
29. P. C. Bell, M. Bergsma, I. P. Dolbnya, W. Bras, M. C. A. Stuart, A. E. Rowan, M. C. Feiters, J. B. F. N. Engberts, J. Am. Chem. Soc. 2003, 125, 1551-1558.
30. E. J. R. Südholter, J. B. F. N. Engberts, J. Am. Chem. Soc. 1980, 102, 2467.
31. E. J. R. Südholter, J. B. F. N. Engberts, W. H. de Jeu, J. Phys. Chem. 1982, 86, 1908-1913.
32. J. H. Felgner, R. Kumar, C. N. Sridhar, C. J. Wheeler, Y. J. Tjai, R. Border, P. Ramsey, M. Martin, P. L. Felgner, J. Biol. Chem. 1994, 269, 2550-2561.
33. I. S. Zuhorn, V. Oberle, W. H. Visser, J. B. F. N. Engberts, U. Bakowsky, E. Polushkin, D. Hoekstra, Biophys. J. 2002, 83, 2096-2108.
34. 2O.
35. W. J. Baumann, H. K. Mangold, J. Org. Chem. 1964, 29, 3055-3069.
36. I. Muizebelt, P. Oosting, C. van der Pol, A. Wagenaar, J. Šmisterová, E. Bulten, C. Driessen, I. S. Zuhorn, D. Hoekstra, R. Hulst., J. B. F. N. Engberts, Eur. J. Org. Chem., manuscript accepted.
37. M. Kristiansen, J. Eriksen, K. A. Joergensen, J. Chem. Soc., Perkin Trans. 1 1990, 1, 101-103.