Improved transport of nucleotide monophosphates by lipophilic phosphonium–nucleobase conjugates

Abstract

Lipophilic phosphonium–nucleobase conjugates 3 and 5 showed improved transport of AMP and GMP in comparison with lipophilic phosphonium salts, lipophilic complementary nucleobases, or a joint co-carrier system consisting of a lipophilic phosphonium salt and a nucleobase.

References

1. Nucleotide Analogues as Antiviral Agents, ed. J. C. Martin, American Chemical Society, Washington, D.C., 1989.
2. D. M. Rudkevich, Z. Brzozka, M. Palys, H. C. Visser, W. Verboom and D. N. Reinhoudt, Angew. Chem., Int. Ed. Engl., 1994, 33, 467; M. W. Hosseini, A. J. Blacker and J.-M. Lehn, J. Am. Chem. Soc., 1990, 112, 3896; V. Jubian, R. P. Dixon and A. D. Hamilton, J. Am. Chem. Soc., 1992, 114, 1120; G. Deslongchamps, J. Rebek, A. Galan and J. de Mendoza, Angew. Chem., Int. Ed. Engl., 1994, 33, 467; B. L. Iverson, K. Shreder, V. Kral and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11 022; F. P. Schmidtchen, Tetrahedron Lett., 1989, 30, 4493; S. Nishizawa, P. Buhlmann, M. Iwao and Y. Umezawa, Tetrahedron Lett., 1995, 36, 6483.
3. (a) I. Tabushi, Y. Kobuke and J.-i. Imuta, J. Am. Chem. Soc., 1980, 102, 1744; (b) I. Tabushi, Y. Kobuke and J.-i. Imuta, J. Am. Chem. Soc., 1981, 103, 6152; (c) K. Maruyama, H. Tsukube and T. Araki, J. Am. Chem. Soc., 1982, 104, 3197; (d) H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677; (e) V. Kral, J. L. Sessler and H. Furuta, J. Am. Chem. Soc., 1992, 114, 8704; (f) F. Diederich and T. Li, J. Org. Chem., 1992, 57, 3449; (g) T. Li, S. J. Krasne, B. Persson, H. R. Kaback and F. Diederich, J. Org. Chem., 1993, 58, 380; (h) J. L. Sessler, H. Furuta and V. Kral, Supramol. Chem., 1993, 1, 209 and references cited therein; (i) V. Kral and J. L. Sessler, Tetrahedron, 1995, 51, 539; (j) C. Andreu, A. Galan, K. Kobiro, J. de Mendoza, T. K. Park, J. Rebek, A. Salmeron and N. Usman, J. Am. Chem. Soc., 1994, 116, 5501; (k) K. Yasuhisa, H. Hatekayama, H. Seshimo and H. Ogoshi, Supramol. Chem., 1994, 3, 267.
4. S. B. Lee, H. Choo and J.-I. Hong, details will be published elsewhere.
5. J.-P. Behr and J.-M. Lehn, J. Am. Chem. Soc., 1973, 95, 6108; H. Tsukube, J. Chem. Soc., Perkin Trans. 1, 1983, 29.
6. H. Furuta, T. Morishima, V. Kral and J. L. Sessler, Supramol. Chem., 1993, 3, 5.