A versatile synthesis of tetraester polyamine lipids for gene transfection

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 8985-8988

  Lizarzaburu, Mike E ^a   Kurth, Mark J ^a   Nantz, Michael H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; DIAMINE DERIVATIVE; LIPID;

ARTICLE; CHEMICAL MODIFICATION; GENETIC TRANSFECTION; PARTIAL DRUG SYNTHESIS;

EID: 0033579645     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01934-6     Document Type: Article

References (18)

1. (a) Bally, M. B.; Harvie, P.; Wong, F. M. P.; Kong, S.; Wasan, E. K.; Reimer, D. L. Adv. Drug Delivery Rev. 1999, 38, 291.
2. (b) A. D. Miller, Angew. Chem. Int. Ed. 1998, 37, 1768.
3. (a) Lee, R. E.; Marshall, J.; Siegel, C. S.; Jiang, C.; Yew, N. S.; Nichols, M.; Nietupski, J. B.; Ziegler, R. J.; Lane, M. B.; Wang, K.X.; Wan, N.C.; Scheule, R.K.; Harris, D.J.; Smith, A.E.; Cheng, S.H. Human Gene Therapy 1996, 7, 1701.
4. (b) Bennett, M. J.; Aberle, A. M.; Balasubramaniam, R. P.; Malone, J. G.; Malone, R. W.; Nantz, M. H. J. Med. Chem. 1997, 40, 4069.
5. (a) Behr, J.P.; Demeneix, B.; Loeffler, J.P.; Perez-Mutul, J. Proc. Natl. Acad. Sci., USA 1991, 86, 6982.
6. (b) Remy, J.S.; Sirlin, C.; Vierling, P.; Behr, J.P. Bioconjugate Chem. 1994, 5, 647.
7. (c) Byk, G.; Frederic, M.; Scherman, D. Tetrahedron Lett. 1997, 38, 3219.
8. (e) Geall, A. J.; Blagbrough, I. S. Tetrahedron Lett. 1998, 39, 443.
9. Aberle, A. M.; Tablin, F.; Zhu, J.; Walker, N. J.; Gruenert, C. D.; Nantz, M. H. Biochemistry 1998, 37, 6533.
10. Abdun-Nur, A. R.; Issidoridies, C. H. J. Org. Chem. 1962, 27, 67.
11. Lizarzburu, M. E.; Jones, R. M.; Nantz, M. H.; Kurth, M. J. Org. Prep. Proc. Int. 1999, 31, 0000.
12. Leplawy, M. T.; Jones, D. S.; Kenner, G. W.; Sheppard, R. C. Tetrahedron 1960, 11, 39.
13. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 889.
14. Srisiri, W.; Lamparski, H.G.; O'Brien D.F. J. Org. Chem. 1996, 61, 5911.
15. Johansson, R.; Samuelsson, B. J. Chem. Soc., Chem. Commun. 1984, 108, 201.
16. For an analogous reaction, see: Pastor, S. D.; Togni, A. Tetrahedron Lett. 1990, 31, 839.
17. 3) δ 14.1, 22.6, 24.9, 29.1-29.6 (5 signals), 31.9, 34.2, 55.1, 62.9, 68.2,72.9, 113.6, 129.0, 130.3, 159.1, 173.3. Anal.
18. 1H NMR signals at δ 3.53-3.57, presumably corresponding to hydroxymethyl groups (e.g., as in precursors 12 and 13).