Cationic transport reagents

For use in transporting biologically active species into and through membrane barriers, a symmetrical cationic diamine compound having the general structure ##STR1## wherein m=1-10; R.sub.1 is a hydrogen, an alkyl group, an alkenyl group, a hydroxylated alkyl or alkenyl group, or an ether containing alkyl or alkenyl group; R.sub.2 is an alkyl group, an alkenyl group, or an alkyl or alkenyl containing acyl group; R.sub.3 is a hydrogen, an alkyl group, an alkenyl group, a hydroxylated alkyl or alkenyl group, or an ether containing alkyl or alkenyl group; R.sub.4 is a hydrogen, an alkyl group, an alkenyl group, a hydroxylated alkyl or alkenyl group, or an ether containing alkyl or alkenyl group; and X.sup.- is an anion.

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Claims

1. A compound having the structure: ##STR24## wherein n=0-10;

R.sub.2 is an acyl group;
R.sub.3 is an alkyl group, an alkenyl group, or a hydroxylated alkyl or alkenyl group; and
X.sup.- is an anion.

2. A compound according to claim 1, wherein n is between 0 and three and R.sub.3 is an alkyl group of from 1 to 10 carbons.

3. A compound according to claim 1, wherein n is between 0 and 3 and R.sub.3 is a methyl group.

4. A compound having the structure: ##STR25## wherein n=0-10;

R.sub.1 is an alkyl group, an alkenyl group, or a hydroxylated alkyl or alkenyl group;
R.sub.2 is an acyl group;
R.sub.3 is an alkyl group, an alkenyl group, or a hydroxylated alkyl or alkenyl group;
R.sub.5 is an alkyl or alkenyl group from 1 to 10 carbons; and
X.sup.- is an anion.

5. A compound according to claim 4, wherein n is between 0 and three, R.sub.1 is an alkyl group of from 1 to 10 carbons, R.sub.3 is an alkyl group of from 1 to 10 carbons, and R.sub.5 is an alkyl or alkenyl group from 1 to 10 carbons.

6. A compound according to claim 4, wherein n is between 0 and 3, R.sub.1 is a methyl group, R.sub.3 is a methyl group, and R.sub.5 is a methyl group.

7. A compound according to claim 4, wherein n is 1, R.sub.1 is a methyl group, R.sub.3 is a methyl group, and R.sub.5 is a methyl group.

8. A compound having the structure: ##STR26## wherein n=0-10;

R.sub.2 is an acyl group;
R.sub.3 is an alkyl group, an alkenyl group, or a hydroxylated alkyl or alkenyl group;
R.sub.5 is an alkyl or alkenyl group from 1 to 10 carbons;
R.sub.6 is an alkyl or alkenyl group from 1 to 10 carbons; and
X.sup.- is an anion.

9. A compound according to claim 8, wherein n is between 0 and three, R.sub.3 is an alkyl group of from 1 to 10 carbons, R.sub.5 is an alkyl or alkenyl group from 1 to 10 carbons, and R.sub.6 is an alkyl or alkenyl group from 1 to 10 carbons.

10. A compound according to claim 8, wherein n is between 0 and 3, R.sub.3 is a methyl group, R.sub.5 is a methyl group, and R.sub.6 is a methyl group.

11. A compound according to claim 8, wherein n is 1, R.sub.3 is a methyl group, R.sub.5 is a methyl group, and R.sub.6 is a methyl group.

12. A compound having the structure: ##STR27## wherein R is an alkyl or alkenyl group and

X.sup.- is an anion.

13. A compound according to claim 12, wherein X.sup.- is a halide.

14. A compound having the structure: ##STR28## wherein R is an alkyl or alkenyl group and

X.sup.- is an anion.

15. A compound according to claim 14, wherein X.sup.- is a halide.

16. A compound having the structure: ##STR29## wherein R is an alkyl or alkenyl group and

X.sup.- is an anion.

17. A compound according to claim 16, wherein X.sup.- is a halide.

18. A compound having the structure: ##STR30## wherein n=0-10;

R.sub.1 is an alkyl group, an alkenyl group, or a hydroxylated alkyl or alkenyl group;
R.sub.2 is an acyl group;
R.sub.3 is an alkyl group, an alkenyl group, or a hydroxylated alkyl or alkenyl group; and
X.sup.- is an anion.

19. A compound according to claim 18, wherein n is between 0 and three, R.sub.1 is an alkyl group of from 1 to 10 carbons, R.sub.2 is an alkyl or alkenyl containing acyl group, and R.sub.3 is an alkyl group of from 1 to 10 carbons.

20. A compound according to claim 18, wherein n is between 0 and 3, R.sub.1 is a methyl group, R.sub.2 is an alkyl or alkenyl containing acyl group, and R.sub.3 is a methyl group.

21. A compound according to claim 18, wherein n is 1, R.sub.1 is a methyl group, R.sub.2 is an alkyl or alkenyl containing acyl group, and R.sub.3 is a methyl group.

22. A compound having the structure: ##STR31## wherein m=1-10;

R.sub.1 is an alkyl group, an alkenyl group, a hydroxylated alkyl or alkenyl group, or an ether containing alkyl or alkenyl group;
R.sub.2 is an acyl group;
R.sub.3 is an alkyl group, an alkenyl group, a hydroxylated alkyl or alkenyl group, or an ether containing alkyl or alkenyl group;
R.sub.4 is a hydroxylated alkyl or alkenyl group, or an ether containing alkyl or alkenyl group; and
X.sup.- is an anion.
Referenced Cited
U.S. Patent Documents
4812449 March 14, 1989 Rideout
5171678 December 15, 1992 Behr et al.
5186923 February 16, 1993 Piwnica-Worms et al.
5208036 May 4, 1993 Eppstein et al.
5264618 November 23, 1993 Felgner et al.
5277897 January 11, 1994 Piwnica-Worms et al.
5279833 January 18, 1994 Rose
5334761 August 2, 1994 Gebeyehu
5527928 June 18, 1996 Nantz et al.
Other references
  • RN 113114-79-7, and RN 113091-72-8, 1960. Seebach et.al., Helv. Chim. Acta, 60(2), 301-25, 1977. Ann et.al., Huaxue Xuebao, 49(5), 507-12, 1991. Niemer et.al., Zh. Physiologic. Chimie, 204-207, 1954. Epsztein et.al., Academie Des Sciences, 2910-2911, 1960. "Hydrophobic domain of cationic lipids influence respiratory epithial cell DNA transfection," Balasubramaniam, R.P. et al. Manuscript in Preparation, 1994.
Patent History
Patent number: 5892071
Type: Grant
Filed: Sep 15, 1995
Date of Patent: Apr 6, 1999
Assignee: The Reagents of The University of California (Oakland, CA)
Inventors: Michael H. Nantz (Davis, CA), Michael J. Bennett (Davis, CA), Robert W. Malone (Davis, CA)
Primary Examiner: Shailendra Kumar
Attorney: James M. Ritchey
Application Number: 8/528,733