Amphiphilic Janus-dendrimers
The invention concerns compounds of the formula: X—(Y) t wherein: X is Formula (X), each Y is the same or different and is Formula (Y) —O—[CH 2 —CH(OH)—CH 2 —O—] m —H; or —C(OR 5 ) 3 ; R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 9 , R 10 are each, independently, —(CH 2 CH 2 O) m —R 4 , —[CH 2 CH(OH)CH 2 O] n H, OR 11 , —O(CH 2 ) P R 13 , or —(CH 2 )R 12 ; each R 4 is independently OR 5 or OH; R 5 , R 11 and R 12 are each, independently, H or C 1 -C 30 alkyl; R 13 is —NH 3 + Cl − or —NHBoc; t is an integer from 2 to 6; m, n, and p are each, independently, an integer from 1 to 12; and each q, r, and s is 0 or 1 and the sum of q+r+s is at least 2.
1. An amphiphilic Janus dendrimer having of the formula:
(X) t -A-(Y) z
wherein:
each t and z is independently an integer from 1-6;
A is
each X is independently selected from:
and —O—[CH 2 —CH(OH)—CH 2 —O—] m —H; or —C(OR 5 ) 3 ;
wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , are each, independently, C 1 -C 30 alkyl, —O(CH 2 ) p R 13 , or —(CH 2 ) p R 12 ;
each R 12 is, independently, H or C 1 -C 30 alkyl;
R 13 is —NHBoc;
m and p are each, independently, an integer from 1 to 12;
each q, r, and s is 0 or 1 and the sum of q+r+s is at least 2;
each Y is independently selected from
—O—[CH 2 —CH(OH)—CH 2 —O—] m —H; or —C(OR 5 ) 3 ;
R 1 , R 2 , R 3 , R 6 , and R 7 are each, independently, —(CH 2 CH 2 O) m —R 4 or —[CH 2 CH(OH)CH 2 O] n H,
each R 4 is independently R 5 or H;
each R 5 is independently H or C 1 -C 30 alkyl;
m and n are each, independently, an integer from 1 to 12; and
each q, r, and s is 0 or 1 and the sum of q+r+s is at least 2;
provided that when X is
wherein when A is —CH 2 OC(═O)—, —NHC(═O)— or —O—C(═O)—, at least one of
(a) X is
or
(b) Y is
2. The amphiphilic Janus dendrimer of claim 1 having the formula:
3. The amphiphilic Janus dendrimer of claim 1 having the formula:
wherein R′ is OH or OCH 3 .
4. The amphiphilic Janus dendrimer of claim 3 :
wherein m is an integer from 1 to 6.
5. The amphiphilic Janus dendrimer of claim 1 having the formula:
6. The amphiphilic Janus dendrimer of claim 1 having the formula:
7. The amphiphilic Janus dendrimer of claim 1 having the formula:
8. The amphiphilic Janus dendrimer of claim 1 having the formula:
9. The amphiphilic Janus dendrimer of claim 8 , wherein m is an integer from 1 to 6.
10. The amphiphilic Janus dendrimer of claim 1 having the formula:
11. The amphiphilic Janus dendrimer of claim 1 having the formula:
12. The amphiphilic Janus dendrimer of claim 11 , wherein m is an integer from 1 to 6.
13. The amphiphilic Janus dendrimer having the formula:
wherein X is —CH 2 —NH—CO— or —NH—CO—; or
wherein X is —CH 2 —NH—CO— or —NH—CO—; R′ is —NHBoc or —NH 3 + Cl − .
14. The amphiphilic Janus dendrimer of claim 1 , wherein n is 4 or 12.
15. The amphiphilic Janus dendrimer of claim 1 having the formula:
16. A liposome comprising a plurality of amphiphilic Janus dendrimers of claim 1 .
17. A method of forming a liposome comprising contacting a mixture of an alcohol and a plurality of amphiphilic Janus dendrimer of claim 1 with water.
18. The method of claim 17 , wherein the alcohol is ethanol.
19. A method of delivery of a therapeutic composition comprising contacting a liposome comprising a plurality of amphiphilic Janus dendrimers of claim 1 and said therapeutic composition with a mammal under conditions effective to deliver said liposome to a cell or tissue within said mammal.
20. The method of claim 19 , wherein said mammal is a human.