Amphiphilic Janus-dendrimers

Patent metadata

Field	Value
Publication number	US-9623046-B2
Application number	US-201013388587-A
Country	US
Kind code	B2
Filing date	Aug 5, 2010
Priority date	Aug 6, 2009
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

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.

First claim

What is claimed:

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.

Assignees

• Percec Virgil
• Hughes Andrew D
• Leowanawat Pawaret
• Wilson Daniela A
• Wilson Christopher J
• Univ Pennsylvania

Inventors

• Percec Virgil
• Hughes Andrew D
• Leowanawat Pawaret
• Wilson Daniela A
• Wilson Christopher J

Classifications

• A61K31/74 Primary

  Synthetic polymeric materials · CPC title

• A61K49/0028

  Oxazine dyes · CPC title

• A61P35/00

  Antineoplastic agents · CPC title